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$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
$2,549,000
5 Beds ⋅ 5 Baths ⋅ Lake Knowles Terrace Add 02 SubDv. ⋅ 32789 Zip Code
Under Construction. Nestled along a quiet street in Winter Park’s coveted Tree Streets, this stunning coastal farmhouse new build delivers the perfect combination of timeless architecture, luxury finishes, and an unbeatable location. From the moment you arrive, the home captivates with its warm and inviting facade, charming architectural details, and exceptional curb appeal. Step inside to an impressive open layout where natural light, designer finishes, and meticulous craftsmanship set the tone. The spacious living room serves as the heart of the home, showcasing a sleek electric fireplace, custom built-in bookshelves with LED accent lighting, and expansive pocketed glass sliding doors that create a seamless connection to the outdoor living space. The chef’s kitchen is a true centerpiece, beautifully appointed with Taj Mahal countertops, custom cabinetry with LED underlighting, a premium Thermador appliance package, and a hidden walk-in pantry that blends functionality with luxury. Flowing effortlessly from the kitchen, the dining area offers the perfect setting for hosting, complete with a custom dry bar, additional cabinetry, and a dedicated wine fridge. Designed with a highly desirable layout rarely found in Winter Park, the first-floor features both the primary suite and an additional guest suite. The primary retreat offers generous proportions, beautiful natural light, and private sliders opening directly to its own lanai. The spa-inspired bathroom provides a true escape with marble mosaic flooring, dual vanities, and an elegant wet room featuring a spacious walk-in shower and freestanding soaking tub. Completing the suite is an expansive walk-in closet with its own stackable washer and dryer for ultimate convenience. Upstairs, a spacious loft creates an additional living area accompanied by a full laundry room and three generously sized bedrooms, providing flexibility for family, guests, or additional workspace. Step outside and experience Florida living at its finest. The covered lanai is designed for year-round enjoyment with a fully equipped summer kitchen overlooking the sparkling pool and spa, along with additional green space perfect for relaxing or entertaining. Located in the heart of Winter Park’s iconic Tree Streets, this residence offers one of the area’s most desirable lifestyles. Enjoy the ability to walk to Phelps Park while being just minutes from the Winter Park YMCA, Park Avenue’s renowned shopping and dining, and everything that makes this community one of Central Florida’s most sought-after destinations. Don’t miss this rare opportunity to own a brand-new construction residence in Winter Park’s highly coveted Tree Streets!

1823 Sunset Drive, Winter Park
$1,625,000
4 Beds ⋅ 4 Baths ⋅ Charmont SubDv. ⋅ 32789 Zip Code
Virtually Staged. A rare opportunity to live on a quiet one-way street overlooking a park in the heart of Winter Park. Built in 2007 and meticulously maintained, this exceptional 4-bedroom, 4-bath pool home with a dedicated office offers timeless design, thoughtful updates, and an unbeatable location. A welcoming covered front porch provides the perfect spot to enjoy your morning coffee. Inside, soaring ceilings, extensive moldings, travertine and hardwood floors, and abundant natural light create an elegant first impression. Just off the foyer, French doors open to a private office, ideal for working from home. A secondary bedroom and full bath with a walk-in shower are conveniently located on the main level. The spacious kitchen flows seamlessly into the family room and features granite countertops, solid wood soft-close cabinetry, a gas cooktop, wall oven, breakfast bar, wet bar, walk-in pantry, and a sunny breakfast nook overlooking the lanai and pool. The adjoining family room is anchored by a gas fireplace and French doors leading outdoors. The covered lanai showcases a tongue-and-groove ceiling and remote-controlled screens, creating the perfect setting for year-round entertaining. The generous first-floor primary suite offers space for a sitting area and features two custom walk-in closets, dual vanities, a soaking tub, separate shower, and private water closet. A beautiful wrought-iron staircase leads upstairs to two generous en-suite bedrooms and a cozy loft. The private backyard is designed for relaxation and entertaining, featuring a saltwater pool and spa surrounded by lush landscaping. Additional highlights include two newer HVAC systems (2022 and 2023), a gas water heater (2022), central vacuum system, built-in Home Team pest defense system, and plantation shutters throughout. Located within the highly sought-after Audubon K-8 and Winter Park High School districts, this exceptional home is ideally situated between Park Avenue and Corrine Drive, with downtown Orlando just minutes away.

341 E Reading Way, Winter Park
$5,600,000
5 Beds ⋅ 6 Baths ⋅ Maitland Shores First Add SubDv. ⋅ 32789 Zip Code
This elegant transitional French Provincial residence was the feature home in the Orlando Museum of Art's 2022 "mystery home tour" and is located on a large, elevated corner lot in a quiet and secluded area in the Via’s of Winter Park. This residence has been significantly enhanced inside and out by the current owner. The home features 5,200 square feet of living space and 800+ square feet of outdoor space with 5 bedrooms, 5 bathrooms ensuite, 1 half bathroom, 3 car garage, pool, patio and professionally landscaped yard and lighting. Upon entry, you are welcomed through the exquisite foyer where you instantly notice the craftsmanship and expert care that went into the custom carpentry and crown molding details throughout. To the left of the foyer is an elegant and intimate parlor with grass cloth wallpaper, a gas vented fireplace and built-in bookshelves. To the right of the foyer is the formal dining room with beautiful hand painted wallpaper and an adjacent butler’s pantry. Past the foyer you are led to a spacious and grand formal living room with 6 new French iron doors that flow out to a covered brick porch and picturesque back yard & pool. Designed with entertainment in mind, the adjoining chef’s kitchen includes newly painted custom cabinetry, a Sub-Zero/Wolf appliance package, a grand center island and a walk-in pantry. Built in desk and casual dining area all open to the adjoining beamed ceiling family room with gas vented fireplace and additional French doors that lead to street side patio with new awnings. First floor master retreat overlooks the pool & yard and features 14-foot wood beam vaulted ceilings. The oversized master bath with double custom lacquered vanities made in Palm Beach, mosaic marble shower and a Waterworks free standing tub, brushed brass fixtures, and walk in closet. The second-floor features nine-foot ceilings with four bedrooms (one which was converted to a beautiful women’s dressing room) and four ensuite bathrooms, covered balcony adjoining two bedrooms, two built in desks and bookshelves for office/study time and large media room with big screen tv and wet-bar. There are also two laundry rooms, one upstairs and one downstairs. Attic space inside the home and inside the garage. Recent upgrades include slate roof/swooped decorative copper roof with chimney caps, complete chimney rebuild, nine iron French doors, white oak tongue and grove hardwood floors, renovated master bath and two ensuite baths, two new HVAC home units and a new garage mini-split air conditioner. This home offers boat access to the Winter Park chain of lakes and is within short distance of the Winter Park Racquet Club. It’s also a bike ride away and a short drive to the Interlachen Country Club and Park Avenue shopping and dining district. The property is zoned for Dommerich Elementary, Maitland Middle School, and Winter Park High School. One or more rooms virtually staged

2228 Azalea Place, Winter Park
$1,025,000
3 Beds ⋅ 3 Baths ⋅ Virginia Heights Rep SubDv. ⋅ 32789 Zip Code
Georgetown-style 'Brownstown' in the Heart of Winter Park, walking distance to Downtown, PLUS deeded Lake Access to Lake Virginia! This spacious property has 3 bedrooms, 3 full baths, 2434 sq ft, 10' ceilings custom details throughout and natural lighting. Foyer with slate flooring, enjoy the double-sided gas fireplace in the Living & Dining areas, beautiful wood floors, crown molding, plantation shutters, a butler bar with custom cabinetry & wine refrigerator. Cooking inspired Kitchen with a lengthy granite island and sitting bar overlooks the Family room. Upgraded stainless appliances, including gas cooktop with griddle, microwave/convection oven, hanging pot rack with lighting, and soft close cabinets with pullouts. French doors to the covered 'English Garden' courtyard with pavers & stainless grill for entertaining. Guest suite or home office with a custom closet and full bath overlooks brick street, Pennsylvania Ave. Large laundry room near the garage with granite countertops, cabinets & utility sink, plus washer & dryer. Upstairs is a spacious Primary bedroom with French doors to a private covered balcony; also, 2 large walk-in closets with closet systems, Jacuzzi tub, huge walk-in shower, dual vanities with granite countertops & more. An additional ensuite bedroom, more wood floors, plus a built-in dehumidifier. Attached 2-car, rear alley access garage, plus an additional side parking pad. Walk to Park Ave. for dining, shopping, WP Tennis Center, outdoor park & Rollins College. Neighborhood Lake Virginia access for paddleboard & kayak launching to the Winter Park Chain of Lakes. Top schools, Audubon K-8 seconds away, and WPHS. NEW TPO membrane roof w/ metal coping March 2026. HOA maintains: landscaping, irrigation, building maintenance & outdoor lighting. Won't last!

1138 S Pennsylvania Avenue, Winter Park
$1,099,000
4 Beds ⋅ 3 Baths ⋅ Northwood Terrace SubDv. ⋅ 32789 Zip Code
Reinvented from the ground up for modern living while honoring its 1953 mid-century modern roots, this 4-bedroom, 3-bath Winter Park home blends authentic MCM character with all-new finishes and systems. An open living, dining, and kitchen core opens to a light-filled sitting area, with white oak floors and designer lighting and ceiling fans throughout. The kitchen stuns with Taj Mahal quartzite counters and KitchenAid stainless appliances. Out back, an expanded patio overlooks a private, fenced yard built for gathering. Everything is new: roof, windows, 200-amp electrical, plumbing with new water heater, HVAC ductwork, and Nest thermostat. Best of all, you can live it on foot: walk to East End Market, Kelly's Homemade Ice Cream, Redlight Redlight, Sushi Lola's, and top-rated Audubon Park K-8. Zoned for Winter Park High, and minutes to Park Avenue and Rollins College. A turnkey classic in one of Winter Park's most established, walkable 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
$2,475,000
5 Beds ⋅ 5 Baths ⋅ Kenilworth Shores Sec 01 SubDv. ⋅ 32789 Zip Code
Nestled within the highly sought-after Kenilworth Shores neighborhood, this extraordinary new construction home represents a rare opportunity to own one of Winter Park's finest new builds. Thoughtfully designed with an exceptional floor plan and uncompromising level of craftsmanship, detail, and finishes. This home is located just minutes from everything Winter Park has to offer. Step through the front doors into a breathtaking two-story foyer where soaring ceilings, and a statement chandelier create an unforgettable first impression. Designed for both everyday living and effortless entertaining, the floor plan is one of the home's most desirable features. Rare for Winter Park, the residence offers a luxurious primary suite, private guest suite, and dedicated office all on the main level. The expansive living room serves as the heart of the home, showcasing extensive custom trim work, an electric fireplace, and bespoke built-in cabinetry with LED underlighting. Walls of glass create a seamless connection to the outdoor living spaces while filling the home with natural light. The chef's kitchen is a true showpiece, designed to satisfy even the most discerning culinary enthusiast, featuring stunning Calacatta quartz countertops, custom cabinetry, a paneled built-in refrigerator, and a complete suite of Thermador appliances. Adjacent to the kitchen, the formal dining room creates an elegant setting for entertaining, featuring a custom dry bar complete with a wine refrigerator. Privately tucked away, the primary suite serves as a true retreat, featuring sliding glass doors leading directly to the backyard oasis, creating a seamless indoor-outdoor connection. The spa-inspired primary bath features marble mosaic tile, floating mirrors above dual vanities, a freestanding soaking tub, an oversized walk-in shower, and a generous walk-in closet. The upper level continues the home's thoughtful design with a spacious loft, accompanied by three generously sized bedrooms. Outdoor living is equally impressive, a covered lanai creates the perfect setting for year-round entertaining and is fully equipped with a summer kitchen. The beautifully designed backyard retreat showcases a sparkling pool and spa surrounded by lush green space, offering the ideal balance of recreation, relaxation, and privacy. Perfectly positioned in the heart of Winter Park, residents enjoy tree-lined streets while remaining just a golf-cart ride from the boutiques, award-winning restaurants, and cafés, of Park Avenue. The home is also conveniently located near Winter Park High School, Advent Health Winter Park, and the beloved Cady Way Park, where tennis courts, soccer fields, baseball fields, walking trails create one of Central Florida's most desirable active lifestyles. Don't miss out on this amazing new home!

426 Worthington Drive, Winter Park
$1,799,000
4 Beds ⋅ 5 Baths ⋅ Winter Park Place 45/148 SubDv. ⋅ 32789 Zip Code
Nestled on one of Winter Park’s most exclusive streets, this exceptional residence is located within Park Place—the only gated neighborhood in the coveted 32789 ZIP code—and is zoned for highly sought-after Audubon Park K–8 School. From the moment you arrive, you'll appreciate the rare combination of privacy, charm, and convenience that defines this remarkable home. Designed with both everyday living and effortless entertaining in mind, the versatile floor plan features elegant formal living and dining rooms, creating a welcoming setting for gatherings both large and small. The spacious primary suite is conveniently located on the first floor, along with a secondary bedroom ideal for guests or multigenerational living. Upstairs, you'll find two additional bedrooms, a full bath, and a generous bonus room perfect for a home office, media room, playroom, or fitness space. At the heart of the home is a beautifully appointed kitchen featuring granite countertops, crisp white cabinetry, a center island, and a sunlit breakfast nook surrounded by windows. The kitchen flows seamlessly into the inviting family room, where custom built-ins, a cozy fireplace, and French doors create the perfect blend of comfort and sophistication. Step outside to your own private Florida oasis. The covered paver lanai, summer kitchen, and sparkling saltwater pool provide an ideal backdrop for year-round entertaining, weekend gatherings, or peaceful evenings at home. Rich hardwood floors extend throughout the entire residence—there’s not a stitch of carpet anywhere. Architectural details such as crown molding, plantation shutters, 10-foot ceilings, and 8-foot doors enhance the home’s timeless elegance and spacious feel. Additional conveniences include a first-floor laundry room with pantry storage and a guest powder bath. A standout feature is the oversized detached two-car garage, complete with a private upstairs studio and full bath—perfect for a home office, guest suite or creative space. Surrounded by lush professional landscaping and shaded by magnificent mature oak trees, the fully fenced backyard offers beauty, privacy, and natural cooling throughout Florida’s warmer months. Tucked away on a quiet cul-de-sac, the property also benefits from added privacy provided by the neighborhood’s surrounding brick wall and direct access to a nearby open field. Park Place is more than a neighborhood—it’s a rare opportunity to enjoy a secure, friendly lifestyle.

2625 Park Place Drive, Winter Park
$1,399,000
3 Beds ⋅ 3 Baths ⋅ Vilasa Twnhms SubDv. ⋅ 32789 Zip Code
Vilasa Homes — Winter Park’s Expression of Modern Luxury. Perfectly positioned just steps from Park Avenue, this architecturally stunning residence blends refined design with the effortless elegance of Winter Park living. Crafted by Nasrallah Architectural Group, Ted Maines Interiors, and Jordan Builders, this home showcases an Alys Beach–inspired aesthetic with warm wood accents, wrought iron detailing, and two-story block construction for enduring quality. Interiors exude sophistication: soaring 13' ceilings on the main level, 10' upstairs, level-four wall finishes, all-wood flooring, Pella double pain windows and curated designer lighting. The chef’s kitchen is a showpiece— high-end flat panel cabinetry, quartz surfaces, Thermador appliances, and an expansive quartz waterfall island overlooking lush greenery. A private in-unit elevator provides effortless access to the second-floor, enhancing both convenience and sophistication. The second-floor primary retreat offers a serene escape with a loft for office or wellness space, a spa-caliber bath with soaking tub and oversized shower, and generous closet options. Two additional bedrooms provide versatile accommodation for guests, a private office, or fitness space, complemented by a thoughtfully designed shared bath. Outdoor living is exceptional with an expansive 40' x 20' private fenced-in backyard, including a covered patio which extends from the sliding glass doors. A 2-car garage with insulated doors completes the residence. Moments from Winter Park’s finest dining, boutiques, museums, lakes, Hannibal Square and Rollins College. Vilasa Homes offers a rare opportunity to live at the center of it all—wrapped in luxury, design, and timeless style.

512 W Swoope Avenue, Winter Park
$1,795,000
4 Beds ⋅ 4 Baths ⋅ Winter Park Village SubDv. ⋅ 32789 Zip Code
Under contract-accepting backup offers. Virtually Staged. A rare new construction offering in the heart of Winter Park — 2501 Lafayette Ave is a 2,810 sq ft architectural residence crafted by curated design firm - Catalyst Design, with 25-year experience and Parade of Homes judge across Naples, Daytona & Southwest Florida. 4 bed | 4 bath | office | 2-car garage | saltwater pool. Every detail built to a single standard: the highest one. Step through the custom pivot front door into a home that immediately announces its intentions. Soaring 10-ft ceilings throughout rise to a dramatic 22-ft volume in the great room, framed by sliding glass walls that dissolve the line between interior living and the private outdoor retreat beyond. Level 5 smooth drywall finish — the standard reserved for the finest custom builds — runs throughout, while wide-plank hardwood flooring flows across every living area. Italian porcelain tile anchors all bathrooms and the laundry room with precision and permanence. Every window and exterior door is imported from Germany — Unilux® precision-engineered for thermal performance, acoustic excellence, and longevity that no domestic product can match. Grohe® plumbing fixtures, also made in Germany, carry that same philosophy through every bathroom. Countertops are Cambria or Silestone® quartz with a thickened 3cm mitered edge throughout. Custom solid wood cabinetry is built to plan in the kitchen, laundry, and all bathrooms, finished with Emtek® hardware and 8-ft solid core architectural doors with 7" baseboard throughout. The Winter Park Chain of Lakes — 12 interconnected lakes spanning 2,781 acres of pristine Florida waterways — is moments away, offering boating, paddleboarding, and the beloved Winter Park Scenic Boat Tour. Over 70 parks, Kraft Azalea Gardens, Mead Botanical Garden, and more than a dozen walkable green spaces define the outdoor lifestyle. The Winter Park Farmers' Market, held every Saturday at the historic train station, is a community institution. Rollins College, one of the South's most respected liberal arts institutions, sits lakeside just minutes away, bringing cultural programming, the Bach Festival, and vibrant intellectual energy to the neighborhood year-round. Families are served by highly rated Orange County public schools, with Winter Park High School renowned for its academic rigor and championship programs, as well as exceptional private options, including Trinity Preparatory School and St. Margaret Mary. New construction in 32789 is genuinely rare — historic preservation standards and limited land availability make it so. For international buyers, Orlando International Airport is 30 minutes south. Disney, Universal, and the theme park corridor are under 30 minutes via I-4. Atlantic beaches are under an hour away. This is not a production home dressed up with upgrades. It is a ground-up, custom-built, German-engineered, the most coveted zip code in Central Florida. Schedule your private showing today.

2501 Lafayette Avenue, Winter Park
$1,849,900
3 Beds ⋅ 4 Baths ⋅ Winter Park Residential SubDv. ⋅ 32789 Zip Code
Discover luxury living in this exquisitely renovated two-story condominium, ideally situated on the third floor of the highly sought-after Douglas Grand in the heart of Winter Park. This elegant three-bedroom, three-and-one-half-bath residence seamlessly blends sophisticated design with everyday comfort. Immediately captivating, the light-filled open floor plan showcases stunning new wide-plank white oak flooring, high ceilings, detailed crown molding, and all-new designer lighting throughout. The chef’s kitchen is a showpiece, featuring crisp white cabinetry, luxurious white quartz countertops, a spacious breakfast bar island, elegant gold hardware, and a built-in desk. A charming breakfast nook offers the perfect setting for morning coffee or casual dining. French doors open to a private enclosed atrium, creating a versatile outdoor retreat ideal for alfresco dining, relaxing, or entertaining guests in style. The expansive living and dining spaces flow effortlessly, while a private first-floor bedroom with en suite bath and walkout balcony provides an ideal space for guests, multigenerational living, or a home office. Upstairs, the primary suite serves as a peaceful sanctuary, complete with an indulgent soaking tub, dual vanities, an oversized walk-in closet, and French doors leading to a large private balcony with sweeping views of Winter Park's iconic Park Avenue—perfect for enjoying sunrise coffee or evening sunsets. A second upstairs en suite bedroom offers its own private bath and generous walk-in closet. Thoughtful features include an upstairs laundry room, a spacious storage closet with potential elevator conversion for future accessibility, and a secure gated garage with two reserved parking spaces. Perfectly positioned in the heart of Winter Park, Douglas Grand places you just steps from Park Avenue, the Winter Park Farmers’ Market, Rollins College, Hannibal Square, Winter Park Golf Course, the Winter Park Tennis Center, Winter Park Village, and an array of renowned dining, shopping, and cultural attractions. Enjoy an unparalleled walkable lifestyle in one of Central Florida's most desirable communities. Notable improvements include an interior renovation (2026), front elevation windows and French doors (2024), interior paint (2024), and HVAC system (2022).

101 S New York Avenue Unit 311, Winter Park
$2,350,000
3 Beds ⋅ 3 Baths ⋅ Landmark Winter Park Condo SubDv. ⋅ 32789 Zip Code
Discover an exceptional opportunity to own a penthouse residence at The Landmark, one of downtown Winter Park's exclusive addresses. Directly along the desired brick streets of Park Avenue, this boutique condominium community consists of only 13 residences and offers an unparalleled blend of privacy, sophistication and accessible convenience. Just outside your door, enjoy acclaimed dining, boutique shopping, art galleries, sidewalk cafés, Central Park and the year-round events that have made Winter Park one of Central Florida's sought-after destinations. Behind The Landmark's secure wrought-iron gates, residents are welcomed into a beautifully landscaped courtyard centered around a timeless fountain and illuminated by dozens of gas lanterns, creating a warm and elegant atmosphere reminiscent of a European enclave. Impeccably maintained and thoughtfully designed, the community provides a peaceful retreat while remaining moments from the vibrant energy of Park Avenue. Residence J occupies a premier penthouse position and is filled with natural light, enhanced by soaring ceilings, expansive windows, and multiple French doors that open to private terraces overlooking Morse Boulevard and the surrounding downtown streetscape. The spacious floor plan is designed for comfortable daily living and effortless entertaining. The living and dining areas are anchored by a gas fireplace and flow seamlessly into the kitchen, where integrated appliances, a gas cooktop, generous workspace, and a charming breakfast area create a functional and inviting gathering space. The primary suite serves as a private sanctuary, featuring dual vanities, separate water closets, an oversized walk-in shower and a custom-designed walk-in closet. Two additional guest bedrooms provide flexibility for family and visitors. One bedroom is connected to a Jack-and-Jill bath, while the third enjoys a private en-suite bath and a Juliet balcony that captures the charm and character of downtown Winter Park from above. Additional amenities include two deeded underground parking spaces, a private climate-controlled storage room, and access to the community's shared outdoor entertaining area, complete with a summer kitchen and courtyard gathering space. Whether enjoyed as a full-time residence or a lock-and-leave retreat, this penthouse offers a rare combination of luxury, security and an unmatched Park Avenue lifestyle in the heart of Winter Park.

140 E Morse Boulevard Unit J, Winter Park
$1,300,000
3 Beds ⋅ 3 Baths ⋅ Sylvan Lake Shores SubDv. ⋅ 32789 Zip Code
Set on a rare double lot in one of Winter Park's most coveted locations, this charming 1940 Craftsman-style residence presents an extraordinary opportunity to enjoy one of Central Florida's most celebrated lifestyles while envisioning the future. Just moments from the Winter Park Chain of Lakes, the boutiques and acclaimed dining of Park Avenue, and the timeless beauty of Rollins College, the property offers a setting that few locations can rival. The existing residence features approximately three bedrooms, two-and-a-half bathrooms, and generously proportioned living spaces filled with warmth and character. Lovingly maintained over the years, the home provides a comfortable foundation for renovation, restoration, or reimagination. Outdoors, a screened pool creates a private retreat for year-round enjoyment, while a detached two-car garage and separate studio shed offer exceptional flexibility for hobbies, creative pursuits, a home office, fitness space, or guest accommodations. What truly distinguishes this offering is the double lot itself. Opportunities of this scale within the heart of Winter Park are increasingly rare, providing the space and flexibility to construct a custom estate tailored to your vision while preserving ample room for outdoor living, gardens, and recreation. Life here extends far beyond the property lines. Enjoy morning walks beneath majestic oak canopies, afternoons on the Chain of Lakes, outdoor concerts, art festivals, sidewalk cafés, and some of Florida's most picturesque streetscapes. Whether renovating the existing residence or creating the home of your dreams, this exceptional property represents a rare chance to secure a legacy homesite in one of the most desirable addresses in Central Florida.

321 Sylvan Boulevard, Winter Park
$5,500,000
4 Beds ⋅ 5 Baths ⋅ Sylvan Park SubDv. ⋅ 32789 Zip Code
Pre-Construction. To be built. This extraordinary lakefront residence on beautiful Lake Sylvan, set on a .37-acre (16,603± square foot) homesite, presents a rare opportunity to own a thoughtfully curated custom home by renowned builder Floridian Custom Homes, brought to life in collaboration with Winter Park Design, Brianna Michelle Interior Design and Signature Landscape. Offering 4,775 heated square feet of expertly crafted living space, this four-bedroom plus office, four-and-one-half-bath home blends timeless architecture, elevated finishes and effortless lakefront living. Designed with an open-concept floor plan ideal for everyday living and entertaining, the home showcases stunning European white oak hardwood flooring throughout all main living areas and bedrooms. The heart of the home is the spectacular chef’s kitchen, featuring two oversized islands, custom-designed wood cabinetry, an expansive walk-in pantry, and a premium Sub-Zero and Wolf appliance package highlighted by a 48-inch, eight-burner range. The private first-floor primary suite serves as a luxurious retreat, complete with an expansive walk-in closet and a spa-inspired bath adorned with marble tile shower walls and flooring. Also on the main level is a versatile office/den with a built-in closet. Upstairs, an expansive media/family room provides additional gathering space, accompanied by a dedicated office and three generously sized secondary bedrooms, each featuring en-suite baths and walk-in closets. The fourth bedroom offers exceptional flexibility and may easily serve as a secondary primary suite, ideal for guests or multigenerational living. Designed to embrace seamless indoor-outdoor living, expansive glass sliders extend from the gathering and dining rooms to a covered lanai overlooking the resort-style custom pool. Retractable screens create a setting for year-round enjoyment, while the fully equipped summer kitchen and generous lounge and dining areas make entertaining effortless. Expertly designed by Signature Landscape, the pool features a sun shelf, LED lighting and elegant travertine limestone decking, all surrounded by lush professional landscaping, Zoysia grass and privacy hedging for a serene outdoor setting. Additional notable features include a Brava slate tile roof and a striking custom glass front entry door, further elevating the home’s exceptional curb appeal. Ideally just minutes from the vibrant shops and dining of Park Avenue, this remarkable residence also offers convenient access to major roadways, leading area hospitals and top private schools, all within an A-rated school district. An exceptional opportunity to enjoy luxury lakefront living in one of Central Florida’s desirable settings.

313 Sylvan Drive, 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
$1,450,000
4 Beds ⋅ 4 Baths ⋅ Windsong Elizabeths Walk 43/81 SubDv. ⋅ 32789 Zip Code
Welcome to 1421 Chapman Circle, an elegant Spanish-Mediterranean home nestled within the highly coveted Windsong community in the heart of Winter Park. From the moment you arrive, the classic barrel tile roof and timeless architectural character set the tone for what awaits inside — a home with enduring style, gracious proportions, and tremendous potential to be personalized for its next chapter. Spanning over 3,500 square feet, this 4-bedroom, 3.5-bath residence offers a formal, well-appointed layout with soaring high ceilings, rich crown molding, and a thoughtful floor plan designed for both comfortable daily living and effortless entertaining. A dedicated first-floor office provides the ideal work-from-home space, while the separate formal dining room adds an air of sophistication perfect for hosting family and friends. The gourmet kitchen is the heart of the home, featuring granite countertops, premium Thermador appliances, and bartop seating — a space equally suited for casual mornings and lively gatherings. The living room opens through French doors to a generous wrap-around screened patio, seamlessly blending indoor and outdoor living in true Florida fashion. The first-floor primary suite is a private retreat, complete with French door access to the patio, a spacious walk-in closet, and a well-appointed en suite bath featuring a double sink vanity, a separate soaking tub, and a walk-in shower. Upstairs, three generously sized guest bedrooms share a hall bath, and a large bonus room and landing offer flexible space for a playroom, media room, or additional lounge area. A large upstairs utility room and additional walk-in storage beneath the stairs ensure that function is never sacrificed. The home is served by two HVAC units, both dated 2017. Beyond the front door, the Windsong community is nothing short of exceptional. Residents enjoy access to two resort-style pools, a splash pad for the little ones, scenic parks, a fishing dock, and coveted chain-of-lakes access complete with use of a community boat — a lifestyle that truly sets Windsong apart. Zoned for A-rated schools and ideally situated just minutes from the vibrant energy of Baldwin Park, Audubon Park, the Mills District, Downtown Orlando, and all that Winter Park has to offer, this address places you at the center of everything. Whether you're drawn to its classic architecture, its unmatched community amenities, or the incredible opportunity to update and truly make it your own, 1421 Chapman Circle is a rare find in one of Central Florida's most beloved neighborhoods.

1421 Chapman Circle, Winter Park
$1,400,000
4 Beds ⋅ 4 Baths ⋅ Woodmere Terrace Rep SubDv. ⋅ 32789 Zip Code
Welcome to 1220 Woodmere Drive, where timeless elegance and modern luxury come together in one of Winter Park’s most coveted neighborhoods. This exceptional 4-bedroom, 3.5-bath residence offers 2,815 square feet of thoughtfully designed living space, blending classic charm with today’s most desirable comforts. The spacious first-floor primary suite serves as a private retreat, complete with dual walk-in closets and a spa-inspired bath designed for relaxation. Rich solid hardwood floors flow throughout the main downstairs living areas, creating warmth and sophistication at every turn. Upstairs, a smart split-bedroom layout provides three additional bedrooms and two full baths, offering privacy and flexibility for family and guests alike. A detached two-car garage adds even more versatility, featuring an expansive bonus room above—perfect as a home office, fitness studio, creative space, or hobby room. Ideally positioned on one of Winter Park’s most sought-after streets, this home places you just moments from the Winter Park Racquet Club, the scenic Chain of Lakes, and the vibrant shops and dining of downtown Winter Park. With top-rated public schools nearby and an unbeatable location, this is a rare opportunity to enjoy the very best of Winter Park living. 1220 Woodmere Drive isn't just a home—it's a lifestyle.

1220 Woodmere Drive, Winter Park
$1,595,000
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. 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
$2,150,000
5 Beds ⋅ 5 Baths ⋅ Sylvan Heights SubDv. ⋅ 32789 Zip Code
A striking expression of modern luxury, this brand-new residence offers nearly 3,000 square feet of thoughtfully designed living space in one of Winter Park's most desirable locations. From the moment you step inside, a dramatic two-story foyer and soaring ceilings set the tone for a home that seamlessly blends sophisticated design with everyday comfort. The open-concept living areas are filled with natural light and anchored by a stunning feature wall with a sleek fireplace, creating an inviting space for both intimate gatherings and large-scale entertaining. At the heart of the home, the kitchen showcases a statement island, European-style cabinetry, premium finishes, and quality appliances, while a custom wine display tucked beneath the staircase adds a distinctive architectural touch. Designed with flexibility in mind, the first floor features a private guest suite with en-suite bath, a dedicated home office, and convenient laundry room. Expansive sliding doors open to a fully equipped outdoor kitchen, creating a seamless indoor-outdoor lifestyle perfectly suited to Florida living. Upstairs, the primary suite serves as a private retreat, complete with a custom walk-in closet and spa-inspired bath featuring a freestanding soaking tub, oversized walk-in shower, and elegant finishes throughout. Three additional bedrooms provide exceptional accommodations, including a Jack-and-Jill layout and an additional en-suite bedroom. Ideally positioned just minutes from Park Avenue, residents enjoy effortless access to Winter Park's renowned dining, boutique shopping, cultural attractions, parks, and top-rated schools. Combining exceptional craftsmanship, modern design, and an unbeatable location, this is a rare opportunity to own a brand-new luxury home in the heart of Winter Park.

240 N Phelps Avenue, Winter Park
$4,950,000
4 Beds ⋅ 7 Baths ⋅ Forest Hills SubDv. ⋅ 32789 Zip Code
Residing among the treelined streets of Winter Park, this stunning, contemporary pool home, designed and built by renowned Phil Kean, truly captures the essence of luxury living. Showcasing his signature aesthetic, the home emphasizes sleek architectural lines, refined finishes, and a seamless connection between indoor and outdoor spaces. Expansive walls of glass flood the interior with natural light and create a striking façade that embodies its contemporary elegance. The main living areas are designed for both entertaining and everyday living. A dramatic two-story living room is anchored by designer furnishings, which extend throughout the home, while the spacious dining area comfortably accommodates large gatherings. The adjacent family room continues the modern aesthetic with a built-in media wall, sleek fireplace, textured design elements, and a triple sliding door connecting the indoor and outdoor spaces. Ready for any caliber of chef, the kitchen boasts Thermador appliances, along with extensive cabinetry and countertop space, soft-close drawers, a waterfall edge island, generously sized pantry, and reverse osmosis water filtration. A private home theater on the main level offers a true cinematic experience with surround sound, custom seating, and blackout shades, along with a stylish wet bar, providing additional space for entertaining. The home’s Crestron automation system is discreetly integrated, allowing full control of lighting, climate, and technology from a single interface. Upstairs, a striking floating staircase leads to a gallery-style landing overlooking the living space below. For those exhausting days, you can instead take a ride on the elevator. The expansive primary suite features a sitting area, a custom closet, and terrace access. The spa-inspired primary bath includes dual rain showers with body sprays, a soaking tub, and dual vanities with elegant finishes. Additional second-floor amenities include a fitness room with steam shower and sauna, an additional en-suite bedroom, one of the two laundry rooms, and access to an upper-level terrace overlooking the landscaped grounds and pool. Two en-suite guest bedrooms are conveniently tucked away on the first floor for maximum privacy. Offering four bedrooms, five full bathrooms, and two half baths, the home delivers both comfort and sophistication at every turn. Thoughtfully integrated automated shades provide effortless privacy, while the advanced air purification systems and whole-home water softener complement the home's advanced smart features. This residence is offered fully furnished with curated Restoration Hardware pieces, including custom-selected furniture, lighting, rugs, and artwork that enhance its cohesive design. Outdoor living is equally impressive, with covered lanai spaces enhanced by automated roll-down screens, designer furnishings, a summer kitchen with gas grill and ventilation, and tranquil poolside views. The property also includes a split, three-car garage with a large driveway protected by a gated entrance. Completing this extraordinary dwelling is its location in the heart of Winter Park. This lakeside residence sits minutes from Park Ave Shopping, Rollins College, AdventHealth, multiple Botanical Gardens and Museums, well-rated grade schools, and highway access. Schedule your private showing today and experience the Winter Park lifestyle firsthand.

231 Chelton Circle, Winter Park
$1,429,000
5 Beds ⋅ 4 Baths ⋅ Orwin Manor Westminster Sec SubDv. ⋅ 32789 Zip Code
LOCATION LOCATION LOCATION. Discover exceptional new construction in the heart of Winter Park. Completed in 2025, this stunning Mediterranean-inspired residence offers 5 bedrooms, 4 bathrooms, and nearly 2,900 square feet of thoughtfully designed living space. Situated on a charming, tree-lined street, the home combines timeless elegance with modern luxury. The open-concept floor plan features 10-foot ceilings, 8-foot doors, luxury vinyl plank flooring throughout, and an expansive great room with an electric fireplace. The gourmet kitchen is designed to impress with quartz countertops, custom cabinetry, stainless steel appliances, a large center island, and abundant storage. A unique under-stair wine cellar adds character and sophistication, while a first-floor guest suite provides privacy and flexibility. Upstairs, the spacious primary suite overlooks the backyard and pool area and includes a spa-inspired bathroom with dual vanities, a soaking tub, walk-in shower, and generous walk-in closet. Three additional bedrooms comfortable accommodations, including a Jack-and-Jill layout and a private In-suite bedroom. A conveniently located upstairs laundry room completes the second level. Step outside to your private outdoor retreat featuring a beautifully landscaped backyard, sparkling in-ground pool, covered lanai, and summer kitchen with built-in grill—perfect for entertaining year-round. Ideally located just minutes from Winter Park’s renowned shopping, dining, parks, and cultural attractions, this exceptional home offers the rare opportunity to enjoy the benefits of brand-new construction in one of Central Florida’s most sought-after communities. Schedule your private showing today.

1473 Berkshire Avenue, Winter Park
$5,125,000
5 Beds ⋅ 6 Baths ⋅ Virginia Heights Rep SubDv. ⋅ 32789 Zip Code
Owner/Agent - Properties of this caliber are exceptionally rare in Winter Park — in a neighborhood defined by its walkability to Park Avenue, top-rated schools, and exclusive deeded access to the Winter Park Chain of Lakes. While new construction continues to emerge throughout Winter Park, few can approach the level of intention, artistry and personal investment found here. Named best custom home in the entire Southeast, this grand award-winning residence was conceived and executed by Master Custom Homebuilder Chris Salhab of Valdara Custom Homes as his own family home. Every element of this home reflects a standard of craftsmanship and care that is immediately felt upon entry and discovered anew in every room. The open-concept floor plan flows effortlessly between interior and exterior living spaces, where a summer kitchen, covered entertaining areas and a signature rain curtain that doubles as an outdoor movie screen create an experience unlike anything else on the market. Intelligent design, smart home integration and refined finishes complete a residence that is as functional as it is extraordinary. Offered with the added benefit of premium lease income through early 2027, this is a rare chance to secure one of Winter Park's finest homes as both a trophy asset and an immediate income-producing investment. Private showings by appointment only.

1221 Richmond Road, Winter Park
$2,695,000
3 Beds ⋅ 4 Baths ⋅ Town Of Winter Park SubDv. ⋅ 32789 Zip Code
LUXURIOUS LIVING WITH FANTASTIC LOCATION This Winter Park three story townhouse is within walking distance to all the fun amenities of the city- the many restaurants, boutique shops, banks, post office, farmers market, Central Park and Rollins College. Designed by architect Phil Kean and built in 2017 the owners have embellished this townhome with custom millwork and finishes, wood floors, sound system, full house generator and a private elevator to all floors. The first floor has a two car garage with storage lift above, large laundry room/home office and a downstairs guest suite. The second floor features a stylish and comfortable living room with lovely custom ceiling detail and moldings, gas fireplace, a sophisticated powder bath, and a beautiful dining room that opens to an eat-in chef's kitchen with Subzero, Wolfe and Bosch appliances and light Taj Mahal quartzite countertops. The third floor offers the spacious master bedroom and bath and also has the additional guest bedroom suite. Take the elevator to the roof top for great views of the city and here find even more potential space for fun entertaining. If your dream is to own a townhome in the heart of Winter Park, here is a stunning one for you!

413 W Morse Boulevard, Winter Park
$2,875,000
3 Beds ⋅ 5 Baths ⋅ Conwill Estates SubDv. ⋅ 32789 Zip Code
Beautifully renovated and thoughtfully designed, this exceptional residence is nestled in the heart of Winter Park’s sought-after Tree Streets neighborhood. Privately behind entry gates, the home welcomes you with a picturesque front courtyard highlighted by a tranquil water feature, setting the tone for the sophisticated living experience that awaits. Expansive walls of glass and disappearing sliders flood the interiors with natural light while creating a seamless connection between indoor and outdoor living spaces, all while maintaining a remarkable sense of privacy. Designed for both everyday living and effortless entertaining, the open-concept floor plan showcases a spectacular custom entertainment bar featuring a stunning stone countertop, handcrafted cabinetry, an ice maker, a wine tower and a beverage cooler. The great room, dining area and kitchen flow together in one expansive space, framed by pocketing glass doors on both sides that open completely to the front courtyard and the rear lanai, pool and backyard beyond. The chef’s kitchen is a true centerpiece, outfitted with an impressive suite of Wi-Fi-enabled Thermador appliances, including a six-burner gas range with a steam oven and warming drawer and an integrated refrigerator with freezer drawers and additional refrigerated storage drawers. Thoughtfully designed for both functionality and style, the kitchen also features an appliance garage, a dedicated coffee bar, custom cabinetry and a large pass-through window that pockets into the wall, providing convenient service access to the covered lanai. A fully equipped secondary kitchen and butler’s pantry offers abundant storage, a built-in oven, a microwave and an additional refrigerator, making entertaining on any scale effortless. Privately situated on the first floor, the luxurious primary suite serves as a peaceful retreat with direct access to the lanai and outdoor living areas. The spa-inspired primary bath features a sculptural stone soaking tub, an oversized shower with multiple rain shower heads and a secluded outdoor patio complete with an open-air shower. A beautifully customized walk-in closet completes the suite. Additional first-floor amenities include a dedicated office, an elegant powder bath, and a unique dog room. A versatile flex space currently utilized as a spa room with laundry offers endless possibilities as a fitness room, expansive mudroom, storage area or wellness retreat, with direct access to one of the garage bays. The second level features a spacious family room along with two generously sized bedroom suites, each offering walk-in closets and private ensuite baths. One of the home's most remarkable features is the expansive rooftop balcony, complete with a gas fireplace and panoramic views overlooking both the front courtyard and backyard. Whether hosting guests or enjoying a quiet evening sunset, this elevated outdoor living space provides an unforgettable setting. Situated on a sprawling half-acre lot, the property offers exceptional outdoor space with room for future expansion or simply enjoying the privacy and beauty of the backyard, pool and lanai. Ideally located just minutes from vibrant Park Avenue, residents enjoy convenient access to Winter Park’s renowned dining, shopping, parks and cultural amenities, while major roadways provide easy commutes to downtown Orlando, Orlando Executive Airport and Orlando International Airport.

1724 Pine Avenue, Winter Park
$3,500,000
4 Beds ⋅ 4 Baths ⋅ Maitland Shores 1st Add SubDv. ⋅ 32789 Zip Code
Virtually Staged. Positioned on a quiet canal, this exceptional property features a covered boat dock with lift, offering effortless access to the renowned Winter Park Chain of Lakes. This home, built by Liberty Development, with 4-bedrooms plus two bonus rooms blends elegance with comfortable everyday living. The main level offers a dedicated office area, formal dining room, and an inviting gathering room with gas fireplace, all flowing seamlessly into the stunning chef’s kitchen. Designed for entertaining, the kitchen features two large islands, exotic granite countertops, under-cabinet lighting, and premium Thermador appliances including a 6-burner gas range with griddle. The walk-in butler’s pantry has a beverage cooler and ice maker adds both style and functionality. The adjoining breakfast area is framed by grand windows overlooking the pool, cabana, and canal. The luxurious downstairs primary suite enjoys tranquil water views and a spa-inspired bath with travertine stone floors, marble counters, custom cabinetry, soaking tub, walk-in shower with steam and generous closet space. Upstairs you’ll find three additional bedrooms and a spacious bonus room, while a separate bonus suite above the garage provides future space for a media room, gym or guest retreat. The interior of the home is highlighted by hardwood floors, plantation shutters, decorative moldings and designer lighting throughout. The outdoor living area is equally impressive. French doors open to a covered porch with classic Old Winter Park brick, leading to a travertine-surrounded pool and private cabana with a wood-burning fireplace. Exterior highlights include a metal roof, durable cement board siding and wooden shutters. Don’t miss this limited opportunity to have immediate and easy access to the coveted Winter Park Chain of Lakes. *Some photos have been virtually staged*

2240 Venetian Way, Winter Park
$2,150,000
5 Beds ⋅ 4 Baths ⋅ Charmont SubDv. ⋅ 32789 Zip Code
JUST LISTED! Located in the highly sought-after Winter Park Lake Sue area, this exceptional contemporary residence offers a rare opportunity to enjoy luxury living among some of the most architecturally significant and beautifully designed homes in Central Florida. Positioned within one of the region's most desirable neighborhoods, the property combines modern design, exceptional functionality, and an outstanding lifestyle location. From its prominent presence to its thoughtfully executed interior spaces, the home offers a seamless blend of modern esthetics and comfort. The open-concept floor plan is designed for both everyday living and entertaining, with expansive living areas that transition effortlessly into the covered outdoor living space, summer kitchen, resort-style pool, and heated spa. A highly desirable layout places both the luxurious primary suite and an additional bedroom/flex room on the main level, providing exceptional flexibility for guests, a home office, fitness space, or multi-purpose living. Upstairs, additional bedrooms and a large bonus room create ample space for family and entertaining. The private first-floor primary suite serves as a true retreat, featuring direct access to the outdoor living areas and a beautifully appointed spa-inspired bath. Throughout the home, quality finishes, extensive wood flooring, designer lighting, custom window treatments, and carefully curated details create an elevated living experience. The kitchen serves as the centerpiece of the home, featuring premium appliances, generous workspace, and a large entertaining island that connects seamlessly to the main gathering spaces. Perhaps most compelling is the location. Zoned for highly regarded Audubon Park K-8 and Winter Park High School, the home enjoys convenient access to Park Avenue, Rollins College, East End Market, Winter Park Village, Downtown Winter Park, and Downtown Orlando. Residents enjoy the unique advantage of being positioned between the charm and sophistication of Winter Park and the energy of Orlando's most vibrant dining, cultural, and lifestyle destinations. Opportunities to secure a fantastic residence at this price point in the Winter Park Lake Sue area are increasingly rare. This is a unique opportunity to enjoy a wonderful lifestyle and home in one of Central Florida's most desirable neighborhoods.

230 E Rockwood Way, Winter Park
$2,280,000
Winter Park SubDv. ⋅ 32789 Zip Code
An exceptional new development opportunity in the heart of Downtown Winter Park. On a slightly over one-quarter-acre homesite along a charming brick street, this property offers an enviable location just one block from renowned Park Avenue and one block from picturesque Interlachen Avenue. Enjoy a highly accessible lifestyle with some of Winter Park’s finest shopping dining, and entertainment just a short distance away. Stroll to Central Park, the Winter Park Farmers’ Market, Rollins College, museums, galleries, sidewalk cafés, and a vibrant collection of boutiques and restaurants. Whether you envision building a custom residence or investing in one of Central Florida’s sought-after neighborhoods, this property presents a rare opportunity to create something special in an unmatched location.

436 N Knowles Avenue, Winter Park
$1,250,000
2 Beds ⋅ 2 Baths ⋅ Alabama Condo SubDv. ⋅ 32789 Zip Code
Under contract-accepting backup offers. Nestled along one of Winter Park's most cherished brick-lined streets, this elegantly appointed two-bedroom, two-bath residence at the prestigious Alabama offers a rare opportunity to experience the very best of lakeside luxury living. With 1,574 square feet of thoughtfully designed interior space, this exceptional unit captures the timeless charm and sophistication that have made the Alabama one of the most coveted addresses in the heart of Winter Park. From the moment you step through the gracious foyer entry, complete with a coat closet, you are welcomed by an atmosphere of warmth and refined taste. Reclaimed wood floors flow seamlessly throughout the entire residence, lending an organic richness that perfectly complements the grass cloth covered walls and classic crown molding found in every room. Recessed lighting adds a soft, curated ambiance, while the expansive living and dining area serves as the heart of the home, offering sweeping views of the beautifully maintained gardens and the shimmering waters of Lake Maitland just beyond. The well-appointed kitchen is a chef's delight, featuring stainless steel appliances, an induction range, a Subzero refrigerator, stone countertops, a charming penny tile backsplash, and a central island ideal for both casual dining and entertaining. A dedicated interior laundry room adds a layer of everyday convenience that is rarely found in residences of this era and character. The primary bedroom is a true retreat, featuring double built-in closets and a beautifully finished en suite bath with a walk-in shower. The second bedroom is comfortably proportioned and well-suited for guests, a home office, or whatever lifestyle demands require. The hall bath offers a classic tub and shower combination to serve residents and visitors alike. One reserved covered parking space is included, and monthly HOA dues of $1,600 cover the care and maintenance that keep this distinguished property in impeccable condition. The location is simply unmatched. Kraft Azalea Park, one of Central Florida's most scenic and beloved green spaces along the shores of Lake Maitland, is just moments away, offering a tranquil setting for morning walks and golden-hour evenings. The legendary shops, restaurants, and galleries of Park Avenue are easily accessible, placing world-class dining and boutique retail practically at your doorstep. Tennis enthusiasts will appreciate the proximity to the Winter Park Racquet Club, while golf aficionados will find the storied Interlachen Country Club well within reach, rounding out a lifestyle that is as active as it is refined. This is Winter Park living at its most authentic, offering history, elegance, and an unbeatable sense of place in one of the most desirable communities in all of Central Florida.

1600 Alabama Drive Unit 402, Winter Park
$3,500,000
3 Beds ⋅ 5 Baths ⋅ Park Hill SubDv. ⋅ 32789 Zip Code
Park Hill is one of Winter Park's most coveted addresses, a distinguished collection of luxury brownstones situated at the northern end of Park Avenue, moments from the city's finest boutiques, restaurants, cultural landmarks and the historic Winter Park Golf Course. Within this exclusive enclave, residence 649 occupies one of the community's most private settings. Beyond the stately brick courtyard and gas lantern-adorned entrance, this three-story home with a private elevator is thoughtfully scaled for refined living. Not oversized, but extraordinarily well-appointed. Ten-foot ceilings, intricate millwork and moldings and generous windows establish an ambiance of quiet elegance, while hardwood floors and designer fixtures carry that standard throughout. The open-concept main living area is built for effortless entertaining. The chef's kitchen features Wolf and Sub-Zero appliances, custom wood cabinetry, marble accents, a center island with bar seating and a wet bar with a beverage refrigerator and ice maker. The space opens directly to a private courtyard with a summer kitchen and dedicated alfresco dining area, creating a genuinely tranquil retreat that feels removed from the energy of the avenue. Upstairs, two guest suites each offer walk-in closets and en-suite baths. A dedicated laundry room and a covered terrace with a fireplace, wet bar and half bath complete the level. The third-floor primary suite provides a true sense of retreat, with two custom walk-in closets, a private balcony and a spa bath filled with natural light from windows and skylights. Dual vanities, a glass-enclosed steam shower and a soaking tub are finished throughout in premium materials. Constructed of Old Carolina brick with three-story block construction, precast exterior trim and a slate mansard roof, the residence features a two-car air-conditioned garage, ample storage and soundproof hollow core floors. With exterior maintenance managed by the association, the lifestyle here is genuinely lock-and-leave. This is a rare opportunity to own in one of Central Florida's most prestigious communities, in a location that simply cannot be replicated.

649 N Park Avenue, Winter Park