32789 Zip Code FL Real Estate, Homes with Awning(s) for Sale

1 Beds ⋅ 1 Baths ⋅ Chateaux Du Lac SubDv. ⋅ 32789 Zip Code

Lakefront Community! Enjoy Glorious Sunsets, Cocktails on the Deck and the Peace of Water and the Amazing Joy of Nature! All this near the heart of Winter Park and walking distance to all kinds of Shopping! One of few 1 Bedrooms and an Upstairs End Unit! Enjoy Spacious Room Sizes for easy Furniture Placement, Compact Kitchen, Bright Master Bedroom with additional Built-in Closets, Vanity and Mirrored Closets and updated Bath, accessible for Guests and close to Master! Updated Windows! Private Balcony! Owner is providing a One-Year Home Warranty and a $3,000 Flooring Credit. Make this affordable Unit your own!

1500 Gay Road Unit 4D, Winter Park

$1,995,000

4 Beds ⋅ 4 Baths ⋅ Tantum Add SubDv. ⋅ 32789 Zip Code

Truly a rare Winter Park offering. Perfectly positioned along the dogleg of the fourth fairway of the historic Winter Park 9-Hole Golf Course, this beautifully renovated four-bedroom, four-bath Mediterranean residence seamlessly blends timeless architectural character with sophisticated modern living. Rich in charm and thoughtfully updated throughout, the home welcomes you with an elegant living room featuring a gas fireplace, classic built-in shelving and abundant natural light. At the heart of the home is a stunning chef's kitchen, complete with custom floor-to-ceiling cabinetry, premium Thermador appliances, a charming breakfast nook and an inviting bar with wine refrigeration that flows effortlessly into the formal dining room, ideal for entertaining. A distinguished first-floor office offers an exceptional work-from-home environment, showcasing a breathtaking custom wall of built-in shelving, cabinetry and an integrated desk. This versatile space also serves beautifully as a library or den. Upstairs, all four bedrooms provide privacy and comfort. The luxurious primary suite features two separate closets, a spacious spa-inspired bath with a soaking tub overlooking the golf course and a private covered balcony perfect for enjoying peaceful morning coffee or evening sunsets. A generously sized secondary suite offers exceptional flexibility with its own custom walk-in closet, en suite bath and private rear staircase, making it ideal for guests, multigenerational living or a secluded retreat. Two additional bedrooms and a well-appointed full bath complete the second level. Updated features include smart house lighting, cabinet and shelving accent lighting, custom built-ins and much more. Designed to embrace Florida's indoor-outdoor lifestyle, the home offers a screened porch accessible from both the dining room and breakfast nook, creating an inviting space for year-round entertaining. Two additional open patios provide the perfect setting to relax while enjoying picturesque golf course views and the tranquil surroundings. Perhaps the home's greatest luxury is its exceptional location. Just steps from the boutiques, acclaimed restaurants, sidewalk cafés and vibrant atmosphere of Park Avenue, this residence offers an unmatched Winter Park lifestyle. Convenient access to downtown Orlando, major hospitals, world-renowned attractions and both Orlando International and Orlando Executive airports makes everyday living as effortless as it is elegant. This is a rare opportunity to own a beautifully updated Mediterranean home in one of Winter Park's most coveted and locations.

922 N Pennsylvania 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

$300,000

2 Beds ⋅ 1 Baths ⋅ Karolina On Killarney SubDv. ⋅ 32789 Zip Code

Under contract-accepting backup offers. Perfect Property for Builder or Investor Nestled in the sought-after Karolina on Killarney neighborhood, this classic 1935 bungalow offers timeless character and an exceptional opportunity to create your dream home in one of Central Florida's most desirable locations. Situated on a generous lot, this 2-bedroom, 1-bath residence features approximately 1,408 square feet of living space with a flexible floor plan ready for your personal vision. Original architectural details provide a warm foundation for renovation, restoration, or expansion, while the spacious backyard offers ample room for outdoor entertaining, gardening, or future additions. Whether you're a homeowner looking to customize a historic property or an investor seeking your next project, this home presents outstanding value in a neighborhood surrounded by beautifully updated residences. Ideally located just minutes from Park Avenue's renowned dining, boutique shopping, museums, and year-round events, you'll also enjoy convenient access to Downtown Orlando, College Park, Winter Park Village, major hospitals, and top commuter routes. With no HOA and a prime location in the heart of Winter Park, opportunities like this are increasingly rare. Bring your imagination and unlock the incredible potential this charming property has to offer!

1960 Biscayne Drive, 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

$1,189,000

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

Reimagined from the ground up for modern living while honoring its original mid-century modern heritage, this 1953 Winter Park residence pairs authentic MCM character with the ease of all-new finishes and systems. Four bedrooms and three full bathrooms are arranged around an open living, dining, and kitchen core that opens to a light-filled sitting area. White oak floors run throughout, while designer lighting and ceiling fans, clean horizontal lines, and warm natural finishes carry the home's MCM soul. The kitchen anchors the home with Taj Mahal quartzite counters and brand new KitchenAid stainless steel appliances. Step out to an expanded rear patio overlooking a private fenced backyard, ideal for entertaining or quiet evenings at home. Move in with confidence: new roof, all-new windows, new 200-amp electrical service, all-new plumbing with new water heater, new HVAC ductwork, and a new Nest thermostat. The attached garage and dedicated interior laundry complete the layout. The location is the rare kind you can live on foot: walk to East End Market, Kelly's Homemade Ice Cream, Redlight Redlight, Sushi Lola's, and the sought-after Audubon Park K-8 School. Winter Park High and the shops and dining of Park Avenue are just minutes away. A thoughtfully rebuilt classic in one of the area's most established and connected neighborhoods.

3006 Northwood Boulevard, Winter Park

$2,800,000

3 Beds ⋅ 4 Baths ⋅ Morse & Pennsylvania Twnhms SubDv. ⋅ 32789 Zip Code

Hidden Gem! Designed and built by the acclaimed Phil Kean Design Group, this exceptional luxury townhome offers modern living in one of Downtown Winter Park’s most desirable locations. Situated in the heart of Hannibal Square and just three blocks from Park Avenue, this residence places premier dining, shopping, galleries, museums, Central Park and year-round community events within easy walking distance. Thoughtfully designed with both style and functionality in mind, the home showcases high-end finishes throughout including rich Brazilian walnut flooring, oversized 24 x 48 ceramic tile, coffered ceilings, quartz countertops, custom cabinetry and premium stainless-steel appliances. The chef’s kitchen is anchored by an eight-burner Wolf gas range and a Sub-Zero refrigerator, paired with a hidden pantry discreetly concealed behind custom cabinetry. A striking metal staircase serves as a central architectural feature, adding a contemporary design element that complements the home’s clean lines and sophisticated aesthetic. The open-concept floor plan is filled with natural light, enhanced by expansive windows throughout that frame peaceful green views and mature tree-lined surroundings. The main living areas extend seamlessly to the outdoors, where a first-floor entertaining wet bar with a wine refrigerator opens directly to the private courtyard, creating an effortless indoor-outdoor flow ideal for hosting. The courtyard features a fire pit surrounded by greenery, while the balcony off the main living area includes a summer kitchen. A fenced yard offers privacy and space for pets to enjoy. Designed for today’s lifestyle, the home includes a PRIVATE ELEVATOR servicing all three floors, dual HVAC systems, two tankless water heaters hardwired security cameras and a spacious three-car garage with an electric vehicle charging station and generous storage space. RARELY AVAILABLE in Downtown Winter Park, the oversized THREE CAR GARAGE offers exceptional functionality and flexibility. The private driveway provides additional parking while abundant guest parking nearby makes entertaining easy, an uncommon convenience in a downtown setting. The primary suite occupies the third floor, offering a private retreat with separation from the main living areas. It features a very large owner’s closet filled with natural light and a dedicated vanity area, creating a functional yet refined dressing space. Two additional bedrooms and a dedicated office or den provide flexibility for working from home, accommodating guests or creating additional living space. Each bathroom has been thoughtfully appointed with quality finishes and timeless design. Tucked within a quiet enclave , this residence offers a unique balance of privacy and walkability. The property is adjacent to the recently completed $6.1 million residence of internationally respected architect Kamal Rizk further underscoring the caliber of the surrounding neighborhood. Homes of this quality and location rarely come to market, presenting a truly limited opportunity to own in one of Winter Park’s most sought-after addresses. Combining the architectural vision and craftsmanship of Phil Kean Design Group with luxury finishes, modern conveniences and an exceptional location, this residence offers sophisticated low-maintenance living in the heart of Winter Park’s most vibrant neighborhood. Furniture may convey and pricing upon request. New 10 yr. termite bond will convey with the sale.

660 W Morse Boulevard, Winter Park

$3,500,000

5 Beds ⋅ 7 Baths ⋅ Kenilworth Shores Sec 06 SubDv. ⋅ 32789 Zip Code

Experience resort-style living at 1836 Whitehall Drive! Inspired by the warm breeze and seaside elegance of a tranquil island paradise, this new custom home by Urban Perch, A Boutique Home Builder, offers a timeless front elevation, exquisite finishes inside and out, and unobstructed views of the beautiful outdoors from almost every room. Totaling 4,168 square feet, this five-bedroom, five-bath residence (and casita!) features a unique U-shaped floor plan ensuring natural light shines through every gathering space. Channeling the natural sands of a sunny retreat, the kitchen features white marble countertops and backsplash with blush pink undertones. A custom plaster hood, La Cornue gas range, a wall of cabinets with paneled GE Monogram appliances and a scullery with additional prep space create a kitchen ideal for entertaining. The marble island overlooks one of the main living rooms, where white oak trim highlights the precast stone surrounding the gas fireplace. A vaulted ceiling with natural wooden beams accentuates the bubble chandelier and level 5 drywall finish. Full-height sliding glass doors invite you to soak in the saltwater pool, summer kitchen, landscaped grounds and detached casita beyond. With accordion-style doors and a side entrance, the casita can serve as a pool house, personal home gym or additional bedroom with full bath. Sightlines from the main entrance lead you to the outdoors but also serve as observation points for the color-drenched first floor bedroom and primary suite with arched entry. A freestanding tub with smart glass window, zero-entry shower and extra thick Taj Mahal quartzite countertops elevate the primary bath to pure relaxation. Outside the primary suite, a concealed under-stairs laundry closet appears elegant, as impeccable millwork provides seamless transitions to the adjacent accent wall. Completing the first floor is a formal living room and dining room, a bold powder room, and a charming mudroom with custom cabinets. Follow the wrought-iron railing and engineered wood flooring to the expansive second floor. A flex room, three additional bedrooms and baths, a large laundry room, and built-in closets and benches keep everything organized and beautiful. This exceptional Winter Park home, crafted with intention and experience from award-winning local custom home builder, Urban Perch, elevates everyday living to approachable luxury.

1836 Whitehall Drive, Winter Park

$849,900

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

Virtually Staged. Welcome to 1265 Arlington Place, a beautifully appointed townhome nestled in the heart of Winter Park's coveted College Quarter - just steps from Rollins College, Park Avenue, and all the dining, shopping, and culture that downtown Winter Park provides. The main level features an open living area flowing into a well-equipped kitchen with granite countertops and solid wood cabinetry, a wet bar for effortless entertaining, a dining room, and a convenient half bath - all finished with rich hardwood floors. French doors lead to a private, fenced yard with two deck spaces, one covered with an awning, perfect for outdoor entertaining or quiet mornings outside. Also on the main level, the spacious primary suite offers an oversized walk-in closet and direct yard access. The luxurious primary bath features double vanities, a soaking tub, and a separate standing shower. Upstairs, a generous bonus living space is flanked by two additional bedrooms, one of which includes an en-suite bath and two walk-in closets - ideal for guests or a home office setup. A full hall bath completes the upper level. Throughout the home, storage has been thoughtfully considered, with generous closet space at every turn. Smart home features including remote-controlled outdoor lighting, garage door, irrigation, and alarm system make this the ultimate lock-and-leave lifestyle home. Residents also enjoy exclusive access to Virginia Heights Park, a private lakefront park reserved for neighborhood use only - a rare amenity in the heart of Winter Park. Come see what makes this property so special!

1265 Arlington Pl, Winter Park

$249,900

2 Beds ⋅ 2 Baths ⋅ Chateaux Du Lac SubDv. ⋅ 32789 Zip Code

MAJOR PRICE ADJUSTMENT! Fantastic Winter Park Location on Lake Killarney. This 2 Bedroom 2 Bath Upstairs Unit has Lake and Pool Views. Spacious Living Spaces and Generously-sized Bedrooms. Unique Updated Kitchen has Sub Zero Refrigerator, Bosch Dishwasher, Solid Surface Counters, unbelievable amount of Storage with Corner Cabinets, Drawers, pull-out Shelving and 3 Tiers of Lighting! Updates include: Water Heater in 2023, Range 2019, Refrigerator in 2020, A/C in 2020, Double-Pane Windows and Sliding Door in 2016, Updated Electric Panel, Replaced Ductwork and added Attic Insulation. Master Bath has Double-Sink Vanity. Guest Bath has newer Vanity and Retiled Shower with replaced Shower Pan. Unit recently Replumbed. Plantation Shutters, recently Repainted and Carpeted. Short Walk to Shopping, Restaurants, Theaters, and minutes to Park Avenue with it's Village Style Shopping, Central Park with Bandstand, Spring and Fall Art Festivals, Farmer's Market and Downtown Train Station. Drive into the Community, catch a view of the Lake, watch a Sunset on the Deck and you will know "you're Home"! OWNER WILL CONSIDER REPLACING CARPET IN LIVING AREA WITH LUXURY VINYL FLOORING WITH ACCEPTABLE CONTRACT!

1500 Gay Road Unit 17D, 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

$640,000

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

Beautiful income-producing duplex located in the highly desirable Winter Park area! This well-maintained property features two units, each offering 2 bedrooms, 1 bathroom, and a dedicated utility room for added convenience. Both sides provide functional layouts with comfortable living spaces, making it ideal for tenants or owner-occupants looking to offset their mortgage. Situated on Indiana Ave, this property is just minutes from Park Avenue, shopping, dining, and major roadways, offering both convenience and strong rental appeal. Whether you're looking to expand your investment portfolio or live in one unit while renting the other, this duplex presents a fantastic opportunity in a prime location.

1618 Indiana Avenue, Winter Park

$3,799,000

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

JUST COMPLETED....WINTER PARK / LAKE SUE DISTRICT — A TRUE STANDOUT IN TODAY’S LUXURY NEW CONSTRUCTION MARKET Proudly presented by RARE Builders, a name synonymous with design-forward custom homes that continue to help set and raise the standard in Orlando and Winter Park, this newly completed residence represents a rare opportunity to secure a fully realized custom home in one of the area’s most sought-after neighborhoods. Positioned just steps from Lake Chelton and Lake Sue, and located within a highly desirable Winter Park school district, the setting delivers an exceptional lifestyle in one of Central Florida’s most dynamic and tightly held areas. While new construction inventory exists in today’s market, this home stands apart offering a fresh, cutting-edge architectural vision brought to life through exceptional planning, material selection, and execution. Prominently sited on an elevated homesite with a striking front elevation, the home offers 4,500 square feet of living space, including nearly 3,000 square feet on the ground level alone... a rare and highly functional configuration. The layout is both expansive and intentional, featuring multiple large living spaces, a private ground-floor primary suite, and a well-appointed guest suite/study/flex space. Upstairs, each bedroom is thoughtfully designed with either an en-suite bath or direct access to a full bath, delivering both comfort and privacy throughout. The defining feature of this home...and one rarely seen in the market... is the massive Renlita Floataway door system, which opens an entire wall of the home to seamlessly connect the interior Florida room with the resort-style outdoor living environment. This creates a true four-season entertaining space, transforming the way the home lives and offering a level of indoor-outdoor integration that is both dramatic and highly functional. The outdoor setting is designed as a private resort, complete with a pool, spa, fire and water features, pergola, and summer kitchen... all curated to complement the home’s architectural vision. Inside, the level of finish and design is exceptional. From breathtaking Venetian plaster walls to a dramatic two-story foyer, the home is defined by a refined and highly curated selection of materials, fixtures, and hardware. Every element has been intentionally sourced and executed, resulting in a level of craftsmanship and aesthetic cohesion that is rarely achieved and immediately recognized by discerning buyers. A well-appointed kitchen with walk-in butler’s pantry and thoughtfully designed secondary spaces further enhance both function and livability. Integrated Control4 home automation, audio, and security systems complete the offering. Located just minutes from Downtown Orlando, Winter Park, Park Avenue, Winter Park Village, AdventHealth, and Orlando Health, this home delivers a rare combination of location, design, and execution at the highest level. This is not simply new construction, it is a distinct, design-driven custom residence offering a level of detail, presence, and livability that is truly rare in the current Winter Park market.

150 Dana Way, Winter Park

$261,000

2 Beds ⋅ 2 Baths ⋅ Chateaux Du Lac SubDv. ⋅ 32789 Zip Code

Welcome to the most beautifully updated 2 Bedroom 2 bath End Unit in a Lakefront Community on Lake Killarney. This home features Quartz counter tops with a Granite Island and stainless steel appliances, along with a beverage refrigerator, and luxury vinyl flooring through out the whole unit. A huge living room offers loads of gathering and entertaining space in this cheerful home. Enjoy Florida outdoor living in the private patio. Home is move in ready!! The Community includes a private Boat Ramp and Dock, On-site Boat Parking, Heated Pool and Sauna, and a community grill. Enjoy Sunsets on Lakefront Deck and short walking access to Winter Parks Shops, Restaurants, Movies, Park Avenue, Farmers Market and Downtown Art Festivals. Come see this inviting home and make it yours today!

1500 Gay Road Unit 8D, Winter Park

$2,650,000

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

Timeless elegance meets boutique craftsmanship at 541 W Canton Ave., an exceptional new construction home by Urban Perch, proudly featured in the 2025 Parade of Homes Orlando. Near Winter Park’s iconic Park Avenue, this French Quarter-inspired residence blends historic charm and rich character with elevated modern living and a refined sense of calm. From its dormer windows and custom-carved wood entry door, to its charming striped awnings and the flicker of gas lanterns, every detail of the exterior is carefully curated. Classic marble-paved patios frame the home, and a courtyard-style pool with fountain and sandblasted marble decking invites quiet relaxation or festive gatherings. Inside, soaring ceilings, beautiful hardwood floors and immersive color-drenched rooms create an inviting space that is luxurious but unpretentious, bold yet serene. The stunning staircase features a custom wrought-iron railing with an antique finish, offering a striking architectural focal point. The chef’s kitchen, a culinary sanctuary and social hub, is complete with graphite La Cornue range and pot filler, Monogram paneled refrigerator, custom plaster hood, quartzite countertops and backsplash, and grand center island that opens to a gathering room with a gas fireplace. This more relaxed living area flows effortlessly through French doors to the pool and patios, creating an ideal indoor-outdoor lifestyle. A butler’s pantry with a second refrigerator, cabinetry and prep space adds functionality, while the formal dining room, living room, and bar area with sink and built-in beverage cooler are ideal for entertaining. A beautiful downstairs powder bath features designer wallpaper, elegant sconces and custom cabinetry. The upstairs primary suite offers spa-like serenity, including a wet room complete with soaking tub framed by a picture window. Three additional bedrooms include one with an en-suite bath, while the other two share a hallway-accessible bath with double vanity and walk-in tiled shower. This masterpiece set in the heart of Winter Park, thoughtfully surrounded by lush landscaping and carefully placed privacy screens, offers polish and presence in an ideal location.

541 W Canton Avenue, Winter Park

$612,500

2 Beds ⋅ 2 Baths ⋅ Village Winterset Inc SubDv. ⋅ 32789 Zip Code

Experience elevated living in this rare fifth-floor corner residence, perfectly positioned just one block from the iconic Park Avenue in the heart of Winter Park. With sweeping views of the downtown skyline and abundant natural light from multiple exposures, this residence offers an exceptional blend of comfort, elegance, and location. The thoughtfully updated kitchen features custom shaker cabinetry, granite countertops, and stainless-steel appliances, seamlessly connecting to the spacious living and dining areas. A charming sunroom provides the perfect setting for morning coffee, reading, or enjoying the city views. The generously sized primary suite offers a peaceful retreat, complete with an updated bath and a large walk-in closet with custom built-ins. The second bedroom has been thoughtfully opened to create a stylish office or den, ideal for working from home or relaxing with guests. Refined interior details include crown molding, bamboo flooring, and abundant natural light throughout, creating a warm and sophisticated atmosphere. Residents enjoy the security and convenience of a well-maintained mid-rise building featuring secure key entry, guest call box access, and a welcoming lobby. Perfectly suited for a lock-and-leave lifestyle, this residence is just steps from Park Avenue’s boutiques, acclaimed restaurants, museums, cafés, and the Winter Park Golf Course. Additional features include: • Private storage unit • Covered carport parking space • Guest parking and community pool. An exceptional opportunity to enjoy refined living in one of Central Florida’s most desirable locations. Please note: NO RENTALS, NO PETS.

259 E Canton Avenue Unit 259, Winter Park

$258,000

2 Beds ⋅ 2 Baths ⋅ Chateaux Du Lac SubDv. ⋅ 32789 Zip Code

LAKEFRONT COMMUNITY WITH SPECTACULAR SUNSETS OVER BEAUTIFUL LAKE KILLARNEY. LOCATED IN THE CHARMING AND ELLEGANT NEIGHBORHOOD OF WINTER PARK, IN A FULLY REVITALIZED AREA. CONVENIENT TO I-4, PARK AVENUE, FARMER'S MARKETS, TRADER JOE'S, AS WELL AS A MOVIE THEATER, BOUTIQUE SHOPS, RENOWNED RESTAURANTS AND A NATIONALLY RATED ART FESTIVAL - ALL WITHIN A SHORT WALKING DISTANCE. BRIGHT SUN-FILLED 2 BEDROOM, 2 BATH USTAIRS UNIT WITH AN OPEN FLOOR PLAN AND PRIVATE BALCONY. THE PRIMARY BEDROOM IS A SUITE, AND THE SECOND BEDROOM FEATURES A SPACIOUS WALK-IN CLOSET. SOFT, WARM COLORS, TILE AND LUXURY VINYL FLOORS, RAISED KITCHEN CEILING AND GRANITE COUNTER ENHANCE THE SPACE. BRAND NEW WATER HEATER 6/2026! LARGE ROOMS MAKE IT EASY TO ARRANGE FURNITURE. ENJOY BOATING, SKIING AND WILDLIFE OF LAKE LIVING. COMMUNITY DECK, BOAT RAMP, HEATED POOL AND SAUNAS. MAKE AN APPOINTMENT TODAY TO SEE WINTER PARK'S BEST KEP SECRET!

1500 Gay Road Unit 20D, Winter Park

$1,200,000

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

Discover refined, modern living in the heart of Winter Park. Built in 2020, this beautifully designed four-bedroom, 2.5-bath pool home offers over 2,500 square feet of thoughtfully curated living space and is zoned for A-rated Audubon Park schools, combining newer construction, location, and top-tier education in one exceptional opportunity. The first floor offers an open, light-filled layout with a natural flow that feels both comfortable and functional. A sleek contemporary kitchen anchors the space with clean lines, generous storage, and a large island that naturally becomes the gathering point. It flows seamlessly into the main living and dining areas, creating an effortless environment for entertaining or everyday life. Upstairs, the primary suite feels like a true retreat, complete with a spacious en-suite bath and ample closet space. Three additional bedrooms provide flexibility for guests, a home office, or growing families. A versatile loft at the top of the stairs adds even more usable space, perfect for an office or secondary lounge. Beyond the doors, a private, fenced yard surrounds your pool, offering a seamless indoor-outdoor flow that’s ideal for weekend entertaining or everyday relaxation. Live steps from everything that makes Winter Park special, in a location that also provides fast access to I-4 for effortless connectivity throughout the city.

950 Aragon Avenue, Winter Park

$1,595,000

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

Exceptional opportunity in the heart of Winter Park — a truly premier and irreplaceable homesite offering rare scale, privacy, and extraordinary future build potential. The primary value is in the land, presenting an unparalleled canvas for a custom luxury residence, with virtually no comparable vacant land available in the immediate vicinity. Set on a tranquil small lake that provides remarkable serenity and picturesque water views, this property combines peaceful natural surroundings with unbeatable walkability. Ideally positioned just steps from the Racquet Club, moments to Park Avenue’s renowned dining, boutiques, and cultural venues, and within easy reach of the Winter Park Chain of Lakes. The location also offers the distinct prestige of residing within the coveted “Vias” of Winter Park, a collection of streets long regarded as one of the city’s most established and desirable residential enclaves. The existing residence is perfectly livable and has benefited from numerous upgrades, offering flexibility for immediate occupancy while planning a future custom build. The home also presents excellent rental potential. Please note the interior is currently being utilized for storage and does not reflect its full presentation potential, providing an opportunity for cosmetic refresh or personalization. Whether envisioned as a modern architectural statement or an elegant estate home, this site delivers the location, setting, and versatility sought by discerning builders, investors, and end¦users alike — a rare chance to secure one of Winter Park’s most desirable land offerings in a highly established neighborhood.

1113 Via Del Mar, Winter Park

$168,500

1 Beds ⋅ 1 Baths ⋅ Chateaux Du Lac SubDv. ⋅ 32789 Zip Code

Welcome to Chateaux du Lac, a lakefront community in the heart of Winter Park, FL, offering an active and convenient lifestyle. Residents enjoy an impressive array of amenities including a heated community pool, clubhouse, lakefront community deck, BBQ area, resident-only boat ramp, community laundry facilities, and two on-site saunas. This second-floor one-bedroom, one-bath apartment features laminate flooring throughout, creating a modern and cohesive living space. The unit is ideally located close to shopping, dining, and everyday conveniences, making daily living easy and enjoyable. With lake access just steps away, you can take in the serene waterfront setting while still being minutes from everything Winter Park has to offer. Lawn care is included, ensuring a well-maintained and picturesque community year-round. Don’t miss this opportunity to enjoy lakefront living with resort-style amenities in one of Central Florida’s most desirable areas.

1500 Gay Road Unit 5, Winter Park

$1,449,999

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

BRAND NEW CONSTRUCTION COMPLETED APRIL 2026, MOVE-IN READY. 2-year builders' warranty! This 3,164 sqft home at 1523 Miller Ave, Winter Park, FL 32789 combines modern design, high-end finishes, and an unbeatable central location. Featuring 5 bedrooms, 4 full bathrooms, and a private salt-water pool, the home is designed for both everyday comfort and effortless entertaining. The open L-shaped living, kitchen, and dining area is filled with natural light and anchored by a 4-panel grand pocket slider that fully retracts, opening the entire living space to the covered patio for true indoor-outdoor living. The chef’s kitchen overlooks the main living area and flows seamlessly outside to a fully equipped outdoor kitchen with grill, sink, and fridge, complemented by a spacious seating area and pool—ideal for hosting year-round. Additional highlights include a shingle roof with metal accents, a pergola accenting the front of the garage, and clean architectural lines that elevate the curb appeal. The floor plan offers flexibility with generous bedroom sizes and well-appointed full baths, while the backyard retreat centers around the sparkling salt-water pool. Location is a major advantage—2 minutes to I-4, 4 minutes to Mills Avenue, 5 minutes to Park Avenue, 10 minutes to Downtown Orlando, and approximately 20 minutes to Disney, placing dining, shopping, nightlife, and major employers all within easy reach. A rare opportunity to own a brand-new construction home in one of Winter Park’s most connected neighborhoods.

1523 Miller Avenue, Winter Park

$1,115,000

4 Beds ⋅ 4 Baths ⋅ Temple Estates SubDv. ⋅ 32789 Zip Code

In the heart of Winter Park, this extensively renovated modern farmhouse offers exceptional value for the location. A circular drive and inviting front porch welcome you into light-filled living spaces enhanced by all-new energy-efficient windows, custom millwork and designer finishes throughout. The functional layout includes a first-floor guest suite, additional well-appointed bedrooms and updated baths. The kitchen is updated, featuring custom cabinetry, stone countertops and stainless appliances. The family room flows to a covered lanai and summer kitchen, overlooking a paver deck, pool, fire pit and putting green, ideal for year-round entertaining. The fully fenced backyard offers privacy and access to a detached garage with additional storage. Upstairs, the primary suite features a private balcony, a sitting area, a walk-in closet, and a spa-inspired bath with a freestanding tub and an oversized shower. An additional upstairs fourth bedroom en suite, used as a gym, offers flexibility for a home office or nursery. Renovated with quality and intention, including updated systems and recent roofs. Ideally, across from Phelps Park and just a few blocks from Interlachen Country Club and Winter Park Racquet Club.

1673 Mayfield Avenue, Winter Park

$4,250,000

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

Steeped in history and masterfully reimagined, this 1926 Winter Park estate blends architectural provenance with modern refinement. Thoughtfully restored by E2 Homes, the residence honors its past while offering contemporary sophistication. Unlike many historic properties, it is free from preservation restrictions, allowing for seamless enhancements. On the shores of Lake Virginia along the desirable Winter Park Chain of Lakes, this 3,181-square-foot estate features four bedrooms, three full baths and two half baths, with three bedrooms in the main house plus a detached one-bedroom guest cottage. The second-floor primary suite is a private retreat with a Juliet balcony, dual closets and an elegantly appointed bath with an expansive dual-sink vanity, a separate water closet, and a washroom with a shower-tub combination. A Jack and Jill bath, adorned with Maharam wallpaper, serves the additional upstairs bedrooms. The Poliform Twelve kitchen showcases European craftsmanship with Gaggenau and Sub-Zero appliances, sleek Italian cabinetry and natural basalt countertops. The formal dining room, framed by arched windows and French doors, opens to a vine-covered courtyard, while the sunroom offers uninterrupted lake views. A fireplace in the living room, flanked by custom built-ins, adds warmth to the home’s contemporary aesthetic. Beyond its striking interiors, the estate is an architectural rarity, featuring original woodwork by Gene Leedy, a key figure in the Sarasota School of Architecture. The home is crowned with sought-after Ludowici-Celadon Imperial roof tiles. Poliform built-ins extend throughout, including a dedicated upstairs office/library. An integration of art and architecture, the property features site-specific installations by acclaimed artist Matt Olson. His No Separation project finds a compelling continuation here. The entryway, designed by Olson’s firm OOIEE and inspired by Sol LeWitt, makes a striking first impression. Designed for seamless indoor-outdoor living, the estate’s exterior spaces are as refined as its interiors. A covered deck overlooks a heated saltwater pool. A wood-clad pergola shelters the lanai. The boathouse includes a partial bath, creating a waterfront sanctuary. A Sonos-integrated sound system extends from the main house to the patio, guesthouse and boathouse, ensuring a seamless sensory experience. The detached guesthouse is a private retreat with a full bedroom, bath, kitchenette and Poliform built-ins. Floor-to-ceiling windows frame manicured grounds and lake views, while a private covered porch provides a tranquil space for relaxation. Every detail has been meticulously curated, from designer lighting to motorized roller shades and a wood-burning fireplace anchoring the living room. A private wine library enhances the home’s sophisticated appeal. Meticulously maintained by E2 Concierge services, the residence undergoes routine wellness checks and meticulous upkeep. A distinctive home of this caliber is rarely available, a residence where history, architecture and art converge in harmony. This is a once-in-a-lifetime opportunity to own one of Winter Park’s architecturally and artistically significant properties.

1336 College Point, Winter Park

$1,500,000

2 Beds ⋅ 2 Baths ⋅ Trovillion Condo SubDv. ⋅ 32789 Zip Code

Located on the second floor of Villa Siena, this two-bedroom, two-bath residence offers 1,511 square feet of elegantly appointed living space with two balconies overlooking New England Avenue’s tree-lined brick streets in the heart of Winter Park. A split-bedroom layout ensures privacy, with wood flooring and tray ceilings defining the open-concept living and dining areas. The kitchen features solid wood cabinetry, granite countertops, a Sub-Zero refrigerator, and Wolf gas cooktop and oven. Both bedrooms include walk-in closets, tray ceilings, and direct access to private balconies via French doors. The primary bath is designed with dual vanities, a deep soaking tub, and a walk-in shower finished in natural stone. Travertine flooring continues through the entry, kitchen, and baths, while the full laundry room includes built-in cabinetry and utility closet storage. This residence includes one assigned space in the secured below-ground garage, and an additional ground-level garage space. Villa Siena amenities include a fitness center, rooftop terrace, club room with bar and outdoor seating, conference room, guest parking, and on-site management. Enjoy direct access to Park Avenue’s boutique shopping, dining, museums, and Central Park, with the Alfond Inn’s restaurant, café, and lounge just across the street.

315 E New England Avenue Unit 7, Winter Park

$2,150,000

4 Beds ⋅ 4 Baths ⋅ Maitland Shores SubDv. ⋅ 32789 Zip Code

Under contract-accepting backup offers. BACK ON MARKET. Picture yourself unwinding in your private 0.41-acre yard, taking a dip in the pool, flipping through a good book, or hosting friends on a sunny afternoon. From there, stroll over to the Winter Park Racquet Club for tennis, pickleball, or lunch (kids are covered—there’s a sidewalk the whole way), or head to the deeded lake access launch for a day of kayaking on the Winter Park Chain of Lakes. Welcome to 2299 Via Tuscany, an opportunity priced 4-bedroom, 3.5-bath home to get into the coveted Winter Park Vias while adding your final touches to personalize this home while prioritizing location, schools, privacy and connectivity. With 3,986 square feet on a 0.40-acre lot, it offers the perfect blend of luxury and comfort, featuring a super spacious kitchen, a new architectural shingle roof (2023), Pebble Tec-style pool finish, and lush landscaping. Inside, enjoy solid hardwood and modern tile floors, soaring ceilings, and two wood-burning fireplaces. The chef’s kitchen shines with SubZero refrigeration and a Viking 6-burner gas cooktop. The main floor offers a private primary suite, a guest suite, and a study/library with built-ins, while upstairs you’ll find two more bedrooms and a full bath. Modern perks include zoned A/C, a new EV charger, and epoxy-coated floors in the 2-car garage. Close to parks, the Racquet Club, and downtown Winter Park’s shops, dining, and culture, this home suits families and active lifestyles alike. Deeded lake access through the Maitland Shores Lakefront Preservation Association gives you a private ramp for kayaks, canoes, and more, plus easy access to schools, trails, and green spaces—a perfect mix of charm, amenities, and location.

2299 Via Tuscany, Winter Park

$266,000

2 Beds ⋅ 2 Baths ⋅ Chateaux Du Lac SubDv. ⋅ 32789 Zip Code

Beautifully updated and meticulously maintained. Improvements done in late 2020. Kitchen Ceiling raised and recessed lights installed, new Cabinets, Quart Counters, Stainless Steel Samsung Appliances including Counter-depth Refrigerator. Wall opened into Living Room and Breakfast Bar Installed. Updated Master Bath includes new Vanity, Mirror and Lights, Commode and beautiful new Shower, Barn Door installed for Privacy. Guest Bath also updated. Luxury Vinyl and Bathroom Tiles replaced throughout. New Double Paned Windows and Sliding Door, 6" Floor Moldings, Knock-down Ceilings and Decorator Paint. A/C and water Heater done with rest of updates. This 2 Bedroom 2 bath End Unit is centrally located in Lakefront Community with covered Patio in private Courtyard! Enjoy Sunsets on Lakefront Deck, Private Lakefront Ramp Access to skiable Lake Killarney, Heated Pool, Saunas and walking access to Shops, Restaurants, Movies and short distance to Park Avenue, Farmers Market and Downtown Art Festivals. Don't miss seeing this "little bit of heaven"! Call today for private viewing!

1500 Gay Road Unit 9B, Winter Park

$2,925,000

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

This beautiful Mediterranean style home offers a rare opportunity for prime waterfront living on Lake Mizell, part of the highly sought out after Winter Park Chain of Lakes. The property is just a short walk or drive to Park Avenue’s restaurants, boutiques, and local attractions. The main home features three bedrooms and five bathrooms, each bedroom offering its own en suite bathroom. A separate guest house (ADU) provides an additional 932 square feet with two bedrooms, one bathroom, newly refinished original hardwood floors, fresh paint and a wood burning fireplace perfect for guests or extended family. Inside the main residence, you’ll find solid wood and travertine flooring throughout the first floor, surround sound speakers, a wood burning fireplace and freshly painted interiors. The living room features large windows overlooking the lake, with an open floor plan that flows seamlessly into the dining room and kitchen. The gourmet kitchen showcases a beamed ceiling, Busby custom three tone cabinetry with granite countertops, a six burner gas cooktop, and a built in ice maker. The dining area offers easy access to the outdoor entertaining spaces, perfect for enjoying lakeside gatherings. The primary suite occupies the entire second level, offering dual bathrooms, individual walk in closets, and a private balcony with unobstructed lake views. Additional features include an inviting office/den with french doors and custom built ins, as well as a spacious laundry room with ample cabinetry, a 120 bottle wine fridge, and a secondary refrigerator for added convenience. An expansive paver driveway leads to covered parking that accommodates up to three vehicles. Traditional gas lanterns and built in landscape lighting enhance the home’s Mediterranean charm and highlight its mature, manicured grounds. Outdoor living is the centerpiece of this property, featuring durable composite board decking, a summer kitchen with an infrared grill, and a hot tub for relaxing and entertaining. Enjoy multiple inviting seating areas with stunning east facing lake views. The private boat dock includes a storage closet, boat lift, and the boat itself is included. This home offers relaxed luxury and timeless lakefront living in one of Winter Park’s most desirable neighborhoods.

516 Henkel Circle, Winter Park

$879,000

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

Experience the best of Winter Park living at 451 Fairfax Avenue, an exceptional townhouse in the sought-after Virginia Heights neighborhood. This elegant residence offers timeless style and the rare advantage of no HOA. Designed for comfort and convenience, this home features three spacious bedrooms, three full baths and a private two-car garage. Upon entry, you are greeted by an open-concept living and dining area that flows seamlessly into the well-appointed kitchen, creating the perfect space for everyday living and entertaining. A bedroom and full bath on the main level provide flexible living options for guests. The main level also features a well-equipped laundry room with a sink, ice maker and generous storage. A bright sunroom with abundant natural light offers a versatile space for an office, reading nook or cozy sitting area. Upstairs, the primary suite features a spacious bath and walk-in closet, along with a secondary suite with its own en-suite bath. Beyond its inviting spaces, this home has been meticulously maintained, with new landscaping and drip-line irrigation for all patio planters. Enhancements include a tankless gas water heater, newer windows and doors with transferable warranties, new air-conditioner heat pumps (2024 and 2025), interior/exterior painting, and honeycomb roll shades throughout. In one of Winter Park’s most desirable neighborhoods, you’re a short distance from Lake Virginia, Mead Botanical Garden, and the Winter Park Tennis Center. Stroll to Rollins College or enjoy the boutiques and dining along Park Avenue, all less than a mile away. A rare opportunity to own a low-maintenance, luxury residence in the heart of Winter Park. Zoned for Audubon K-8 and WP High School. Schedule your private showing today to experience 451 Fairfax Avenue for yourself.

451 Fairfax Ave., Winter Park

$490,000

3 Beds ⋅ 2 Baths ⋅ Shores Lake Killarney Sec 02 SubDv. ⋅ 32789 Zip Code

No HOA! Fully Renovated Home with Deeded Lake Access to Lake Killarney in Prime Winter Park Location! Welcome to this move-in ready gem nestled in one of Winter Park’s most coveted neighborhoods. This solid concrete block home has been thoughtfully updated with timeless finishes, featuring a brand-new kitchen with freshly painted cabinetry, quartz countertops, stainless steel appliances and a custom paver driveway. The layout is filled with natural light, showcasing refinished flooring and modern bathrooms with stylish upgrades. Key improvements include: new roof and AC (2019), re-piping (2005) and energy-efficient windows (2010). Enjoy the charming front porch, lush landscaping and unbeatable location, just minutes from I-4, Park Avenue, and Winter Park Village. Whether you’re looking for a primary residence or a smart investment, this home checks all the boxes. **This property also qualifies for a closing cost credit of up to 1% of the loan amount through the Seller’s preferred lender.** Schedule your showing today and make it yours!

259 Blossom Lane, Winter Park

$745,000

3 Beds ⋅ 2 Baths ⋅ Northwood - Winter Park Oasis SubDv. ⋅ 32789 Zip Code

An incredible location close to Park Avenue, this freshly renovated home exudes modern style and the walkable lifestyle that Winter Park is known for. This timeless Florida ranch features one-level living and is in a charming downtown neighborhood that is fresh and turnkey. Experience an open living concept with seamless flooring and designer selections throughout creating great spaces and function. The kitchen features clean-lined, neutral-toned cabinetry with a large island topped with quartz counters and bar seating with gold-toned, oversized pendants that take center stage. The adjacent bar area includes a built-in pantry, open shelving and a wine refrigerator, adding a touch of luxury to your everyday life. Just beyond the kitchen/living room, you'll discover a fantastic dining area and two well-appointed bedrooms. The shared bath is fully renovated with current selections, making it a retreat for family and guests. A desirable split plan with owner's suite is on opposite side of the home, adorned with beautiful light and airiness. A space-saving built-in wardrobe lines one wall, while the en-suite bath showcases stunning design elements, including a walk-in shower, dual sinks and a private water closet. The backyard invites you out through clear glass sliders to a charming backyard with a brick patio and a fully fenced backyard, lined with bamboo, which offers the privacy you desire. Entertain with shaded dining and lounging on sunny days with newer retractable awning (2021) controlled by a convenient remote. Additional features that make this home stand out include a newer roof (2020), newer air conditioner (2020), plumbing updated 2018, electrical panel update (2023), new backyard sod and irrigation (2025), freshly painted, a two-car garage with a new electric car charger (2022), a custom workbench and storage cabinets added in 2021. And let's not forget the incredible location, a couple of blocks from Winter Park 9 Golf Course, Park Avenue, Winter Park Village and Saturday farmers market, with Whole Foods, Publix and the Enzian just minutes away, this home is your private oasis in the heart of Winter Park.

630 Northwood Circle, Winter Park

$3,200,000

4 Beds ⋅ 5 Baths ⋅ Forest Hills SubDv. ⋅ 32789 Zip Code

Don't miss the opportunity to own this stunning lakefront property on Lake Sue in Winter Park! Over an acre with 125+ feet of frontage, private dock with lift, and breathtaking sunsets. Features include a chef’s kitchen, multiple entertaining spaces, spa, and expansive lake views. **New build plans by Winter Park Designs (Gary Hancock) and Urban Perch – A Boutique Home Builder – available upon request.

1900 W Fawsett Road, Winter Park

$259,500

2 Beds ⋅ 2 Baths ⋅ Chateaux Du Lac SubDv. ⋅ 32789 Zip Code

Under contract-accepting backup offers. ANOTHER PRICE REDUCTION! OWNER WILL CONSIDER ALL REASONABLE OFFERS! Highly Desirable Winter Park Lakefront Community on Skiable Lake Killarney. Enjoy Peaceful Water Views and Million-Dollar Sunsets on Lakefront Deck! Private Community Ramp, Heated Pool, Men's and Women's Saunas! Don't miss this! Beautifully Renovated 2 Bedroom 2 Bath End Unit. New Kitchen Cabinets and Quartz Counters, Stainless Steel Appliances, Raised Ceiling with Lighting, Kitchen Island/Bar! Enjoy the Ease of Luxury Vinyl Plank Flooring, Crown and Wide Floor Moldings, Plantation Shutters, Upgraded Energy Saving Windows and Sliding Glass Door. Modernized Master Bath with Raised Vanity, Open Layout with Spacious Shower with Seat and Barn Door for Privacy. Guest Bath also Updated with New Raised Vanity and Shower. Second Bedroom Walk-in Organized Closet. New Master Bedroom Carpet in 2025, New Water Heater in 8/2025 A/C replaced 4-5 years ago. Sit on Private Covered Patio and enjoy Pool Views and Landscaped Vistas. Walk to Shopping, Restaurants, Movies, Trader Joe's. Minutes from Park Avenue and Farmer's Market. Centrally located, close to I-4. One of Winter Park's "Best Kept Secrets"! Make an Appointment to view today!

1500 Gay Road Unit 24B, Winter Park

$655,000

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

Welcome to 2825 Mulford Avenue, 'Memorable Mulford,' a charming two-bedroom, two-bath bungalow ideally located in Winter Park. Blending classic character with thoughtful updates, this move-in-ready home is just minutes from shopping, dining and top-rated schools. Inside, you’ll find a bright, inviting layout with spacious living areas highlighted by beautiful hardwood floors and recessed lighting. The well-designed kitchen connects to a versatile bonus room—perfect for a dining area, office or playroom. Recent improvements include a newer roof (2021), new A/C unit and updated plumbing and electrical systems. Outside, a spacious lanai is ideal for relaxing or entertaining, while the backyard offers ample room for a pool or custom outdoor living. A detached storage shed adds flexibility for a gym, workshop or hobby space, and the garage provides even more convenient storage. With a prime location just steps to East End Market and minutes to Baldwin Park, Mills 50, Park Avenue, downtown, and more—paired with stylish updates and endless potential—this bungalow is ready to welcome its next owners to enjoy the best of the Winter Park lifestyle. Zoned for Audubon K-8 and WP High School. Showings are now being scheduled!

2825 Mulford Avenue, Winter Park

$299,000

1 Beds ⋅ 1 Baths ⋅ Phillips Circle Rep SubDv. ⋅ 32789 Zip Code

Charming Downtown Winter Park Pied-à-Terre – Steps from Park Avenue! Welcome to Whispering Waters, a beautifully maintained mid-century community nestled on the shores of Lake Osceola. This light-filled corner studio offers a rare opportunity to own a piece of Winter Park’s most coveted location—just steps from Park Avenue, Central Park, and all the cultural charm the city has to offer. Located on the second floor, this spacious studio boasts an updated kitchenette, generous storage, and abundant natural light. Enjoy secure garage access, mail and package delivery to your door, and a relaxing retreat with sunrise views, osprey sightings, and even rocket launches visible from the community patios. Community Amenities: Sparkling pool, Club room for social gatherings, Peaceful outdoor patios overlooking Lake Osceola and Professional on-site management. Location Highlights include being one block to Park Avenue’s boutiques, cafes, and fine dining. Close to The Alfond Inn, museums, and galleries. Walkable to SunRail & Amtrak station. Moments from the Winter Park Farmers’ Market. This is a rare opportunity to own a stylish, low-maintenance home in the heart of downtown Winter Park where ELECTRIC, GAS, WATER, SEWER and TRASH are included in condo fee. Whether you're looking for a weekend retreat or full-time residence, this pied-à-terre is truly one-of-a-kind. Call today for your private viewing of this condo.

311 E Morse Boulevard Unit 7-11, 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

$2,700,000

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

$385,000

3 Beds ⋅ 2 Baths ⋅ Shores Lake Killarney Sec 02 SubDv. ⋅ 32789 Zip Code

Charming Winter Park Block Home with Deeded Access to Lake Killarney – Solid, Updated Systems & Priced for Your Personal Touch! Welcome to this well-built 3-bedroom, 2-bath cement block home in one of Winter Park’s most desirable and established neighborhoods. . . . . . Built in 1954 and lovingly cared by the same owner for almost 40 years, this home offers strong bones, a functional layout, and major system updates already completed—including roof (2019), AC (2019), re-piping (2005), window replacement (2010), and custom paver driveway (2005). . . . . . The kitchen was updated in 2008 and offers a great starting point for further personalization. This home is priced to reflect the need for cosmetic updates, giving buyers the opportunity to renovate and style the home to their taste, without worrying about costly behind-the-walls repairs. . . . . . Whether you're a first-time buyer, investor, or someone looking to downsize into a home you can make your own, this property is full of potential. The layout is warm and inviting, with plenty of natural light and the timeless durability of concrete block construction. . . . . . Located just minutes from top-rated schools, parks, shopping, dining, and major roadways, this home is perfectly positioned for convenience and community. . . . . . A wonderful opportunity to own in Winter Park—move in now, update at your pace, and build equity as you go!

259 Blossom Lane, Winter Park

$980,000

3 Beds ⋅ 3 Baths ⋅ Lake Knowles Terrace SubDv. ⋅ 32789 Zip Code

Nestled in the desirable Tree Streets of Winter Park, this stunning Mid-Century Modern residence offers timeless style, thoughtful updates, and effortless indoor-outdoor living. With over 2,100 square feet of beautifully designed space, this 3-bedroom, 2.5-bath home delivers modern functionality with elegant character—just minutes from the heart of Park Avenue. Inside, you'll find an open floor plan with engineered hardwood flooring, high ceilings, crown molding, and abundant natural light. The kitchen is a chef’s dream, featuring a convection oven, cooktop, range hood, and brand-new appliances—ideal for both daily living and entertaining. A wet bar with wine fridge, cozy sunroom, and custom closets in all three bedrooms elevate the home’s comfort and convenience. The primary suite is located upstairs, offering privacy and retreat. The backyard is a true Florida oasis, complete with a newly resurfaced saltwater pool, expansive artificial turf, a custom putting green, and a deck with a retractable awning—all within a fully fenced yard designed for privacy and year-round enjoyment. Additional upgrades include a new roof (2020), updated A/C system (2021), garage storage solutions, and lush front landscaping. With no HOA, a 2-car garage, and extended driveway parking for 4+ vehicles, this home offers both style and flexibility in one of Winter Park’s most coveted neighborhoods. A rare opportunity to own a turnkey home in a prime location—schedule your private showing today.

1610 Chestnut 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

$3,350,000

4 Beds ⋅ 3 Baths ⋅ Timberlane Shores SubDv. ⋅ 32789 Zip Code

Welcome to 641 Virginia Drive, a rare and remarkable lakefront property located in the highly sought-after Timberlane Shores neighborhood of Winter Park. This expansive .48-acre lot offers approximately 100 feet of frontage on Lake Virginia, one of the most desirable lakes on the prestigious Winter Park Chain of Lakes. The existing 4-bedroom, 3-bath home features 3,223 square feet of living space and showcases Country French architectural charm, offering an ideal opportunity to renovate and enhance its timeless appeal—or build new and design a custom estate that takes full advantage of this exceptional lakefront setting. Whether modernizing the current layout or crafting an architectural masterpiece from the ground up, this property offers limitless potential. The home enjoys northern lakefront exposure, providing breathtaking views to the northeast of Winter Park’s protected Genius Preserve and to the west of the iconic Rollins College shoreline, creating a picturesque backdrop with year-round natural beauty and unforgettable sunsets. Significant recent improvements have already been made, including a new roof installed in 2023 with 50-year composite cedar shake shingles, offering the charm of natural materials with enhanced durability. In addition, the dock was redecked in 2023, making this waterfront ready for immediate enjoyment. A rare enclosed boathouse and private dock offer direct access to Lake Virginia and the entire Winter Park Chain of Lakes—ideal for boating, paddleboarding, and lakeside entertaining. Few properties in Winter Park feature this level of water access and historic charm on such a prime stretch of shoreline. Set among multimillion-dollar estates and located just minutes from Park Avenue’s renowned shopping and dining, Rollins College, the Winter Park Golf Course, and a variety of cultural amenities, this property provides the perfect balance of privacy and accessibility. Zoned for top-rated Audubon Park K-8 and Winter Park High School, it offers an ideal location for those seeking the best in lifestyle and education. Whether you're seeking a peaceful lakefront retreat, a renovation opportunity with character, or the perfect site to build your dream home, 641 Virginia Drive offers a once-in-a-generation opportunity in one of Central Florida’s most distinguished communities.

641 Virginia Drive, Winter Park

$1,825,000

4 Beds ⋅ 4 Baths ⋅ Woodmere Terrace Rep SubDv. ⋅ 32789 Zip Code

A rare gem in the heart of the Vias – Nestled in one of Winter Park’s most sought-after neighborhoods, this beautifully designed home is the epitome of comfort, luxury, and convenience. Located just minutes from Park Avenue, top-rated schools, and the best dining and shopping in Central Florida, this property offers an unbeatable lifestyle in a truly prime location. Inside, the home impresses with an open-concept first floor that’s tailor-made for entertaining. The seamless flow between the spacious living room, dining area, and chef’s kitchen makes it easy to host gatherings of any size—from intimate dinners to lively celebrations. Natural light pours in through large windows, highlighting designer finishes and a thoughtful floor plan that blends elegance with everyday functionality. With four oversized bedrooms and four full bathrooms, there's ample space for everyone to spread out comfortably. The private office on the main level is perfect for working from home, while upstairs, a versatile loft offers flex space that can be used as a playroom, reading nook, or creative studio. The true showstopper is the expansive theater room, offering endless possibilities—use it as a media lounge, game room, fitness center, or whatever your lifestyle demands. Step outside to your resort-inspired backyard oasis, featuring a sparkling pool and spa, lush, professionally landscaped grounds, and a covered patio that’s perfect for summer BBQs and year-round outdoor living. Whether you're relaxing with family or entertaining guests, this outdoor space delivers the feel of a luxury getaway right at home. Don’t miss your chance to own a home that offers exceptional space, stylish design, and one of the most desirable locations in Winter Park.

1665 Temple Drive, 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

$2,800,000

5 Beds ⋅ 4 Baths ⋅ South Lakemont Shores SubDv. ⋅ 32789 Zip Code

Welcome to a rare opportunity to embrace the Winter Park lakefront lifestyle in this custom-built masterpiece that blends timeless architecture with relaxed coastal sophistication. Crafted by Hanson Custom Homes and thoughtfully curated by Kate Voss Interiors, this modern coastal residence offers the perfect setting for those who value both refined living and a vibrant, connected lifestyle. With top-rated Winter Park schools, endless parks, bike paths, and the shopping, dining and events at Park Avenue and Baldwin Park just minutes away, the owners of this home spared no expense in creating a unique blend of luxury and livability in one of Central Florida’s most desirable communities. Step inside to soaring 14-foot ceilings, custom millwork, and a 20-foot Euro glass wall that disappears into a hidden pocket—blurring the line between indoors and out and filling the home with lake breezes and natural light. Whether you're hosting birthday parties by the lake, poolside barbecues, or just soaking in the serenity of a morning coffee on the water, this home was built to bring people together. The open-concept kitchen features exotic quartzite counters, a touchless faucet, Thermador appliances, and a full butler’s pantry and flows seamlessly into an expansive outdoor living space with motorized screens, a full summer kitchen, and views that stretch across your private beach and dock. Just steps from the pool, the lake becomes your playground—ideal for paddleboarding, fishing, or sunset cruises on your boat or jet ski. The primary suite comes complete with water views, motorized drapery, and spa-worthy bath finishes—including a steam shower, soaking tub, and private porch access. The main living areas are built for both entertaining guests and cozy family nights in, while the resort-style pool and spa deliver year-round fun with dual heat sources, LED lighting, and coral stone decking. Upstairs, every bedroom features lake views, walk-in closets, and smart layouts that offer both privacy and togetherness. The bright, central loft is perfect as a media room, homework space, or game lounge, keeping the family connected without sacrificing space. Energy-efficient spray foam insulation, an EV-ready oversized 3-car garage, smart-home integration, impact-rated glass, and commercial-grade soundproofing are just a few of the features that make everyday living seamless and secure. This one-of-a-kind property is ideally positioned with easy access to both Winter Park’s iconic charm and Baldwin Park’s family-friendly amenities—a true gem that offers the rare combination of newer construction, world-class craftsmanship, and a lifestyle built for generations to enjoy. There’s simply nothing else like this on the market. If you’ve been waiting for a newly built custom lakefront home that combines relaxed luxury with the best of Winter Park family living—this is the one. Call today to schedule your private showing.

1891 Lake Spier Drive, Winter Park

$489,020

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

Here is the opportunity to own this beautiful remodeled bungalow in the desirable town of Winter Park. This meticulously maintained two-bedroom, 1.5-bath home is just steps from Hannibal Square and Park Avenue. Enjoy the convenience of Rollins College, shopping, dining and vibrant nightlife, all within short distance. Enter inside this charming bungalow to discover a newly updated kitchen that features granite countertops, stainless steel appliances and a center island. The enclosed Florida room is off the kitchen and is where you will entertain or just relax, as it provides sun all day. The fully fenced yard creates a delightful retreat, and the turf grass requires no maintenance but provides a year-round manicured look. In 2023, significant enhancements were made, including addition of a new rear deck and a new front porch, further enhancing the overall charm and appeal of the property. The roof was updated in December 2023, and the air conditioning unit was replaced in 2019, the air-conditioning compressor in 2022, and the water heater in 2019.

674 Douglas Avenue, Winter Park

$343,000

4 Beds ⋅ 2 Baths ⋅ Dubsdread Heights SubDv. ⋅ 32789 Zip Code

One or more photo(s) has been virtually staged. **Seller is motivated and encourages all serious offers—bring your buyers!** Welcome to your cozy Winter Park retreat! This charming 4-bedroom, 2-bath home blends comfort and convenience in one perfect package. Nestled on a spacious lot with a large backyard—ideal for entertaining, gardening, or playing fetch—this home also features a unique drive-through garage, perfect for weekend projects or extra parking flexibility. Step inside to find a warm and inviting layout filled with natural light and space for the whole family. Plus, enjoy peace of mind knowing the roof is only 4 years old—one less thing to worry about! Located just minutes from I-4 and surrounded by popular shopping centers, dining, and more, you'll love how easy it is to get anywhere you need to go. Don’t miss your chance to own a piece of Winter Park charm—schedule your showing today! <iframe src="https://my.matterport.com/show/?m=n9WcP2miBTq&brand=0&mls=1&" width="640" height="360" style="border: 0;" allow="fullscreen"></iframe>

657 Overspin Drive, Winter Park

$482,500

3 Beds ⋅ 1 Baths ⋅ Carver Town First Addition SubDv. ⋅ 32789 Zip Code

Bungalow with metal roof approximately one block from Winter Park mall. Considered an excellent location.

710 W Swoope Avenue W, Winter Park

$2,220,000

4 Beds ⋅ 3 Baths ⋅ Kenilworth Shores Sec 06 SubDv. ⋅ 32789 Zip Code

Contemporary Lakefront Estate in Winter Park! Nestled along the serene shores of Lake Berry, this spacious single-story, 4-bedroom, 3-bathroom home offers a perfect blend of comfort and natural beauty. With expansive living spaces bathed in natural light, this home invites you to experience relaxed lakefront living at its finest. Offering over 2,600 sf of luxurious living space, the open-concept layout allows for an expansive great room with large sliding doors that frame breathtaking lake views and create an airy and inviting atmosphere. Recently updated to include enhanced finishes that compliment the homes modern aesthetic, the neutral tile floors, vaulted ceilings and glass tile fireplace reflect the home’s cool tones. A sophisticated kitchen with white cabinetry and granite counters is a chef’s dream with its large island and high-end Viking appliances and gas-range. An oversized primary suite overlooks the water and has a private en suite with a double-sink vanity, step-in shower, and walk-in closet. With a coveted split-bedroom layout, 3 guest bedrooms, each comfortably sized, and with ample closet space, and two full baths are located at the opposite side of the home. Step outside to your private oasis, where a sparkling pool awaits. The backyard is well-suited for enjoying Florida’s sunny weather year-round and for hosting gatherings with friends and family. The fenced yard keeps the backyard nice and private, while also providing unobstructed views of Lake Berry. A docks with covered boathouse and lift is perfect for storing a boat or wave runner or jet skis. Located within one of Winter Park’s quiet and charming neighborhoods, this home offers an incredible opportunity to live on one of Winter Park’s pristine waterways and is just a short distance to Park Avenue, Baldwin Park, Advent Health, Rollins College, and many other nearby businesses. Zoned for the Brookshire/Glendridge/WPHS school district and within 15 mins of Orlando’s top private schools. Don’t miss the opportunity to tour this home – schedule your showing today.

673 Balmoral Road, Winter Park

$5,400,000

5 Beds ⋅ 9 Baths ⋅ J Kronenberger Sub SubDv. ⋅ 32789 Zip Code

Extraordinary Waterfront Neoclassical Italian Estate situated on a prime .72-acre corner lot in one of Winter Park's most sought-after locations. This 7,916 SF property includes a main residence of over 7,100 SF, a detached guest house, and a poolside catering suite. The private covered boat dock is located just steps away, across the street, in the historic Kraft Azalea Garden, providing direct lake access with boat and personal watercraft storage on Lake Maitland, without the upkeep of a waterfront backyard. Inside, fresh neutral interiors and beautiful landscaping frame elegant arrival and living spaces. The thoughtful layout offers 5 bedrooms and 5 full plus 4 half baths, including a 550 SF guest house. Expansive entertaining areas flow seamlessly into a private courtyard with a heated pool and spa, covered dining, an outdoor grill, a wood-burning fireplace, and multiple terraces. Highlights include a grand primary suite with dual bathrooms and closets, a two-story wardrobe with an office in one of the primary closets, an impressive entertainment room, and a gourmet kitchen outfitted with Viking appliances, a newly replaced double oven, and a trash compactor. For large-scale entertaining, the detached pool house doubles as a catering suite with prep sink, refrigerator, and wall-to-wall storage. Built by renowned builder Charles Clayton and designed by Marc-Michaels, the home is a masterpiece of solid block construction and timeless detail featuring imported Parisian fireplaces, solid marble columns, both marble and travertine floors, and Venetian plaster walls. A new barrel tile roof (2023) adds lasting value and peace of mind. Ideally located across from Kraft Azalea Garden and near Rollins College, the estate offers a rare combination of waterfront tranquility and walkable access to Park Avenue’s world-class dining, boutiques, and museums. The Winter Park Racquet Club is also just a short golf cart ride away. A rare opportunity to acquire a legacy property with major aesthetic updates already completed and future equity positioned for growth.

1400 Alabama Drive, Winter Park

$4,273,211

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

Steeped in history and masterfully reimagined, this 1926 Winter Park estate blends architectural provenance with modern refinement. Thoughtfully restored by E2 Homes, the residence honors its past while offering contemporary sophistication. Unlike many historic properties, it is free from preservation restrictions, allowing for seamless enhancements. On the shores of Lake Virginia along the desirable Winter Park Chain of Lakes, this 3,181-square-foot estate features four bedrooms, three full baths and two half baths, with three bedrooms in main house plus detached one-bedroom guest cottage. The second-floor primary suite is a private retreat with a Juliet balcony, dual closets and an elegantly appointed bath with an expansive dual-sink vanity, a separate water closet, and a washroom with a shower-tub combination. A Jack and Jill bath, adorned with Maharam wallpaper, serves the additional upstairs bedrooms. The Poliform TWELVE kitchen showcases European craftsmanship with Gaggenau and Sub-Zero appliances, sleek Italian cabinetry, and natural basalt countertops. The formal dining room, framed by arched windows and French doors, opens to a vine-covered courtyard, while the sunroom offers uninterrupted lake views. A fireplace in the living room, flanked by custom built-ins, adds warmth to the home’s contemporary aesthetic. Beyond its striking interiors, the estate is an architectural rarity, featuring original woodwork by Gene Leedy, a key figure in the Sarasota School of Architecture. The home is crowned with sought-after Ludowici-Celadon Imperial roof tiles. Poliform built-ins extend throughout, including a dedicated upstairs office/library. An integration of art and architecture, the property features site-specific installations by acclaimed artist Matt Olson. His No Separation project finds a compelling continuation here, with a sculptural installation of galvanized steel surrounding a crepe myrtle, accompanied by a matching bike rack. The entryway, designed by Olson’s firm OOIEE and inspired by Sol LeWitt, makes a striking first impression. Designed for seamless indoor-outdoor living, the estate’s exterior spaces are as refined as its interiors. A covered deck overlooks a heated saltwater pool and spa, while a custom cedar hot tub blends into the landscape. A wood-clad pergola shelters the outdoor kitchen, featuring a Röshults system with a professional-grade grill, sink and storage. The boathouse includes a partial bath, creating a waterfront sanctuary. A Sonos-integrated sound system extends from the main house to the patio, guesthouse and boathouse, ensuring a seamless sensory experience. The detached guesthouse is a private retreat with a full bedroom, bath, kitchenette and Poliform built-ins. Floor-to-ceiling windows frame manicured grounds and lake views, while a private covered porch provides a tranquil space for relaxation. Every detail has been meticulously curated, from designer lighting to motorized roller shades and a wood-burning fireplace anchoring the living room. A private wine library enhances the home’s sophisticated appeal. Meticulously maintained by E2 Concierge services, the residence undergoes routine wellness checks and meticulous upkeep. A distinctive home of this caliber is rarely available, a residence where history, architecture and art converge in harmony. This is a once-in-a-lifetime opportunity to own one of Winter Park’s architecturally and artistically significant properties.

1336 College Point, Winter Park

$610,000

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

Welcome to 2812 Mulford Avenue. This updated 3 bedroom and 2 bath home is located perfectly in Winter Park. Walking distance to East End Market, close to Rollins College, steps from Baldwin Park, 1 mile from Mills 50 area, and close to Mead Gardens, Leu Gardens and Loch Haven Park. The neighborhood is quiet with low traffic, oversized lots, and NO HOA, yet surrounded by amazing schools, local coffee shops, incredible restaurants & bars, and world-class shopping. The home itself is completely move-in ready, offering an amazing kitchen and is open to the formal living room/dining room. This open space connects to the den, which is an oversized room that leads to the expansive backyard with a great patio deck for entertaining, and convenient storage shed. The living room also connects via french doors to a great flex space that could morph into a homework station, home office, or new laundry room. Welcome Home!

2812 Mulford Avenue, Winter Park

$230,000

2 Beds ⋅ 2 Baths ⋅ Chateaux Du Lac SubDv. ⋅ 32789 Zip Code

Waterfront Community on beautiful Lake Killarney. Enjoy breathtaking sunsets on Community deck! Private Boat Ramp on this Skiable Lake, limited Boat parking on property. 2 Bedroom 2 Bath second floor Unit has been meticulously maintained by Winter Resident. Furniture purchased in 2020. Many Updates to Unit include new windows and window treatments, 2024 new Hot Water Heater, Baths redone in 2018-2019, New Appliances within last 5 years. Spacious Room Sizes, Private Balcony. Perfect location! Easy walk to Shopping, Restaurants, Movie Theater, close to Park Avenue and Farmers Market, minutes to I-4. One of Winter Park's best kept secrets! Don't miss this opportunity to view and own in this lovely community!

1500 Gay Road Unit 10C, 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

$1,125,000

4 Beds ⋅ 5 Baths ⋅ Hamilton Place SubDv. ⋅ 32789 Zip Code

Welcome to this exquisite Mediterranean-inspired home located in the heart of Winter Park, Florida. This residence offers luxurious living spaces and modern amenities both inside and out, complemented with a detached mother-in-law suite, all nestled on a beautifully landscaped private community with a sprawling park right in your backyard. Upon entering, you'll immediately be impressed by the spacious and open floor plan, featuring elegant finishes, new flooring throughout, and an abundance of natural light. The chef’s kitchen is designed for both functionality and style, with high-end appliances, ample counter space, and a large island that opens up to the living and dining areas. The perfect layout for entertaining and everyday living. Each of the four bedrooms is generously sized, with the primary suite offering a private retreat complete with an ensuite bathroom and an oversized walk-in closet. With four full bathrooms and an additional half bath, there is plenty of space for everyone. A standout feature of this home is the detached mother-in-law suite located above the garage. This private and fully equipped living space provides ultimate flexibility, whether used for guests, a home office, or multi-generational living. Located just minutes from Winter Park Village and the vibrant Park Avenue, you'll enjoy the convenience of boutique shopping, fine dining, and cultural attractions just a short drive away. This home is move-in ready. Built with meticulous attention to detail, offering comfort, privacy, and a prime Winter Park location.

805 Hamilton Place Court, Winter Park

$2,762,500

5 Beds ⋅ 5 Baths ⋅ Winter Park Heights SubDv. ⋅ 32789 Zip Code

This stunning custom home, completed in 2021, is located among the highly desirable “tree streets” in the heart of Winter Park, and was custom-built by M. Lahr Homes, showcasing exquisite craftsmanship and thoughtful design. With high-end finishes and custom details hand-selected by the owners, this home is sure to check every box. Designed with both luxury and functionality in mind, the home is equipped with natural gas for the cooktop, water heater, pool heater, grill, and fireplaces, while smart technology enhances modern living with app-controlled kitchen appliances, thermostats, irrigation, pool equipment, and garage doors. Neutral wood flooring, Restoration Hardware lighting, and custom electronic window treatments by The Shade Store add to the home’s understated sophistication. Additional highlights include copper gutters, level 5 finished walls, designer wall coverings, and custom storage throughout. Offering nearly 4,000 sq. ft. of organic, modern design, the open floorplan blends functionality with timeless elegance. The expansive living and dining areas flow seamlessly into the kitchen, which features Thermador smart appliances, quartz countertops, and a massive island with a stylish open-shelving detail. A hidden walk-in pantry behind the kitchen adds a bar fridge, microwave, and abundant prep space. The downstairs Primary Suite is a serene retreat with pool views through a picture window, a spa-like bathroom with a soaking tub and glass-enclosed shower, and an oversized, custom walk-in closet. A second main-level suite with a full bath and walk-in closet is currently used as an office overlooking the front lawn. Upstairs, a spacious bonus room/living area is surrounded by (3) additional bedrooms, each with walk-in closets, and (2) full bathrooms. The outdoor living space is an entertainer’s dream. The 8 ft sliding glass doors, with 2 ft. transom windows above, open to a covered lanai with motorized screens, a gas grill, and a fireplace for year-round enjoyment. Beyond the lanai is a meticulously landscaped backyard, fully fenced for privacy, with a heated saltwater pool wrapped in artfully laid out artificial turf and travertine pavers. Storage is abundant, with a custom-outfitted mudroom and laundry room, an oversized 2-car garage featuring storage shelves, and custom designed closets throughout. Ideally located, this home offers easy access to downtown Winter Park, Park Avenue, the YMCA, Aloma shopping center, and Whole Foods.

1620 Oneco Avenue, Winter Park

$3,125,000

4 Beds ⋅ 5 Baths ⋅ Forest Hills SubDv. ⋅ 32789 Zip Code

Discover this exquisite lakefront property located in the heart of Winter Park! Nestled on over an acre with more than 125 feet of water frontage, this home offers breathtaking views and absolutely stunning sunsets. As you step through the front door, you’re greeted by captivating lake views that flow from front to back. The spacious foyer leads to a charming living room, complete with a brick wood-burning fireplace. This area seamlessly transitions into the Florida room, an entertainer’s paradise featuring a wet bar, seating area and pool table, with easy access to a full bathroom that is equipped with a steamer shower. Open the French doors to reveal a tranquil outdoor oasis, where mature landscaping ensures privacy for the heated spa, creating a resort-like atmosphere in your own backyard. The heart of the home is a state-of-the-art chef's kitchen, boasting a large island, oversized GE refrigerator, Thermador dual ovens, elegant custom cabinetry, granite countertops, and a cozy breakfast nook. The spacious formal dining and living rooms offer beautiful lake views and lead out to a tranquil front terrace. For those who work from home, a private office on the main floor with a lake view provides an ideal and serene workspace. The large family room is perfect for everyday gatherings and is conveniently located next to a half bath. Upstairs, the primary suite overlooks the lake and features a walk-in closet and ensuite bathroom with a standalone Jacuzzi tub and separate shower. Two additional bedrooms share a full bath, while a generous fourth bedroom serves as a secondary primary suite with its own ensuite and walk-in closet. The property includes a paver circular driveway leading to a side-entry two-car garage. Cross the brick paved road to a sprawling lakefront lawn, leading to a private boat dock with a lift, perfect for enjoying all the water activities. Located on Lake Sue, a private ski lake, this home is just minutes from Park Avenue's shopping and dining, Downtown Orlando, Baldwin Park, playgrounds, parks and excellent public schools. Don’t miss the opportunity to make this stunning lakefront home your own!

1900 W Fawsett Road, Winter Park

$658,125

3 Beds ⋅ 2 Baths ⋅ Azalea Lane SubDv. ⋅ 32789 Zip Code

Discover the ease of turnkey living in this beautifully renovated 3-bedroom condo, located off Minnesota Ave., between Pennsylvania and Orange Ave. Just steps from the Winter Park Tennis Center and minutes from Park Avenue, the condo offers a prime location with easy access to dining, shopping, and entertainment. Thoughtfully designed by Wolfe-Rizor Interiors, this home showcases gorgeous “rustic” style engineered wood floors, a modern kitchen with a breezy coastal feel, and stylish bathrooms. Elegant blackout drapes and stunning chandeliers throughout the home add an extra layer of sophistication. The sunny living area is delightful yet cozy, with a wood-burning fireplace and (3) sets of French doors opening to (2) balconies, perfect for outdoor dining and relaxing. The spacious primary suite has a walk-in closet and pocket doors opening to a stylish bathroom with dual sinks and a glass shower. 2 additional bedrooms share a 2nd full bathroom, and a laundry closet located in the hallway offers a stackable washer and dryer, plus great storage space. On the ground level, a detached 2-car garage (with new motors) can be utilized for private parking or storage, while a driveway and street parking provide ample space for your guests. Zoned for Audubon K-8 and close to top schools, this condo is directly across the street from the tennis courts and the Azalea Lane park/playground, and minutes from Baldwin Park, the Corrine Drive corridor, and downtown Winter Park. Enjoy a low-maintenance lifestyle in a prime location!

1086 Azalea Lane, Winter Park

$656,000

4 Beds ⋅ 2 Baths ⋅ Cherokee Park SubDv. ⋅ 32789 Zip Code

Highly in demand, charming and rare 2 unit duplex for sale near the “College Quarter” in Winter Park: each unit offers 2 bedrooms and 1 bath plus each side has its own laundry room with washer/dryer included. Surrounded by luxury townhomes, lakefront mansions, and located on a tree lined, brick street close to Winter Park's famed Park Ave, it’s just a short 5 to10 minute walk to the shore of beautiful Lake Virginia and Rollins College campus. White tile floors run throughout unit 1101 & terra cotta tile is in unit 1107, with plenty of light coming through the energy efficient double pane windows. Both units have access to their own private paver patio to enjoy the lovely evening weather in beautiful Winter Park. There’s plenty of off-street parking with 2 dedicated spots in front and 2+ additional dedicated parking spots in back for residents and guests as well. Great value in just the land for future development too with the availability to start fresh and build two very large townhouses for resale, each over 2,000+ sq ft and each having a 1 car garage. The back unit is currently rented for $1,800 per month with lease through May 2025. The other unit is currently vacant and can easily be shown. Too many improvements to list here, please see features/updates attachments.

1101 S Pennsylvania Avenue, 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

$465,000

2 Beds ⋅ 1 Baths ⋅ Osceola Heights SubDv. ⋅ 32789 Zip Code

Authentic 1930 bungalow with detached guest suite in prime Winter Park location, surrounded by $1m+ homes. Great opportunity to build new or renovate. The main house is 640sf with 2 bedrooms/1 bath and has a sunporch with built-ins, living room + dining room with original hardwood floors, kitchen, and utility porch with washer/dryer. The 576sf guest house is a converted garage with family room, kitchen that has cooktop, microwave & refrigerator, 1 bedroom/1 bathroom, and newer roof and AC. 9 x 13 shed is on the property. New fence. Great location within walking distance to the Winter Park YMCA and only minutes to Park Avenue’s shops and restaurants, Interlachen Country Club, Winter Park Racquet Club, the Winter Park Golf Course (WP9), Advent Hospital, and Rollins College. Lot size is 0.15 acres and 50x125sf. House being sold AS IS with no repairs.

1870 Walker Avenue, Winter Park

$1,730,000

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

Presenting an extraordinary custom traditional home crafted by esteemed builder George Driscoll. Situated on Place Vendome, this remarkable property impresses from the moment you arrive. The bricked drive seamlessly continuing into the garage sets the stage for timeless elegance. Boasting four bedrooms and three and a half baths, including a pool bath, this spacious home offers refined living. Spanning approximately 4,049 square feet under air, this residence provides ample space for comfort and relaxation. As the first and only owners, meticulous care and attention to detail are evident throughout. Step through the inviting entryway and experience the artistry of this exceptional home. The primary living spaces, including the family room and living room, exude warmth and sophistication, setting the stage for memorable gatherings. Adjacent to the garage, a mudroom and laundry room combination connects the kitchen, featuring Wolf, Sub-Zero, and Bosch appliances, as well as a dinette and breakfast bar, creating a seamless flow for everyday living. Retreat to the luxurious primary suite, complete with an updated bath and a spacious walk-in closet. From the primary bed, enjoy enchanting views of the pool, creating a serene sanctuary for relaxation. An elegant office space provides a tranquil setting for work or study. Ascend to the second floor, where a versatile living space beckons. Here, a wet bar complements the entertainment possibilities, while a hidden doorway leads to a hallway connecting the areas near the wet bar to the exclusive theater room, enhancing the cinematic experience. Three additional bedrooms offer comfort and privacy, with two bedrooms conveniently sharing a Jack and Jill bath. All bedroom closets are thoughtfully built out to optimize storage and organization. Stepping outside, the motorized screen-enclosed lanai invites you to embrace the Florida lifestyle. The resurfaced heated pool, adorned with beautiful stone accents, includes an integrated jacuzzi for ultimate relaxation. The fully fenced yard provides an expansive and secure space for pets to roam freely. This exceptional property offers an exquisite place to call home with convenient access to the Winter Park Racquet Club, Park Avenue, Maitland, and the picturesque Chain of Lakes.

1350 Place Vendome, Winter Park

$3,150,000

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

Welcome to your dream home on sought-after Park Avenue! This stunning one-story, three-bedroom, three-bath residence is situated on an expansive 18,000 square feet (0.41-acre) lot and has been meticulously renovated to offer everything a discerning buyer could desire. Wonderful curb appeal with its stately front yard and large circular driveway. Step inside to discover gorgeous wood floors that flow throughout the home, a beautiful formal living room with a gas fireplace, a spacious family room and a bonus room (currently used as a playroom) boasting stunning wood vaulted ceilings and a wall of Windsor French doors that open to a honed marble patio and pool deck. The kitchen, renovated by S & W Kitchens, is a chef’s delight with a breathtaking marble waterfall island, a Café appliance package, including a stylish hood vent, and a large walk-in pantry. The primary suite is a true retreat, featuring two closets (one walk-in and one built-in) and an ensuite bath with a large glass shower and dual sinks. Step outside to a bamboo-lined fenced backyard that is an entertainer’s paradise. The zero grout-lined marble patio and sparkling pool with a sun shelf create a serene and luxurious outdoor space. Located on a picturesque brick street in downtown Winter Park, this home offers quintessential Winter Park living. Enjoy a leisurely stroll to shopping and dining on Park Avenue, the historic Winter Park 9 Golf Course, the Farmer’s Market, numerous holiday events and festivities in Central Park, and so much more. Don’t miss the opportunity to own this breathtaking home in one of Winter Park’s most coveted locations on Park Avenue.

931 N Park Avenue, Winter Park

$240,000

2 Beds ⋅ 2 Baths ⋅ Chateaux Du Lac SubDv. ⋅ 32789 Zip Code

This beautifully upgraded, 2 bedroom, 2 bath condo is a ground floor unit, boasts Winter Park Lake access, and is located just 0.4 miles from Winter Park Village. You’ll love the spacious, open floor plan, the natural lighting, the rustic wood plank tiles, and the updated kitchens and bathrooms! Kitchen features white cabinets, granite countertops, brushed nickel hardware, sleek black appliances, ample prep space, and a breakfast bar! The community is tucked back in a quiet corner of Winter Park and hugs Lake Killarney’s shoreline! Your community pool, laundromat, and patio all enjoy beautiful views of the lake! Bring your favorite book and chill by the pool while doing your laundry, or bird watch from your community's lakefront patio! The community also includes a boat ramp onto the lake and a watercraft parking area! You can’t beat this location! Winter Park’s best restaurants and amenities are all at your fingertips! Imagine kayaking to Trader Joe’s for a few groceries or biking to Hillstone for dinner and drinks on the water! Park Ave with all its boutique shopping and fine dining are within 2 miles! Rollins College and Full Sail University are within approximately 3 miles as well! Don’t let this opportunity to live in downtown Winter Park pass you by! Call me today to set up your private showing!

1500 Gay Road Unit 8B, Winter Park

$1,695,000

6 Beds ⋅ 5 Baths ⋅ Temple Estates SubDv. ⋅ 32789 Zip Code

Curb appeal is the first thing you will notice when you pull up to this traditional Charleston style home with a floor plan that will suite the needs for today’s lifestyle. Upon entering the home right past the foyer, you will be greeted with a traditional dining room large enough to sit up to 12 guests, across the hall you will find a study with a full bath and closet. Moving past the dining area you will be taken aback by the family area featuring 18 ft tall ceilings, floor to ceiling window, and a wood burning/gas fireplace!!!! The 2020 renovated kitchen is fully equipped with “5 Star” commercial gas range, 48" stainless refrigerator, second oven and microwave making cooking and serving a delight!! Moving past the kitchen is the laundry room and the spacious downstairs Master suite, 2 closets and a spa like bath with both a jetted tub and a walk-in shower. Upstairs you will find 3 Bedrooms, one with a private bath and the other two share a jack-n-jill. Out back has a side entry garage with an easy back out extension, over the Garage is a Bonus room with a large closet and full bathroom with approx. 400 sq. ft. of living space that works great for a detached office, exercise room, guest room or media room! The backyard comes stocked with a sparking saltwater pool, mature landscape and additional outdoor entertaining space for dining and relaxing. Excellent Winter Park Schools, one block to Winter Park YMCA & Phelps Park and minutes from Maitland, Baldwin Park, Rollins College and Park Ave!! Schedule your private showing today!!!

1611 Mayfield Avenue, Winter Park

$1,629,000

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

Welcome to 1801 Legion Drive, a stunning Southern traditional with a huge front porch and white picket fence in one of the best neighborhoods in Winter Park. The main house has 4 bedrooms and 3.5 baths and a separate office. There is an additional bedroom and full bath in the detached guest quarters. A large gourmet kitchen with white cabinetry, a stainless steel Thermador gas range and GE Monogram built-in refrigerator and microwave. The adjacent family room that opens to the kitchen has custom-built in shelving surrounding the brick fireplace and is the perfect place for family night movies. French doors lead to the large covered porch with another brick fireplace and an open patio for dining al fresco and also leads to the detached guest quarters which makes a perfect place for a home gym. Take a cool dip in the saltwater pool that was installed in 2018 or after a long day jump in the hot tub! The living room is located off the porch as well with French doors and features a wet bar and yet another brick fireplace (3). The master bedroom has French doors and two custom built-shelved closets, one is a large walk-in. A central laundry room is conveniently located between the split bedroom plan. There is a secondary master with en-suite and two more bedrooms and a shared bath. Roof 2019. Conveniently located between Maitland and Winter Park, enjoy easy access to top-rated schools, upscale shopping, dining destinations, and recreational amenities. Embrace the quintessential Florida lifestyle in this prestigious community. Don't miss your opportunity to own this exceptional residence in Winter Park. Schedule your private tour today and discover the luxury and sophistication of 1801 Legion Dr.

1801 Legion Drive, Winter Park

$1,583,000

4 Beds ⋅ 4 Baths ⋅ Robert Dhu Macdonald Park SubDv. ⋅ 32789 Zip Code

Welcome to 1161 Lincoln Circle, a stunning gem nestled in the heart of Winter Park's most desirable area. This charming residence offers the perfect blend of modern comfort and classic elegance, boasting impeccable craftsmanship and attention to detail throughout. As you step inside, you'll be greeted by a spacious and inviting floor plan flooded with natural light. The open concept living area is ideal for entertaining, featuring hardwood floors, soaring ceilings, and a cozy fireplace, creating a warm and inviting atmosphere for gatherings with family and friends. The gourmet kitchen is a chef's dream, equipped with stainless steel appliances, granite countertops, custom built-in banquette with mahogany table, and ample cabinet space, perfect for preparing delicious meals and culinary creations. The adjacent dining area provides a seamless flow for hosting intimate dinners or festive celebrations. Retreat to the luxurious master suite, where relaxation awaits. This private oasis boasts a tranquil atmosphere, complete with a spa-like ensuite bathroom featuring dual vanity, a Jacuzzi tub, and a separate shower. Three additional bedrooms offer comfort and versatility, accommodating guests, family members, or a home office space with ease. Step outside to discover your own private paradise, with a heated swimming pool and lush landscaping and mature trees provide privacy and serenity. Whether you're enjoying a morning coffee on the porch or hosting a barbecue with loved ones you will love the Zen-like atmosphere the tropical Koi Pond offers. Conveniently located just a few steps away from Winter Park's charming downtown area and golf course, you'll enjoy easy access to boutique shops, gourmet restaurants, and cultural attractions. With top-rated schools and recreational amenities nearby, this is more than just a home—it's a lifestyle! Don't miss your opportunity to own this exquisite residence in one of Winter Park's most coveted location, location, locations! Schedule you're showing today and experience the epitome of luxury living at 1161 Lincoln Circle."

1161 Lincoln Circle, Winter Park

$1,700,000

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

Nestled on one of Winter Park's coveted and charming brick streets, this meticulously crafted 5-bedroom residence embodies traditional elegance with modern amenities, offering a NEWER ROOF (2022) and other recent updates for a fresh feel. Its exterior, a testament to Florida living, boasts a sprawling saltwater pool with a sun shelf, surrounded by 900 SF of Chicago brick, and complemented by lush landscaping and enchanting lighting for evenings of magic, while custom-irrigated garden boxes for cultivating fresh herbs and vegetables await those with green thumbs. Inside, natural hardwood floors grace the entire home, accented by updated fixtures. The family room and living areas include built-ins, one gas fireplace, and 4 glass doors that lead to the backyard. An open kitchen awaits, complete with a breakfast bar, walk-in pantry, and bright, sunlit dinette framed by plantation shutters. The front room off the foyer makes a great office or dining room, with access to the kitchen. The large DOWNSTAIRS Main suite treats residents to a renovated, spa-like bathroom, adorned with a large zero-entry shower and separate soaking tub. A massive walk-in closet (Closets by Design), equipped with a dedicated washer & dryer, provides organization and convenience. You will sleep sound with the electronic blackout shades behind the plantation shutters. Upstairs features 4 additional bedrooms with hardwood floors, along with 2 full baths and a second laundry room, affirming practicality and comfort for every member of the household. This is an enchanting traditional home has so much to offer on this brick street. This ideal location is just a few blocks from the WP YMCA, grocery stores, restaurants and shopping off Aloma, and a mile or so from Park Ave!

1333 Mayfield Avenue, Winter Park

$1,800,000

4 Beds ⋅ 4 Baths ⋅ Woodmere Terrace Rep SubDv. ⋅ 32789 Zip Code

Located within the heart of the Vias, this premier property boasts an expansive, almost half-acre lot spanning 19,800 square feet, with dimensions of 120 by 165 feet, all set along a picturesque brick street. Representing a rare find in an "A location" lot, its over 100-foot width opens up a realm of design possibilities, making it an ideal canvas for your dream home. At the heart of this property stands a spacious four-bedroom home, offering over 4,700 square feet of living space. This dwelling is currently vacant and impeccably maintained, presenting a "move-in condition" option for those seeking immediate occupancy or rental income while planning their custom residence. Alternatively, delve into the meticulously crafted proposed remodel plans, designed by Ashley Martin Home and brought to life by M Lahr Homes. These plans, with an investment of approximately $50,000 by the seller, outline a renovation encompassing around 5,400 square feet, promising a blend of modern luxury and timeless charm. While the value lies predominantly in the land and its generous proportions, the existing home exudes a blend of elegance and functionality. Primarily one-level living, it features an owner's suite along with two additional spacious bedrooms, each with en suite facilities, offering the utmost comfort and privacy. A private office, discreetly positioned behind the garage with a separate entrance, adds versatility to the space, catering to various needs from work to creative pursuits. The interior unfolds with an array of captivating features, including soaring ceilings, plantation shutters, crown molding, and solid oak floors throughout. The primary retreat boasts a luxurious en suite and a large walk-in closet, ensuring indulgent relaxation. A gourmet kitchen, adorned with expansive cabinetry and stainless steel appliances, adjoins a charming eat-in area, offering the perfect setting for culinary endeavors. Entertainment options abound with a formal dining room, a living room adorned with a wood-burning fireplace, and a den complete with a wet bar, ideal for hosting guests or unwinding in style. The enclosed Florida room adds a touch of serenity, overlooking the lush backyard oasis. Upstairs, a second potential owner's suite awaits, boasting its own entrance, vaulted ceilings, and a spacious closet. French doors lead to a private covered balcony, offering scenic views of the meticulously landscaped grounds below. Outside, the allure continues with a park-like setting, characterized by mature landscaping, majestic trees, and an expansive brick patio, covered porch, and pergola. This outdoor haven provides the perfect backdrop for al fresco dining, relaxation, and gatherings with loved ones. Situated in the highly sought-after Vias neighborhood of Old Winter Park, this property offers unparalleled convenience and ambiance, with proximity to WPRC, ICC, and downtown Park Avenue. Embrace the opportunity to create your own haven of luxury and sophistication in this coveted locale. Experience the essence of timeless elegance and modern comfort at this remarkable address.

1251 Woodmere Drive, Winter Park

$3,270,500

5 Beds ⋅ 7 Baths ⋅ Parklando 03 SubDv. ⋅ 32789 Zip Code

Sold Data Entry Purpose Only!

2413 Winter Park Road, Winter Park

$730,000

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

Amidst the grandeur of stately magnolias and the delicate beauty of crepe myrtles, this enchanting 1926 Tudor Revival home awaits in the storied embrace of Winter Park, Florida. A homage to architectural elegance, it basks in a symphony of sunlight that enhances its authentic character and charm. As you step inside, be welcomed by the expansive living room where a crackling wood-burning fireplace adds a touch of warmth to the rich hardwood floors underfoot. This inviting space seamlessly unfolds into a dining area and a versatile sunroom, enclosed by elegant French doors. Whether as a serene office, an invigorating gym, or a whimsical playroom, this sun-drenched retreat adapts to your every fancy. The dining room, a prelude to alfresco dining, offers a view through French doors to the deck, inviting visions of starlit dinners in the generous backyard. The kitchen—a stylish masterpiece—features chic shaker cabinets, luxe stone countertops, and a natural gas range, each detail meticulously curated to inspire culinary adventure. Ascend the stairs, past the picturesque window with its cozy seat, to the sanctuary above. Here lies the primary suite, a realm of tranquility with its alluring sitting window and a spa-like bathroom, boasting a dual vanity and an expansive walk-in shower. Two additional bedrooms echo the home's timeless allure, complete with elegant wainscoting and a rejuvenated second bathroom. The vast backyard, a canvas of possibility, whispers promises of a personalized paradise—with ample space for a glittering pool and a luxurious cabana. A detached 2-car garage completes this portrait of suburban bliss. Positioned just minutes from the vivacious Park Avenue, and within a leisurely stroll to Advent Health Hospital, Ivanhoe Village, College Park, Mills 50, and a treasure trove of museums, your connection to culture and convenience is assured. With swift access to I-4, the heart of Orlando is merely a heartbeat away. ***************************************************************************************************************** Appliances 2019 & 2023, Crawlspace joists reinforced in 2020. New window treatments in 2021, HW 2021, Roof 2018, HVAC 2017 Furniture is available for purchase

1355 Devon Road, Winter Park

$1,500,000

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

Unlock the potential of building your dream home with this rare opportunity on an oversized corner lot. The home and property are being sold in as-is condition with all value being placed in the land. An A-plus location and a wonderful setting to embark on the journey of creating a custom masterpiece from the ground up. Situated on almost half an acre along one of Winter Park's most enchanting streets, this property is a canvas awaiting your vision. Enjoy the prime location, offering a swift drive to Winter Park's vibrant Park Avenue. Surrounded by multi-million dollar homes, this property embodies exclusivity and prestige, inviting you to become part of this distinguished neighborhood.

810 Bonita Drive, Winter Park

$452,500

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

Nestled in the highly desirable town of Winter Park, this meticulously maintained and beautifully remodeled two-bedroom, 1.5-bath bungalow welcomes you to a prime location just steps away from Hannibal Square and Park Avenue. Enjoy the convenience of Rollins College, shopping, dining, and vibrant nightlife, all within easy walking distance. Step inside this charming bungalow to discover a newly updated kitchen that features granite countertops, stainless steel appliances and a center island. The all-year enclosed Florida room features an electric fireplace, seamlessly combining functionality with style and the perfect setting to enjoy the outdoors in any season. Adding privacy and security, the fully fenced yard creates a delightful retreat. In 2023, significant enhancements were made, including the addition of a new rear deck and a new front porch, further enhancing the overall charm and appeal of the property. The entire home has been freshly painted, contributing to its vibrant and inviting atmosphere. The recent roof update in December 2023 ensures long-lasting durability, complemented by a series of modern comfort and efficiency upgrades. The air conditioning unit was replaced in 2019, the AC compressor in 2022, and the water heater in 2019.For a detailed overview of all the improvements, please refer to the attached improvement sheet. Don't miss the opportunity to make this residence your own, as it seamlessly combines the convenience of modern updates with the timeless charm of a bungalow lifestyle. Experience the best of both worlds in this impeccably maintained home located in the heart of a thriving community.

674 Douglas Avenue, Winter Park

$140,000

1 Beds ⋅ 1 Baths ⋅ Waterfall Cove At Winter Park SubDv. ⋅ 32789 Zip Code

Spacious FIRST FLOOR condo in sought-after Winter Park! This 1 bedroom, 1 bath condo features a fully furnished kitchen, spacious living room, and sunny dining room. The primary bedroom includes a walk-in closet. For added convenience, a washer and dryer is located inside the condo. Just off the living room is a private outdoor patio with access to a community green space. Waterfall Cove features a community pool and playground, as well as internet and cable included. Within a mile of the community - easily walkable or bikeable - are fantastic Winter Park shopping and dining destinations including Ravaudage Winter Park, Whole Foods, Nordstrom Rack, and more. Also nearby is the recently renovated Winter Park Village. Traveling throughout Central Florida is easy with convenient access to I-4. Perfect investment opportunity as this outstanding condo is leased!

1695 Lee Road Unit D109, Winter Park

$3,100,000

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

Fantastic new home that will take your breath away. Central location, heart of the Via's and steps from the Racquet Club. Completed in 2022 by design build firm Z Properties. This house has a super efficient and well thought out floor plan with thoughtfully designed, flexible spaces and gorgeous interior and exterior details. Four bedrooms - 2 up and 2 down, 4 way split - each with en suite bath. Chef's kitchen with True refrigerator, freezer, ice and beverage along with a Wolf Range and Bosch dishwasher. The kitchen has custom walnut cabinetry. The house glows with Venetian plaster throughout. Variable and multi zone ac make this house comfortable and efficient, cameras and security are top of the line. consider purchasing this house mostly furnished for a turn key experience. Car lift excluded

2080 Sharon Road, Winter Park

$1,650,000

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

Elegant single-story home on an oversized lot in the heart of Olde Winter Park. This home has been meticulously maintained and updated over the years. Interior features include 3 bedrooms and 4 full bathrooms with an office and bonus/TV room that can be used as additional bedrooms, beautiful natural oak floors throughout, higher ceilings with varied heights up to 12 feet, extensive millwork, moldings & built-ins, newer windows, 2 natural gas fireplaces, wet bar, and generous-sized laundry room. The eat-in island kitchen was completely renovated in 2017 designed by Signature Kitchens with Wolf & Bosch appliances, custom cabinets, and quartz countertops. The expansive owner’s suite has a large bedroom with a fireplace, spa-like bathroom with walk-in shower and separate soaker tub, and 2 walk-in closets. Outdoor living areas include a covered porch with a remote-controlled ceiling to enjoy the outdoor living rain or shine, a summer kitchen with natural gas grill, all overlooking a beautiful private and manicured yard with mature landscaping. Natural gas generator. A short distance to Park Avenue, YMCA, and within the top-rated Winter Park school system.

1120 Palmer Ave, Winter Park

$560,000

2 Beds ⋅ 1 Baths ⋅ Lake Knowles Terrace SubDv. ⋅ 32789 Zip Code

A Florida bungalow in the Tree Streets of Winter Park, with lots of character and an unmatched location. Great investment property with such a strong rental market. Buy and hold this property until you are ready to build your dream house. Possibilities are endless an opportunity like this at this price point doesn’t come around very often. Brick drive and walkways welcome you home to this 2-bedroom, 1-bath home, well-maintained, featuring an eat-in kitchen, family room and flex space. Vintage Spanish tile floors and nail-down wood floors warm the spaces and great natural light. Close to Phelps Park, the WPRC and YMCA. A short distance to Park Avenue, medical and hospital are moments away. Winter Park offers a great lifestyle with restaurants, museums, parks, new library, and home to Rollins College. Location is everything.

1425 Chestnut Ave., Winter Park

$685,000

3 Beds ⋅ 2 Baths ⋅ Seville Park SubDv. ⋅ 32789 Zip Code

Completely Renovated Townhouse in the Most Desirable Area in Winter Park. Property Features a Light & Bright Open Living Room and Kitchen Area that Access the Patio Area. Paved Patio is Very Spacious to Enjoy Florida’s Weather & Family Cookouts, with a Direct Connect Gas Grill. Double Master Suites with Renovated Bathrooms. First Floor Master Suite Features Spacious with Dual Sinks & Modern Shower. Modern Kitchen with Upscale Cabinets with Integrated Refrigerator, Top of the Line Appliances. Upstairs Master Suite Features a Garden Tub, Separate Walk-In Shower Area with Door, Dual Sinks. Spacious Third Bedroom Features Doors That Lead You to an Open Balcony. Tile Throughout Except for Stairs that has Carpet. New Roof Installed in 2023. Property is In a Community with Only 4 Units. Located with Walking Distance to Park Avenue, Rollins College, Farmers Market, And Winter Park Village. This Is a Home Built to Enjoy the WINTER PARK LIFESTYLE. Very Conveniently Located & Close to Major Highways I4, 408 & 417. Won’t Last (The roof is on the process of replacement)

970 Aragon Avenue, Winter Park

$700,000

3 Beds ⋅ 3 Baths ⋅ Conwill Estates SubDv. ⋅ 32789 Zip Code

Located on the sought-after Walnut Ave in Winter Park, this nearly quarter acre lot offers tremendous potential for builders and investors. The property's size and zoning classification make it a perfect candidate for a remodel or new construction, catering to the ever-growing demand for housing in the area. With the right vision and plans, you can transform the current structure or completely reimagine it to create a modern, desirable home. Winter Park, FL, is renowned for its upscale living, vibrant community, desirable school system, and proximity to excellent amenities. The neighborhood surrounding 1725 Walnut Ave offers a blend of a serene and active lifestyle with the property located 2 blocks from Phelps Park and the Winter Park YMCA. The convenient location allows for a quick drive to beautiful downtown Winter Park and easy access to the area's major highways, and airports, and attractions. This is a rare chance to seize a fantastic investment opportunity in Winter Park that's not to be missed!

1725 Walnut Avenue, Winter Park

$415,000

3 Beds ⋅ 2 Baths ⋅ Justamere Camp Rep SubDv. ⋅ 32789 Zip Code

Under contract-accepting backup offers. Multiple Offers. Welcome to this charming & cozy cottage on a very quiet tree-lined street in Winter Park! This adorable dwelling invites you in with rich wood laminate flooring throughout, all new fresh interior paint, and an abundance of windows that allows natural light to fill the home. The quaint living space is open to a nicely updated Kitchen that provides plenty of cabinets, granite counters, subway tile backsplash, stainless appliances, a cooking peninsula with breakfast bar, and an eat-in space. You’ll be impressed with the architecturally inspiring sunroom with walls of windows illuminating the room and vaulted ceilings with exposed beams & rafters, accented with uplighting. The home offers a very desirable split plan with a secluded & spacious owner’s retreat beyond the sunroom, and it delivers more of the rich wood laminate flooring, a walk-in closet, a wonderful updated en-suite bath plus French doors for private access to the fully fenced and lushly landscaped backyard. The other side of home has 2 more bedrooms & an updated bath with newly refreshed tub & shower surround. You will also find a convenient laundry closet just outside the bedrooms. All of this is situated on picturesque, landscaped & tree covered .22-acre lot that has irrigation & rear storage shed. This ideal location is only minutes from the newly reinvented Winter Park Village shopping, dining & entertainment and the renowned Park Ave dining and shopping in downtown Winter Park. You’ll find easy access to just about anywhere via I-4.

2600 Lotafun Avenue, Winter Park

$1,995,000

4 Beds ⋅ 4 Baths ⋅ Flora Park 2nd Add SubDv. ⋅ 32789 Zip Code

Stunning Rustic Modern pool home with clean lines and top quality finishes. As you walk through the front door you are welcomed by a spacious Foyer with stack stone and wood paneling detail on the wall. Just off the foyer is the formal living/flex room. As you continue through the foyer you walk into the large open and family room / kitchen / dining room area which overlooks the oversized and private backyard. The family room features a stack stone fire place and double sliding doors leading out to the covered travertine lanai. The gourmet kitchen offers Thermador stainless steel appliances, a large breakfast bar and built-in pantry storage. Just off the Kitchen is the dining room which features 3 large picture windows for amazing natural light and beautiful wood beams on the ceiling. The spacious master bedroom located on the first floor features a trey ceiling with wood beams and sliding doors leading to covered lanai overlooking the large private backyard. The stunning master bath features a large walk-in shower and soaker tub, dual vanity and a large walk-in closet. The main floor also includes a half bath and spacious laundry room. The second floor has 3 bedrooms, 2 full baths, 2 Loft/Flex space areas and Laundry Closet. The spacious lanai, extended patio deck & summer kitchen overlook the sparkling pool, heated spa & private HUGE totally fenced back yard. Additional amenities include: 2 Trane 16 seer A/C dual systems, vinyl Low E insulated windows, core fill in block walls, high density foam insulation in ceilings, Rinnai gas tankless water heater, full security, camera & surround sound pre-wire & more!

2012 Arbor Park Dr, Winter Park

$768,000

3 Beds ⋅ 4 Baths ⋅ Sorensen Heights SubDv. ⋅ 32789 Zip Code

Are you looking for style, space, and comfort in the heart of luxurious Winter Park? Come see this Sorensen Fletcher mid-century modern pool home, strategically located just minutes from Park Ave. Spanning well over 3,000 sq ft, this architectural gem boasts timeless design and abundant living space, providing the ideal setting for luxurious living and entertaining. Spacious Layout: This home offers a well-designed floor plan with 3 bedrooms and 3.5 bathrooms, including two bonus rooms that can be used as additional bedrooms, an office, or a nursery – perfect for accommodating a growing family or hosting guests. Abundant Natural Light throughout: The living room and Florida room are highlighted by ceiling-to-floor windows, allowing natural light to flood the interiors and create a seamless connection with the lush outdoor surroundings. Enjoy the warmth of the fireplace during cozy evenings. Upgraded Kitchen: The kitchen is a host/hostesses dream, featuring modern appliances and a stylish design that will inspire culinary creativity just off the Formal Dining Room and Bar Room. Entertain in style with a formal dining room overlooking a serene side patio, ideal for intimate gatherings. Additionally, a dedicated bar room adds a touch of sophistication to your entertainment space. Luxurious Main Suite: The main suite is a private retreat with a bonus room that can be utilized as a dressing room, home office, or nursery, providing versatility to suit your lifestyle. Step outside to your oversized pool. Mother-in-Law Suite: Offering comfort and privacy, the mother-in-law suite features a bedroom and a separate living room, making it perfect for guests or multigenerational living. Enchanting Outdoor Living: Step outside to your own paradise featuring an enormous pool, expansive outside entertaining area, and multiple enclaves for intimate gatherings and solitude. A fountain, pond, and an adorable red bridge add to the charm of the outdoor space. Garage and Storage: The property includes a 2-car garage and an exterior storage building, ensuring ample space for vehicles and storage needs. Lush Landscaping: The landscaped grounds are a testament to elegance and care, showcasing mature showpiece palms, staghorns, crape myrtles, and a variety of other plantings that enhance the property's curb appeal. Nearby Attractions: Residents will appreciate the convenience of being just minutes away from the vibrant Park Avenue, Rollins College, and Winter Park Hospital. This Sorensen Fletcher mid-century modern home is a rare find, offering the perfect balance of timeless charm, modern amenities, and an enviable location. Don't miss the opportunity to make this masterpiece your own! Contact us for a private showing today.

412 Fletcher Place, Winter Park

$2,750,000

5 Beds ⋅ 7 Baths ⋅ Golfview Terrace SubDv. ⋅ 32789 Zip Code

This fairytale property is located in the gracious neighborhood surrounding Park Avenue known for homes of unique character & historic architecture. The main home was originally built in 1918 & has been thoughtfully renovated to modernize the home’s function while maintaining the architectural integrity. It is located in the heart of Winter Park on a rare half acre, corner lot w/ charming views of the Winter Park Country Club & golf course. The semi-circular driveway that connects to both Webster & Old England provides convenience & enhances the curb appeal. Upon arrival, your guests will immediately appreciate the lush landscape, the dynamic & steeply pitched roof, overlapping, front-facing gables & charming, arched front door popular w/ Tudor style homes. Inside the foyer & through the arched doorway to the left, this home opens to an expansive, formal living space featuring cathedral style, volume ceilings ornamented w/stained, hand hewn oak, wood floors, tall windows, french doors overlooking the brick courtyard & an elegant, floor to ceiling, wood burning fireplace. To the right of the foyer are the formal dining & sitting rooms w/ long, rectangular windows clustered together offering an abundance of natural light to these richly detailed yet comfortable interior spaces. Towards the back, right side of the home, the spacious kitchen opens to an eat-in area, family room & stairs leading down to the basement wine storage. The kitchen features real wood cabinets, black granite counter tops, a sizable island w/seating for five, a Subzero refrigerator, Viking gas range & oven w/stainless steel vent hood, double-bowl, under-mount sinks, commercial style faucet, ice maker, prep sink, under counter microwave, a pantry & a large closet-style storage space allowing for easy access to your favorite serving pieces. The eat-in area & family rooms feature multiple sets of french doors through which you are provided beautiful views of the fountain at the center of the courtyard, pool & backyard haven. The layout of the main house includes a 3-way split plan w/ all bedrooms & bathrooms on the 2nd floor. The primary is located on the left side of the home and is accessed through a rear stairwell. This spacious suite is equipped w/ a walk-in closet, Juliet balcony & charming bathroom featuring a wood vanity, marble countertop & a shower/tub combination w/ floor to ceiling white subway tile. The two alternate bedrooms & bathrooms are accessed from the entry stairwell. The front, right alternate bedroom suite features a spiral staircase w/ loft. The rear, alternate bedroom suite is adjacent to the roof top deck. Both are rich w/ character showcasing wood floors, extensive millwork, renovated baths w/shower-tub combination, white subway tile, bead-board & pedestal sinks. The guest house was built in 1925 & is located on the far side of the courtyard. It includes a full kitchen, general living space, laundry room & half bathroom on the 1st floor as well as 2 bedrooms & 1 ½ bathrooms on the 2nd floor. This flexible space could be used in myriad ways. A rear, gated driveway w/ access from Old England is located at the NE corner of the property & is discretely hidden behind a jasmine covered wall. This is the first time this century that this Old Florida property w/ its storybook exterior architecture, majestic oaks & private courtyards that leaves you w/ a rare feeling of deep connection & an undeniable sense of place is being offered for sale.

341 E Webster Avenue, Winter Park

$1,075,000

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

This exquisite home overlooking Dubsdread golf course is a true gem, offering a perfect blend of classic charm and modern comfort. New roof, new AC units and whole house emergency generator added in 2020! New tankless water heater installed in 2021! The home is on a large corner lot which actually consists of three lots combined, so this spacious yard affords plenty of room for outdoor gatherings, privacy, or possibly even a future additional dwelling unit! From the moment you step inside, you will be captivated by the attention to detail found throughout and the thoughtful design elements that define this residence. Boasting impeccable craftsmanship, this home features beautiful molding, hardwood floors, french doors, and tray ceilings that add a touch of warmth to every room. The custom built-ins throughout the house not only offer convenient storage solutions but also add a unique and personal charm. The formal living room is the perfect place to unwind and relax, with a working wood-burning fireplace that sets the ambiance for intimate gatherings or quiet evenings. The spacious kitchen features granite countertops, custom cabinetry, stainless steel appliances, brand new ice maker and six burner gas stove top. There is also a prep kitchen that includes an additional oven, refrigerator, separate freezer, wine cooler, and second dishwasher. This one-of-a-kind home offers 5 spacious bedrooms and 3.5 bathrooms (two of which have double vanities), providing ample space for accommodating guests or entertaining. The primary suite features a large walk- in closet and a spacious sitting area that overlooks the picturesque backyard view. Step outside to discover a breathtaking outdoor space that is truly a private oasis. The gorgeous backyard showcases a private pool, providing the ideal setting for private outdoor entertainment. With its lush landscaping and serene atmosphere, this space is perfect for creating lasting memories with loved ones or hosting events. With its prime location in a walkable neighborhood, this home allows for easy access to an array of shopping, dining, and activities. Don't miss out on the opportunity to make this unique property your own. Call today to schedule a private tour.

2521 Minnesota Avenue, Winter Park

$235,000

2 Beds ⋅ 2 Baths ⋅ Chateaux Du Lac SubDv. ⋅ 32789 Zip Code

Reduced over $20,000. Make an appointment today! Owner is interested in holding a mortgage with a balloon payment or a Lease Purchase to close beginning of 2024. Owners not interested in Cash offer or financing Contract to close in 2023. Call Jan for more details. Updated 2BR 2 Bath !st Floor Unit in Lakefront Community. Spacious Rooms/Great Layout. Great Winter Park Value! Community Heated Pool. Community Lakefront Deck. Lake Access to beautiful Lake Killarney. Walk to Shopping, Movies, Restaurants. Close to Park Avenue! Easy Access to 1-4.

1500 Gay Road Unit 21B, Winter Park

$330,000

2 Beds ⋅ 2 Baths ⋅ Carver Town SubDv. ⋅ 32789 Zip Code

Winter Park 3/2 Block Home with side entry garage and fenced yard.

730 Callahan Street, Winter Park

$686,000

3 Beds ⋅ 2 Baths ⋅ Northwood - Winter Park Oasis SubDv. ⋅ 32789 Zip Code

Nestled just steps away from the Winter Park 9 golf course and a short stroll from the vibrant Park Avenue, this fabulous home boasts the desirable walkability that everyone is looking for! This modern and stylish one-level home, situated in a charming Winter Park neighborhood, offers the perfect combination of location and updates. Step inside and experience the cozy sophistication of this completely refreshed and upgraded home. The trendy & tasteful finishes create a modern ambiance that will leave you impressed. The open living space is complemented by three bedrooms and two bathrooms, making it the ideal split floorplan for comfortable living. Upon entering, you are greeted with newer tile flooring throughout the entire home. The spacious kitchen is a chef's delight, with a large island adorned with quartz counters and a convenient microwave drawer. The adjacent bar area includes a built-in pantry, open shelving, and a wine fridge, adding a touch of luxury to your everyday life. Just beyond the kitchen/living room, you'll discover a fantastic dining area and two well-appointed bedrooms. The chic fully redone bathroom will impress you with its delightful features and selections. The laundry room, equipped with a newer GE washer & dryer (2021), built-in storage cabinets, a sink, and a tankless water heater, adds convenience to your daily routine. On the opposite side of the home, the owner's suite awaits, exuding brightness and airiness. A space-saving built-in wardrobe lines one wall, while the en-suite bathroom showcases stunning design elements, including a walk-in shower, dual sinks, and a private water closet. Step through the sliding glass doors at the back of the house and be greeted by a rear brick patio and backyard, seamlessly connecting indoor and outdoor spaces for delightful entertaining. Enjoy shaded dining and lounging on sunny days with the newer retractable awning (2021) controlled by a convenient remote. The fully fenced backyard, lined with bamboo, offers the privacy you desire. Additional features that make this home stand out include a newer roof (2020), newer AC (2020), a two-car garage with a new electric car charger (2022), a custom workbench, and storage cabinets added in 2021. And let's not forget the incredible location—a couple blocks from the Winter Park 9 Golf Course, Park Avenue, and the Farmers Market on Saturdays. With Whole Foods, Winter Park Village, and Publix just minutes away, this home truly is your private oasis in the heart of Winter Park.

630 Northwood Circle, Winter Park

$400,000

3 Beds ⋅ 2 Baths ⋅ Howell Heights SubDv. ⋅ 32789 Zip Code

Under contract-accepting backup offers. ***MULTIPLE OFFERS RECEIVED***Vintage home in a well-established Winter Park neighborhood. Refurbished terrazzo floors throughout. Living/dining and family rooms with large enclosed screened porch. Equipped with kitchen appliances, ceiling fans and central electric air conditioning and heating. Covered front porch. Good size 2-car garage with opener and work benches. Big fenced back yard. Driveway with amply parking space. The roof was replaced 9/2021. Back screened porch installed 10/2020, whole house replumbed 2/2022, new garage door opener 4/2012 and the water heater was replaced 3/2012. Superior location in a desirable school district. No homeowners association. Move in ready, it won't last long!

2862 Sanbina Street, Winter Park

$1,251,000

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

Under contract-accepting backup offers. It's a beautiful day in this neighborhood in the heart of old Winter Park with great views and access to Lake Osceola, and just across the street from the home where Rollins grad Mr. Rogers and his wife spent their winters. This 3-bedroom, 2-bath gem on a quiet cul-de-sac is just steps away from Lake Osceola, part of the Winter Park chain of lakes, Rollins College and the Alfond Inn and Park Avenue. A fully updated kitchen includes granite countertops, GE Profile appliances and a stainless-steel hood. The kitchen opens into a naturally lit informal dining area with skylights and sliding glass doors, one of various indoor and outdoor habitats throughout the home. A spacious primary suite includes a walk-in closet, with the bathroom fully updated with a large shower, double vanities, with marble throughout. A formal dining room with custom built-ins opens into a warm and inviting living room complete with a wood-burning fireplace. Classically arched windows and French patio doors that were newly replaced last year open up in the back to a stone patio offering relaxing views of the lake and surrounding tree canopy. Other features include full home surround sound with Pioneer speakers, a climate-controlled attic for extra storage, an air-conditioned, fully finished basement spotlighting a custom wine room, and an electric car charger. Perfect for welcoming guests, the home also includes a detached 1-bedroom in-law suite with bath and laundry, as well as a transferable Orkin termite bond. Don't miss out on seeing this charming, classic Winter Park home.

215 Osceola Court, Winter Park

$2,240,000

5 Beds ⋅ 5 Baths ⋅ Camwood Sub SubDv. ⋅ 32789 Zip Code

Newly updated and ready for new owner to begin building memories immediately as it is move in ready! This stately Winter Park residence by Rex-Tibbs Custom on an oversized corner lot on Park Avenue is available for the first time to welcome it’s new owner to peerless luxury! This 5-bedroom, 5-bath with downstairs office and master, a bonus room and guest wing, is walking distance to restaurants, shops and WP golf course. Double wide circle drive and side garage provide plenty of parking for family and friends to visit. The spacious foyer welcomes guests with the new designer features of lights, fans plus high ceilings, wood floors, crown molding, shutters, abundance of storage, and built-ins all freshly painted. The foyer opens to the separate living and dining room both with picturesque windows having views to the front. Nearby is the heart of the home: a well-appointed chefs eat-in kitchen sporting a large quartz sitting island, stainless built-in appliances including dual ovens and cooktop, walk-in pantry, abundance of cabinetry with new designer selected fixtures, wood floors and a private paver patio- perfect for morning coffee! The kitchen overlooks the family room and lanai area making it an ideal space for relaxing and entertaining. The bright family room has built-ins, fireplace and 2 sets of French doors to the covered lanai with fans and the resort backyard. A hallway leads to a home office with built-ins, full guest/pool bath and private master wing. Spacious master retreat has tray ceilings, customized walk-in closet, soaking tub, oversized shower, dual sinks with granite counters and doors to the lanai area. Upstairs is the ideal bonus space for movies, gaming and homework .2 large bedrooms with walk-in closets share a Jack-n-Jill bath. Another bedroom and full bath complete the area. There is a guest wing nearby also accessed by its own stairs off the kitchen! This guest wing has a spacious bedroom with a Juliet balcony overlooking the resort backyard, updated bath and AC storage. The backyard is ready for year-round enjoyment with the lanai featuring tongue and groove ceiling, fans, speakers and wet bar overlooking the brick lined resort pool and deck. Plenty of green space with new sod and landscape plus beyond the pool area is ideal for gardening, pets or ball throwing. The well-equipped indoor laundry room with washer, dryer, utility sink, built-in cabinetry and 2 closets for storage leads to the oversized 3-car garage: with new epoxy flooring, window panels on garage doors and paint! Zoned for the top WP schools, walk to Park Avenue, and easy access to all of central Florida including downtown, the parks, beaches and airport. Immaculately cared for and improved for the new owner to enjoy immediately!

1300 Raintree Place, Winter Park

$965,000

3 Beds ⋅ 4 Baths ⋅ Osceola Shores Sec 01 SubDv. ⋅ 32789 Zip Code

PRICE IMPROVEMENT! PRIME LOCATION! .45 ACRE HOME SITE with Charming pool home in the Heart and Soul of Winter Park's Osceola Shores neighborhood. Walk to Polasek Museum, Rollins College, Dinky Dock Park and Park Avenue shops and restaurants. Just a great location! BUILD YOUR DREAM HOME or Enjoy This Classic property, originally built for the Miller Hardware family, is truly a one of a kind property. Expansive front lawn, Split floor plan and exceptional renovation offers a range of spaces inside and out. Wood floors, custom tiles and a wood burning fireplace adds warmth and charm to this relaxed and informal gem. Professionally equipped Kitchen featuring granite countertops, Sub Zero built in refrigerator and gas stove. The spacious Owners suite has a Jacuzzi tub, large glass shower and oversized vanity with marble floors. Split plan with All 3 bedrooms having access to their own baths. This home has a nice size Den/ office space as well as a Sunny Florida Room with bright windows and French door overlooking lush landscaping and tree canopy. Custom shutters throughout add a touch of class and sophistication. Have a delicious meal in your formal dining room or step outside to your private rear deck and pool area and enjoy a casual dining experience under your custom pergola. Seperate pool bath as well. Plenty of parking for guests on the long paver driveway. Just under a half acre and set back with an amazing landscaped lawn and garden. Welcome Home!

911 Osceola Avenue, Winter Park

$6,850,000

8 Beds ⋅ 10 Baths ⋅ 0000 SubDv. ⋅ 32789 Zip Code

One or more photo(s) has been virtually staged. This magnificent estate was originally built in 1938 with a major addition in 1999. The estate is nestled on nearly 2 acres of prime property on Lake Maitland on the Winter Park Chain of Lakes and walking distance to all the shops and restaurants on Park Avenue. As you drive up to the estate, you will be impressed by the entry gate that leads to the huge circular paved driveway complete with a fountain. For the car enthusiast, there are 2 separate garages totaling 7 spaces. There is plenty of additional parking as this house was built for luxury living and entertaining! The home spans 19,304 square feet under air and 25,124 square feet under the roof. There are two separate grand foyers to welcome you, with high ceilings, gorgeous staircases, and magnificent lake views. This home was built to showcase the stunning lake views from almost every room. There are multiple patios and balconies to offer the perfect spots to take in the incredible views. With a total of 8 bedrooms, 3 of which are master suites with ensuite bathrooms and massive walk-in closets there is no shortage of space in this home. In total, there are 9 full baths and 5 half baths making sure everyone has plenty of space in this Park Avenue Estate. Plus, there is a caregiver’s suite with private entries for live-in help. This home is equipped with 3 kitchens making any large gathering a breeze to accommodate! As well as 3 elevators so everyone can move about the estate with ease. The expansive estate is perfect for a multi-generational family, with plenty of bedrooms and bathrooms for everyone to comfortably live together. The grounds are simply beautiful, with mature landscaping and expansive lake views there is truly nothing like it. The possibilities are endless with this home! If you are looking for a one-of-a-kind property, this is it! The grandeur of this estate and its prime location makes it a truly unique find. Don’t miss your chance to own a piece of Winter Park history!

1190 N Park Avenue, Winter Park

$1,950,000

3 Beds ⋅ 3 Baths ⋅ Winter Park Old Town SubDv. ⋅ 32789 Zip Code

NEW AND IMPROVED PRICE: Located in the heart of “The Golden Triangle” of Winter Park, this 0.43 acre property is approximately 125 feet wide by 150 feet deep. Discretely hidden behind a wall of podocarpus, this exclusive Georgia Avenue opportunity is only a few short blocks from the retail and restaurants located on Park. Live in the lovely, one-story 2,709 SF Santa Barbara style pool home currently sitting on the property as it is, add on and renovate it to make it your own or tear it down to build the custom home of your dreams. The current home includes a deep covered entry to greet your guests. Beyond the front door is an ample foyer and powder bath. Visible from the foyer are several old-world-style brick walls with gracious arches. Directly through the foyer’s arched opening you will find the entertaining areas — kitchen, dining and family rooms. The dining area is complete with a built-in bar. Updated countertops in the kitchen, lighting and neutral paint allow these flexible spaces to be well received by guests and owners alike. A touch of warmth is added by the masonry fireplace. Multiple sets of french doors and large scale windows allow for an abundance of natural light and a direct view of the enormous backyard. The mature landscaping, pool and broad brick patio area are ideal for entertaining or private enjoyment. Large scale windows also line the galley hallway to the right of the foyer where you will find the master suite featuring a renovated bathroom updated with a soaking tub, designer tile, lighting fixtures and vanities. Continuing down the hall are the two remaining bedrooms, a shared full bathroom and a bonus area. Incredible new house plans designed by the collaborative team of Cynde Norris and Jodie Warrick Konold of Scout & Company Lifestyle + Design are offered with the sale. The Kingston House plans reflect a 6,010 SF estate in a Modern Tudor style with five bedrooms, plus an office and detached Casita as well as an accompanying six full and one half bathrooms.

870 Georgia Avenue, Winter Park

$2,400,000

5 Beds ⋅ 6 Baths ⋅ Kenilworth Shores Sec 01 SubDv. ⋅ 32789 Zip Code

Under Construction. Here is the perfect opportunity to purchase your very own private sanctuary in the heart of Winter Park. This exquisite transitional modern home by Parade of Homes award winning builder Clarkson Concepts was designed with incredible details that will not disappoint. As you drive up to the property you are greeted by a contemporary, West Coast Casual elevation. A private courtyard leads you through the entrance and into your contemporary, open great room with 12’ ceilings. To the left, a relaxing living room with built-ins and fireplace. To the right you’ll find an uncompromising gourmet chef’s kitchen featuring all Subzero/Wolf appliances. The solid wood cabinets are accented by a designer backsplash and Legrand Addorne under cabinet outlets with lighting. The custom pantry features countertops for coffee station, appliances, and storage. You’ll never want to leave your grand first floor owner’s retreat with barrel vaulted ceiling and an en suite where you can soak away in your 6’ freestanding tub. His and hers solid wood vanities along with his and hers closets mean plenty of space for clothing, shoes, handbags, makeup and jewelry. A full guest suite and laundry room complete the first floor. On the second level you will find a relaxing balcony to enjoy views of your backyard, a large bonus room with vaulted ceilings, 3 bedrooms with en suites and a secondary laundry room. The private backyard outdoor oasis will include a large undercover lanai, separate, fully outfitted summer kitchen, pool with hot tub and sun shelf. Relax your days away with privacy, comfort and the best parts of Florida living while being minutes from Park Avenue, Baldwin Park, Rollins College and Advent Health. Zoned for Winter Park Schools. Call today to set your appointment with the Builder!

532 Worthington Drive, Winter Park

32789 Zip Code Real Estate & Homes with Awning(s)

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