32789 Zip Code FL Real Estate, Homes with Formal Living Room Separate for Sale

4 Beds ⋅ 2 Baths ⋅ Glencoe Sub SubDv. ⋅ 32789 Zip Code

Rare opportunity in Winter Park's 32789! Located on a quiet cul-de-sac in one of Central Florida's most sought-after ZIP codes, this spacious 4-bedroom, 2-bath home offers approximately 2,400 square feet of living space, a brand new roof (2025), water heater (2021), and is situated on a generous lot with no HOA. Whether you're dreaming of creating your forever home, searching for your next renovation project, or looking to add a prime rental property to your portfolio, this is one you won't want to miss. With a little vision and updating, this property can truly shine in a neighborhood where beautifully renovated homes and stunning new construction continue to elevate property values. The location is exceptional—minutes from Park Avenue, Winter Park Village, top-rated schools, Rollins College, AdventHealth, downtown Orlando, and convenient access to I-4 and SR 408. Enjoy some of Central Florida's finest dining, boutique shopping, parks, museums, and entertainment, all just moments from your doorstep. Families will also appreciate Killarney Elementary School is just one street away. With endless possibilities to reimagine, renovate, or invest, opportunities to purchase a home like this seldom come along. If you're looking to build equity, generate rental income, or create the home you've always envisioned, this exceptional property is ready for its next chapter.

2323 Devon Court, Winter Park

$795,000

3 Beds ⋅ 2 Baths ⋅ Lakeview Terrace SubDv. ⋅ 32789 Zip Code

This well-cared-for immaculate home features quality workmanship inside and out! In addition to the three bedroom two bath, there is an 'office-bonus' room. The mature tropical oasis landscaping, cozy seating areas, and winding pathways make you feel right at home and at the same time on vacation! Open Kitchen, dining room, living room and bonus room. Located on a quaint street nestled among custom built homes. Have the best of both worlds, family life with upscale restaurants and shopping, and the annual Art and Holiday Festivals, movies in the park, parades, Rollins College, Boat Tours, kayaking and paddleboarding on the Winter Park Chain of Lakes all linked together and easily accessed via an Italian-inspired canal system. Only a mile away from famous ‘Park Avenue’ where visitors travel from all over the world to experience and celebrate our romantic sidewalk cafés and festivities.

1850 Bryan Avenue, Winter Park

$1,150,000

4 Beds ⋅ 3 Baths ⋅ Lake Knowles Terrace 2nd Add SubDv. ⋅ 32789 Zip Code

Located on one of Winter Park's picturesque brick streets in the highly desirable “Tree Streets”, this beautifully updated home offers incredible curb appeal with a circular driveway, charming front porch with brick flooring, and mature landscaping. Inside, a spacious foyer with soaring ceilings welcomes you, while engineered hardwood flooring runs throughout the main living areas. The recently renovated kitchen is the heart of the home, featuring quartz countertops, custom oak cabinetry with gold hardware, a center island with seating, stylish backsplash, and stainless steel appliances, including a gas range. The kitchen opens to the spacious dining room and inviting family room with built-ins, high ceilings, and French doors that fill the space with natural light. One of the home's most unique features is its thoughtfully designed layout. The original 1951 portion of the home offers two bedrooms, including the original primary suite with a large walk-in closet and private bath, plus a beautifully renovated hall bathroom. An addition completed in the early 2000s created an impressive owner's retreat on the opposite side of the home, complete with vaulted ceilings, French doors to the backyard, an oversized walk-in closet with custom organization, and a spacious bathroom with double vanities, soaking tub, separate shower, and private water closet. A fourth bedroom, tucked away in its own wing off the dining room, features built-ins, a large walk-in closet, and is conveniently located near the indoor laundry room. Situated on a generous .24-acre lot, the backyard offers plenty of room to add a pool while still leaving space to enjoy the yard. A long driveway leads to the rear one-car carport and an oversized storage room. Major updates include a 2020 roof and 2021 AC. All of this is just minutes from Park Avenue's renowned shopping, dining, and events, with easy access to top-rated Winter Park schools, parks, and everything that makes this neighborhood one of Central Florida's most sought-after places to call home.

1351 Oneco Avenue, Winter Park

$625,000

3 Beds ⋅ 3 Baths ⋅ Trotters Rep SubDv. ⋅ 32789 Zip Code

Under contract-accepting backup offers. Virtually Staged. Welcome to 786 McIntyre Avenue, Winter Park, FL 32789—a serene retreat perched on a picturesque tree-lined brick street in one of Winter Park's most desirable neighborhoods. Just a short stroll from Rollins College and the renowned shops, restaurants, and charm of Park Avenue, this exceptional single-family townhome offers the perfect blend of comfort, style, and location—SINGLE FAMILY TOWNHOME with NO HOA! A charming driveway leads to the attached two-car garage and private front entrance. Inside, you'll be welcomed by a bright, airy interior featuring soaring ceilings, dramatic high windows, abundant natural light, and a cozy wood-burning fireplace. The spacious living room is surrounded by two private patios, creating a seamless connection between indoor and outdoor living. The updated kitchen boasts modern cabinetry, an open breakfast bar, and a cheerful eat-in dining area with direct access to one of the patios. The formal dining room, currently used as a home office, opens to the second patio, making it the perfect setting for al fresco dining or entertaining. Upstairs, the impressive 23' x 12' primary suite offers a peaceful retreat, complete with a spacious 20' x 8' ensuite bathroom. Two additional guest bedrooms share a convenient Jack-and-Jill bathroom, providing comfort and privacy for family or visitors. Meticulously maintained, this home features numerous recent updates, including a new HVAC system (2025) and beautiful wood shutters throughout. Located in the highly sought-after Audubon K-8 and Winter Park High School districts, this exceptional home combines timeless character, modern updates, and an unbeatable location. WELCOME HOME!

786 Mcintyre Avenue, Winter Park

$600,000

2 Beds ⋅ 2 Baths ⋅ Orangewood Park SubDv. ⋅ 32789 Zip Code

Location, location, location. Wonderful home located in Winter Park besides Baldwin Park. Live in this home now - or purchase for the property and build your custom home! The yard is large. Large shed in the yard to store all of your yard essentials. You will love the area and the convenience to what makes this area special...steps from East End Market, lots of amazing restaurants, shopping, Leu Gardens, and so much more. Updates to the home include: Roof: 2020, HVAC 2019, Elecrical - new utility box, Plumbing: re-plumbed Kitchen and both bathrooms. Welcome Home.

2824 Woodside Avenue, Winter Park

$4,900,000

5 Beds ⋅ 6 Baths ⋅ Woodmere Terrace Rep SubDv. ⋅ 32789 Zip Code

A pristine location in the Vias of Winter Park, this refined Santa Barbara-inspired Mediterranean estate rests on nearly half an acre — a rare double lot. A 2006 custom build by Maroon Fine Homes and renovated in 2024 by Greg Hardwick, this estate blends timeless architecture with comfortable sophistication and functionality. A stone’s throw to the celebrated shops and dining of Park Avenue, Rollins College, Winter Park Golf Course, and the serene beauty of Kraft Azalea Gardens, the location is simply unrivaled. This extraordinary residence spans nearly 5,000 sf with a flowing floor plan designed for entertaining and everyday living. Solid wood artisan arched doors anchor the inviting foyer with porcelain marble tile, volume ceilings, and a sleek iron circular staircase as a focal point. An open dining and intimate living room layout are flanked by windows and clear view doors, which bring in natural light. The spaces share a unique temperature-controlled wine cellar finished with seamless glass and ambient lighting, adding a dramatic touch for the discerning enthusiast. The main level centers around a spacious kitchen that enjoys a dedicated eat-in space and counter seating, with a family room that overlooks the expansive backyard. A dedicated wet bar and first-floor bonus room make this home ideal for hosting at any scale. The outdoor living rivals a 5-star resort, recently reimagined in 2026 by Signature Landscaping. An immense new pool with a sun shelf anchors the outdoor living experience, surrounded by a lush turf courtyard, sport court, and a covered lanai with generous pavered decking and a summer kitchen. A cozy gas fire pit with casual seating invites you to take in the evening breezes. Privacy abounds with mature Japanese blueberry trees and Podocarpus hedges. A dedicated side yard dog run completes this outdoor haven. The main floor is home to the first-floor primary suite, with privacy doors separating this section of the home. It is a true retreat unto itself, offering a sunlit sitting area with doors leading to the backyard, a beautifully appointed bath, a dedicated home office, and two custom-fitted walk-in closets, one of which includes a secondary laundry area. The spa-inspired bathroom has it all, featuring a generous shower with a soaking tub within the enclosure for the ultimate relaxation experience. A first-floor guest suite, thoughtfully designed with a split-plan layout, provides privacy for visitors, while three additional ensuite bedrooms and a bonus landing are located upstairs. The oversized three-car side-loading garage is air-conditioned and features upgraded flooring, while a generous circular drive and mature front hedge offer a gracious arrival experience and an added layer of privacy. A rare convergence of premier location, architectural distinction, and meticulous renovation — this is Winter Park luxury living at its finest.

1180 Via Lugano, Winter Park

$575,000

2 Beds ⋅ 3 Baths ⋅ Quarters At Winter Park Condo SubDv. ⋅ 32789 Zip Code

Under contract-accepting backup offers. Completely reimagined in 2025, this stunning 2-bedroom, 2.5-bath townhome offers the perfect blend of modern luxury and an unbeatable Winter Park location. Just minutes from Rollins College, Park Avenue, boutique shopping, award-winning dining, and everything that makes Winter Park so desirable, this move-in-ready home has been thoughtfully renovated from top to bottom with timeless, designer-selected finishes. The heart of the home is the beautifully redesigned kitchen featuring Sarah Sherman Samuel cabinetry and hardware, gorgeous marble countertops, a custom marble ledge, and all-new appliances. Throughout the home, you'll find new flooring, smooth-finished walls, fresh interior paint, recessed lighting with dimmers, updated electrical, new interior doors and hardware, and new baseboards, creating a clean, sophisticated aesthetic. Upstairs, both spacious bedrooms feature beautifully updated en-suite bathrooms, while the primary suite includes a custom marble-top vanity and a thoughtfully designed built-in closet system. Every bathroom has been fully renovated with high-end finishes that elevate the home's overall design. Step outside to your own private outdoor retreat featuring a large covered patio with low-maintenance turf—perfect for entertaining, relaxing, or enjoying your morning coffee year-round. Major mechanical updates provide added peace of mind, including a 2023 air handler, 2024 water heater, all-new A/C ductwork, and added attic insulation for improved energy efficiency. With nearly every surface and major system thoughtfully updated, this exceptional Winter Park townhome offers luxurious, turnkey living in one of Central Florida's most sought-after neighborhoods.

1122 Washington Avenue Unit 7B, Winter Park

$1,625,000

4 Beds ⋅ 4 Baths ⋅ Charmont SubDv. ⋅ 32789 Zip Code

Virtually Staged. A rare opportunity to live on a quiet one-way street overlooking a park in the heart of Winter Park. Built in 2007 and meticulously maintained, this exceptional 4-bedroom, 4-bath pool home with a dedicated office offers timeless design, thoughtful updates, and an unbeatable location. A welcoming covered front porch provides the perfect spot to enjoy your morning coffee. Inside, soaring ceilings, extensive moldings, travertine and hardwood floors, and abundant natural light create an elegant first impression. Just off the foyer, French doors open to a private office, ideal for working from home. A secondary bedroom and full bath with a walk-in shower are conveniently located on the main level. The spacious kitchen flows seamlessly into the family room and features granite countertops, solid wood soft-close cabinetry, a gas cooktop, wall oven, breakfast bar, wet bar, walk-in pantry, and a sunny breakfast nook overlooking the lanai and pool. The adjoining family room is anchored by a gas fireplace and French doors leading outdoors. The covered lanai showcases a tongue-and-groove ceiling and remote-controlled screens, creating the perfect setting for year-round entertaining. The generous first-floor primary suite offers space for a sitting area and features two custom walk-in closets, dual vanities, a soaking tub, separate shower, and private water closet. A beautiful wrought-iron staircase leads upstairs to two generous en-suite bedrooms and a cozy loft. The private backyard is designed for relaxation and entertaining, featuring a saltwater pool and spa surrounded by lush landscaping. Additional highlights include two newer HVAC systems (2022 and 2023), a gas water heater (2022), central vacuum system, built-in Home Team pest defense system, and plantation shutters throughout. Located within the highly sought-after Audubon K-8 and Winter Park High School districts, this exceptional home is ideally situated between Park Avenue and Corrine Drive, with downtown Orlando just minutes away.

341 E Reading Way, Winter Park

$5,600,000

5 Beds ⋅ 6 Baths ⋅ Maitland Shores First Add SubDv. ⋅ 32789 Zip Code

This elegant transitional French Provincial residence was the feature home in the Orlando Museum of Art's 2022 "mystery home tour" and is located on a large, elevated corner lot in a quiet and secluded area in the Via’s of Winter Park. This residence has been significantly enhanced inside and out by the current owner. The home features 5,200 square feet of living space and 800+ square feet of outdoor space with 5 bedrooms, 5 bathrooms ensuite, 1 half bathroom, 3 car garage, pool, patio and professionally landscaped yard and lighting. Upon entry, you are welcomed through the exquisite foyer where you instantly notice the craftsmanship and expert care that went into the custom carpentry and crown molding details throughout. To the left of the foyer is an elegant and intimate parlor with grass cloth wallpaper, a gas vented fireplace and built-in bookshelves. To the right of the foyer is the formal dining room with beautiful hand painted wallpaper and an adjacent butler’s pantry. Past the foyer you are led to a spacious and grand formal living room with 6 new French iron doors that flow out to a covered brick porch and picturesque back yard & pool. Designed with entertainment in mind, the adjoining chef’s kitchen includes newly painted custom cabinetry, a Sub-Zero/Wolf appliance package, a grand center island and a walk-in pantry. Built in desk and casual dining area all open to the adjoining beamed ceiling family room with gas vented fireplace and additional French doors that lead to street side patio with new awnings. First floor master retreat overlooks the pool & yard and features 14-foot wood beam vaulted ceilings. The oversized master bath with double custom lacquered vanities made in Palm Beach, mosaic marble shower and a Waterworks free standing tub, brushed brass fixtures, and walk in closet. The second-floor features nine-foot ceilings with four bedrooms (one which was converted to a beautiful women’s dressing room) and four ensuite bathrooms, covered balcony adjoining two bedrooms, two built in desks and bookshelves for office/study time and large media room with big screen tv and wet-bar. There are also two laundry rooms, one upstairs and one downstairs. Attic space inside the home and inside the garage. Recent upgrades include slate roof/swooped decorative copper roof with chimney caps, complete chimney rebuild, nine iron French doors, white oak tongue and grove hardwood floors, renovated master bath and two ensuite baths, two new HVAC home units and a new garage mini-split air conditioner. This home offers boat access to the Winter Park chain of lakes and is within short distance of the Winter Park Racquet Club. It’s also a bike ride away and a short drive to the Interlachen Country Club and Park Avenue shopping and dining district. The property is zoned for Dommerich Elementary, Maitland Middle School, and Winter Park High School. One or more rooms virtually staged

2228 Azalea Place, Winter Park

$1,025,000

3 Beds ⋅ 3 Baths ⋅ Virginia Heights Rep SubDv. ⋅ 32789 Zip Code

Georgetown-style 'Brownstown' in the Heart of Winter Park, walking distance to Downtown, PLUS deeded Lake Access to Lake Virginia! This spacious property has 3 bedrooms, 3 full baths, 2434 sq ft, 10' ceilings custom details throughout and natural lighting. Foyer with slate flooring, enjoy the double-sided gas fireplace in the Living & Dining areas, beautiful wood floors, crown molding, plantation shutters, a butler bar with custom cabinetry & wine refrigerator. Cooking inspired Kitchen with a lengthy granite island and sitting bar overlooks the Family room. Upgraded stainless appliances, including gas cooktop with griddle, microwave/convection oven, hanging pot rack with lighting, and soft close cabinets with pullouts. French doors to the covered 'English Garden' courtyard with pavers & stainless grill for entertaining. Guest suite or home office with a custom closet and full bath overlooks brick street, Pennsylvania Ave. Large laundry room near the garage with granite countertops, cabinets & utility sink, plus washer & dryer. Upstairs is a spacious Primary bedroom with French doors to a private covered balcony; also, 2 large walk-in closets with closet systems, Jacuzzi tub, huge walk-in shower, dual vanities with granite countertops & more. An additional ensuite bedroom, more wood floors, plus a built-in dehumidifier. Attached 2-car, rear alley access garage, plus an additional side parking pad. Walk to Park Ave. for dining, shopping, WP Tennis Center, outdoor park & Rollins College. Neighborhood Lake Virginia access for paddleboard & kayak launching to the Winter Park Chain of Lakes. Top schools, Audubon K-8 seconds away, and WPHS. NEW TPO membrane roof w/ metal coping March 2026. HOA maintains: landscaping, irrigation, building maintenance & outdoor lighting. Won't last!

1138 S Pennsylvania Avenue, Winter Park

$1,799,000

4 Beds ⋅ 5 Baths ⋅ Winter Park Place 45/148 SubDv. ⋅ 32789 Zip Code

Nestled on one of Winter Park’s most exclusive streets, this exceptional residence is located within Park Place—the only gated neighborhood in the coveted 32789 ZIP code—and is zoned for highly sought-after Audubon Park K–8 School. From the moment you arrive, you'll appreciate the rare combination of privacy, charm, and convenience that defines this remarkable home. Designed with both everyday living and effortless entertaining in mind, the versatile floor plan features elegant formal living and dining rooms, creating a welcoming setting for gatherings both large and small. The spacious primary suite is conveniently located on the first floor, along with a secondary bedroom ideal for guests or multigenerational living. Upstairs, you'll find two additional bedrooms, a full bath, and a generous bonus room perfect for a home office, media room, playroom, or fitness space. At the heart of the home is a beautifully appointed kitchen featuring granite countertops, crisp white cabinetry, a center island, and a sunlit breakfast nook surrounded by windows. The kitchen flows seamlessly into the inviting family room, where custom built-ins, a cozy fireplace, and French doors create the perfect blend of comfort and sophistication. Step outside to your own private Florida oasis. The covered paver lanai, summer kitchen, and sparkling saltwater pool provide an ideal backdrop for year-round entertaining, weekend gatherings, or peaceful evenings at home. Rich hardwood floors extend throughout the entire residence—there’s not a stitch of carpet anywhere. Architectural details such as crown molding, plantation shutters, 10-foot ceilings, and 8-foot doors enhance the home’s timeless elegance and spacious feel. Additional conveniences include a first-floor laundry room with pantry storage and a guest powder bath. A standout feature is the oversized detached two-car garage, complete with a private upstairs studio and full bath—perfect for a home office, guest suite or creative space. Surrounded by lush professional landscaping and shaded by magnificent mature oak trees, the fully fenced backyard offers beauty, privacy, and natural cooling throughout Florida’s warmer months. Tucked away on a quiet cul-de-sac, the property also benefits from added privacy provided by the neighborhood’s surrounding brick wall and direct access to a nearby open field. Park Place is more than a neighborhood—it’s a rare opportunity to enjoy a secure, friendly lifestyle.

2625 Park Place Drive, Winter Park

$249,900

2 Beds ⋅ 2 Baths ⋅ Lakeside Manor Apts Condo SubDv. ⋅ 32789 Zip Code

At under $250,000, this renovated 2-bedroom, 2-bath condominium is truly move-in ready. The heart of the home is the custom kitchen (2025), which features soft-close cabinetry with a built-in refrigerator surround, matching energy-efficient appliances, quartzite countertops, white granite sink, and antique brass hardware. Additional updates include vinyl flooring throughout, renovated primary shower (2026) with Italian porcelain tile, tankless water heater (2025), renovated hallway bathroom (2024), fresh interior paint (2026), and a new A/C system (2024), which was most recently serviced in June 2026. Enjoy an exceptional HOA package including water, trash, high-speed internet, cable television (150+ channels), and popular streaming services. Set along scenic Lake Killarney, the community features a private dock, boating and kayaking access, abundant guest parking, and new landscaping, with community paving scheduled for August 2026. Schedule your tour today!

2500 Lee Road Unit 104, Winter Park

$6,000,000

5 Beds ⋅ 8 Baths ⋅ Comstock Park SubDv. ⋅ 32789 Zip Code

Experience timeless elegance and deliberate craftsmanship in the heart of prestigious Winter Park. This one-of- a-kind exceptional estate offers more than 7,300 square feet across three beautifully designed levels, blending refined luxury with modern comfort. Rich architectural details include solid red oak flooring with a walnut finish, nearly 10-foot ceilings, stacked crown moldings, custom ironwork, designer lighting, and extensive millwork throughout. The gourmet kitchen is thoughtfully appointed with Viking and GE Monogram appliances, custom Busby cabinetry, an oversized island, and a butler’s pantry. It also includes multiple filtered water and ice zones designed for effortless entertaining. The spacious primary suite offers a true retreat with spa-inspired marble finishes, an oversized walk-in shower, a jetted soaking tub, and exceptional custom closet space. Additional features include a private elevator, Control4 automation, integrated audio/video/security systems, five HVAC systems, a central vacuum system, and a Generac whole-home generator. A fully finished and expansive basement level serves as a unique and exceptional extension of the home’s living and entertaining space. Designed for both relaxation and recreation, it features a game and arcade room, a full beverage center with a dishwasher, microwave, and Scotsman ice machine, a fitness area with a sauna and steam room, an additional laundry room, a creative storage center, and a private 4K theater with seating for multiple guests. Outdoors, resort-style living awaits with a saltwater pool and spa, a summer kitchen with a custom copper hood, an electric gated entry, landscape lighting, lush cascading bougainvillea, and ten mature magnolia trees creating exceptional beauty and privacy. The property also features a dog run with artificial turf. Three ventless gas fireplaces, including one on the private covered porch, add warmth and ambiance throughout the home. This home also features a whole-house water softener system. Top-rated A+ public schools are within a short walk or bike ride. Nearby highly regarded private schools include Park Maitland School, The Christ School, The First Academy, Trinity Preparatory School, Lake Highland Preparatory School, and Bishop Moore Catholic High School. Perfectly positioned within walking distance of the boutiques and dining of Park Avenue, and just minutes from the Winter Park Golf Course, Rollins College, and Advent Health Winter Park, this is a rare opportunity to own an exceptional custom estate in one of Central Florida’s most sought-after communities.

1571 Woodland Avenue, Winter Park

$995,000

3 Beds ⋅ 3 Baths ⋅ Virginia Heights SubDv. ⋅ 32789 Zip Code

Seller is offering a generous $25,000 credit toward price or closing costs, giving the next owner an incredible opportunity to personalize this Winter Park residence to their own taste. While the home could benefit from cosmetic updates, the fundamentals are already in place! A/C system and ductwork (2023), roof (2021), replumb (2026). For the right buyer, this is a rare chance to secure a premier location at a value that’s increasingly hard to find. Welcome to 241 W. Lake Sue Avenue, an exceptional offering in Virginia Heights, one of Winter Park’s most cherished and established neighborhoods. Nestled along a picturesque oak-canopied brick street and surrounded by multimillion-dollar estates, this beautifully updated pool home sits on an oversized 12,000-square-foot lot and delivers the lifestyle that defines Olde Winter Park living. Designed for effortless indoor-outdoor enjoyment, the home features sunlit interiors, soaring ceilings, architectural wood-beam accents, travertine flooring, and inviting gathering spaces that overlook a private backyard retreat. The chef’s kitchen anchors the residence, connecting seamlessly to the living and dining areas while offering serene views of the pool, spa, and lush outdoor living spaces. The spacious primary suite provides a calming escape with vaulted ceilings, a spa-inspired bath, and a generous walk-in closet. What truly sets this property apart is its location within Virginia Heights, where residents enjoy deeded access to a private Lake Virginia waterfront park. Just a short stroll away, homeowners have exclusive use of a private dock, canoe and kayak storage, open green space, and sweeping lakefront views across from Rollins College, an amenity rarely found in Winter Park. Moments from Park Avenue’s boutiques and dining, nearby parks, cultural venues, and top-rated schools, this home blends timeless charm with modern comfort in one of the city’s most coveted enclaves. Opportunities to purchase in Virginia Heights are limited; opportunities with private lake access, an oversized lot, and a resort-style backyard are even rarer. Priced below market value due to cosmetic updates needed, this property invites you to enhance the existing residence or build a new home from the ground up. Either path securing a legacy-worthy homesite in one of Winter Park’s most desirable locations!

241 W Lake Sue Avenue, Winter Park

$1,695,000

4 Beds ⋅ 4 Baths ⋅ Lake Knowles Terrace Add 02 SubDv. ⋅ 32789 Zip Code

On a picturesque brick street in Winter Park, this beautifully designed modern traditional pool home blends timeless architecture with thoughtful, high-end finishes throughout. Built in 2015 and offering over 3,100 square feet, the home features four bedrooms, three full baths, and a flexible three-story layout designed for everyday living and effortless entertaining. A welcoming front porch leads into a bright foyer highlighted by custom millwork and warm wood flooring, setting the tone for the home’s clean, curated style. The open-concept main living space flows seamlessly from the dining area into a spacious family room and a chef’s kitchen designed to impress. Anchored by a generous marble island with seating, the kitchen features Viking stainless steel appliances, a gas cooktop, honed granite perimeter countertops, custom cabinetry with upper and under-cabinet lighting, and stylish tile backsplash. A wet bar with wine refrigerator adds to the home’s entertaining appeal. The first floor also includes a versatile office or playroom with custom built-ins, a functional mudroom/drop zone and abundant storage throughout. Upstairs, the primary suite offers a peaceful retreat with natural light and a spa-inspired bath featuring dual vanities, a soaking tub and a glass-enclosed shower. Secondary bedrooms are well-sized and thoughtfully designed, while the third-floor bonus suite with full bath provides ideal space for guests, a home office or additional living. Outdoor living is equally inviting, with a covered back porch equipped with remote-controlled phantom screens overlooking a private, professionally landscaped yard with artificial turf and a low-maintenance pool, ideal for year-round enjoyment. Additional features include two HVAC systems with Nest thermostats, hardwood flooring on the main level, and designer finishes throughout. Zoned for sought-after schools including Dommerich Elementary, Maitland Middle and Winter Park High. This is a rare opportunity to own a move-in ready home that balances style, function and location in one of Winter Park’s desirable settings.

1420 Magnolia Avenue, Winter Park

$892,500

3 Beds ⋅ 3 Baths ⋅ Charmont SubDv. ⋅ 32789 Zip Code

Discover the perfect canvas for your dream home at 1960 Winter Park Road! With utilities and sewer connected, plus a complete roof replacement in 2019, newer gutters with gutter guards added in 2020, and various new appliances and thoughtful upgrades since, this ¼-acre lot presents the ideal opportunity to either build new, or remodel. Zoned for the highly esteemed Audubon K-8 School, this property offers an ideal location nestled in one of the most coveted pockets of Winter Park. Stroll down the brick-lined street and land at East End market, Kelly’s Homemade Ice Cream, and all the shops and restaurants along the vibrant Corrine Drive corridor; walk around the corner to Blue Jacket Park; or venture North just 2.5 miles to discover the cultural delights of Park Avenue in downtown Winter Park. The existing 1940's home is still bursting with charm and potential. From the moment you arrive, the circular paver driveway and inviting front porch set the tone for a home that balances warmth and functionality. The main residence offers 2 bedrooms and 2 bathrooms across 1,500+ square feet, complemented by a detached 1-bedroom, 1-bath guest cottage. Ideal for extended stays, a private office, hobby space, or flexible living arrangements, the detached cottage presents endless possibilities, with enough space available for creative modifications to suit your needs. A paver 2-car parking pad off the circular drive allows room for temporary or long-term guests, with the added convenience of private entry to the detached dwelling via a paved walkway through the side gate. The main home is well-laid-out, with multiple living & dining spaces to make everyday living and entertaining a breeze, all anchored by hardwood flooring throughout. A spacious, paver side patio and large rear deck offer separate, gated outdoor living areas for versatility and enjoyment, while the rear deck overlooks a private, fenced-in backyard just waiting to be transformed into the perfect Florida oasis. If you are looking to land just a few minutes from downtown Orlando and downtown Winter Park, with easy Access to I-4…this is the location for you!

1960 Winter Park Road, Winter Park

$2,750,000

5 Beds ⋅ 5 Baths ⋅ Comstock Park SubDv. ⋅ 32789 Zip Code

Under contract-accepting backup offers. The seller has just completed a full renovation. Bathrooms have been entirely gutted and updated with new tiles, fixtures, and lighting. All lighting throughout the home has been replaced, and fresh paint has been applied throughout. Situated on a spacious double lot spanning over 1/3 acres, this home offers a private retreat, complete with an impressive 18 x 40 pool. The layout features generous common areas, including a large family room, a formal living room, a separate dining room, a kitchen with an adjacent breakfast room, a dedicated home office, a loft-style office or playroom, and a cozy home theater located above the garage. The kitchen, primary bedroom, and both the family and living rooms provide stunning views of the pool and backyard. The three-car garage offers ample space for large vehicles. Beyond the pool, you’ll find a charming gazebo and a fully equipped outdoor kitchen. Built with block and stucco construction and topped with a durable tile roof designed to last up to 100 years, this home boasts incredible durability and aesthetic appeal. Combining the feel of new construction with a rare, expansive lot in a well-established neighborhood, it provides privacy, mature landscaping, and modern elegance all in one.

1630 Lasbury Avenue, Winter Park

$1,995,000

4 Beds ⋅ 4 Baths ⋅ Sylvan Lake Shores SubDv. ⋅ 32789 Zip Code

Welcome to your private slice of paradise, perfectly positioned on a charming brick-lined street in the heart of historic Winter Park. This custom-built estate exudes casual elegance from the moment you step through the grand double door entry, where soaring 12-foot ceilings, rich architectural details, and exceptional craftsmanship immediately set the tone. Thoughtfully designed with a well-balanced and highly functional floor plan, the home offers a seamless blend of formal and informal living spaces ideal for both everyday living and elevated entertaining. At the heart of the home, the pristine chef’s kitchen opens effortlessly to the family room and is outfitted with a built-in Thermador French door refrigerator, custom lighted cabinetry, granite countertops, a six-burner gas range with pot filler, double ovens with warming drawer, and an oversized island designed for gathering. A beautifully appointed butler’s pantry with wine fridge and wet bar creates the perfect transition to the formal dining space. Tucked away for privacy, a dedicated home office or library offers a quiet retreat for work or study. The first-floor primary suite is a true sanctuary, featuring intricate ceiling detail, expansive windows, and private French door access to the outdoor living space. The spa-inspired primary bath includes a jetted tub, dual vanities, and two oversized walk-in closets. Upstairs, three generously sized secondary bedrooms and two additional baths—including a private en suite—provide comfortable accommodations, while a charming Juliet balcony offers picturesque views of the tree-lined street below. Step outside to an exceptional outdoor living experience designed for year-round enjoyment. The covered lanai features a fully equipped summer kitchen with built-in grill, custom copper hood, and beverage fridge for the warmest Florida days. The saltwater pool creates a resort-style setting, surrounded by lush landscaping and enhanced by upgraded lighting and smart technology. This meticulously maintained home has been extensively upgraded, including new HVAC systems for both levels, on-demand water heater, whole-house surge protection, updated LED lighting with dimmer controls, smart home integrations for pool, irrigation, security, and climate, as well as complete interior and exterior repainting with premium finishes. High-end reclaimed maple and beech wood flooring has been installed and is complemented by refined architectural details such as curved archways, custom millwork, and elevated designer fixtures. Additional highlights include a newly created wine room, epoxy-coated garage flooring, central vacuum system, and enhanced exterior features with added awnings and detailed craftsmanship. Situated on a gorgeous lot with added privacy and with garage doors thoughtfully positioned away from the street, this home offers both presence and practicality. Just a short stroll to Lake Mizell and minutes from the renowned dining, shopping, and cultural experiences of Park Avenue, this exceptional property combines timeless design, modern upgrades, and an unbeatable location.

1398 Grove Terrace, Winter Park

$1,875,000

4 Beds ⋅ 5 Baths ⋅ Lake Virginia Pt Rep SubDv. ⋅ 32789 Zip Code

Welcome to Timberlane Shores—one of Winter Park’s most desirable neighborhoods! This beautiful 4-bedroom, 4.5-bath home sits on over a third of an acre in a quiet, tucked-away location with gorgeous updated landscaping. Inside, you’ll find wide-plank hardwood floors throughout and a thoughtfully designed floor plan with separate living and dining rooms plus a spacious family room. The bright kitchen features white cabinetry with pull-out drawers, marble countertops, subway tile backsplash, and newer appliances (2018), including a Sub-Zero refrigerator and Wolf gas 4 burner range. The kitchen opens to a bright sunroom with beautiful wood-like tile floors laid in a herringbone pattern (2018). Such a great space that is filled with natural light—perfect as a casual gathering space or playroom, making this an ideal home for entertaining. The sunroom overlooks the enormous backyard space and large pool area with custom designed pavers (2023). A downstairs guest suite with full bath provides comfort and privacy, while a dedicated office with built-in desks and brand new carpet adds functionality. Upstairs, the oversized primary suite boasts a beautifully appointed bathroom with dual sinks, marble countertops, soaking tub, and separate walk-in shower, along with a custom walk-in closet. Two additional upstairs bedrooms each offer en-suite baths, including one renovated in 2021. Recent updates include new windows (2017), solid wood front door (2021), renovated bath (2021), two new AC units and duct cleaning (2024), and a new roof (2024). This exceptional home offers the perfect blend of style, comfort, and location—truly a must-see.

543 E Lake Sue Avenue, Winter Park

$2,150,000

5 Beds ⋅ 4 Baths ⋅ Green Oaks Rep 02 SubDv. ⋅ 32789 Zip Code

Welcome to an exceptional opportunity in the highly desirable Park Grove community, an impeccably updated one-story residence ideally situated just moments from the vibrant shops and dining of Park Avenue and all that downtown Winter Park has to offer. With charming curb appeal, pristine landscaping and timeless architectural appeal, this home makes a stunning first impression. Inside, a thoughtfully designed floor plan offers seamless flow, perfectly suited for both everyday living and effortless entertaining. Beautiful wood flooring spans the main living areas, while the Florida room showcases distinctive Mexican tile, adding warmth and character. Designer lighting, curated tile selections and stylish wallpaper accents create a bright, inviting aesthetic throughout. The formal sitting room, complete with custom built-ins and an elegant dining room provide refined gathering spaces. At the heart of the home, a light-filled kitchen opens to the spacious family room, where a cozy wood-burning fireplace serves as a focal point. The adjacent Florida room is lined with windows, offering serene views of the sparkling pool and lush, private backyard. The generously sized primary suite is thoughtfully positioned for privacy, featuring its own wood-burning fireplace, a large walk-in closet and a beautifully appointed ensuite bath with dual vanities and an oversized walk-in shower. Four additional bedrooms are located on the opposite side of the home, two of which include ensuite baths, ideal for guests or multi-generational living. Outdoor living is equally impressive, with a beautifully paved lanai overlooking the pool and ample space for alfresco dining, entertaining and relaxing poolside. Tucked away in one of Winter Park’s sought-after neighborhoods, this home offers tranquility and convenience, with easy access to downtown Orlando, major hospitals, top-rated public and private schools and key roadways. A rare blend of style, comfort and location; this is Florida living at its finest.

800 Juanita Rael, Winter Park

$1,125,000

3 Beds ⋅ 3 Baths ⋅ Orwin Manor Westminster Sec SubDv. ⋅ 32789 Zip Code

Virtually Staged. Set on a prized corner lot in Winter Parks sought after Orwin Manor Neighborhood, 1651 Westchester Ave is a timeless classic with Cape Cod inspired architecture that has been meticulously reimagined with today’s luxury finishes while preserving its original charm. Refinished Original Pine hardwood flooring and a beautifully updated fireplace welcome you into the main living space, while the showpiece kitchen delivers true chef-level design with new Custom European Cabinetry, Quartz Countertops with a Waterfall Island, Porcelain Tile floors, premium lighting, under counter Kitchen Aid Ice Maker and a top-tier appliance suite including Wolf Gas Range-top, Wolf Built-in Oven & Microwave and Bosch Refrigerator and Dishwasher. The primary suite is a serene retreat with a newly redesigned spa style bath with frameless walk-in shower, soaking tub, new double sink vanity and lighting—plus a walk-in closet with California Closet built-in’s and a versatile bonus room ideal for a sitting area, nursery, or additional laundry space. Outdoors, enjoy resort-style living under the expansive 26’ x 24’ covered Lanai featuring vaulted tongue-and-groove ceilings, tile flooring, a striking stone gas fireplace with RealFyre burners, stainless mantle, perfect for effortless entertaining. There is even enough room to customize the outdoor space with your own Pool Oasis. Recent improvements include Roof 2020, New HVAC System, New Double-Pane windows, 4-panel slider & front door, fresh interior/exterior paint, new custom shades, privacy bamboo landscaping, privacy fencing and an extended paver driveway. The attached Garage offers dedicated storage space and a bonus room with mini-split system which could offer space for home gym or office. Just minutes from Park Avenue’s acclaimed dining and shopping, top Winter Park amenities, Advent Health Medical Campus and quick access to key corridors for an easy downtown Orlando commute, this is 32789 living at its most refined—classic architecture, modern systems, and elevated indoor-outdoor lifestyle in one of Winter Park’s most sought-after neighborhoods.

1651 Westchester Avenue, Winter Park

$1,425,000

4 Beds ⋅ 4 Baths ⋅ Park Grove SubDv. ⋅ 32789 Zip Code

Timeless Olde Winter Park charm meets relaxed Florida living at 823 Granville Drive, a true Park Grove gem on an expansive 100' x 135' lot. Nestled among tree-lined streets in this coveted, well-established neighborhood, this single-story residence offers 4 bedrooms, 3.5 baths, and effortless indoor-outdoor living. Thoughtfully designed for entertaining, the home features two fireplaces that anchor inviting living and family spaces, creating a warm, elegant backdrop for gatherings large and small. The open, flowing layout keeps daily living convenient on one level while offering plenty of separation for guests or multi-generational living. Step outside to your own private retreat: a screened, enclosed pool area that feels like an outdoor living room, perfect for morning laps, weekend barbecues, or evening cocktails. The generous lot provides room to play, garden, or simply enjoy the lush surroundings and privacy Park Grove is known for. Practical features include a two-car garage, ample storage, and the rare opportunity to own a pool home in one of Winter Park’s most sought-after neighborhoods, just minutes to Park Avenue shopping, dining, lakes, and cultural venues. This is the Park Grove lifestyle—single-story, pool, charm, and location—all in one compelling property.

823 Granville Drive, Winter Park

$3,100,000

5 Beds ⋅ 5 Baths ⋅ Charmont SubDv. ⋅ 32789 Zip Code

Grand Southern charm and architectural elegance define this stately residence in one of Winter Park’s most desirable neighborhoods, set along a quiet brick-lined street just steps from Lake Chelton. Positioned on nearly half an acre, the home spans over 5,200 square feet, offering 5 bedrooms, 4.5 baths, a designated office, a large, versatile media/game room, a 3-car garage, and an expansive lanai with summer kitchen and resort style pool— all brought together in a smart well-planned layout ideal for effortless everyday living and exceptional entertaining. Step inside to a beautifully curated interior where rich architectural detail and livable design come together. Extensive custom millwork—seen in detailed moldings, trim work, and built-ins—adds depth and character throughout. The entry opens to gracious living and dining spaces, complemented by an impressive 550+ bottle temperature-controlled wine room. At the heart of the home, a beautifully appointed Kitchen, featuring white wood cabinetry, a six-burner gas range, an oversized quartz island, and a delightful breakfast nook that seamlessly connects to the family room featuring custom built-ins and fireplace—creating a natural gathering space. Tucked away, the first-floor primary suite offers a spacious sitting area, a beautifully customized closet with dressing area, and a luxurious bath with marble flooring, a large double-head walk-in shower, dual vanities, a free -standing tub, and built-in linen cabinetry—designed as a calming and private sanctuary. The first level also features a private guest bedroom with en-suite bath, creating an ideal setup for friends & family. A generously sized laundry room offers abundant cabinetry and exceptional storage, making everyday tasks feel effortless. Upstairs, three spacious bedrooms and two full baths provide comfortable accommodations, with two bedrooms opening through French doors to the front double balcony—perfect for enjoying peaceful treetop views. The back of the home unfolds around a beautiful pool and spa, with French doors from multiple rooms opening to the lanai and creating a natural indoor-outdoor connection. Retractable screens allow for year-round enjoyment of the well-appointed summer kitchen, making it ideal for both relaxed evenings and easy entertaining. Other notable highlights: a whole house natural gas generator, extensive brick paver driveway & motor court, automated driveway gate, integrated sound system, security cameras and new roof 2024. Lastly, this profound property offers top rated Winter Park schools and easy access to Park Ave, Downtown Orlando, Audubon Park Garden District and Baldwin Park.

141 Glenridge Way, Winter Park

$2,200,000

5 Beds ⋅ 4 Baths ⋅ Park North SubDv. ⋅ 32789 Zip Code

Under contract-accepting backup offers. WALK TO PARK AVENUE from this RARE nearly HALF ACRE homesite with OVER 4,000 SQUARE FEET and 5 BEDROOMS in one of Winter Park's most desirable locations. Leave your car at home and enjoy Park Avenue's renowned restaurants, boutiques, cafés, parks, and the Winter Park Golf Course just moments from your front door. Tucked away on a quiet cul-de-sac, this timeless two story residence offers the perfect combination of space, warmth, and an exceptional floor plan designed for both everyday living and effortless entertaining. From the moment you step inside, the home feels welcoming with expansive living spaces, soaring ceilings, and abundant natural light. The main level is anchored by a spacious primary suite, while the family room features dramatic ceilings and opens seamlessly to the kitchen and casual dining area, creating the true heart of the home. French doors lead to a screened patio with a charming Southern feel that overlooks the expansive backyard, offering endless possibilities for a pool, outdoor entertaining, or future expansion. A separate formal living room provides additional flexibility, while the formal dining room connects to a butler's pantry, making hosting gatherings both functional and elegant. Upstairs, you'll find four generously sized bedrooms with beautiful original hardwood floors, providing ample space for family, guests, home offices, or a playroom. LOCATION. LOT SIZE. WALKABILITY. Opportunities to own a nearly half acre property this close to Park Avenue are exceptionally rare. Enjoy the very best of Winter Park with premier shopping, award winning dining, parks, golf, and everything that makes this one of Central Florida's most coveted addresses just a short stroll away.

1130 Park North Place, Winter Park

$3,755,000

4 Beds ⋅ 5 Baths ⋅ Dixie Terrace SubDv. ⋅ 32789 Zip Code

Experience the art of luxury living just steps from the boutiques, cafés & celebrated dining of Park Avenue, Winter Park Village, Rollins College & the iconic Winter Park Art Festival. This beautifully crafted custom one-story pool home built in 2024 blends elegant design with an effortless, modern lifestyle. THIS HOME RECEIVED THE 2025 ARDA GRAND AWARD FOR CUSTOM HOME (built). A thoughtful quad split bedroom layout offers 4 bedrooms & 4.5 baths, including a serene primary suite with Hunter Douglas automated light filtering/light blocking shades. The primary suite includes a spectacular custom walk-in closet featuring an island, 36 drawers, built-in benches, dual hampers, a safe, locking jewelry drawers & display shelving. The ensuite bath provides a spa-like retreat. Additionally, two guest suites also enjoy private ensuite baths & large walk-in closets. The showpiece chef’s kitchen is designed for both culinary mastery & entertaining, featuring Dura Supreme cabinetry, a 60" Wolf dual fuel range with griddle, pot filler, 36" Sub Zero Designer Column refrigerator, Sub Zero freezer drawers, two Bosch dishwashers, Wolf microwave drawer, Revati dual tier 57" sink with custom inserts for colander, cutting board & strainer & dual automatic faucets. Dramatic 15-foot waterfall island with Dekton countertops & matching backsplash. A hidden scullery adds even more function with a French door refrigerator, sink, pantry shelving, Dekton counters & floating LED-lit shelves. The stylish wet bar includes white oak floating shelves with LED lighting, Dekton countertops & backsplash, a glass rinser, Scotsman gourmet ice machine & Thermador refrigerator drawers. Dining room has a climate-controlled wine cellar that holds up to 240 bottles. Enjoy picking lemons, limes & oranges from your own mature trees for juicing or garnishes. The expansive family room impresses with six LED-lit floating shelves, a 60" linear gas fireplace & an extraordinary 52 feet of 10-foot-tall sliding stacking patio doors that create seamless indoor-outdoor flow. Step outside to a resort-style outdoor kitchen & living area, complete with a Dekton waterfall countertop, Perlick refrigerator drawers & kegerator, 48" DCS grill with rotisserie & 2 side burners, pizza oven, Ruvati sink with ice chest, bar-height island seating, three 60" Minka Aire remote control fans, outdoor electric fireplace & retractable screens. The app-controlled pool features water elements, bubblers, two ledge loungers with umbrella holder/end table/ice chest & a 9-seat hot tub. Custom closets are found throughout the home, including the media room with built-in Queen Murphy bed & closet & a dedicated exercise room with closet or potential fifth bedroom. Large office filled with natural sunlight. The laundry room includes custom cabinetry with built-ins for pet bowls & bed & a fold-out ironing board. Additional features include Visual Comfort lighting, Guardian security system, Trane home automation, Quantum Fiber, built-in speakers throughout the main living areas & outdoor kitchen, living room & pool, Emtek hardware, PGT casement windows & 8" white oak hardwood floors. The sellers will also provide a one-year home warranty for added benefit. This home delivers a refined, fun & effortless luxury lifestyle in one of Winter Park’s most coveted locations—where every detail is designed to impress. Finding a one-story, almost-new home on a large lot in Winter Park is like finding a rare gem!

1117 Kenwood Avenue, Winter Park

$994,000

4 Beds ⋅ 3 Baths ⋅ Temple Terrace SubDv. ⋅ 32789 Zip Code

Virtually Staged. Temporarily Off the Market to replace driveway and sidewalks. PRICE IMPROVEMENT! NO HOA! Experience refined living in this renovated custom designed home on a corner lot in one of the area’s most peaceful and private neighborhoods. Tucked away at the end of a quiet dead-end street, this residence offers an exceptional blend of craftsmanship, sophistication, and modern comfort. With soaring 10-foot ceilings throughout and a stately wood-burning fireplace which sets a welcoming feeling in the family room. The fully reimagined chef’s kitchen is a true showpiece, featuring solid maple cabinetry, quartz countertops, programmable Bosch stainless steel range and refrigerator and a striking brick backsplash—an elevated space designed for both culinary creativity and effortless entertaining. All three bathrooms have been luxuriously renovated, and new carpeting adds a soft, refined touch throughout all four bedrooms. French doors from the master suite, formal living room, and family room open to a breathtaking screened-in pool retreat. Surrounded by lush tropical landscaping, this private oasis has been thoughtfully upgraded with a new pool pump, a conversion to a sparkling saltwater system, and a beautifully refinished pool deck. An outdoor shower with both hot and cold water adds a resort-level convenience, perfect after a swim or a day in the sun. Every major system has been meticulously updated for peace of mind, including a new programmable HVAC system, a complete replumb of the entire home, all new ductwork, and an upgraded water heater. Additional enhancements—such as fresh interior and exterior paint, a new garage door opener in the over-sized garage, irrigation system and refreshed landscaping — ensure a truly turnkey experience. With its luxurious finishes and meticulous improvements, this residence is ready for the next family to make it their own. This property is located just 2 miles to AdventHealth Winter Park Hospital, less than 10 minutes to Park Ave, and zoned for top-rated schools: Dommerich Elementary, Maitland Middle, and Winter Park High School. Just minutes from Winter Park’s boutiques, acclaimed restaurants, and the cultural charm of Park Avenue, this home offers a rare opportunity to enjoy elevated living in a setting that’s both secluded and connected. A truly private sanctuary designed for comfort, style, and the best of Florida living.

1800 Magnolia Avenue, Winter Park

$1,905,000

5 Beds ⋅ 5 Baths ⋅ Thomas M Henkels Add SubDv. ⋅ 32789 Zip Code

Walk to Park Avenue from this stylish and impeccably maintained Winter Park home, tucked along a charming brick street just minutes from the shops, dining, and vibrant energy of downtown Winter Park. Designed for both effortless living and entertaining, the main residence offers 3,410 SF with 4 bedrooms and 3.5 baths, while a detached studio apartment sits above the two-car garage, adding 300+ SF of living space. Complete with a full bath, separate AC unit, and oversized storage room, this flexible space is perfect for in-laws or guests, a gym, art studio, game room, or the home office of your dreams. Truly turnkey, this home comes with an impressive list of recent improvements... And when we say NEW, we mean BRAND NEW! Major updates include a NEW gas tankless water heater (2026), THREE NEW HVAC systems - 2 in the main home (2026) & 1 in the studio apartment (2025) - and a NEW roof (2025). Additional recent improvements include a freshly painted interior (2026), new light fixtures (even in the closets) and NEW LED ceiling lighting throughout (2026), a newly re-screened rear patio (2026), dishwasher (2025), garage door motor (2025), and a whole-home Reverse Osmosis water purification system. The exterior was painted in 2018, and a beautiful saltwater pool with a sun shelf and waterfall feature was built in 2017. The ideal floor plan centers around the kitchen, featuring a gas cooktop, stainless steel appliances, and walk-in pantry. The kitchen flows effortlessly into the spacious family room, highlighted by vaulted ceilings and a gas fireplace, then around to the bright sunroom lined with windows and charming built-in window benches that create the perfect space to relax or gather. A bar/butler’s area connects the kitchen to the front-facing dining room, while a 2nd living/sitting room, with a second gas fireplace, sits just across the foyer. The downstairs primary suite offers a peaceful retreat with 2 walk-in closets, a vaulted wood-plank ceiling, and a large picture window overlooking the resort-style pool and backyard. Upstairs are 3 generously sized bedrooms with large walk-in closets, and 2 full bathrooms. Outdoor living is just as inviting, with a newly screened, brick patio that spans over 500 square feet for covered dining or lounging, including a dedicated grilling station that is ready for your grill and beverage refrigerator. Just outside the screens, an open courtyard leads to the saltwater pool with a sun shelf and soothing waterfall feature, all surrounded by a spacious backyard with gated access and room to discreetly store a boat trailer. A rare combination of prime location, thoughtful design, and extensive upgrades, this charming and fresh Winter Park home is the perfect blend of elevated entertaining and everyday comfort…all just a short stroll to Park Avenue.

501 Henkel Circle, Winter Park

$1,500,000

2 Beds ⋅ 2 Baths ⋅ Robert Dhu Macdonald Park SubDv. ⋅ 32789 Zip Code

Welcome to 246 Palmer Avenue! Build your dream home or live in this charming home As-Is. Situated on a 14,252 sq.ft (0.33) corner lot on a beautiful brick street in the heart of Winter Park, this charming cottage offers timeless character, thoughtful updates, and a highly desirable location just minutes from Park Avenue, Rollins College, and the Winter Park Chain of Lakes. This well-maintained home features a layout with warm and inviting living spaces and abundant natural light. The original front door faces Palmer Avenue, while a later addition created the day-to-day entrance along Old England Avenue. Two separate living areas provide versatility for both relaxing and entertaining, and both the family room and the original living room, currently used as an office, feature wood-burning fireplaces. Just off the family room, a screened porch overlooks the lap pool and backyard, creating an easy connection between indoor and outdoor living. The dining room is lined with built-in bookcases, one of several thoughtful details found throughout the home. The kitchen enjoys views of the backyard and opens to a breakfast area with built-in cabinetry and French doors leading outside. A walk-in pantry adds practical storage. Off the original living room, an enclosed sunroom with original tile and additional built-ins offers a cozy space for reading, working, or unwinding. The primary bedroom opens to the backyard through French doors and includes built-in drawers in addition to closet storage. Its bath features a pedestal sink and clawfoot tub. A second bedroom is located across the home with access to a bathroom off the hallway, providing comfort and privacy for guests or family. Recent updates include a 2014 roof, gas water heater (2022), HVAC systems (2022 and 2023), and updated plumbing and electrical panels. A sprinkler system adds convenience for maintaining the grounds. This is a rare opportunity to build your dream home or enjoy this charming property as-is, ideally located just a couple of blocks from Park Avenue.

246 Palmer Avenue, Winter Park

$3,100,001

5 Beds ⋅ 5 Baths ⋅ Park Grove SubDv. ⋅ 32789 Zip Code

Artistry and exquisite style are brilliantly showcased in this renovated Winter Park masterpiece. Located in the coveted neighborhood of Park Grove, this magical home is sure to take your breath away, with stunning surprises around every corner. Since 2022, the home has undergone an extraordinary transformation in thoughtful renovations, upgrades, and enhancements throughout. Highlights include refinished and new hardwood floors extended across the entire first floor and continued onto the second level with sound-reducing underlayment, renovated bathrooms with designer plumbing fixtures, and new door hardware throughout for a cohesive, high-end finish. A dramatic 16-foot sliding glass door was added by removing the former wall, opening the living spaces to the outdoors with a sleek modern system. Elevated by designer lighting, sophisticated wall coverings, and custom window treatments, the thoughtful floor plan leaves nothing to be desired. At the center of the home, the open family room seamlessly converges with a polished kitchen, separated by an expansive breakfast bar. Sub-Zero, Wolf, and Bosch stainless steel appliances, including a gas cooktop and built-in dual convection ovens, surround a separate prep island. A sun-filled dinette with pool views sits at the far end. Ample storage, a walk-in pantry, built-in workstation, and wet bar/butler’s area with icemaker enhance functionality and entertaining. Lounge or dine beneath two covered lanai areas with electronic screens, or enjoy the newly redesigned & resurfaced pool and deck completed in 2023. Improvements include an expansive sun shelf with bubbler and umbrella sleeve, conversion to a saltwater system, and updated marble pool deck, all surrounded by a newer vinyl fence and block walls lined with tall hedges for privacy. Defined front living and dining rooms feature floor-to-ceiling windows with custom window treatments, while a perfectly placed powder room and coat closet are off the grand foyer. The spacious laundry room, with a laundry chute, is bursting with natural sunlight. The floor plan further enhances functionality with a downstairs Primary Suite featuring French doors that provide direct access to both covered lanais and the backyard. The newly renovated primary bath offers an LED-lit glass shower, soaking tub beneath a window, water closet, and large custom boutique-style walk-in closet. Tucked behind the dinette is the secondary guest bedroom wing currently used as a private office, with French doors, and a renovated full bath accessible from the pool deck. Upstairs features three large bedrooms, two full bathrooms, and a gym equipped with a built-in mini fridge, all centered around an enormous bonus room with built-in cabinetry. The oversized side-facing two-car garage sits off Summerland Avenue’s charming brick street and includes epoxy floors, workshop space or room for bikes & strollers, a second refrigerator, storage cabinets, and extensive hanging storage. The westside lawn was designed with a trellis over the garden area, perfect for homegrown produce. The garden area includes dedicated irrigation lines that feed from the well irrigation system. Other luxury elevated features include a home audio system (inside and out), a whole-house generator, whole-home water filtration system, and integrated security system with hard-wired cameras. This home truly has it all.

611 Williams Drive, Winter Park

$3,000,000

5 Beds ⋅ 6 Baths ⋅ Charmont SubDv. ⋅ 32789 Zip Code

Set along a picturesque brick street, 2040 Randall Circle is a beautifully crafted residence that pairs timeless architecture with elevated, designer finishes and a functional floor plan. Framed by manicured landscaping and connected to a detached two-car garage by a covered walkway, the home offers classic curb appeal in an idyllic setting just minutes from vibrant shopping and dining on Park Avenue. Inside, rich hardwood floors run throughout the living spaces, complemented by Restoration Hardware lighting that brings a refined, cohesive feel to every room. The welcoming foyer opens to a gracious formal living room with a gas fireplace and custom built-ins, an elegant yet comfortable space for entertaining or relaxing. Just beyond, the formal dining room is well proportioned for hosting holiday gatherings and dinner parties with ease. The heart of the home is the expansive chef’s kitchen, thoughtfully designed for everyday living and effortless entertaining. An oversized island anchors the space, topped with Carrara marble counters and offering generous seating. A dual Wolf oven with six-burner range plus French cooktop, custom cabinetry, walk-in pantry, and a butler’s pantry complete with under-counter wine refrigerator provide beauty and functionality. A spacious breakfast room filled with natural light overlooks the backyard and flows seamlessly into the family room. Here, a gas fireplace, custom built-ins and three sets of French doors create a warm focal point while inviting in the outdoors. The first-floor primary suite serves as a private retreat, featuring large windows with tranquil views of the pool and direct access to the covered lanai. Dual walk-in closets provide ample storage, and the spa-like primary bath is finished in Carrara marble, offering a large soaking tub and an expansive glass-enclosed shower with dual shower heads. Two powder baths, one thoughtfully designed as a pool bath, along with one of two laundry rooms complete the main level. Upstairs, four additional bedrooms and a dedicated office provide generous space for family and guests. Two of the bedrooms feature private en-suite baths, while the remaining two share a well-appointed Jack & Jill bath. One of these rooms is arranged as a bonus lounge, offering flexibility to serve as a fifth bedroom, media room or additional gathering space if desired. The thoughtful second-floor layout easily adapts to a variety of lifestyle needs, whether accommodating guests, growing families or multi-generational living. A secondary laundry room upstairs adds an added layer of everyday convenience. Outdoor living is equally impressive. The spacious covered lanai with summer kitchen overlooks the saltwater, heated pool and spa, creating an extension of the interior living space. Brick paver flooring continues from the lanai to the open patio, offering multiple areas for lounging, dining and entertaining beneath the Florida sky. Ideally in a desirable location and zoned for sought-after Audubon Park K-8, 2040 Randall Circle offers timeless style, thoughtful design and seamless indoor-outdoor living in one of the area’s charming neighborhoods.

2040 Randall Circle, Winter Park

$6,900,000

6 Beds ⋅ 7 Baths ⋅ J Kronenberger Sub SubDv. ⋅ 32789 Zip Code

Rarely does a property of this caliber grace the Winter Park market. Nestled along the coveted Venetian Canal with 95 feet of pristine waterfrontage, this magnificent masonry estate is the pinnacle of refined Florida living — offering 6,396 square feet of meticulously crafted space, a private boathouse, resort-style grounds, and an address mere steps from the best of Park Avenue. From the moment you arrive, the circular driveway, porte-cochère, and motor court signal that something extraordinary awaits. Solid brick construction and lush, manicured landscaping frame a grand entrance that sets the tone for every detail within. Step through the dramatic grand foyer into a home defined by elevated ceilings, rich hardwood floors, and exquisite crown moldings throughout. The formal living and dining rooms offer elegant spaces for entertaining, while a beautifully appointed wine room with stunning glass doors adds an unmistakable touch of sophistication. A chef's kitchen that truly inspires — outfitted with professional WOLF, Sub-Zero, and Miele appliances, dual islands with breathtaking countertops, a prep sink, built-in nugget ice machine, and a butler's hallway with floor-to-ceiling storage — flows effortlessly into the warm and inviting family room (complete with fireplace) and informal dining area. Bright, sun-drenched interiors and French doors open to a spectacular covered outdoor kitchen and a beautifully landscaped turf backyard, where a stunning saltwater pool and spa invite you to unwind in style. The first-floor primary suite is a sanctuary unto itself — featuring a private office, den, or sitting room anchored by a stunning double-sided fireplace, and a spa-caliber en suite with double vanities, jetted soaking tub, walk-in shower, and an oversized custom-built walk-in closet. A true retreat from the world. Upstairs, four generously sized bedrooms offer comfort and privacy for family and guests alike. One bedroom enjoys its own private en suite and a delightful secret bonus room — a magical hideaway perfect for children. Two bedrooms share a beautifully appointed Jack-and-Jill bath, each with its own private vanity area, and the fourth bedroom is spacious and well-served by the hall bath. The pièce de résistance of the upper level is a state-of-the-art home theater, complete with projector and screen, ceiling surround sound speakers, and a built-in dry bar with wine fridge — the ultimate in at-home entertainment. A detached guest casita with a full bath and wet bar provides ideal accommodations for visitors, while a detached three-car garage offers ample space for vehicles and storage. Two laundry rooms — one per floor — add everyday convenience, and custom storage solutions are found throughout. The whole-house Lutron lighting system and full-house generator ensure comfort, security, and seamless living at every turn. And then there is the water. The private boathouse along the Venetian Canal, with 95 feet of serene waterfront, offers a lifestyle that simply cannot be replicated — direct access to Winter Park's legendary chain of lakes, all from your own backyard. Located just a short stroll to the boutiques and dining of Park Avenue, the beauty of Kraft Azalea Gardens, and the Winter Park Racquet Club, this estate offers not just a home — but a way of life that the most discerning buyers have only dreamed of.

1260 Alabama Drive, Winter Park

$1,100,000

4 Beds ⋅ 4 Baths ⋅ Tangerine Court SubDv. ⋅ 32789 Zip Code

Charming, exquisite, unique; get it all with this beautiful cottage situated on the upscale corner of Mizell and Phelps Avenue in Winter Park. Originally restored and expanded by Carlos Posada for his family in 1998, this single level 4-bedroom, 2 full and 2 half-bathroom split plan. The common areas flow seamlessly throughout the home, and are highlighted by natural light. The kitchen has granite counter space, complemented by gorgeous 42" wood cabinets, and new stainless appliances. The primary suite provides an exclusive retreat, complete with a spacious walk-in closet, and well appointed master bath. Throughout the home, original hardwoods blend seamlessly with slate flooring. A completely renovated jack and jill bathroom (2020) adjoins 2 of the bedrooms opposite the primary suite and the 4th bedroom can be used as an office if desired. The outdoor space is truly serene, providing an expansive yet private patio and courtyard surrounded by mature landscaping with afternoon shade compliments of the eastern exposure. You’ll find plenty of space surrounding this home with sprawling front and side yards, and an expansive brick paver driveway that accommodates 6-8 vehicles, with space for 2 more inside the garage. Additional updates include (2) new HVAC units (2021), complete repipe below the home including drainage (2022), new water heater (2022), new water filtration system (2022). Located within the esteemed Winter Park School District, this home offers an ideal blend of sophistication and practicality.

1700 Mizell Avenue, Winter Park

$1,500,000

3 Beds ⋅ 4 Baths ⋅ Fontainebleau SubDv. ⋅ 32789 Zip Code

Set on an oversized 1/3-acre lot in the heart of Winter Park, this one-owner home was custom built in 1997 and has been meticulously maintained ever since. Solid block construction, timeless stone accents, and mature landscaping give it great curb appeal from the moment you arrive. Step inside to a spacious foyer with hardwood floors that carry through most of the main living areas. To the right, the living room features built-in shelving and a bay window that fills the space with natural light. It flows into the formal dining room, also with hardwood floors, plantation shutters, and plenty of room to host. A conveniently located powder bath serves this side of the home. To the left is the heart of the house - a generously sized kitchen with abundant white cabinetry, stone countertops, a center island, double ovens, a built-in pantry with pull-out storage, and a breakfast bar. The separate eat-in area overlooks the backyard and opens to the screened porch through French doors. The kitchen connects to a large family room with coffered ceilings, a gas fireplace, built-ins, and additional French doors leading outside. The home offers a three-way split floor plan for privacy. The primary suite sits on its own wing and is very spacious, featuring crown molding, a bay window, and French doors to the patio. The en-suite bath includes double vanities, large "His & Hers" walk-in closets with custom closet systems, a soaking tub, separate shower, and private water closet. On the opposite side of the home, you’ll find a generously sized secondary bedroom with its own en-suite bathroom and walk-in closet. Toward the back of the house is a third bedroom with a built-in desk, French doors to the exterior, and an en-suite Jack-and-Jill bath that also serves the family room. The first floor also includes an indoor laundry room with ample cabinetry and a utility sink. Upstairs, a huge bonus room offers incredible flexibility - game room, media room, office, or potential fourth bedroom. There is also space to add a bathroom if desired. Out back, a large screened porch with high ceilings overlooks a peaceful, lushly landscaped yard with plenty of room to enjoy Florida living. Additional features include plantation shutters throughout, a spacious two-car garage, and an unbeatable location just minutes from Park Avenue’s shopping and dining. Zoned for highly rated Dommerich Elementary, Maitland Middle, and Winter Park High. Call today to schedule your private showing!

1340 Place Picardy, Winter Park

$599,900

3 Beds ⋅ 2 Baths ⋅ Karolina On Killarney SubDv. ⋅ 32789 Zip Code

TRANSFERABLE TERMITE BOND INCLUDED. Welcome home to the charm and character of the bygone days. This 3-bedroom, 2-bathroom home offers 2,556 square feet, with the historic main home originally built in 1922. Featuring original antique wood floors, a classic fireplace, and a one of a kind upstairs loft, there's nothing quite like it! A charming front porch welcomes you into the living room with a fireplace. A front room currently used as a formal parlor or sitting room doubles as the third bedroom, also ideal for entertaining or reading. Two additional bedrooms and full baths are located down the hall. The dining room sits just off the main living space, with French doors opening into the hallway. The kitchen is positioned toward the back of the home with a tucked away laundry closet. Accessed by an interior staircase off the kitchen, the HIGHLIGHT of the home is the handcrafted upstairs loft with design in a class of itself. Currently used as an exquisite billiards room and library, this flexible space can serve as a library, office, or creative retreat, and features a balcony with views of Lake Killarney. Additional features include 42-inch kitchen cabinets, stone countertops, a roof replaced in 2018, AC replaced in 2019. Wind mitigation passed April 2024, septic pumped October 2025, and on top of it all, no HOA! Conveniently located minutes from Downtown Winter Park, Park Avenue, Rollins College, and just minutes from I-4, this is a truly unique property offering craftsmanship and character rarely found today.

1951 Staunton Avenue, Winter Park

$13,000,000

6 Beds ⋅ 9 Baths ⋅ --- SubDv. ⋅ 32789 Zip Code

Elegant Mediterranean estate, masterfully crafted by Akers Custom Homes and set within the heart of the Vias. Privately tucked behind a gated drive, the approach unfolds to a grand circular motor court framed by lush, manicured grounds spanning over two acres with impressive sunset views across Lake Maitland. Every element of the estate is thoughtfully connected by covered walkways, including five garages (three-car and two-car) and two motor courts, a detached office or seventh bedroom suite, and a lakeside pool cabana, creating a seamless blend of function, elegance and architectural harmony in this one-owner Lake Maitland residence. A dramatic arrival sets the tone as a flowing water feature guides guests along the walkway to the front entry. Inside, the grand foyer opens to a breathtaking gathering room, anchored by soaring two-story windows that frame panoramic lake views, the expansive terrace and terraced outdoor space. A dedicated space for a grand piano enhances the home’s capacity for elegant entertainment and memorable gatherings. The spacious kitchen overlooks the family room and is positioned alongside a dedicated bar, breakfast room and dining room. The family room, warmed by a gas fireplace, is filled with natural light and opens through a wall of French doors to the open terrace, blurring the line between indoor and outdoor living. The first-floor primary suite is a serene retreat with French doors to a covered outdoor space, a fireside sitting area wrapped in custom bookshelves, and a spa-inspired bath featuring a large glass shower, soaking tub, expansive walk-in closet, and a versatile flex room ideal for yoga, massage or expanded wardrobe space. A full guest suite with en-suite bath and walk-in closet is also on the main level. Upstairs, a grand mezzanine overlooks the gathering room, offering a dramatic extension of the living areas. French doors open to a front balcony, while the west wing features two bedrooms with a shared private living room and full bath. The east wing hosts two additional bedroom suites, each with walk-in closets and en-suite baths, one enhanced by a private sitting area and access to a spacious rear balcony. Off the kitchen, a wrought-iron gate leads to the basement level, where a refrigerated wine cellar, theater room, and generous storage space await. Outdoors, the stunning terrace showcases a heated spa, sparkling lakeside pool, expansive gas fire pit and an extraordinary 700-square-foot pool cabana that offers a wraparound screened porch with summer kitchen, a full bar, gaming area and full bath, ideal for lakeside entertaining. Elevated above the water for commanding views and shielded from the main road for complete privacy, this remarkable estate is a masterpiece, designed for multi-generational living and destined to create lasting memories for generations to come.

2203 Via Tuscany, Winter Park

$625,000

3 Beds ⋅ 2 Baths ⋅ Orwin Manor Westminster Sec SubDv. ⋅ 32789 Zip Code

Welcome to this beautifully renovated historic home in the heart of Orwin Manor, one of Winter Park’s most treasured neighborhoods. Thoughtfully updated while preserving its timeless character, this 3 bedroom 1 and a half bath home blends classic architectural charm with today’s modern conveniences. Major system improvements include updated plumbing and electrical, a new roof in 2025, new HVAC in 2025, exterior painting completed in 2024, original hardwood floors, hot water heater within the last two years, and much more offering true peace of mind for years to come. The inviting renovated kitchen features updated cabinetry, granite surfaces, stainless steel appliances, and a spacious island perfect for everyday living and entertaining. A generous 18’ x 16’ screened porch expands the living space and overlooks a lush, beautifully curated garden, creating a serene indoor-outdoor retreat. All bedrooms are spacious outfitted with built-in closets, beautiful updated windows and blinds. An added bonus is the electric vehicle charging station with driveway privacy gate, ideal for modern lifestyles. This property is individually registered on the City of Winter Park Historic Registry, a rare distinction that celebrates its architectural significance and heritage. The home has been meticulously cared for and retains the warmth and craftsmanship that make historic properties so special. Orwin Manor offers an unbeatable location between Winter Park, College Park, and Downtown Orlando just minutes from AdventHealth, Loch Haven Park, the Orlando Museum of Art, Orlando Science Center, and multiple theaters. Enjoy easy access to Park Avenue, Ivanhoe Village, and Mills Park, all filled with exceptional dining and boutique shopping, with convenient routes that avoid I-4 when desired. A true blend of history, beauty, and modern living, this is a home you’ll fall in love with the moment you arrive. Schedule your private showing to experience this beautiful home today!

1500 Berkshire Avenue, Winter Park

$1,005,000

4 Beds ⋅ 3 Baths ⋅ Osceola Court SubDv. ⋅ 32789 Zip Code

Set in one of Winter Park’s most sought-after locations, this 1940 home delivers something that’s hard to recreate: walkability, character, and flexibility. Just steps from Downtown Winter Park, iconic Park Avenue, and Rollins College, with private access to Lake Osceola, the location alone sets this property apart. The home offers the charm of a historic build without the restrictions of a historic designation, giving the next owner freedom to update, expand, or personalize as they choose. Inside, you’re welcomed by a proper foyer with original hardwood floors (currently painted white and able to be refinished) and crown molding throughout. A thoughtfully used desk nook sits beside the staircase, making great use of the space. To the left, the formal living room features a true masonry, natural gas fireplace and flows into a bright dining room that connects to a cozy family room—an enclosed former porch with French doors opening to the screened porch beyond. The renovated kitchen is stunning, featuring Carrara marble countertops, stainless steel appliances including a gas range, a pantry with custom storage, breakfast bar, and dry bar. The primary suite is located on the first floor and was formerly a garage conversion, now offering high ceilings, an en suite bath, built-in dressers, a walk-in closet with stackable washer and dryer, and French doors leading to a charming private courtyard. Upstairs are three additional bedrooms and a full bath with double sinks, subway tile and bead-board accents. The largest upstairs bedroom, once the original primary, includes a half bath, generous space for a seating area or desk, and French doors opening to a covered balcony. The fourth bedroom includes access to a full-size walk-in attic with ventilation and heat removal system—offering future expansion potential. Outdoor living is just as inviting, with a screened porch complete with natural gas grill hookup and sink, plus a fully fenced backyard featuring artificial turf, a circular paver patio, and an adorable shed designed to match the home. Major updates include a metal roof (2020), updated plumbing, electrical, windows, and doors (2012), tankless gas water heater, and whole-house generator. Additional perks include a transferable termite bond and covered parking pad. A rare opportunity to own a true Winter Park home where location, charm, and long-term potential come together. Motivated Seller!! Call today to schedule your private showing.

244 Osceola Court, Winter Park

$4,800,000

5 Beds ⋅ 6 Baths ⋅ Comstock Park SubDv. ⋅ 32789 Zip Code

An extraordinary opportunity on the shores of Lake Osceola on one of Winter Park's most charming streets. This architecturally interesting lakefront estate offers breathtaking panoramic sunset views and an irreplaceable setting. Thoughtfully designed with the beautiful finishes. First time available in over three decades, this is rare chance to own a legacy property!

641 Bonita Drive, Winter Park

$1,250,000

3 Beds ⋅ 3 Baths ⋅ Morseland Sub SubDv. ⋅ 32789 Zip Code

Experience the charm and endless convenience of Beloit Avenue, one of Winter Park’s most coveted streets! Just steps from the WP-9 Golf Course, and 2 blocks from the lively, renowned Park Avenue, this 3-bedroom/2.5-bath residence presents a unique opportunity for reimagination in a location that is simply unmatched. The 1-story home provides the ideal framework for function yet stylish living, with the existing open floorplan, detailed crown molding, and timeless hardwood floors. French doors off the rear family room lead to an open side courtyard, offering plenty of space to create an outdoor oasis that's perfect for relaxing or entertaining, all wrapped in a masonry wall for added privacy. Access the rear-facing two-car garage from a private brick-paved alley exclusive to Beloit homeowners. Combining charm, convenience, and the added perks of natural gas and a 4-year-old roof, this opportunity is a rare find in the very heart of Winter Park.

359 Beloit Avenue, Winter Park

$369,900

3 Beds ⋅ 2 Baths ⋅ Temple Terrace SubDv. ⋅ 32789 Zip Code

MULTIPLE OFFER SITUATION - Welcome to this classic ranch home offering 3 bedrooms, 2 baths, and a wonderfully livable floor plan designed for everyday comfort, work-from-home flexibility, and easy entertaining. With 1,584 sqft of living space this home lives large and offers generous room sizes, plenty of storage, and a layout that simply makes sense. From the big front patio, step inside to a bright living area with cathedral ceilings and natural light, leading into an updated kitchen featuring granite countertops and newer cabinetry. Stacked bedroom layout, and the bathrooms feature tile finishes and oak cabinetry. Flooring includes tile throughout most of the home, wood laminate in the primary bedroom, and carpet in two bedrooms. The home also features updated double-pane insulated windows. Some of the highlights of this home are the expansive screened-in Florida room, perfect for relaxing, dining outdoors, or hosting friends —while enjoying fresh air. Outside, you'll find a huge, fully fenced backyard with mature oaks, palms, bananas, flowering cactus, and an aloe garden. There’s ample room for a pool, future expansion, and RV / trailer storage. A storage shed with electric adds even more convenience. The location truly can’t be beat — centrally located near downtown Winter Park, Maitland, Casselberry, restaurants, theaters, lakes, bike paths, museums, five golf courses, and endless shopping and recreation. Zoned for highly regarded schools including Dommerich Elementary, Maitland Middle, and Winter Park High, this is a setting many buyers specifically seek out. The neighborhood is on city utilities; this home currently uses septic which may not function properly and may need to be connected to city sewer which is already on the street. This is a conventional and cash-only sale and is being offered As-Is, with buyers responsible for their due diligence including verifying fees, taxes, and property details.

1816 Azalea Avenue, Winter Park

$540,000

3 Beds ⋅ 2 Baths ⋅ Waterbridge SubDv. ⋅ 32789 Zip Code

Beautifully situated on an elevated 50-by-106-foot lot in the Waterbridge community, this spacious single-story home enjoys a quiet cul-de-sac setting overlooking a small neighborhood park and is adjacent to a green space that enhances privacy. The property has wonderful curb appeal with mature trees, a wide driveway, an oversized two-car garage, and an inviting entrance courtyard that creates a sheltered transition into the home. Inside, the floor plan offers generous room sizes and excellent flow, beginning with a large foyer that opens to both the formal living room and the formal dining room. The 17’ x 12’ living room features a vaulted ceiling and large-format windows. The formal dining room is spacious and opens through sliding glass doors to a private side courtyard ideal for container gardening or quiet outdoor seating. The kitchen is sizable and well designed, with extensive counter space and abundant cabinetry, and offers convenient access to the side courtyard. The kitchen opens to the family room, allowing easy interaction between the two spaces, and extends into the Florida room beyond. The Florida room is one of the most charming areas of the home, with a brick façade along one wall, sliding glass doors, and views of the brick-covered and maturely landscaped backyard. This light-filled space is perfect for casual dining, a reading nook, or year-round indoor–outdoor living. The bedroom wing is thoughtfully spaced away from the main living areas. The primary suite is generously proportioned at roughly 21’ x 17’, with a vaulted ceiling, walk-in closet, and a spacious bathroom that includes a standalone tub, separate shower, long vanity with significant counter space, and a dedicated makeup area. Two additional bedrooms are comfortable in size with reach-in closets and share a full hallway bath with a long vanity and a tub-shower combination. Closet space and storage are abundant throughout the home, including hall storage, bedroom closets, built-ins, and a deep garage with workshop potential. Outdoor living is a highlight of the property. In addition to the front entrance courtyard and the private dining courtyard, the home features a lovely brick-paved backyard framed by mature landscaping, planting beds, and established greenery. The space is low-maintenance and provides multiple areas for seating, gardening, and relaxation. Recent updates include replacement of the electrical panels, which is set for final permit closing inspection; a 2017 HVAC; and a 2018 full home replumb. A current four-point inspection is available and will be updated to reflect the electrical panel replacement once the permit is closed. With its cul-de-sac location, elevated lot, multiple courtyards, flexible living areas, and desirable proximity to Park Avenue, Baldwin Park, the Cady Way Trail, the nearby dog park, and Downtown Orlando, the home enjoys an exceptional setting within a highly regarded Winter Park school zone. Meticulously maintained and built on excellent bones, it offers the uncommon opportunity to move right in or renovate with vision and create something extraordinary.

1817 Jessica Court, Winter Park

$2,000,000

3 Beds ⋅ 3 Baths ⋅ Sevilla SubDv. ⋅ 32789 Zip Code

Once closed, call LA for Effective sales price. Totally traditional luxury single-story home is located in the desirable Sevilla neighborhood in Winter Park. Sitting high and dry on approximately a half-acre beautifully landscaped lot. Original home was mostly gutted down to the studs in 2011-2012 and COMPLETELY re-done. Multi-generational potential as this home has a complete attached guesthouse. Interior layout boasts formal living with bay window and tall ceilings, dining room with antiqued mirror set into extensive moldings and trim, plus a library/den with a tongue and groove wood vaulted ceiling and a wall of bookshelves and built-ins. The spacious family room with a white-washed brick, wood-burning fireplace wall and vaulted ceiling is all open to the breakfast area and kitchen. The gourmet kitchen features custom inset cabinet drawers and doors, white marble slab backsplashes, Kohler farmhouse sink and a large island with a deep prep sink. The kitchen is a chef’s delight with a 48-inch Viking gas range, Viking warming drawer, Jenn-Air refrigerator, wine refrigerator and a Bosch dishwasher. The kitchen also has amazing storage and two large pantries. There are a total of four bedrooms (the 4th is currently the living room of the in-law suite suite) and three full baths. Throughout the home are beautiful real ¾-inch-thick and 5-inch-wide plank walnut floors, beam and coffered ceilings, French doors, oversized picture windows and designer accents lighting. French doors off the family room open to seamlessly blend indoor and outdoor living, leading to a covered lanai with travertine stone tile overlooking a resort and entertaining backyard. Huge swimming pool and a 30-by-15-foot pergola with Bistro lighting, which is a wonderful spot to relax, dine and play, all on a tiny pebble surface, like an Italian driveway! French garden fountain, rose garden and synthetic turf for pets make the backyard a haven. The home’s floor plan offers a desirable layout with huge primary bedroom with a generously sized un-suite bath with dual sink counters, amazing Roman walk-in shower, jetted tub with bubblers and two large walk-in closets. Guest wing features a spacious bedroom and bath and the West Wing is a full In-law apartment, including a bedroom, handicapped bath, full kitchen and its living room (which would be easy to be converted back into the 4th bedroom - plans available). Imagine having a wonderful space for in-laws or an adult family member that needs space of their own. Just a short drive or bike ride from Park Avenue, this open and inviting home has easy access to downtown Winter Park, AdventHealth, downtown Orlando and is zoned for A-rated schools. Surround sound through most of the house and CAT 6 wiring throughout. Recent additional remodeling and updating have taken place including all new windows, paint inside and out, as well as a new roof and gutters in 2022. A detailed list of all renovations is available upon request.

1624 Barcelona Way, Winter Park

$800,000

3 Beds ⋅ 4 Baths ⋅ Virginia Heights Rep SubDv. ⋅ 32789 Zip Code

Welcome to this rare find in the heart of Winter Park — a beautifully updated 3-bedroom, 3.5-bath townhome that lives like a single-family home, and best of all, there’s no HOA. Step inside to soaring 20-foot ceilings in the foyer and living room, complemented by elegant hardwood floors, crown molding, and expansive windows that fill the space with natural light. The open-concept design is both spacious and versatile, offering seamless flow and plenty of room to relax, entertain, and enjoy the Florida lifestyle. At the center of the home is a chef-inspired kitchen featuring crisp white cabinetry, solid granite countertops, stainless steel appliances, and a central island with built-in outlets and custom pull-out storage. The light-filled living room opens effortlessly into the dining area, where French doors lead out to a wood deck and a fully landscaped backyard oasis. Mature trees, curated garden beds, and decorative stone walkways create a peaceful retreat — perfect for indoor-outdoor entertaining. Upstairs, the generous primary suite is a true sanctuary, complete with double entry doors, a spa-like bath with jetted tub and shower, a walk-in closet, and a private balcony ideal for morning coffee or evening relaxation. Two additional guest suites each include their own ensuite bath, providing comfort and privacy for family, visitors, or a home office. A conveniently located upstairs laundry room completes the second floor. Additional Features: • Underground propane tank powering the stove, fireplace, BBQ grill, and new (2023) hot water heater • New roof (2022), new carpet (Nov. 2025) • Upstairs A/C replaced in 2023 • Tesla car charging station • Long private driveway with ample parking • No HOA — enjoy added freedom and low-maintenance living. Prime Location: Situated in Virginia Heights, one of Winter Park’s most coveted neighborhoods just minutes from Park Avenue’s renowned dining, shopping, and Central Park, along with Seven Oaks Park, Mead Botanical Garden, and Azalea Lane Tennis Center with adjacent kiddie park. Zoned for top-rated Audubon K–8 and Winter Park High School. Call today to schedule your private tour of this exceptional home in a premier Winter Park location. Floor Plan Attached!

1251 Arlington Place, Winter Park

$6,300,000

4 Beds ⋅ 6 Baths ⋅ Camwood SubDv. ⋅ 32789 Zip Code

Quintisential Lake Maitland Estate - first time available. Classic architecture with incredible and thoughtful details throughout. Private setting on over an acre captures sweeping views of Lake Maitland. Sought after location close to Park Avenue. This legacy property embodies the best of Winter Park Lakefront Living.

1308 Green Cove, Winter Park

$5,700,000

5 Beds ⋅ 6 Baths ⋅ Thomas M Henkels Add SubDv. ⋅ 32789 Zip Code

SOLD DATA ENTRY.. Welcome to this timeless lakefront estate located on the shores of Lake Virginia, offering approximately 143 feet of private waterfront along the highly sought-after Winter Park Chain of Lakes. Situated on over an acre, this beautifully updated residence blends classic architecture with modern luxury and an exceptional indoor-outdoor lifestyle. Thoughtfully renovated in 2016, the home features spacious formal and informal living areas, high ceilings, custom millwork, and stunning lake views throughout.The chef’s kitchen is equipped with Wolf and Sub-Zero appliances, double ovens, built-in Miele coffee system, wine refrigeration, and additional refrigerator/freezer drawers. The kitchen opens to the main living space and flows seamlessly to the outdoor entertaining areas. The primary suite offers a serene lakefront setting with a spa-inspired bath and generous closets. Additional bedrooms are well-appointed and offer both privacy and flexible living arrangements.Step outside to a resort-style waterfront setting, complete with a large pool and spa, expansive terrace, summer kitchen, gas fire pit, and private boat dock with lift. Enjoy boating, paddleboarding, or sunset cruises right from your backyard. The property’s elevation provides exceptional views stretching across Lake Virginia toward downtown Orlando and Rollins College.Located on a quiet, private street just moments from Park Avenue dining, shops, and Winter Park’s most desirable amenities, this is a rare opportunity to enjoy lakefront living in one of Central Florida’s most distinguished neighborhoods.

374 Henkel Circle, Winter Park

$470,000

3 Beds ⋅ 2 Baths ⋅ Glencoe Sub SubDv. ⋅ 32789 Zip Code

One or more photo(s) has been virtually staged. Live the Winter Park dream in this freshly updated 3-bedroom, 2-bath home—just steps from Lake Killarney and minutes to I-4, boutique shopping, and top dining spots. The interior has been freshly painted, creating a bright and welcoming feel throughout. The updated kitchen shines with white shaker cabinets, quartz countertops, a subway-tile backsplash, and stainless-steel appliances. It’s perfect for everyday cooking and effortless entertaining. Wood-look laminate floors flow through the spacious living and dining rooms and into the bedrooms, while the family room offers wood-look tile, a cozy fireplace, and sliding doors that open to the screened patio. Outside, a long driveway extends beyond the fenced yard to a side-entry oversized two-car garage with workshop area. Surrounded by mature trees, the backyard is a private retreat with a cozy firepit, utility shed, and a versatile concrete pad—ideal for basketball games or weekend gatherings under the stars. Zoned R-1A, the property also allows for an accessory structure such as a guest suite or studio (no kitchen permitted) Thoughtful updates, generous outdoor space, and an unbeatable location near Lake Killarney make this home a rare find. Come experience comfort, character, and convenience in the heart of Winter Park.

2381 Roxbury Road, Winter Park

$8,950,000

7 Beds ⋅ 11 Baths ⋅ Windsong-Preserve Point SubDv. ⋅ 32789 Zip Code

In the exclusive community of Windsong on Lake Berry, this magnificent 1.6-acre gated Mediterranean estate is a private oasis. With over 11,000 square feet of living area and a beautifully landscaped lakefront lot, this residence offers an exceptional blend of elegance, charm and privacy rarely found in Winter Park. The home features seven spacious bedrooms and nine full and two half baths. Entertain in the all-glass conservatory, dedicated theater room with motorized seating and a fully equipped game room. Modern conveniences throughout including gas-powered generators, an elevator and dumbwaiter. Two above-garage apartments provide ideal accommodations for guests and family. Outdoors, enjoy an expansive covered lanai, infinity edge pool and spa, boat dock with jet ski lift, and a summer kitchen complete with wood-burning fireplace, gas grill, refrigerator and icemaker, all overlooking the beautifully landscaped yard and lake. With its private gated entrance, this home is a one-of-a-kind opportunity to enjoy all the amenities Winter Park and Windsong have to offer.

1120 Preserve Point Drive, Winter Park

$2,325,000

4 Beds ⋅ 4 Baths ⋅ Windsong Lookout Landing 43/79 SubDv. ⋅ 32789 Zip Code

Stunning custom residence in the highly sought-after Windsong community, built by Hal George of Parkland Homes and designed by architect Steve Feller. This one-owner home blends timeless architecture with exceptional craftsmanship and thoughtful design. From the moment you arrive, the storybook curb appeal is undeniable—brick exterior and driveway, lush landscaping, and charming gardens create a warm welcome. Inside, luxury finishes abound: herringbone wood floors, crown molding, cased openings with arched doorways, custom built-ins, and plantation shutters. The highly functional floor plan offers a downstairs owners’ suite plus a secondary bedroom (currently used as an office) with adjacent full bath. Upstairs, a spacious bonus room anchors two private bedroom suites. Soaring 10’ ceilings enhance the sense of space, with lots of natural light. The gourmet kitchen is a chef’s dream, featuring wood custom cabinetry, stainless steel appliances including a six-burner gas cooktop and Dacor double ovens, and an oversized island with sink. The kitchen flows seamlessly into the sunlit dining room with a dramatic vaulted 14’ beamed ceiling, comfortably seating 15. Set on a generous 0.38-acre lot, the outdoor living is equally impressive. The resort-style backyard showcases a covered patio with Pennsylvania Bluestone pavers, tongue-and-groove ceiling, and a charming detached garden house for storage. A serpentine wall winds gracefully through the landscaped grounds, offering privacy and charm. Additional highlights include an oversized two-car garage, indoor laundry with sink, and abundant storage throughout. A rare opportunity to own a meticulously maintained, beautifully appointed home in one of Winter Park’s most desirable communities.

1268 Preserve Point Drive, Winter Park

$1,300,000

4 Beds ⋅ 3 Baths ⋅ Park Grove SubDv. ⋅ 32789 Zip Code

For data entry only.

857 Brock Street, Winter Park

$1,000,000

4 Beds ⋅ 4 Baths ⋅ Sevilla SubDv. ⋅ 32789 Zip Code

Welcome home to this lovely four-bedroom, three-and-a-half-bath pool home in the gorgeous Sevilla neighborhood of Winter Park! Tucked off a charming brick road lined with mature oak trees, this .40-acre property combines privacy and convenience in the heart of Winter Park. Just a 7-minute drive to Park Avenue and moments from Mead Botanical Gardens and scenic Lake Sue, it's perfectly situated for the lifestyle you love. Inside, you’ll find timeless details such as marble and parquet flooring, crown molding and plantation shutters throughout. The heart of the home is the kitchen and family room — both overlooking the pool and anchored by a cozy wood-burning brick fireplace with built-in shelving. Two bedrooms share a Jack-and-Jill bath, while another offers custom shelving — perfect for a home office or study. The primary suite features a spacious walk-in closet and an en-suite bath framed by elegant architectural columns, with private access directly to the pool area. Step outside to your own tropical retreat — an expansive screened, heated pool that lights up in the evenings, surrounded by lush landscaping, multiple seating areas, a covered brick patio, and a charming brick outdoor kitchen waiting for your personal touch. This well-built concrete block home also features a double-door entry and an extended covered front patio — ideal for welcoming guests, relaxing in rocking chairs, or adding seasonal décor throughout the year. Additional highlights include a circular driveway, oversized side-entry garage, fenced yard, spacious laundry room, low HOA, Blink security system, and a roof replaced in 2007. Close proximity to Rollins College, top-rated Winter Park schools, and private schools, this home has been lovingly cared for by the same owner for 33 years. With your personal updates, it has the potential to become a true showpiece in one of Winter Park’s most desirable neighborhoods. Enjoy all that Winter Park living has to give — fine dining, boutiques, museums, art festivals, lakes, and cultural events — just minutes from your front door.

215 Salvador Square, Winter Park

$2,078,500

5 Beds ⋅ 4 Baths ⋅ Palmer Ave Lakeside Prop SubDv. ⋅ 32789 Zip Code

Tucked away on a quiet cul-de-sac lined with multi-million-dollar estates, this Winter Park residence offers an enviable blend of privacy, lifestyle, and location. Less than a mile from Park Avenue, the Winter Park 9 Golf Course, and the Racquet Club, this address puts you at the center of the city’s most coveted amenities. A deeded greenbelt easement to Lake Osceola—just 100 yards from the front door—provides effortless access for boating, kayaking, or paddle boarding on the Winter Park Chain of Lakes. The two-story brick home spans 4,328sf with 4 bedrooms, 4 baths, and a 2-car garage. Inside, character and craftsmanship shine with brick archways, custom millwork, tongue-and-groove ceilings, and two wood-burning fireplaces. The gourmet kitchen features Thermador appliances, marble counters, and a walnut-topped island, while the expansive primary suite boasts a private screened patio, a fully built-out oversized walk-in closet, and a spa-like bath. Two bonus rooms upstairs provide flexible space for work or play, while updated systems—including a 2018 roof, three HVAC units, dual-pane windows, updated drainage, whole house generator, mosquito misting system, whole house alarm, and smart home upgrades—ensure comfort and peace of mind. Equally impressive are the grounds. The front garden is graced with jasmine, mature oaks, and manicured plantings, while a Chicago brick horseshoe driveway easily accommodates six or more cars. Out back, a private retreat unfolds with a lagoon-style saltwater pool and spa surrounded by flagstone decking, a summer kitchen, covered patio with fans and lighting, and a dedicated pool bath. Living here is about more than a home—it’s about lifestyle. With gardens and stunning architecture at every turn, culture, shopping, and dining just minutes away, and lake access at your fingertips, this property offers a rare opportunity to experience the very best of Winter Park.

715 Via Bella, Winter Park

$2,144,000

4 Beds ⋅ 4 Baths ⋅ Pennsylvania Place SubDv. ⋅ 32789 Zip Code

Wonderful home in sought-after Pennsylvania Place. Newer roof (2019), HVAC and Water Heaters

1077 N. Pennsylvania Ave, Winter Park

$2,700,000

5 Beds ⋅ 5 Baths ⋅ Windsong Lakeside SubDv. ⋅ 32789 Zip Code

Experience Mediterranean charm in this fabulous five-bedroom, five-bath pool home built by Cahill Builders. On the north side of Windsong, this home features an open floor plan with spacious living areas that flow seamlessly and provide warm natural light. The living room with cozy gas fireplace overlooks the spacious and open dining room while the light-filled family room with French doors has wonderful views of the covered lanai and pool. You will love entertaining in the chef’s eat-in kitchen with many updates and upgrades completed in 2024. Kitchen features include stainless appliances, natural gas cooktop, double ovens, large center prep island and large walk-in pantry. The first-floor luxurious owner’s retreat features vaulted and hand-crafted wood beam ceilings, wide plank wood floors and bath with dual vanities, walk-in shower and spa tub. Bedroom Suite 2, which is also on the main level is ideal for guests, home office or nursery. As you go upstairs, the second floor offers a thoughtfully designed retreat for both relaxation and entertainment. There are three spacious bedrooms each with their private baths. This layout offers comfort and privacy for family or guests. The media room provides the ideal setting for movie nights or immersive gaming and includes an additional room for a playroom, library or large air-conditioned storage space. Whether you are entertaining or unwinding, this upper-level layout delivers functionality and privacy. Go outside to enjoy the covered lanai which overlooks the private and expansive yard filled with a vibrant mix of citrus trees, tropical plants and year-round flowering garden. The fabulous landscape was designed by a landscape architect with the concept to provide continuous blooms and inviting sitting areas under the sun. The sparkling pool and spa, large surrounding patio and firepit area invite year-round enjoyment. Additional amenities include custom molding and trim work, an entry fountain and three-car garage (one with split air conditioning). Windsong, one of Winter Park's sought-after neighborhoods, offers exclusive amenities to their residents including a pontoon boat to enjoy Winter Park Chain of Lakes, two community pools, a splash park, playground, a lakefront clubhouse and a scenic pier for fishing. Ideal location is minutes from hospitals, schools, golf courses, and Park Avenue’s amazing dining and shopping.

1445 Holts Grove, Winter Park

$1,770,000

3 Beds ⋅ 4 Baths ⋅ Park Grove SubDv. ⋅ 32789 Zip Code

Welcome to this picturesque 3 bedroom, 4 bath pool home nestled in the highly sought-after neighborhood of Park Grove. Overflowing with charm and character, this naturally light-filled home features white oak hardwood floors and plantation shutters throughout. Upon entry, a formal living room with a cozy wood-burning fireplace greets you, offering serene views of the sparkling heated pool and lush backyard oasis. The elegant formal dining room leads to a chef's kitchen adorned with marble countertops, wood cabinetry, a spacious island with seating, and top-of-the-line appliances. A well-appointed wet bar adds to the home's entertainment appeal, while an informal dining space flows seamlessly into the expansive family room, where floor-to-ceiling windows invite the beauty of the outdoors in. Step outside to a covered porch and summer kitchen- perfect for hosting. Enjoy al fresco dining under the shade of a covered pergola or relax by the glistening pool in complete privacy. The home features two secondary bedrooms, each with its own en-suite bath, and a full guest bath off the hallway. The primary suite is a true retreat, offering a private sitting area, his-and-hers closets, and a luxurious bath with dual vanities and a large walk-in shower. Located just minutes from the vibrant shops and fine dining of Park Avenue in downtown Winter Park, and zoned for top-rated schools- this home is an exceptional opportunity you won't want to miss!

690 Williams Drive, Winter Park

$4,500,000

6 Beds ⋅ 6 Baths ⋅ Dyer Susan Resub SubDv. ⋅ 32789 Zip Code

Offered for the first time in over 50 years, this distinguished Winter Park estate is a true traditional gem, nestled on a picturesque brick street and situated on a full 1-acre lot. Exuding timeless charm with a subtle New England ambiance, this residence represents the best of historic Winter Park living—all within walking distance to Park Avenue. This stately 6-bedroom, 5.5-bathroom home offers 5,759 square feet of thoughtfully designed living space, plus an additional 1,859-square-foot unfinished basement that spans the entire length of the home, offering endless possibilities for expansion or customization. Upon entry, you'll be welcomed by coffered ceilings in the spacious formal living room, rich dark oak floors, and one of the home’s three gas fireplaces. This elegant yet inviting room overlooks the lush gardens, making it an ideal setting for both entertaining and quiet relaxation. Adjacent to the living room is a cozy, beautifully appointed den featuring another gas fireplace and natural jute flooring—undoubtedly one of the most beloved spaces in the home. The kitchen is filled with natural light and includes a large casual dining area, a charming butler’s pantry, and direct access to both the laundry room—complete with a full-size refrigerator and half-bath—and the oversized 2-car garage. The formal dining room showcases lattice-framed bay windows with views of the back garden and pool area, creating a warm and elegant space perfect for holiday dinners and family gatherings. The home features two primary bedroom suites on the main level, including one expansive L-shaped suite with its own gas fireplace and views of the pool, gardens, and outdoor terrace. The primary bathroom includes a dressing area and marble finishes throughout. Upstairs, the south wing includes two generous bedrooms with a shared full bathroom, while the north wing—located above the kitchen—offers two additional bedrooms and a charming full bath. The expansive backyard is a private sanctuary, framed by majestic oak trees, bamboo, and thoughtfully designed gardens, with several inviting sitting areas for outdoor relaxation. An extra-large swimming pool completes the setting—perfect for warm Florida days or evening gatherings under the stars.

887 Georgia Avenue, Winter Park

$1,575,000

4 Beds ⋅ 4 Baths ⋅ Sylvan Lake Shores SubDv. ⋅ 32789 Zip Code

Beautiful Sylvan Lake Shores Mediterranean home. Ideally located in quintessential Old Winter Park with its tree lined, brick streets that surround Lake Mizell. This 4 bedroom 3 ½ bath, plus office home features timeless architectural features such as classic wide molding, repeated archways and a custom ironwork stairway. The soaring 10 foot ceilings accentuate the classic feel of this elegant home. The designer inspired kitchen features custom cabinets and spacious pantry. The spa like master suite is located on the first floor and has an en-suite bath and custom designed closet. Just recently completed, the luxurious master bath has an inviting soaking tub and separate, relaxing rain shower. The executive office is located on the first floor. Up the custom staircase are three bedrooms including a private guest room with its own en-suite bath. The open floor plan is perfect for entertaining with multiple, solid wood French doors surrounding the welcoming back yard pool with cooling fountains. Outside, a custom awning shades the patio as you relax by the pool. There is a convenient pool bath as well. This bright and sunny home is in a prime location of Winter Park with an easy walk or bike to Park Avenue with its upscale restaurants, stores and Rollins College. Excellent Winter Park Schools. This amazing move in ready home is an excellent opportunity to live in the heart of Winter Park and enjoy Central Florida living.

1394 Grove Terrace, Winter Park

$1,600,000

4 Beds ⋅ 3 Baths ⋅ Osceola Summit SubDv. ⋅ 32789 Zip Code

Charming Opportunity in Prime Winter Park – 446 Alberta Drive, Winter Park, FL! First time ever on the market and sits on a double lot that is .35 acres. Only a mile stroll to the famous Park Ave shops, dining and entertaining. Home site over looks Lake Osceola and the multi million dollar homes all around!! A neighborhood lot, a few doors down, allows residents to have walking access to Lake Osceola for paddle boarding, fishing, swimming or just to enjoy the view!! This home has only had one owner and is uniquely positioned not to see a next-door neighbor to your left or right!! Embrace the mid century modern style of this home or it is priced to be a tear down to build your dream home around the other multi million dollar homes. Nestled in the heart of highly sought-after Winter Park, this spacious 4-bedroom, 2.5-bath home offers over 3,260 square feet of living space on an oversized .35 acre lot with gorgeous lake views—ideal for enjoying sunsets from a future second-story balcony or out your current kitchen window!! The 4 bedrooms are very generous in size, have ample natural light and each one has oversized closets. The bathrooms have been updated with style in mind. The luxury vinyl floors were recently installed along with new kitchen appliances. Featuring a distinctive Mansard-style roof, this residence boasts strong architectural character and a versatile layout designed for modern living. Inside, you’ll find new luxury plank flooring, large windows that invite abundant natural light, and generously sized rooms with ample closet and storage space. Home offers a lot of character and charm with the present architectural features of a Chicago brick wall, ceiling accent beams and for the art lover a huge paneled art gallery wall!! The home includes two separate living areas, a formal dining room, an eat-in kitchen, and an office area with abundant storage and desk work space —perfect for work-from-home needs, student study session or family organization. The 2-car garage adds both storage and convenience and has a large utility closet inside the garage to stay organized. While the home is ready for your personal touch, it presents a rare chance to customize and elevate a spacious property in a top-rated school district, just minutes from parks, shopping, dining, and lakefront recreation. Whether you're looking to renovate, invest, expand upward, or build your dream home — the potential here is truly exceptional.

446 Alberta Drive, Winter Park

$1,300,000

4 Beds ⋅ 4 Baths ⋅ Comstock Park SubDv. ⋅ 32789 Zip Code

**DON'T LET THIS OPPORTUNITY PASS YOU BY, BACK ON MARKET DUE TO BUYERS FINANCING.** Luxurious Retreat in the Heart of Winter Park’s Premier Neighborhood – Minutes from Park Ave! Discover timeless elegance in this stunning 4-bedroom, 3.5-bathroom home offering 2,953 square feet of thoughtfully designed living space. Nestled on tree-lined streets in one of Winter Park’s most coveted areas, surrounded by multi-million-dollar estates and just moments from the Winter Park Chain of Lakes, this home defines luxury living. Step through the impressive cut beveled glass double front doors into an interior filled with natural light, featuring hardwood floors, crown molding, recessed lighting, and blinds and Roman shades throughout. Formal living and dining rooms provide an elegant backdrop for entertaining, while the fireplace in the family room adds a cozy touch. Sliding French doors and two sets of large sliders seamlessly extend the living space to the private pool area. A sunroom (added in 2024) with a mini split system offers additional space to relax and unwind. Enjoy modern upgrades including a monitored security system, intercom system, reverse osmosis water filtration, and a water softener system. The gourmet kitchen is a chef’s dream with custom wood cabinetry, wavy tiled backsplash, granite countertops, stainless appliances including a newer refrigerator (2024) and newer dishwasher (2022), a gas stove, and two pantries, including a walk-in pantry. The breakfast nook and breakfast bar with seating for three creates plenty of space for gathering. Retreat to the luxurious primary suite with wood floors, a large walk-in closet, and a spa-like ensuite bathroom featuring double split vanities, a garden soaking tub, a large tiled shower, and a private water closet. Enjoy your own private backyard paradise on a .26-acre lot with a resort-style in-ground pool (2021), waterfall feature, sun shelf, lush landscaping, and irrigation system. An electronic front gate provides peace of mind for security as you're guided to a paved driveway and parking pad with a 2-car garage to complete this exceptional property. All this in a highly sought-after location, just minutes from Park Avenue’s high end shops and fine dining restaurants, Rollins College/Dinky Dock public boat ramp, Winter Park 9 Golf Club, Winter Park Racquet Club, Interlachen Country Club, Winter Park YMCA and WP Phelps Park and playground and so much more! Don’t miss your chance to own a piece of Winter Park’s finest! Schedule your private tour today. (Roof: 2019, HVAC 2017, Mini Splits (2) 2024, Electrical 2004, Plumbing 2004)

1420 Palmer Avenue, Winter Park

$1,400,000

5 Beds ⋅ 4 Baths ⋅ Waterbridge SubDv. ⋅ 32789 Zip Code

This 5 bedroom, 4 full bathroom one story refreshed ranch estate boasts nearly 4,200 sq ft and features 3 fireplaces, double primary suites, and sprawls out on an oversized .36 acre lot, overlooking an open air salt water & solar heated pool. Updates & upgrades include: full roof replacement with transferable warranty (2023), new windows with transferable warranty (2023), 4 newer ACs (2 are 2023 & 2 are 2017), pool resurfaced with new waterline tiles and stacked stone (2023), pool salt cell replaced with 3 year warranty (2025), new carpet in bedrooms (2025), fresh sod in the backyard (2025), new turf in atrium (2025), exterior paint (2023), plantation shutters throughout, tile floors (2016), closets by design. The kitchen has undergone a full remodel & is the heart of the home. It features quartz countertops, a 10' quartz peninsula, a Bosch cooktop, Bosch oven with a top built-in microwave, a GE cafe smudge proof fridge and a farmers sink. The kitchen opens up to the family room, with a stacked stone feature wall and built-in shelving, all surrounding the cozy wood burning fireplace. The primary bedroom is split on one side of the home, offering privacy, is oversized and features a seating area with it's own wood burning fireplace. The ensuite primary bathroom has been remodeled with dual sinks, a deep soaking tub and a separate shower stall with floor to ceiling tile & glass frame. The second primary bedroom, which would function perfectly as an in-law or nanny suite, is split on the other side of the home and features it's own AC & water heater, with an ensuite bathroom. The additional 3 bedrooms can also be found on this side of the home, 2 of which share a jack n jill bathroom, and the final & 5th bedroom, measuring 25X12, has enough room for double office spaces or could be utilized as an office & work out space. While the home features a formal living, formal dining, family room & dining nook, there is also a secondary living space, off the secondary primary suite, complete with a wet bar, wine chiller and an electric fireplace. It's the perfect flex room and could serve as a separate in-law living area or a game room. The pool is a show stopper and has been resurfaced, including the install of new waterline tiles and stacked stone. With a sun shelf & bubbler, this pool offers resort style relaxation and is surrounded by a resealed paver deck. The side yard is ample space to play and has been freshly sodded. Zoned Winter Park High, Glenridge Middle & Brookshire Elementary, and just minutes from Advent Health Winter Park Hospital, the East End Market, which serves as a hub of market & culinary delights, and less than 4 miles from the popular Park Avenue, where you can enjoy acclaimed eateries and some of Orlando's best shopping, the location is highly desirable. Move right in, everything has been done.

1327 Bridgeport Drive, Winter Park

$1,825,000

5 Beds ⋅ 4 Baths ⋅ Temple Heights SubDv. ⋅ 32789 Zip Code

One or more photo(s) has been virtually staged. Welcome to 1361 Palmer Avenue, a beautifully updated five-bedroom, 3.5-bath residence in the heart of Winter Park, Florida, 32789. This exceptional home has been meticulously maintained and extensively renovated, blending classic charm with modern design. Inside, you'll find a reimagined designer kitchen with premium finishes, ideal for everyday living and entertaining, as well as an elegant home office with timeless wood paneling. The spacious interior features custom woodwork, generous living areas with abundant natural light, and sweeping views of the pool that create a seamless connection between indoor and outdoor living. The first-floor primary suite is a private retreat, complete with a luxurious en-suite bath offering dual vanities, a spa-like shower and two custom walk-in closets. French doors open to a serene backyard oasis, where a resurfaced, oversized pool and spa await, alongside a fully equipped summer kitchen, cozy firepit, and a pergola ideal for outdoor dining and relaxation. Upstairs, four additional bedrooms and two remodeled full baths provide ample space for family and guests. This home offers numerous high-end upgrades, including new air-conditioning units, a tankless water heater, energy-efficient PGT doors, improved insulation, lush landscaping with outdoor lighting and a whole-home water softener system—providing comfort, style and lasting peace of mind. Ideally in the Winter Park school district and just minutes from Phelps Park, Park Avenue, Interlachen Country Club, Winter Park Racquet Club and Rollins College, this home presents an unparalleled opportunity to enjoy refined living in one of Central Florida’s desirable communities.

1361 Palmer Ave., Winter Park

$2,100,000

4 Beds ⋅ 3 Baths ⋅ Cortland Park SubDv. ⋅ 32789 Zip Code

Commanding an elevated position with tranquil views of Lake Mizell, this quintessential 1926 estate artfully fuses period elegance with refined, modern enhancements. Moments from the boutiques and restaurants of Park Avenue, the residence welcomes with a paver circular drive and a private, gated side entry leading to a detached two-car garage. A brick-clad front porch and mature landscaping frame the formal entry, setting a tone of architectural distinction. Inside, a gallery-style foyer showcases designer wallpaper and salvaged pew rail detailing from a New York City church. The formal living room offers a stately gas fireplace, bespoke built-ins, and a large fixed window framing the lake, ideally suited for a quiet reading nook. The adjacent sunroom, encased in fixed glass, captures the surrounding canopy and lake vistas in all seasons. A generous dining room with custom dry bar, underlit floating shelving, and beverage refrigeration provides an ideal setting for elegant entertaining. The gourmet kitchen is thoughtfully appointed with paneled appliances including refrigerator and freezer columns, refrigerator drawers and a microwave drawer. Additional features include natural gas cooking, double ovens, and a sun-drenched breakfast room opening to the rear terrace and lap pool. A Dutch door entry offers functional access for daily living, while the basement below presents an opportunity for climate-controlled wine storage. The upstairs primary suite exudes comfort and sophistication with its gas fireplace, walk-in closet illuminated by a lake-facing window, a private covered balcony, and a spa-inspired bath with dual vanities, soaking tub, steam shower and private water closet. Two additional guest rooms with a Jack and Jill bath complete the upper level. Extensive renovations include a newer roof, Andersen windows and doors, two HVAC systems, full re-piping and rewiring, fresh paint, lighting, a newly installed pool heater and Hardie board siding—all executed within the last five years. The walk-up attic and pristine basement offer rare additional storage. Refinished hardwood floors throughout provide a consistent, elegant backdrop. This residence is a compelling blend of character, craftsmanship and contemporary living.

104 Cortland Avenue, Winter Park

$3,200,000

6 Beds ⋅ 6 Baths ⋅ Windsong Lakeside Sec 01 43/70 SubDv. ⋅ 32789 Zip Code

**This stunning estate just became an unbeatable opportunity--luxury living at a dramatically reduced price! Don't miss your chance to own this exceptional home in the highly coveted Windsong community with access to the gorgeous Winter Park chain of lakes. Prepare to be impressed as you enter this almost 6,000 square foot home adorned with custom high-end features throughout, plus a fabulous guest apartment with a full bathroom and kitchenette fully renovated to be enjoyed as a private poker/bourbon room. This exceptional residence has been converted to a full Smart Home with integrated controls for lighting, audio/video, security system with cameras, intercom, thermostat and sun shade. The beautiful chef's kitchen boasts a brand new 48” Sub-Zero refrigerator, and all new Wolf appliances including double 30” electric ovens, microwave, gas cooktop, hood insert, and warming drawer. For added convenience, a fully appointed Butler's pantry is adjacent to the kitchen. Retreat to the stunning first floor owner's suite featuring a newly installed electric fireplace, sitting area, a walk-in closet with custom cabinetry, a separate office/home gym and a spa-inspired bathroom with a jetted tub and steam shower. Just outside, step into your own personal wellness retreat with a new Polar Monkey brand cold plunge and a four-person sauna. Also, guests will enjoy the convenience of another private first floor bedroom suite. Upstairs are the additional three spacious bedrooms and bathrooms, a huge loft area, and hidden stairs leading to a generous air conditioned storage room, great for a home theater. The outside oasis greets you with a fully reimagined expansive covered lanai with an outdoor kitchen complete with a 60" Fire Magic grill, 60" Fire Magic vent hood, Summit refrigerator, and stainless steel cabinets. Relax by the sparkling saltwater pool with its sun shelf, retractable screen, and travertine deck surrounded by lush tropical landscaping and artificial turf for carefree living. The extensive renovations to this luxury estate continue with the installation of a new roof, new gutters with leaf guards, freshly painted exterior, new wood trellis, all new saltwater pool equipment, and epoxy garage flooring with added custom cabinets. Embrace this luxury lifestyle with exclusive access to the Windsong Residence Club overlooking the Winter Park Chain of Lakes, with amenities including lake access, community pools, splash park, playground, and use of the pontoon boat. This home may be purchased fully furnished. Don't miss the opportunity to own this spectacular home in one of Winter Park's most sought after neighborhoods with its top-rated schools, and proximity to shopping and dining on Park Avenue in picturesque downtown Winter Park!

141 S Phelps Avenue, Winter Park

$2,550,000

5 Beds ⋅ 6 Baths ⋅ Fontainebleau SubDv. ⋅ 32789 Zip Code

1440 Place Picardy, Winter Park, FL Custom-Built Elegance with Timeless Finishes A custom-built residence completed in 2008 that blends classic craftsmanship with luxurious, modern living. From the moment you step inside, the superior millwork, solid hardwood floors, and elegant design details make a lasting impression. The gourmet kitchen is a chef’s dream, featuring marble countertops, an oversized gas range, and premium DCS and Sub-Zero appliances. It opens seamlessly to a warm and inviting living area, complete with custom built-ins and a cozy gas fireplace—perfect for entertaining or quiet evenings at home. The spacious primary suite is located on the main floor and boasts generous walk-in closets and a versatile adjoining room, ideal for a home office, nursery, or private retreat. Upstairs, you'll find three expansive bedrooms, three full bathrooms, and a versatile bonus room—perfect for guests, hobbies, or a playroom. Lovingly maintained, this home received a new roof in 2021 and features high-quality windows and doors throughout, bathing every room in natural light. No detail was overlooked. Step outside to your private, beautifully landscaped backyard, which includes a second gas fireplace and a detached flex room—currently used as a gym, but easily converted into a private office or studio space. The oversized three-car side-entry garage offers abundant storage and includes a Tesla charger—ideal for electric vehicle owners. Nestled on a peaceful street, this home is just minutes from everything Winter Park has to offer and is located within the highly sought-after Dommerich, Maitland, and Winter Park school zones. Don’t miss this rare opportunity to own a truly exceptional home in one of Central Florida’s most desirable communities.

1400 Place Picardy, Winter Park

$1,115,000

3 Beds ⋅ 4 Baths ⋅ Park North SubDv. ⋅ 32789 Zip Code

Endless Potential in the Heart of Park North! Just steps from the charm and energy of Winter Park’s Park Avenue—where boutique cafés, fine dining, art galleries, museums, Central Park, and the Winter Park 9 Golf Course await—this rare Park North gem offers the ultimate opportunity to create your dream home. Nestled at the end of a peaceful cul-de-sac, this expansive .38-acre lot (16,534 SF) is a true find in one of Winter Park’s most desirable neighborhoods. Whether you're looking to build new or renovate the existing residence, the possibilities here are limitless. The current single-story block home spans nearly 3,100 square feet, with strong bones and a layout designed for easy living. Inside you’ll find oversized rooms, a cozy fireplace, a spacious eat-in kitchen, an indoor laundry room, private office off the primary suite, and a 2-car garage. Recent updates—new roof (2023), updated electrical panel (2023), one A/C (2019) and modernized windows and doors—set the stage for your vision to come to life. Natural light fills the home, and the beautifully landscaped backyard offers a serene retreat with a private patio, rear privacy wall, and metal fencing—ideal for both everyday relaxation and stylish entertaining. Located in the coveted Winter Park school district, this is a rare chance to invest in a premium property with endless upside. Whether you choose to reimagine the existing home or build brand new, this is a canvas just waiting for your personal touch. Schedule your private showing today and explore the possibilities! ** SURVEY AVAILABLE IN ATTACHMENTS **

309 Park North Court, Winter Park

$1,050,000

4 Beds ⋅ 4 Baths ⋅ Dommerich Cove SubDv. ⋅ 32789 Zip Code

A RARE Winter Park Estate Blending TIMELESS CRAFTSMANSHIP with MODERN FLEXIBILITY & RESORT-STYLE Living comes to market for the FIRST TIME. 2923 Cove Trail is nestled between the best of Winter Park & Maitland. Masterly created by the renowned Charlie Clayton it blends unmatched craftsmanship with modern design & flexibility craved by you, today’s discerning buyer. REIMAGINED in 2011 this 4-bedroom, 4-bath home features WHITE OAK FLOORS, SOLID WOOD CABINETS, CARRERA MARBLE & TRAVERTINE finishes, along side preserved architectural details like SKIP TROWEL CEILINGS & CROWN MOLDING. Updates fashioned TWO PRIMARY SUITES offering ultimate privacy & flexibility.These SPLIT PLAN suites pack personality. The first provides a POOL VIEW, large WALK-IN CLOSET & SHOWER, while the second basks in the PRIVACY of its own SCREENED GARDEN PATIO & access to a COZY FLEX ROOM with BUILT-INS. Whether used as a SERENITY ROOM, craft space, or restyled into a KITCHENETTE this space adds rare flexibility. Flexibility & MULTIGENERATIONAL living in a ONE STORY home aren’t the only rarities you’ll marvel over. A LARGE SEPARATE OFFICE with PRIVATE EXTERIOR ENTRANCE provides an ideal location for professionals to consult with clients or social media influencers & podcasters to ply their trades. Imagine the freedom & peace of mind you’ll gain not having to worry about traffic while also freeing your business from overhead & lease costs. When the workday ends, entertaining begins & other shiny facets of this home sparkle. A 2,500-BOTTLE CLIMATE-CONTROLLED WINE CELLAR sets the stage for unforgettable gatherings. Whether selecting a vintage for a romantic dinner, indulging guests with formal tastings or kicking back for a relaxed evening you’re sure to savor these moments especially when you move the party outdoors to your PAVERED PATIO adjoining the cool blue waters of your 18x36 RESORT-STYLE POOL all tucked within the PRIVACY of lush 8-foot WALLS. Don’t forget the patio is plumbed for an OUTDOOR BBQ & the pool for SOLAR HEAT when you’re ready to add them.The outdoors isn’t the only place you & your guests will gravitate to. Indoors, enjoy seamless FLOW between the SUNROOM, LIVING room, & FAMILY rooms. BUILT-IN SPEAKERS & STEREO SYSTEMS effortlessly deliver music to your ears. FIREPLACES in both living areas add warmth & ambiance for every season. Some properties claim to have a CHEF'S KITCHEN. This one delivers. Beyond the aesthetic updates, your cooking talents will flourish as you pivot between the island PREP SINK, professional grade 6-BURNER GAS COOKTOP with POT FILLER exceptional overhead VENT, BUILT IN OVENS & stainless steel FRENCH DOOR REFRIGERATOR. For those extra busy celebrations, just around the corner in the laundry room a complement of CABINETS,2ND FULL FREEZER & 2nd REFRIGERATOR await your handiwork while the WASHER & DRYER stand ready for tidying. There’s so much more, but here are a few more highlights:IMPACT-RESISTANT WINDOWS, a PARTIAL HOME GENERATOR, IRRIGATION ON WELL, owned SECURITY SYSTEM & 3 BUILT-IN SAFES— all contributing to your long-term comfort & the home’s efficiency. There’s NO DOUBT this property DELIVERS UNMATCHED VALUE, & QUALITY in one of Winter Park’s MOST DESIRABLE neighborhoods. Homes of this CALIBER RARELY COME TO MARKET— AND WHEN THEY DO THEY DON'T LAST. SCHEDULE your private showing TODAY. This is more than a home — IT'S the LIFESTYLE UPGRADE You've been WAITING FOR. *CLICK on Virtual tour link for 3D Walk Through.*

2923 Cove Trail, Winter Park

$8,900,000

8 Beds ⋅ 9 Baths ⋅ Green Oaks Rep 02 SubDv. ⋅ 32789 Zip Code

Discover an extraordinary lifestyle at this one-of-a-kind estate, elegantly situated on the shores of Lake Maitland in the distinguished Winter Park area. This remarkable property is unlike any other in the market, seamlessly blending sophisticated Mediterranean and Spanish architectural elements to create a serene and inviting retreat. Upon entering through the stately steel gates, you are welcomed by a picturesque, tree-lined driveway that leads to a formal motor court, enveloped in lush, mature landscaping that ensures complete privacy. Spanning an expansive 2.10 acres with an impressive 217 feet of lake frontage, this estate offers a breathtaking park-like setting that is perfect for both relaxation and vibrant entertaining. The primary residence encompasses six generously sized bedrooms and 6.5 luxurious baths, featuring exquisite traditional custom details and an abundance of elegant living space. Outside, indulge in the stunning waterside rose garden and pavilion, alongside an expansive pool designed for year-round enjoyment and perfect for hosting guests. This estate also boasts a delightful gatehouse, which includes a one-bedroom, one-bath suite and a dedicated two-car garage, providing an ideal retreat for visitors. Additionally, a separate lake house, constructed in 2004, features richly hued wooden vaulted ceilings, a cozy stone fireplace, and a generously sized covered porch that spans the length of the home showcasing spectacular views of the water and gardens. This property transcends the notion of a mere home; it embodies a truly unique lifestyle. Whether you desire serene lakeside tranquility or a sumptuous entertainer's haven, this exceptional offering presents an unmatched opportunity to own a slice of paradise in Winter Park. As you step through the grand double-door entry of the main residence, you are enveloped in elegance and comfort. This thoughtfully designed home balances functionality with style, featuring dual office suites, a game room, and ample storage space throughout, catering to the demands of modern living. The awe-inspiring 22.5-foot ceilings in the grand foyer and dining room create an impressive ambiance, illuminated by uniquely designed windows that flood the space with natural light. The smartly designed floor plan ensures both privacy and convenience, with the primary suite thoughtfully positioned in a secluded area of the home, while an additional main-level bedroom provides flexibility for guests or family. The expansive kitchen is a culinary dream, boasting a spacious island, breakfast bar, a walk-in pantry, and a gas cook range, all seamlessly connected to a cozy dinette area. Upstairs, you’ll find four additional bedrooms and three beautifully renovated bathrooms that prioritize comfort and space. Step outside to an oversized screened and covered lanai, complete with multiple skylights that invite the beauty of the outdoors inside, perfect for relaxation or entertaining. Enjoy captivating views of the pool area, rose garden with Tea House, and tranquil lake, creating an idyllic backdrop for both peaceful moments and lively gatherings. This main residence is a sophisticated blend of luxury and practicality, designed for those who truly appreciate the finer things in life. Don’t miss this rare opportunity to claim this stunning residence as your own—schedule a private showing today to experience the unparalleled elegance and uniqueness of this extraordinary estate!

2001 Bett Mar Lane, Winter Park

$645,000

3 Beds ⋅ 3 Baths ⋅ Trotters Rep SubDv. ⋅ 32789 Zip Code

Welcome to 796 McIntyre Avenue, Winter Park, FL 32789. This stunning and serene retreat is the ideal place to call home, perfectly situated on a tree-lined brick street within walking distance to Rollins College and all that Park Avenue has to offer. A charming driveway leads to your two-car garage and private front entrance. Upon entering, you'll be greeted by a bright and airy townhome that will instantly impress. The living room features a wood-burning fireplace, soaring ceilings with high windows, and is surrounded by two peaceful patios, bringing in abundant natural light. The updated kitchen offers modern cabinetry, an open breakfast bar, and a delightful eat-in area that opens to a patio. The formal dining room, currently used as a home office, provides access to the second patio, ideal for al fresco dining. Upstairs, you'll find an AMAZING 23x12 primary bedroom with a spacious 20x8 ensuite bathroom. Two guest suites with a Jack-and-Jill bathroom complete the second floor. The owner has meticulously maintained this lovely home, with new patio decks in 2018, a new HVAC, water heater, washer/dryer in 2019, new ceiling fans and refrigerator in 2020, and a new roof and skylights in 2021. Zoned for Audubon K-8 and Winter Park High School. Welcome home!

796 Mcintyre Avenue, Winter Park

$1,450,000

6 Beds ⋅ 5 Baths ⋅ J Kronenberger SubDv. ⋅ 32789 Zip Code

Welcome to your private slice of paradise—a beautifully renovated home with a brand new 2024 pied-à-terre guest retreat, nestled just steps from the iconic Kraft Azalea Garden on the shores of Lake Maitland, and walking distance to the renowned boutiques and dining of Park Avenue. Positioned on a beautiful 0.30-acre lot, this residence is enveloped with manicured landscaping, meandering brick pathways, and outdoor living spaces designed for effortless entertaining. This home captivates with exceptional curb appeal—complete with vibrant florals, a stately new blue front door, and architectural charm. The total square footage is 3784sf with the main home 5 bedrooms/4 bathrooms and 3304sf; the guest retreat is 1 bedroom/1 bathroom with 480sf. Recent updates include new flooring, fresh interior and exterior paint, a renovated kitchen, three new bathroom renovations, almost all new windows, and numerous decorative touches like new crown molding and plantation shutters. The heart of the home features a spacious open-concept layout ideal for entertaining. The living room with an updated gas fireplace flows into the kitchen, which boasts new Bosch appliances, bar seating, a walk-in pantry, and a charming picture window with garden views. The elegant dining space, with 11-foot ceilings and a wall of windows, frames the picturesque backyard. The first floor offers three bedrooms and two full bathrooms, including an en-suite, as well as an office. The second floor includes two large bedroom suites with high ceilings and a laundry room. The upstairs luxurious primary suite impresses with a tray ceiling, cozy fireplace, dual walk-in closets, and a renovated bathroom with granite dual vanities, a freestanding soaking tub, and an oversized walk-in shower. The secondary suite includes its own walk-in closet, spacious bath with double vanities, and a large climate-controlled storage area for ultimate flexibility. Features include French doors, hardwood floors, custom built-ins, crown molding, and plantation shutters throughout. But the crown jewel of the property is the brand-new 2024 detached pied-à-terre—a versatile studio suite with a full bedroom and bathroom, a refreshment area, and a private balcony with tranquil views, ideal as a guest house, executive office, fitness studio, or artist’s retreat. Outdoor living is a dream with a screened brick patio beneath a beamed ceiling, a charming open-air terrace, an enchanting fountain, and complete privacy thanks to a 6-foot concrete wall surrounding the grounds. With ample space to add a custom pool, the possibilities are endless. Located just steps from the 5-acre Kraft Azalea Garden with lakefront trails and a fishing dock, and a short stroll to Park Avenue to enjoy a scenic boat tour or one of the many museums—this is a truly exceptional offering in one of Winter Park’s most sought-after enclaves.

1299 Harding Street, Winter Park

$1,250,000

5 Beds ⋅ 6 Baths ⋅ Galloway Place Rep SubDv. ⋅ 32789 Zip Code

Discover luxurious lakeside living in prestigious Winter Park, where this extensively updated pool home offers the perfect blend of sophisticated main residence and private guest cottage. Just minutes from Park Avenue's renowned shopping and dining, this property provides coveted access to Lake Osceola, creating an ideal setting for the Florida lifestyle. The main residence showcases elegant living spaces, including a grand room with hardwood floors and a welcoming fireplace. The gourmet kitchen is a chef's dream, featuring premium Wolf and Sub-Zero appliances, gleaming granite countertops, and a distinctive bead-board center island that opens to a spacious family room. A wall of French doors in the formal dining room creates seamless indoor-outdoor flow to the screened pool and spa area. The thoughtful floor plan includes a downstairs master suite with custom walk-in closet, dual-sink bathroom, and versatile 13x12 flex space. Two additional en-suite bedrooms upstairs provide comfortable accommodations for family or guests. The separate guest cottage adds tremendous value with two bedrooms, a full kitchen, and bathroom – perfect for long-term guests or home office. Recent updates ensure peace of mind: new roof (2025), two new AC units (2023), complete replumbing (2015), and updated electrical. The property offers abundant parking with a two-car garage plus an additional one-car garage with full bath. Located in Winter Park's prestigious school district, this home represents the perfect combination of luxury, convenience, and long-term value.

1370 Alberta Drive, Winter Park

$1,810,000

4 Beds ⋅ 4 Baths ⋅ Charmont SubDv. ⋅ 32789 Zip Code

Experience modern luxury in this stunning custom-built residence by LunDev Custom Homes, positioned in the heart of Winter Park. Built in 2015, this contemporary home offers four bedrooms, 3.5 baths and 3,440 heated square feet, seamlessly blending elegant design with state-of-the-art smart home technology. The first-floor primary suite is a serene retreat featuring a spacious walk-in closet and a spa-like en-suite bath with dual sinks, a glass-enclosed shower, a separate soaking tub and a private water closet. The formal living room is highlighted by French doors opening to a beautifully designed side yard with low-maintenance artificial turf, creating an indoor-outdoor flow. At the heart of the home, the open-concept kitchen is a chef’s dream, boasting a large island that overlooks the dining and family rooms, ideal for everyday living and entertaining. A dramatic wall of glass doors seamlessly extends the living space to the covered lanai, complete with motorized screens for year-round enjoyment. Recent upgrades, including fresh interior and exterior paint, Philips Hue smart lighting, smart wall switches and new smart locks, enhance style and convenience. Step outside to your private resort-style oasis, where a sparkling pool, built-in gas grill, ceramic Coyote Asado smoker and pergola-covered seating area set the stage for unforgettable gatherings. An outdoor shower and a lush Vistafolia artificial green wall system, illuminated by Philips Hue backlighting, add to the ambiance. A covered walkway connects the home to a detached two-car garage, offering functionality and architectural charm. Upstairs, a versatile bonus room/loft with gym flooring provides endless possibilities, accompanied by three additional bedrooms, two featuring walk-in closets and one with dual closets and an en-suite bath. Additional enhancements include a Ring security system, a new pool filter and skimmer, and upgraded front yard landscaping, ensuring this home is move-in ready. Just minutes from downtown Winter Park’s Park Avenue, Baldwin Park Village Center, and premier dining and shopping, with easy access to downtown Orlando and Orlando International Airport, this residence offers the ideal balance of luxury, comfort and convenience. Don’t miss this opportunity and schedule your private showing today!

1970 Laurel Road, Winter Park

$3,600,000

4 Beds ⋅ 4 Baths ⋅ Winter Park SubDv. ⋅ 32789 Zip Code

Nestled on a sprawling 0.89-acre estate, this luxurious home offers the perfect balance of privacy and convenience, just moments from the vibrant downtown Winter Park. A rare gem, this 1935 James Gamble Rogers masterpiece blends Old World charm with European influences, creating an inviting, character-rich ambiance. The main home features 3 bedrooms, 2 1/2 bathrooms, and 3,908 square feet of elegant living space, complemented by a 1-bedroom, 1-bathroom guest cottage, adding 406 square feet, for a total of 4,314 square feet. Accessed via a long, secluded driveway, this estate seamlessly blends indoor and outdoor living with lush gardens, expansive courtyards, and tranquil patios. Inside, arched doorways, reclaimed doors, and rounded stucco walls evoke a Santa Barbara Mediterranean feel. The kitchen is outfitted with stainless steel appliances, granite countertops, and a butler’s pantry—ideal for entertaining. The formal dining room opens to a living room with a curved barrel ceiling, a fireplace, and French doors leading to a garden patio. A sunlit sunroom offers panoramic garden and pool views, perfect for relaxation. The expansive downstairs owner's suite features vaulted ceilings, French doors to the patio, a cozy fireplace, and a lavish marble bath with a Jacuzzi tub, double sinks, and a dressing area with custom cabinetry and two large walk-in closets. Upstairs, two bedrooms share a beautifully renovated marble bath. The detached 2-car garage is adjacent to the laundry room, while the guest house offers a studio layout with terra-cotta floors, a kitchenette, a full bath, and French doors overlooking the pool. The backyard is an oasis of tranquility with a stunning resort-style pool, an expansive patio, and lush landscaping, providing ultimate privacy. This home offers the best of both worlds: a rare opportunity to own a piece of Winter Park history, yet lovingly maintained with modern updates and conveniences throughout.

851 Georgia Avenue, Winter Park

$1,305,000

4 Beds ⋅ 4 Baths ⋅ Sevilla SubDv. ⋅ 32789 Zip Code

Back on the market at no fault of the seller. Step into the charm of old Florida with this stunning historic home in the heart of Winter Park's exclusive Sevilla neighborhood. Built in 1973 by Charles Clayton, this beautifully preserved residence seamlessly blends timeless elegance with modern comforts. Featuring original hardwood floors, intricate crown molding, and a cozy wood-burning fireplace, every detail reflects meticulous craftsmanship and a timeless aesthetic. The updated gourmet kitchen boasts high-end appliances while maintaining its classic appeal. Nestled on a tree-lined brick street, the home sits on a lushly landscaped lot with a spacious backyard, including a 64,000 gallon custom pool, perfect for enjoying Florida's warm evenings. Just minutes from Park Avenue's boutiques, restaurants, and within walking distance of A-rated schools, this rare gem offers the perfect blend of history, luxury, and location. Don't miss your chance to own a piece of Winter Park's rich heritage!

1600 Barcelona Way, Winter Park

$1,850,000

5 Beds ⋅ 5 Baths ⋅ Windsong Elizabeths Walk 43/81 SubDv. ⋅ 32789 Zip Code

This Mediterranean-style, Windsong pool home is sure to check every box, with a 3-car garage, screened rear patio, heated spa and pool, and an ideal, 3-way split-bedroom floorplan on the 1st floor. The large kitchen sits at the heart of the home with a dinette showcasing pool views, an island with a gas cooktop, and a breakfast bar overlooking the sunny family room. Separate living and dining rooms off the foyer offer flexibility and additional space to entertain with ease. To the left of the foyer, enjoy a large, private office with a storage closet. Just past the office, the Primary Suite is situated on one end of the home for optimal privacy and features his and hers walk-in closets, a renovated bathroom, and access to the screened rear patio. At the other end of the home, a secondary bedroom with a full en-suite bathroom makes a great guest or in-law suite, while 2 additional bedrooms, a full hall bath, storage closet, and spacious laundry room complete the 1st floor. Upstairs, the private bonus room, complete with a walk-in closet and full en-suite bathroom, makes a perfect 5th bedroom. French doors from the family room, living room, and Primary bedroom all lead to a screened rear patio that overlooks a fully-fenced backyard where lush landscaping wraps around the resort-style heated pool and spa with water features. In addition to the massive driveway and expanded parking pad, the oversized 3-car garage provides extra parking and storage space. As one of the most coveted neighborhoods in Winter Park, Windsong offers countless amenities, including private lake access for residents. This premium location is just steps from Baldwin Park, East End Market, the Corrine Drive corridor, and minutes from downtown Park Avenue.

1627 Elizabeths Walk, Winter Park

$3,550,000

3 Beds ⋅ 5 Baths ⋅ Osceola Shores Sec 03 SubDv. ⋅ 32789 Zip Code

This single-story home offers serene lakefront living with approximately 95 feet of prime water frontage on beautiful Lake Osceola. Whether you enjoy watersports, boating, or simply relaxing by the water, this property can provide the true joy of lakefront living. The grandfathered boat dock provides a rare opportunity for transformation, perfect for customizing your ideal lakeside retreat. The home boasts breathtaking lake views from the primary retreat, family room, dining room, and Florida room, providing a seamless connection to nature. Upon entering, you're greeted by a spacious living room that flows effortlessly into the family room. Adjacent to the living room is a formal dining room, ideal for entertaining guests. The expansive primary retreat has dual closets. Across from the primary, a generously sized bedroom features its own ensuite bathroom. The kitchen, located off the dining room, also captures stunning views of the lake, making it a delightful space. An additional bedroom with an ensuite bathroom provides privacy and comfort, while a half bath is conveniently located near this bedroom. A second half bathroom is situated in the garage. A recent update includes a new roof installed in 2022. The property spans .61 acres, providing plenty of room for future development. Located on one of Winter Park's most beautiful streets, this home is just a short walk from the charming shops and restaurants of Park Avenue and Rollins College. Experience the best of lakeside living and the vibrant Winter Park community from this stunning property. Opportunity awaits the buyer of this gorgeous property!

443 Lakewood Drive, Winter Park

$1,835,000

4 Beds ⋅ 4 Baths ⋅ Charmont SubDv. ⋅ 32789 Zip Code

A timeless masterpiece, this 1935 English Cottage, designed by the renowned Gamble Rogers, stands as a testament to classic elegance and enduring craftsmanship. Nestled on nearly half an acre in one of Winter Park’s most coveted neighborhoods, this home has been thoughtfully updated with modern luxuries while preserving its original charm. Inside, warm Heart of Pine floors, beadboard vaulted ceilings, restored period hardware, and custom built-ins create an inviting ambiance. Spacious formal and casual living areas include a dining room, separate living and family rooms, an office, and a versatile flex space. The expanded and renovated kitchen is a chef’s dream, now featuring marble countertops, custom white cabinetry, a Wolf gas range, stainless steel appliances, a built-in Miele espresso machine, and a farmhouse sink. The thoughtful redesign includes a custom range hood, a new ventilation system, and an integrated refrigerator/freezer drawer in the island. The first-floor primary suite is a private retreat with serene backyard views, two walk-in closets, and a bathroom with dual vanities, a clawfoot tub, and a separate shower. Upstairs, two bedrooms share a charming bathroom. Outside, a lushly landscaped backyard offers an idyllic escape with a newly installed pool heater (2023), a restored koi pond, and extensive hardscape additions. A covered porch and a newly added summer kitchen with plumbing make this home an entertainer’s paradise. The fully fenced property is surrounded by mature landscaping, refreshed with new perennials and heirloom camellias. Additional recent upgrades include a new roof (2021), restored siding, new gutters with leaf guards, and a new irrigation system. A detached guest house with a sitting area and loft provides the perfect private space for visitors. Located just minutes from Park Avenue, downtown Orlando, and zoned for the sought-after Audubon Park K-8 and Winter Park High School, this home embodies the perfect blend of historic elegance and modern convenience.

160 Glenridge Way, Winter Park

$2,495,000

5 Beds ⋅ 4 Baths ⋅ Cortland Park SubDv. ⋅ 32789 Zip Code

Welcome to this beautifully renovated century home on one of the most picturesque brick streets in Olde Winter Park. Take a leisurely stroll down to Lake Mizell or enjoy the views from its large front patio. This classic pool home is filled with charm, natural light and is designed for easy entertaining. The spacious layout offers multiple rooms for every occasion, including a bright sunroom, cozy living room with a fireplace, and a large welcoming family room. The gourmet kitchen features custom wood cabinets, quartzite counters, a convenient office nook and an adjoining breakfast room, while the formal dining room boasts elegant moldings and built-in corner cabinets. A secret basement presents options for additional storage or a wine cellar. The second floor features a generously- sized master suite, two additional bedrooms, two updated baths, and a versatile nursery or bonus room, perfect for a study or home office. The property includes a detached two-car garage and a charming guest house with a bedroom, bath, and loft area. Newly renovated resort back yard includes heated salt water pool and spa, multiple seating areas, complete with gas hookups for fire pit and outdoor kitchen and a maintenance-free travertine and turf pool scape. You’ll love the inviting ambiance of both this home and its vibrant Winter Park location.

140 Cortland Avenue, Winter Park

$1,075,000

4 Beds ⋅ 3 Baths ⋅ Winter Park Heights SubDv. ⋅ 32789 Zip Code

Step into this stunning one-story Spanish Mediterranean home, beautifully renovated in 2006 by renowned E2 Homes. Offering four bedrooms and three baths, this thoughtfully designed residence seamlessly blends timeless charm with modern comforts. The inviting living room features a cozy gas fireplace, setting a warm tone for the home. A formal dining room connects to the spacious kitchen through a convenient butler’s pantry. Designed for the chef at heart, the kitchen boasts a large island with a gas range and hood, abundant cabinetry, and generous counter space, along with a breakfast nook that overlooks the family room. Beautiful brand new (May 2025) Silestone countertops in kitchen, butler's pantry, office/study & laundry room, making each space light & bright. French doors open from the family room to a covered lanai, creating a space for indoor-outdoor living. A dedicated office/study or flex space leads to the private primary suite. The primary bedroom has its own set of French doors opening to the lanai and includes a custom walk-in closet. The primary bath is a serene retreat with dual sinks, a large soaking tub and a walk-in shower. The second bedroom enjoys an en-suite bath, while two additional bedrooms feature custom closet systems for maximum organization. The large fenced backyard offers ample space for a future pool, providing endless possibilities for outdoor enjoyment. Close proximity to the shopping and dining district of Park Avenue in downtown Winter Park, this remarkable home offers the ideal blend of comfort, convenience and style. ***NOTE: all interior walls recently painted neutral soft white... also, this home has accessible elements to it, including a handicapped ramp in garage.

1690 Oneco Avenue, Winter Park

$1,877,500

5 Beds ⋅ 6 Baths ⋅ Orwin Manor Westminster Sec SubDv. ⋅ 32789 Zip Code

Nestled in the highly sought-after Orwin Manor neighborhood of Winter Park, this stunning Spanish Revival home at 1446 Berkshire Ave, offers a luxurious lifestyle with unparalleled proximity to Winter Park’s finest amenities including Historic Park Avenue and Rollins College. Located on a tree-lined street, this residence exudes timeless elegance, complemented by a circular driveway that leads you to its impressive facade. The home has been thoughtfully updated with fresh interior and exterior paint, along with the addition of three new HVAC systems, ensuring modern comfort throughout. Boasting over 4,000 square feet of living space, the home features five generously sized bedrooms, including a second-floor Primary Suite that offers both luxury and privacy. The suite is complete with a private sitting area, a terrace overlooking the lushly landscaped grounds, and a spa-like bath with dual sinks, jetted tub, and a walk-in shower. A spacious walk-in closet provides ample storage space and custom built-ins. In addition to the three bedrooms, the second-floor features a spearate bonus room that is perfect for a private office, or could be converted to an in-law/guest suite, adding versatile living space to the property. The chef’s kitchen is a culinary dream, featuring solid wood 42” cabinetry, elegant granite countertops and a new subway tile backsplash. Adding to the Kitchen's functionality and sophistication are Copper prep and main sinks, Wolf Natural Gas Range, dual dishwashers, under counter ice maker and a walk-in pantry, A separate casual dining space and an island/breakfast bar seamlessly open into the family room, creating an ideal setting for everyday living and entertaining. Off the Kitchen and family room is a full guest bathroom with built in desk area and a multifunctional game room that could convert to a 6th bedroom. Outside, the private oasis is designed for both relaxation and entertainment. A resort-style pool with tranquil fountains serves as the centerpiece, while a beautifully crafted Spanish styled privacy wall, accented with lighting and peaceful bamboo, offers a serene atmosphere. Enjoy the cooler evening relaxing around the piped natural gas fire pit. Enjoy the expansive Cabana area includes a summer kitchen, as well as dedicated seating and dining areas, all overlooking the pool and lush landscaping. With its prime Winter Park location, exceptional privacy, and resort-style amenities, this remarkable home offers the perfect blend of style, comfort, and convenience in one of Winter Park’s most desirable neighborhoods.

1446 Berkshire Avenue, Winter Park

$1,555,000

4 Beds ⋅ 3 Baths ⋅ College Place Rep SubDv. ⋅ 32789 Zip Code

Iconic Winter Park treasure! Welcome home to 817 Antonette, an architecturally inviting residence that exudes quality and charm. This thoughtfully designed home boasts detailed moldings and millwork, wood floors, high ceilings, and beautiful oversized windows throughout. A grand foyer leads to a central gallery with an atrium and a custom-designed bannister, while a unique glass ceiling allows for an abundance of natural light. Perfect for entertaining, the home features a large dining room and a chef's kitchen equipped with professional-style appliances, a walk-in pantry, and a built-in banquette. The spacious family room, complete with a fireplace, has French doors that open to a charming outdoor terrace. The versatile floor plan incorporates both formal spaces and options for a home office, nursery, or music room. The main home includes four bedrooms and three baths. The upstairs primary suite is a luxurious retreat, offering a spa-like bath, an oversized closet with built-ins, and a separate room perfect for an office or nursery. The large secondary bedrooms have walk-in closets and are connected by a Jack and Jill bath. Your guests will appreciate the detached apartment, which offers privacy with a full bath, kitchen, and separate courtyard—ideal as a fifth bedroom. Situated on one of Winter Park’s most charming brick streets in the historic College Quarter, this home is just a short stroll to a private neighborhood dock on Lake Virginia. Walk to Park Avenue’s shops and restaurants, Rollins College, the farmer's market, and the Sunrail station. The home celebrates its Federalist architecture with precise and thoughtful details while seamlessly integrating modern amenities. Additional features include an oversized side-entry two-car garage, a new roof installed in 2022, and many windows replaced in 2020. This property is zoned for top-rated schools, including Audubon K-8 and Winter Park High School. Don't miss the opportunity to schedule a private viewing of this unique, one-of-a-kind treasure!

817 Antonette Avenue, Winter Park

$1,625,000

5 Beds ⋅ 6 Baths ⋅ Fontainebleau SubDv. ⋅ 32789 Zip Code

Elegant 5-Bedroom Estate in the Heart of Winter Park. Nestled on a picturesque double lot in the highly sought-after Via’s, this stunning 5-bedroom, 4 full bath, 2 half bath traditional home offers over 4,200 sq. ft. of refined living space. With timeless architectural details, modern upgrades, and an unbeatable location just minutes from Park Avenue’s shops and restaurants, this home is a rare find. Step inside to find newly refinished Brazilian Rosewood floors throughout the main living areas. The formal living room features a wood-burning fireplace and two sets of French doors that open to a covered lanai with a remote-controlled motorized screen, perfect for seamless indoor-outdoor living. The formal dining room sets the stage for elegant entertaining, while the spacious open-concept kitchen overlooks the family room. Designed for the culinary enthusiast, the kitchen boasts an Italian porcelain island, a brand-new Kucht Professional 8-burner gas range/oven, double ovens, and a walk-in pantry. The family room offers another wood-burning fireplace and French doors leading to the screened-in saltwater heated pool, refinished just three years ago with new equipment. The first-floor primary suite is a true retreat, featuring serene pool views, a large walk-in closet with California Closet system, and a spacious en-suite bath. Two additional first-floor bedrooms, each with walk-in closets, provide comfort and convenience. Upstairs, a private bedroom, full bath, and large bonus room offer the perfect space for guests or a secondary living area, with easy access to walk-in attic storage. A two-car attached garage includes built-in storage and a private staircase leading to a guest apartment/bedroom suite complete with a wet bar and full bath—ideal for multi-generational living or an au pair. Outdoor living is at its finest with a covered lanai, new tile flooring, and a remote-controlled motorized screen, plus a poolside half bath and outdoor shower. Situated in a Grade A school district and offering easy access to major roadways, this exquisite home blends elegance, comfort, and prime location. Please see attachments for the full list of improvements.

1470 Place Picardy, Winter Park

$745,000

4 Beds ⋅ 3 Baths ⋅ Orwin Manor Westminster Sec SubDv. ⋅ 32789 Zip Code

This beautiful 4 bedroom, 2.5 bath home with an oversized 1-car garage is truly special, offering a perfect blend of charm, modern upgrades, and thoughtful design in the highly desirable Orwin Manor neighborhood. Upgrades include a FULL RENOVATION in 2016 (Kitchen, Bathrooms, Electrical, Plumbing, HVAC, Water Heater and most of the Windows) PLUS a new Roof, Electric Gate, new pavered Driveway and Front Walkway in 2022, and new Hardie Plank Siding and Exterior Paint in 2018. From the moment you pull up, you’ll love the curb appeal with new landscaping, a beautiful pavered driveway with an electric gate, and a welcoming pavered walkway that leads you to the front door. Inside, the open floor plan has an abundance of natural light, showcasing beautiful floors, tall ceilings, and an inviting, spacious layout. The family room is the perfect space to relax or entertain. It flows seamlessly into the dining room and gourmet kitchen, which is a dream for any chef. The kitchen features quartz countertops with a breakfast bar, an induction cooktop with a sleek vent hood, stainless steel appliances, and 42” solid wood cabinetry with plenty of storage and counter space. On the first floor, you’ll also find a convenient powder room for guests and a home office, ideal for working remotely or creating your own private retreat. On the second floor, you’ll find three of the four bedrooms, including the spacious primary suite. The primary suite boasts custom window treatments, generous closet space, and a beautifully updated ensuite bathroom featuring a custom vanity with quartz countertops and a custom glass-enclosed tiled shower. The two additional bedrooms are bright and spacious, conveniently located near the upgraded second full bathroom and the laundry room. The fourth bedroom is located on its own level, running the full length of the home. This versatile space can easily serve as a bonus room, home gym, playroom, or whatever fits your needs! Step outside into your private, fenced backyard, with a Trex planked deck, lush green space, and an oversized detached 1-car garage for additional storage. The extended driveway offers plenty of parking, perfect for family and guests. This home is centrally located, just a short drive to I4, and a quick walk or bike ride to nearby shops and restaurants in Winter Park, Downtown Orlando and College Park. If you’ve been looking for the perfect home in a wonderful neighborhood, this is it. Don’t miss your chance to see it - schedule your showing today!

1375 Suffolk Road, Winter Park

$2,100,000

4 Beds ⋅ 3 Baths ⋅ N/A SubDv. ⋅ 32789 Zip Code

Discover your own slice of paradise on this extraordinary property spanning nearly five acres, perfectly nestled between two serene lakes in Winter Park. Offering unmatched privacy and tranquility, this retreat is ideal for those who value seclusion, natural beauty, and convenience—all within city limits, yet feeling a world away. With motorized boats allowed on both lakes, you can spend afternoons cruising, water skiing, tubing, or simply enjoying the water. A newly constructed custom dock, located just behind the home, ensures your boating experience is effortless and enjoyable. From the moment you arrive, the journey begins with a picturesque 1,000-foot gravel driveway that winds through lush woods, crosses a charming creek, and leads to a private gated entrance. The property is perfectly positioned between Lake Bell to the east, offering breathtaking sunrises, and Lake Wilderness to the west, showcasing spectacular sunsets. With over 1,000 feet of combined lake frontage, this setting is as rare as it is stunning. The outdoor space is a true haven, highlighted by a custom-designed pool inspired by Florida’s natural beauty, complete with solar heating for year-round comfort. Private gardens have been thoughtfully crafted to enhance the property’s serenity, providing peaceful retreats throughout the grounds. An expansive open field offers endless opportunities for family games, outdoor adventures, or quiet relaxation. This meticulously crafted home was built with exceptional attention to detail. The family room features dual walls of sliding glass doors, flooding the space with natural light and providing uninterrupted views of the lakes. The kitchen is a chef’s dream, boasting custom cabinetry, a handcrafted stone and wood hood, a gas cooktop, double ovens, and a unique center island. A cozy breakfast nook with a stone fireplace overlooks the pool, while the formal dining room exudes sophistication. The living room, complete with a gas fireplace, is the perfect place to unwind. Newly installed flooring, featuring rich and elegant Italian custom tiles, adds warmth and style throughout the home. Additionally, a brand-new roof was installed in 2024, ensuring long-lasting durability. With no HOA and ample space for vehicles, boats, and recreational toys, this property is as practical as it is beautiful. This home is also equipped with a whole house generator. Opportunities to own a lakeside estate like this are incredibly rare—don’t miss your chance to experience stunning views, abundant wildlife, and timeless charm in your own private sanctuary. SECURITY CAMERAS ON PREMISE. ALL INFORMATION IS ASSUMED ACCURATE BUT NOT GUARANTEED. MEASUREMENTS ARE APPROXIMATE. BUYERS AND THEIR AGENTS MUST VERIFY ALL INFORMATION THAT IS IMPORTANT TO THEM.

1032 Early Avenue, Winter Park

$615,000

3 Beds ⋅ 3 Baths ⋅ Trotter Rep SubDv. ⋅ 32789 Zip Code

Welcome to this elegant three-story townhouse in the heart of Winter Park! Step through French doors into a welcoming foyer leading to a bright and open living room, seamlessly connected to the dining area. Adorned with crown molding and charming Spanish tile, this space is bathed in natural light from sliding glass doors that open to a private outdoor patio. The kitchen features white cabinets, stainless steel appliances, a pantry, and a cozy eat-in nook. A convenient half bath completes the main floor. The second floor opens with a wonderful family room featuring a fireplace and French doors that lead to a picturesque balcony overlooking the street. Two generously sized bedrooms, one with custom built-ins, share a spacious bathroom, and there’s also an indoor laundry closet for added convenience. The third-floor primary retreat is a sanctuary, with a large bathroom boasting travertine details, a jetted tub, a separate shower, dual sinks, and a large walk-in closet. The oversized bedroom is bright and airy, with French doors that open to a private balcony. A dedicated office with built-in furniture completes the third floor. This home is as functional as it is beautiful, featuring a metal lifetime roof - installed 12 years ago, whole-house replumbing in 2022, and premium new carpeting with the thickest padding installed throughout the home in 2022. Additional updates include a new water heater and irrigation system added in 2023. A two-car carport and an unbeatable location short distance to Rollins College and the iconic dining and shopping of Park Avenue complete the package. Experience the best of Winter Park living! Motivated Seller all reasonable offers will be considered.

735 Maryland Avenue, Winter Park

$1,500,000

4 Beds ⋅ 4 Baths ⋅ Virginia Heights SubDv. ⋅ 32789 Zip Code

On one of Winter Park's most desirable streets, this charming two-story, four-bedroom, 3.5-bath home offers over 4,200 square feet of a bright-open floor plan with high ceilings, and lots of glass walls of windows and doors. Featuring wood and tile floors in the main living areas, this home has been well maintained by owners! Roof replaced 2019, Pella windows replaced 2019 and pool redone 2020. The main level includes all living areas such as kitchen, family room, living room, dining room, half bath and laundry, plus two secondary bedrooms that share a bath. The open kitchen with a cozy breakfast area opens to French doors that lead to a private paver patio and a sparkling pool with spa, ideal for outdoor entertaining. The expansive primary suite includes room for a sitting area and a generous walk-in closet. Across from Lake Virginia lakefront homes on the Winter Park Chain of Lakes, enjoy leisurely days on the pool deck or visit nearby Park Avenue’s vibrant shopping and dining scene. Note: Tremendous value in the land alone at this price as well, with lots of redevelopment in and around this neighborhood. This property is not subject to the historical district and under standard City of Winter Park building codes, to be verified with the city building department again by buyer/builder during any inspection period. Just a short distance from Rollins College and downtown Winter Park. Additionally, well located only 10-15 minutes to downtown Orlando, hospitals and major roadways, this home offers luxury and convenience in one of Winter Park’s most sought-after neighborhoods.

1321 Lakeview Drive, Winter Park

$670,000

2 Beds ⋅ 2 Baths ⋅ Park West Condo SubDv. ⋅ 32789 Zip Code

One or more photo(s) has been virtually staged. This lovely 2 bedroom/2-bathroom condo is in the newest building in gated community of Park West Winter Park. The unit has 9ft ceilings, crown molding, and beautiful hardwood floors, and a private office. The primary bedroom is spacious with a large walk-in closet. The bathroom includes a large soaker tub and a walk-in shower with dual vanities. The second bedroom utilizes the hallway bathroom, which is complete with a shower/tub combination. The kitchen has wood cabinets, granite countertops, and newer stainless steel appliances. There is one covered parking space and additional open parking spaces. The community amenities include a large clubhouse, pool, and tennis/pickleball courts. Located just one block from beautiful Park Avenue, you're just steps away from an array of upscale boutiques, gourmet restaurants, and cultural attractions. <iframe src="https://my.matterport.com/show/?m=WqHS8ffboym&brand=0&mls=1&" width="640" height="360" style="border: 0;" allow="fullscreen"></iframe>

350 Carolina Avenue Unit 304, Winter Park

$3,900,000

4 Beds ⋅ 4 Baths ⋅ Virginia Heights SubDv. ⋅ 32789 Zip Code

This custom lakefront home on Winter Park's Chain of Lakes offers stunning views of Lake Virginia and is in the historic Virginia Heights neighborhood, just a short walk from Rollins College and downtown Park Avenue. Facing north, it provides picturesque sunrise views over the lake, highlighting Rollins College and its chapel. Lovingly maintained and improved over time, the 4279 square feet does not include an additional 310 square foot finished bonus room with separate HVAC, perfect for game room or office. Upon entering, you are greeted by lake views and a foyer that leads to separate formal living and dining spaces, featuring wood floors, crown molding, plantation shutters, and 10’ ceilings throughout the first floor. The main living space showcases an open-concept kitchen and family room, and flows to the outdoor patio. The spacious kitchen has a gas cooktop, a built-in desk, island seating, an eat-in breakfast space, a walk-in pantry, and a built-in bar with beverage refrigerator. The family room has custom built-ins and a gas fireplace, and overlooks the manicured backyard, pool, and lake. The large downstairs owners’ retreat with picture windows overlooks the lake and a private screened porch with unobstructed views, and the updated bathroom has double vanities and sinks, glass shower, spa tub, and custom walk-in closet. Upstairs there are three bedrooms with attached bathrooms, two bonus spaces, and a media room, offering abundant flex space and storage. Comfort, luxury, and tranquility abound in the backyard with a pool surrounded by paver patio, grassy yard, and boathouse with a lift. The property also includes an oversized two-car garage. Improvements include new roof/2023, whole-house generator/2021, boathouse deck replaced with Trex decking and new roof/2021.

1341 College Point, Winter Park

$1,630,000

3 Beds ⋅ 4 Baths ⋅ Winter Park Residential Condominium 9541/3489 Unit SubDv. ⋅ 32789 Zip Code

One or more photo(s) has been virtually staged. This one-of-a-kind duplex in the heart of Winter Park stands out as the best value in town. Discover an unparalleled living experience in over 3,100 square feet of sophisticated space. Every detail- from the exquisite wood craftmanship which exudes classic Americana to the meticulously finished gourmet kitchen, this home truly speaks of timeless elegance. The stunning condo features three spacious ensuite bedrooms, including a primary suite with a charming fireplace and generous setback terrace. A private elevator ensures seamless access, while a lovely atrium, perfect for morning coffee or an evening glass of wine, enhances the serene ambiance. Pella windows and beautiful wood plantation shutters provide both tranquility and refined style. Step outside, and you’re immersed in the heart of Winter Park, surrounded by charming boutiques, renowned restaurants, lush parks, and vibrant entertainment. Prefer a lighter aesthetic? A paint quote and virtual renderings with lighter wood tones are available upon request.

101 S New York Ave Unit 302, Winter Park

$805,000

5 Beds ⋅ 3 Baths ⋅ Osceola Heights SubDv. ⋅ 32789 Zip Code

*** IN-LAW SUITE *** The highlight of this 95% NEW CONSTRUCTION home is the IN-LAW SUITE, perfectly positioned at the rear with a PRIVATE ENTRANCE, two bedrooms, and a full bathroom. Whether used for family, guests, or as an income-producing rental, this suite offers flexibility and added value. The in-law suite is connected to the main residence via artificial grass breezeway. This meticulously reconstructed Winter Park residence is perfectly situated minutes from Park Ave. The home offers 5 bedrooms, 3 bathrooms, 1,813 square feet of living space, and an attached 1-car garage. As you approach the home, you will be welcomed by a charming front porch adorned with custom railing and Flora cement tile. You'll find an open dining room that seamlessly flows into the kitchen upon entering. The home is enhanced with newly installed real hardwood flooring throughout. The brand-new kitchen features Ferrara Quartz countertops, blue Lioher cabinets with gold hardware, new GE Café appliances, and a spacious kitchen island. Adjacent to the kitchen is a laundry nook, and access to the home from the newly added attached one-car garage. All bathrooms have been fully renovated with high-end finishes. Two renovated bedrooms complete the front footprint of this home. As you move through the house, you'll find the spacious primary suite on your left, featuring double doors, a brand-new primary bathroom, and a walk-in closet with custom built-ins. The primary suite opens into the living room, where you can step through new sliding doors into the breezeway, which is covered with artificial turf and is perfect for outdoor entertaining. The breezeway connects to the in-law suite, which can also be used as an income-producing suite, with two additional bedrooms and a full bathroom, complete with a private side entry door. This home also has a nicely sized backyard, new landscaping, and an irrigation system. Upgrades include a NEW ROOF with gutters, NEW ELECTRICAL and PLUMBING SYSTEMS, a new one-car garage, new HVAC, a new driveway, and new pavers. Located just minutes from Interlachen Country Club, Winter Park Racquet Club, and Winter Park Golf Course, this home is ideally positioned for leisure and recreation. Fine dining and upscale shopping on Park Avenue, Advent Health Hospital, and Rollins College are also minutes away. This beautifully reconstructed home is 95% new construction! Don't miss out on this opportunity—act quickly!

1795 Walker Avenue, Winter Park

$3,325,000

4 Beds ⋅ 6 Baths ⋅ Virginia Heights SubDv. ⋅ 32789 Zip Code

Welcome to 1391 Richmond Road, a true work of art and a surreal living experience now on the market. The most discerning buyer will fall in love with the optimal location, an unusually private lot right in the heart of Winter Park, a short stroll to Park Avenue along the stunning shores of Lake Virginia. This handcrafted Georgian style home, designed to emulate New York City townhouse living was masterfully crafted on a magical lot abundant with pristine natural vegetation. Enjoy the Florida lifestyle with frontage on Howell Creek…kayak or paddleboard amongst incredible wildlife to the Winter Park Chain of Lakes. As you arrive, you are greeted by an enticing mix of traditional and old Florida plantings, highlighted by Bevolo exterior lighting and gas lanterns leading the way to your custom mahogany/iron work front entry door. The grand foyer with soaring ceilings, stunning black and white marble flooring, and grand staircase which was built in place, with hand molded railing providing a welcoming signature. Flanked by separate formal living and dining areas on either side, the formal dining room features custom hand painted Gracie brand wallpaper and leads to the butler’s pantry with wine refrigerator. The gourmet kitchen boasts Busby cabinetry, new six burner Decor gas range, new Bosch dishwasher, Subzero refrigerator, large island with prep sink, built-in oven, and naturally lit breakfast area overlooking the backyard oasis. The kitchen opens to the spacious family room with extensive venetian painted millwork, gas/wood burning fireplace with custom Italian made marble surround, 11’4” ceilings, and French doors leading to the terrace and backyard retreat. The formal living room complete with venetian plaster, gas fireplace with custom marble is connected to the family room with a stunning barreled ceiling hallway conveniently located to a chic powder bath. The main floor also includes a full pool bath with access to one of the two garages with air conditioned work room, and a 2nd back staircase. The upstairs primary suite is a sanctuary, graced with an antiqued mirror entry, gas fireplace, double French doors leading to the serene balcony overlooking the statement backyard, and two custom closets with vast cabinetry and lighting. The spa-like bath features Walker Zanger flooring, generous walk-in shower, soaking tub and dual vanities with make-up area. Two additional ensuite bedrooms are also upstairs along with an office/flex room, full bath and laundry room. The second detached garage features a bonus room/convenient home gym. No expense was spared when building which displays antique and unique lighting fixtures, custom millwork, surround sound, central vacuum, reverse osmosis water filtration, and extensive storage throughout. Notable window treatments from the finest textile manufacturers worldwide (Clarence House, Elitis, Nancy Corzine, Carragio), wallcoverings (Fornasetti, Gracie, Schalamandre), lighting (Aerin, Niermann Weeks). This bespoke home is an entertainer’s dream with multiple outdoor areas to relax amongst the secret garden of terraced landscaping and four thoughtfully placed fountains. Celebrate nature’s wildlife which range from owls, great white egrets, blue herons, hawks, bunnies, and otters in your private sanctuary minutes to Winter Park’s premier dining, upscale shopping, Mead Botanical Garden, and the highly coveted Audubon K-8, and Winter Park High!

1391 Richmond Road, Winter Park

$1,000,000

3 Beds ⋅ 2 Baths ⋅ Tuscany Place SubDv. ⋅ 32789 Zip Code

Located in the Tuscany Place neighborhood in the heart of Winter Park, this home offers endless potential for those looking to create their dream residence. With its classic ranch architecture and original features, this property is a blank canvas awaiting your personal touch, or provides a great opportunity to build new on its 0.39-acre corner lot. The home includes 3 bedrooms and 2 bathrooms, a formal living room, separate dining room, family room, sunporch, and kitchen with a breakfast nook. It also has a two-car rear entry garage. The spacious backyard provides room for outdoor gatherings and gardening, with mature landscaping. The location is excellent, within walking distance to Winter Park Racquet Club, and just moments from Winter Park and Maitland's vibrant dining, shopping, and cultural scene. Zoned for Dommerich Elementary, Maitland Middle School, and Winter Park High School. This home is perfect for investors or homeowners seeking a project in a sought-after neighborhood. Being sold AS IS, please see Realtor Remarks for comments.

1001 Tuscany Place, Winter Park

$1,330,000

5 Beds ⋅ 4 Baths ⋅ Sylvan Lake Shores SubDv. ⋅ 32789 Zip Code

Lakefront living in Winter Park! Enjoy serene views from this single-story ranch charmer, featuring 5 beds, 4 baths and 3,446 sq ft nestled behind a front block wall on the shores of Lake Sylvan. With 150 ft of frontage on a sprawling oversize lot, this lakefront estate provides a tranquil oasis within walking distance to downtown Winter Park. Perfect for multi-generational families, with an attached spacious mother in-law suite addition done in 2016. Seamlessly blending charm and newer construction, this house is light and bright with many living and entertaining options. The original house, with wood flooring throughout, consists of a 3-bedroom split plan and 2 baths (jack n jill and en suite) with a formal living room, dining room and sunroom. The galley kitchen has granite counters and stainless appliances and plenty of storage. A 9 x 7 bonus space connects to the mother-in law wing which consists of 1,300 sq ft including a family room/kitchen combo, primary bed and bath, guest room, guest bath, office, and laundry room with a private side entrance for easy accessibility. Other improvements include roof in 2020, whole house generator and windows on the east side replaced in 2018, AC and windows on the west side in 2016. Enjoy captivating panoramic views of the grounds, lake, and saltwater lap pool from the expansive covered, and screened, back patio. Private dock facilitates canoeing, paddleboarding or fishing. Zoned for top-rated Winter Park schools. Conveniently located to shopping and restaurants of Park Ave, Winter Park Advent Health, Winter Park YMCA, and Rollins College. Welcome home!

1458 Aloma Avenue, Winter Park

$4,100,000

5 Beds ⋅ 7 Baths ⋅ Cloister Grove Sub SubDv. ⋅ 32789 Zip Code

Experience the pinnacle of luxury living in this stunning five-bedroom estate situated on an oversized 120-foot wide lot on a tranquil and premier Vias brick street. This elegant Tuscan Mediterranean enjoys over 5,600 square foot of living space offering an exceptional blend of elegance and comfort, ideal for both intimate gatherings as well as grand entertaining. As you step through the foyer, you are welcomed to the open formal living and dining areas, with a wall of glass straight ahead capturing grand views of the sparkling pool and beautifully landscaped backyard. The heart of the home is the spacious, chef-inspired island kitchen, featuring top-of-the-line appliances, a hidden walk-in pantry, and a 12-by-12 breakfast nook. This space seamlessly connects to the main casual gathering room and additional flex/media room beyond, making it perfect for hosting large gatherings. The gathering area is anchored by gorgeous built-ins and a modern linear fireplace, with large sliding glass doors that open to the expansive covered lanai, blending indoor and outdoor living. The flex/media room is bathed in natural light, thanks to oversized picture windows that frame lush backyard/pool views as well. It also features a glass-enclosed, temperature-controlled wine room and a powder/pool bath that leads to an outdoor shower. On the opposite side of the main level, there is a stately office/library, with its wall of built-ins, providing a peaceful workspace with full views of the front courtyard. The grand primary suite is a true retreat, the gracious space includes a sitting area, a spa-like primary bath, two ample walk-in closets, and access to a private, trellis-covered courtyard with a fountain. The first floor also includes a hidden full guest suite with an ensuite bath. Upstairs, you'll find a large loft/bonus room with built-ins, along with three additional bedroom suites, each boasting ensuite baths and walk-in closets. The private backyard is an oasis, featuring a beautiful, tropical pool with a waterfall feature, a relaxing spa and lush mature grounds. The covered lanai extends your living space outdoors, complete with a seating/lounging area with a gas fireplace and TV, a summer kitchen, and room for alfresco dining. A split three-car garage and a picturesque brick paver driveway enhance the home's curb appeal. Situated in the highly sought-after The Vias neighborhood of Winter Park, 1231 Via Salerno offers the perfect blend of privacy and convenience, just minutes from upscale dining and shopping on Park Avenue, the Winter Park Racquet Club, Interlachen Country Club, and top-rated schools. This is a rare opportunity to own a truly exceptional home in one of Winter Park's most desirable locations.

1231 Via Salerno, Winter Park

$3,625,000

3 Beds ⋅ 6 Baths ⋅ Winter Park SubDv. ⋅ 32789 Zip Code

Welcome to an exquisite 3-bedroom, 5.5-bath plus office pool home in the heart of Winter Park. Set back 150 feet from the picturesque brick street, this stunning residence offers unparalleled privacy and elegance, exuding sophistication from the moment you arrive. Stately double-front doors open into a grand foyer with direct views of the beautiful pool and meticulously landscaped backyard. Step inside to discover a magnificent custom concrete and iron staircase that sets the tone for the remarkable craftsmanship throughout the home. The spacious open kitchen overlooks the family room and breakfast area, providing seamless access to the covered lanai. Outfitted with sleek European custom cabinetry by NEFF, double islands, two dishwashers, and top-of-the-line Wolf/Subzero/Miele appliances, the kitchen is a chef’s dream with ample storage for all your needs. The inviting family room features a stunning gas fireplace, coffered ceilings, and a large custom bar complete with a wine refrigerator. Designed for grand entertaining, the home offers large-scale rooms with soaring ceilings that create an open and airy ambiance. The formal living and dining areas are enhanced by large picture windows that bathe the rooms in natural light, offering picturesque views of the sprawling grounds. The outdoor living space is nothing short of extraordinary, featuring a cozy outdoor living room with a gorgeous gas fireplace, a dining area, and a built-in grill. Motorized screens open to reveal the pool and manicured backyard, creating an idyllic setting for relaxation and entertainment. The primary suite on the first floor is a sanctuary of luxury, offering two separate baths, each with its walk-in closet and access to the pool area. An elegant office or optional fourth bedroom and a secondary bedroom with an en-suite bath are also on the first floor. Upstairs, you'll find a secondary primary suite with a spacious en-suite bath, featuring dual vanities, a luxurious spa-like soaking tub, and a glass-enclosed shower. For added convenience, there’s an upstairs wet bar perfect for refreshments, alongside ample cabinetry providing extra storage and space for hanging clothes. Additional features include a full-house generator, well irrigation system, a five-zone A/C system for optimal climate control, and a three-car attached garage with a brick paver-gated driveway leading to a motor court, ensuring ample parking and privacy. This truly unique property has been done and maintained to the highest standards, offering an unparalleled lifestyle. Situated in a top-notch location, just a short distance from vibrant shopping and restaurants on Park Avenue and the iconic Winter Park Golf Course, this home is a rare opportunity to experience the epitome of luxury living in Winter Park.

850 Georgia Avenue, Winter Park

$585,000

2 Beds ⋅ 2 Baths ⋅ Orwin Manor Westminster SubDv. ⋅ 32789 Zip Code

Located in the highly sought-after neighborhood of Orwin Manor, where Winter Park meets Orlando, this inviting 2-bedroom, 2-bathroom home with a versatile den offers comfort, style, and an unbeatable location. From the moment you arrive, the bright exterior and welcoming pathway set the stage for what’s inside. Sitting on a spacious 0.20-acre corner lot, this home offers both curb appeal and plenty of outdoor space to enjoy. Step inside the living room, where a cozy wood-burning fireplace and a charming built-in cabinet add warmth and character. The living room flows seamlessly into the dining room, a bright space filled with natural light—perfect for everyday meals or hosting guests. Just off the dining room, you’ll find the kitchen, featuring stone countertops and white cabinets. The primary bedroom is a standout, with high ceilings, barn doors, and direct access to a covered patio with a brick floor. The ensuite bathroom is roomy, with double sinks, a soaking tub, a large shower, and a walk-in closet. The second bedroom is also generously sized, making it comfortable for guests or family. The Florida room, with its French doors and natural light, offers flexibility—whether you need a family room, office, or playroom. Outside, the oversized backyard is a great space for entertaining or just relaxing, with both a covered patio off the primary bedroom and an open patio with pavers. Just minutes from Downtown Winter Park, College Park, and Orlando, and with quick access to I-4, getting around town couldn’t be easier. You’ll love the convenience of this location, close to shopping, dining, AdventHealth, and the Orlando Science Center. This home is ready for you to make it your own—schedule a tour today and see all it has to offer!

1600 Berkshire Avenue, Winter Park

$1,825,000

4 Beds ⋅ 4 Baths ⋅ Fontainebleau SubDv. ⋅ 32789 Zip Code

EXPERIENCE THE ART OF LIVING IN THE HEART OF WINTER PARK! This stunning home, built in 2015 by LunDev Custom Homes, is located on a quiet, tree-lined, cul-de-sac street in Fontainebleau, a desirable area of Winter Park. The 2-story residence is situated on an oversized, manicured lot with mature landscaping and features 4 bedrooms, 3 1/2 baths, formal living room, office, gourmet kitchen, great room, bonus room, and playroom. The wide-plank wood flooring, plantation shutters, Restoration Hardware light fixtures, crown molding, wainscoting, and neutral paint colors are just some of the numerous exquisite aspects of this home. The primary bedroom suite is on the first floor and has patio doors leading to the covered lanai and pool area. The primary bathroom has 2 separate vanities with quartzite countertops, frameless glass-enclosed shower, and soaking tub. The gourmet kitchen has wide-plank wood flooring, 42-inch upper cabinets and quartzite countertops, under cabinet lighting, large center island with stainless-steel undermount sink, decorative pendant lighting, vented range hood, gas grill, and Bosch stainless-steel appliances. Additional features include mudroom, laundry room with washer and dryer, walk-in pantry, and butler's pantry with quartzite countertops and wine cooler. Kitchen opens to great room and dining area, overlooking pool and impeccably landscaped backyard. The great room has a gas fireplace and wide-plank wood flooring, with patio doors leading outdoors. The fenced backyard has extensive landscaping transforming it into a secluded and tranquil private retreat with a large inground pool and spa! The paver area surrounding the pool can accommodate ample furniture. The expansive covered lanai has motorized, retractable screens, an outdoor kitchen with gas grill, refrigerator, sink, polywood cabinets with quartzite counters, and a wood-plank ceiling with fans, recessed lighting, and sound speakers. **Irrigation well** **Outdoor shower** **Ring doorbell and cameras** **Extensive outdoor lighting** **New roof in 2022**. Conveniently located near Park Ave with shops, restaurants, Central Park and SunRail station. Close proximity to Rollins College, University of Central Florida, downtown Orlando, hospitals and employment centers, museums, art galleries, entertainment venues, lakes, parks, and tourist attractions. The meticulous workmanship and obvious pride of ownership make this a must see home!

2415 Versailles Avenue, Winter Park

$842,500

3 Beds ⋅ 3 Baths ⋅ Virginia Heights Pt Rep SubDv. ⋅ 32789 Zip Code

ENJOY ALL DOWNTOWN WINTER PARK OFFERS INCLUDING LAKE ACCESS WITH THIS MOVE-IN READY TOWNHOUSE! This spacious abode has 3 bedrooms and 3 baths with 2284 sq. feet, 10’ ceilings, custom details throughout and natural lighting-all ready for immediate enjoyment. Foyer with slate flooring welcomes guests to enjoy the doubled sided gas fireplace in the living and dining area with wood floors. Nearby a butler bar with custom cabinetry and wine refrigerator is ready for your beverages. Chef-inspired kitchen has a long granite sitting bar overlooking the family room. GE Monogram ovens and refrigerator, gas cooktop with griddle, specialty lighting and soft close cabinets with pullouts will inspire your cook! Through French doors is the covered courtyard with stainless gas grill: perfect for entertaining. Nearby is an ideal guest suite or office with a customized closet and full bath. Large laundry room near the garage has granite countertops, cabinets, utility sink and LG Smart washer/dryer! Upstairs is a spacious primary bedroom with French doors to a private covered balcony! Also 2 walk-in closets with custom shelving, jacuzzi bath, oversized shower, and dual vanities with granite countertops. Additional ensuite bedroom and laundry area. Attached 2-car garage with epoxy flooring , and an additional parking pad in rear makes this true maintenance free living in the heart of WP. Walk to Park Ave for dining and shopping, WP Tennis Center, new WP outdoor park, and Rollins College! Neighborhood Lake Virginia access for kayak and paddleboard launching to the Winter Park Chain of Lakes. Top schools: Audubon K-8 and WPHS. New Roof- 7/2024; 2 HVAC- 7/2021; outdoor grill serviced yearly. HOA maintains landscape, irrigation, building maintenance and outdoor lighting.

1134 S Pennsylvania Avenue, Winter Park

$755,000

4 Beds ⋅ 2 Baths ⋅ Hills SubDv. ⋅ 32789 Zip Code

Established Winter Park neighborhood - a hidden gem! Located on a quiet cul-de-sac, this ranch-style one story home w/pool was solidly constructed in 1968 and still retains many original mid-century architectural features. Fully fenced private back yard has a large pool and landscaping that features chemical-free gardens and native butterfly plantings - safe for children and pets. The home features birchwood and tile floors throughout with a light-filled split plan. 2024 and other recent updates include new patio roof, new interior/exterior electrical panels, new LED lights in kitchen and baths, new hot water heater, laundry appliances, custom fence and more. The kitchen, updated in 2012, overlooks the patio and pool and opens to the den, which features a large built-in bookshelf, skylight and red brick wall w/fireplace for gathering on Winter nights. The Laundry room, accessed through the two-car garage or the bedroom/office, has washer, wash tub and dryer with overhead cabinets and shelved storage area. The garage has plastic tile flooring and a workbench, as well as drawers, shelves and pegboard walls for storage. This community is a friendly neighborhood with sidewalks, lovely tree canopies and no through streets, making it peaceful and safe. The Neighborhood Association invites voluntary participation with a small $80 annual fee to help maintain a sense of community and keep the entrances attractive. Winter Park Hills is centrally located - just a short distance to historic Park Avenue, Kraft Azalea Gardens, many cultural institutions, major highways and is zoned for some of the area's best schools - Dommerich Elementary, Maitland Middle and WPHS. Four bedrooms, two baths, fireplace, pool, wonderful porch, 2030 sf - SINGLE STORY!! Definitely worth a look if you are in the market for a nice home!

2436 Tioga Trail, Winter Park

$1,200,000

3 Beds ⋅ 3 Baths ⋅ Park Grove SubDv. ⋅ 32789 Zip Code

Under contract, accepting backup offers. Welcome to 1417 Williams Drive, in the highly desirable Park Grove neighborhood in the heart of Winter Park. This home has been lovingly maintained, having only one set of owners. This well-maintained home sits in a cul-de-sac, with an oversized lot of 0.37 acres. It additionally boasts 2,080 square feet, three bedrooms, 2.5 baths, with pool, covered patio, as well as ample additional backyard space for whatever your vision desires. This is a rare opportunity to be in the desired and secluded Park Grove neighborhood, which is a short distance or brief drive to Park Avenue, Winter Park Golf Course, Winter Park Village and Enzian Theater. It's all at your fingertips! Schools are all A-rated with Dommerich Elementary, Maitland Middle and Winter Park High School all the zoned schools. Additionally, Park Maitland K-8 is within short distance. Don't miss this amazing opportunity to make this house your dream home, as well as be a part of the highly sought-after 32789 community.

1417 Williams Drive, Winter Park

$2,560,000

5 Beds ⋅ 7 Baths ⋅ Windsong Lakeside Sec 01 43/70 SubDv. ⋅ 32789 Zip Code

Prestigious Windsong community-Discover luxury living at its finest in this exquisite 5-bedroom, 5 full and 2 half-bathroom estate built by renowned Hal George (Parkland Homes). Boasting a traditional, red brick exterior and surrounded by a private 12 ft hedge, this meticulously maintained, light-filled home offers unparalleled privacy and modern elegance. Upon entry, you're greeted by a grand foyer, setting the tone for the home's impeccable craftsmanship and attention to detail. The main level features a well-appointed office and a spacious primary bedroom retreat that opens gracefully to the pool lanai, offering a seamless indoor-outdoor lifestyle. Beautiful primary bath features travertine marble, a spacious soaking tub, and a large shower, epitomizing luxury and relaxation. The heart of the home revolves around an open yet distinct layout, perfect for daily living and entertaining. The family, dining, and living rooms flow effortlessly, enhanced by new LED lighting and a gas fireplace for added ambiance. The gourmet kitchen is a chef's dream, showcasing granite countertops, pale oak cabinetry, and top-of-the-line appliances including a Wolf gas range, Subzero refrigerator, Bosch dishwasher, and Perrin and Rowe faucets; a window wall behind the dining banquette floods the kitchen with natural light and looks out onto the pool area and private backyard. Dual pantries provide ample storage space. Upstairs, a separate staircase on one side of the house leads to the fifth bedroom/bonus room with walk-in closet and bathroom, ideal for guests or a private retreat. Upstairs from the main living area are three bedrooms with en-suite bathrooms and a fourth “loft” room, perfect for a library, studio or playroom. Outdoors, indulge in resort-style amenities including a recently resurfaced, heated saltwater pool with a gas-heated spa, fiberoptic light tower, and Jandy Digital Assistant controller. The pool deck is at the center of a private, beautifully landscaped, backyard “room” surrounded by walls of green hedges, perfect for early morning coffee and birdsong or a glass of wine in the evening as the sun sets, washing the pool with color. The 2022 designer summer kitchen boasts marble countertops and a stainless steel Wolf gas grill. A pool bathroom adds convenience for guests. A mudroom and laundry area offer practicality and organization. Additional features include completely refinished wood floors throughout, a new security system with video cameras, a central vacuum, three AC units installed between 2015-2018, a whole house dehumidifier installed in 2023, and two hot water heaters. Outside, enjoy immaculate landscaping, a long driveway leading to a three-car garage with Tesla charging station, and serene touches like a Buddha garden. Located in the highly desirable Windsong, residents benefit from exclusive access to the Winter Park Chain of Lakes, pools and water park area for entertaining, and playgrounds. Minutes away from Park Avenue shopping and restaurants, Baldwin Park, parks, playgrounds, and excellent public schools including Brookshire Elementary, Glenridge Middle, and Winter Park High School. Don’t miss this rare opportunity to own a masterpiece in one of Winter Park’s most coveted neighborhoods. Contact us today to schedule your private tour and experience luxury living at its finest.

1450 Mizell Avenue, Winter Park

$850,000

3 Beds ⋅ 3 Baths ⋅ V H Musselwhites Sub SubDv. ⋅ 32789 Zip Code

One or more photo(s) has been virtually staged. Expect to be impressed! Situated in a fabulous locale and within minutes to downtown Park Avenue, this mid-century modern beauty has numerous details taken into consideration. As you enter the home you can’t help but notice the gorgeous wood flooring with custom two-tone design accents…and a peek of the backyard oasis that awaits you. Creating a seamless expansive space, the wood floors flow through the living and dining areas, the kitchen, hallway and bedrooms. Another impressive feature as you come into the living area is the openness of the floor plan and space that each room offers. The substantial size kitchen with its extensive and sleek, modern styled cabinets, Corian countertops and stainless appliances, including the Sub-Zero refrigerator, truly makes the space one to love. As the floor plan flows to the dining room and Florida room, you have the best views of the natural beauty of the backyard, the tremendous open pool and spacious patios. Flooded with a great deal of natural light, these spaces allow you to enjoy day to day or when you are entertaining. The master suite is a private retreat, boasting ample space, a luxurious ensuite bathroom with a spacious shower and 2 separate vanities along with a custom-designed walk-in closet. The additional bedrooms are generously sized offering flexibility for guests or a home office. Trimmed in mature landscaping that enhances the property’s privacy and natural beauty, and along with a fully fenced yard, the outdoor patio area provides a serene sanctuary for outdoor dining and relaxation. And whether you take a dip or take in the view, the remarkable pool is truly an enjoyable experience. You will love the timeless design and relaxing comfort in this beautiful home! *NEW ROOF & AC - 2018*

1771 Windsor Drive, Winter Park

32789 Zip Code Real Estate & Homes with Formal Living Room Separate

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