Winter Park FL Homes for Sale | 250 Listings

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3 Beds ⋅ 2 Baths ⋅ Elizabeth Heights Sub SubDv. ⋅ 32789 Zip Code

Welcome to a beautifully renovated 3-bedroom, 2-bath residence offering approximately 1,700 square feet of thoughtfully designed living space in the heart of Winter Park. Step inside to a fresh, inviting interior where timeless travertine flooring complements a beautifully updated kitchen featuring new cabinetry, new appliances, and a spacious new pantry. Both bathrooms have been tastefully renovated, while new lighting and ceiling fans throughout add a polished finishing touch. Thoughtfully added storage provides both style and functionality for everyday living. Ideally situated near some of Winter Park’s favorite restaurants, coffee shops, shopping, museums, and local attractions, this home provides exceptional convenience with easy access to major roadways and hospitals. Beautifully refreshed and move-in ready, this home combines modern updates, comfortable living, and an exceptional Winter Park location.

1313 S Denning Drive, Winter Park

3 Beds ⋅ 1 Baths ⋅ Winter Park Village SubDv. ⋅ 32789 Zip Code

An opportunity to build new in an established Winter Park neighborhood. The existing home remains on the property and is offered for its land value only, allowing a buyer to design from the ground up on a street where redevelopment is already underway. Within a half mile, seven custom single-family homes are in their final phase of construction, most starting near $1.5 million. Border Drive itself is a mix of longtime homes and newer builds, shaded by mature trees and free of through traffic. Once the site is prepared, the parcel supports a custom plan with room to work in a pool, covered lanai, and summer kitchen. Bring your own builder, or ask for an introduction to builders already working in the area. Park Avenue shops and restaurants, Rollins College, the Farmers Market, and the chain of lakes are all a short drive away. Property sold as is. Buyer to verify setbacks, utilities, impact fees, demolition requirements, and permitted building dimensions with the City of Winter Park.

1416 Border Drive, Winter Park

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

Welcome home to this charming 2-bedroom, 1-bathroom gem nestled in the heart of Winter Park AND College Park. This charming single-story concrete-block home blends timeless character with everyday convenience. It has a dimensional-shingle roof, and a full-length driveway leading to a covered carport deliver lasting value and practical, protected parking with an attached laundry & storage room. Located just minutes away from Downtown Orlando, Disney, Universal and Advent Health, this sought-after location offers convenience and comfort. This home boasts not only a prime location but also a cozy ambiance that will make you feel right at home. With its Terrazzo floors adding warmth and character, and the spacious fenced-in backyard providing privacy and room for outdoor activities, this property is ideal for those seeking the perks of Winter Park and College Park living as well as the fun outgoing, Orlando attractions.

1941 Oglesby Avenue, Winter Park

3 Beds ⋅ 3 Baths ⋅ Magnolia Gardens Sub SubDv. ⋅ 32789 Zip Code

Completely Remodeled 2026 | Single-Story | Prime Location | Dual Suites | The redesigned kitchen features 42" shaker cabinetry, Calcutta quartz countertops, and new stainless steel appliances. Bathrooms have been completely remodeled with updated finishes. Luxury vinyl flooring extends through all common areas, complemented by LED recessed lighting and updated fixtures throughout. The open layout provides clear sight-lines between the kitchen and family room, creating a connected main living area. The pavers meet manicured lawns and fresh landscaping for a clean, contemporary finish that is 100% move-in ready. Additional features include an interior laundry closet and a fully fenced backyard. Enjoy being just 4 minutes from both Orlando Avenue and Park Avenue where you'll find farmers markets, local dining, and boutique shopping. This prime location also puts you just minutes from Lake Lily, and Maitland City Centre. With easy access to I-4, 417, and the Maitland Exchange, you're well connected to everything Central Florida has to offer.

900 Carver Street, Winter Park

1 Beds ⋅ 1 Baths ⋅ Lake Killarney Condo SubDv. ⋅ 32789 Zip Code

Location, location, location! Bring your boat, enjoy lake views and the best of Winter Park from this beautifully updated, move in ready 1 bedroom, 1 bathroom condo in the desirable Lake Killarney community. This top floor beauty features two private entrances and an enclosed patio overlooking Lake Killarney, perfect for morning coffee or relaxing at the end of the day. Inside, you’ll find new flooring, a brand new kitchen, and a beautifully updated bathroom. Lake Killarney Condominiums offers fantastic lakeside amenities including a waterfront pool, private community boat dock and ramp, fitness room, clubhouse, laundry facilities, shuffleboard, picnic areas, and grills. Bring your boat, water ski, jet ski, paddle board, wake board or go fishing on this beautiful lake. The monthly HOA also includes water, sewer, trash, pest control, and exterior and grounds maintenance for easy, low maintenance living. One of the best parts is the incredible walkability! Stroll to Trader Joe’s, Hillstone, and the newly revitalized Winter Park Village with shopping, dining, cafes, and a luxury movie theaters. Park Avenue, the Winter Park Farmers’ Market, and the SunRail station are just minutes away, with convenient access to I 4, downtown Orlando, and Maitland. Whether you are looking for a primary residence, Winter Park getaway, or investment property, this is a rare opportunity to enjoy lake views, fantastic amenities, and an unbeatable location in the heart of Winter Park.

151 N Orlando Avenue Unit 261, Winter Park

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

New Construction! New photos coming soon! First photo is a rendering of the new home and the following photos are interiors of a similar model by the builder. Discover Modern Luxury in Winter Park's Latest Neighborhood, Winter Park Grove! Step into a world of refined living with this breathtaking new construction pool home, located in the vibrant heart of Winter Park. Just moments away from the eclectic energy of Park Avenue, this modern masterpiece seamlessly blends sophistication, style, and convenience — all within a short distance of premier restaurants, cafés, boutique shops, and entertainment venues. Designed for both daily comfort and elevated entertaining, the open-concept floor plan boasts thoughtful design and high-end finishes throughout. Luxury details abound, including engineered wood floors, smooth finish Level 4 drywall, and designer-selected light fixtures, Delta plumbing finishes and a bright open great room accentuated by LED mood lighting in the coffered ceiling. Designed for culinary excellence, the gourmet kitchen features sleek custom cabinetry and top-tier Bosch appliances, including a 36” gas cooktop, wall oven, built-in microwave, French door refrigerator, and a dedicated wine fridge, all enhanced by contemporary accents. The residence hosts four spacious bedroom suites, highlighting a main-level primary retreat alongside a flexible second suite on the ground floor that works well as a guest space or home office. On the upper level, two additional suites frame a versatile bonus room suited for a fifth bedroom, second living room, fitness space, or private office. Step outside to your private outdoor oasis, featuring a covered lanai with a fully-equipped summer kitchen (complete with grill, sink, and refrigerator drawers), and a sparkling pool — perfect for year-round Florida entertaining. Don’t miss your opportunity to own this exquisitely crafted home in one of Orlando’s most sought-after neighborhoods. Schedule your private showing today and experience the pinnacle of luxury living in Winter Park!

1526 Miller Avenue, Winter Park

4 Beds ⋅ 2 Baths ⋅ Arrowhead Cove SubDv. ⋅ 32792 Zip Code

Welcome to this fully renovated four-bedroom, two-bathroom pool home offering close to 2,000 square feet of beautifully updated living space on an expansive .36-acre pie-shaped lot in the established Arrowhead Cove neighborhood. Thoughtfully renovated throughout, this move-in-ready residence combines modern finishes, an ideal split floor plan and exceptional outdoor living with a location zoned for top-rated Winter Park schools. Inside, brand-new windows and sliders, installed in 2026, fill the home with natural light while wood laminate flooring, fresh interior paint, and recessed lighting create a polished, comfortable atmosphere. The renovated 2025 kitchen features crisp white shaker-style cabinetry, quartz countertops, brand-new stainless steel appliances and a spacious stainless sink, creating a stylish and functional centerpiece for everyday living and entertaining. The private primary suite is thoughtfully separated from the secondary bedrooms and offers dual built-in closets and an updated ensuite bathroom with a double quartz vanity, beautifully tiled shower and separate water closet. Three additional bedrooms share a renovated hall bathroom featuring a double quartz vanity, tiled tub/shower and convenient direct access to the pool area. Step outside to your own private backyard retreat, where a spacious screened lanai overlooks the sparkling in-ground pool. Resurfaced in 2025, the chlorine-generated pool also features a new pump, light, steps and filter. A separate gazebo provides another inviting space for outdoor dining or relaxing, while the fully fenced .36-acre pie-shaped lot offers plenty of room to enjoy the outdoors. A two-car garage adds everyday convenience and storage. Ideally located just five minutes from Full Sail University and SR 417, approximately 15 minutes to UCF and 20 minutes to Orlando International Airport, this exceptional home also offers easy access to Target, Costco, grocery stores and abundant retail. With extensive 2025-2026 renovations, a private pool and an oversized lot in a highly desirable Winter Park school zone, this is a rare opportunity to enjoy turnkey living in a prime Central Florida location. ROOF - 2023 HVAC - 2018 PLUMBING - 2025 WATER HEATER - 2017

7525 Lodge Pole Trail, Winter Park

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

Welcome to 2333 Westminster Court, a stunningly reimagined residence that perfectly captures the effortless elegance of Winter Park living. A thoughtful and meticulous renovation in 2020 offers piece of mind showcasing a new roof, HVAC, plumbing, and a complete septic system and drain field. Step inside to find a bright, cohesive interior featuring modern flooring and a chef-inspired kitchen outfitted with sleek appliances and contemporary finishes. The open layout flows seamlessly to the outdoors, where your own private oasis awaits. The backyard was elevated in 2025 with a brand-new travertine paver deck surrounding a tropical-style pool, creating a resort-like atmosphere perfect for weekend lounging or evening gatherings under the stars. Situated in one of the most sought-after pockets of the area, you are just moments away from the scenic beauty of Lake Killarney and the vibrant energy of Park Avenue. Whether you’re looking for high-end shopping, acclaimed dining in Winter Park and Maitland, or a quick coffee at a local bistro, everything that makes this community so special is right at your fingertips. This is more than just a house; it’s a turn-key lifestyle in the heart of it all. Schedule your private viewing today.

2333 Westminster Court, Winter Park

2 Beds ⋅ 2 Baths ⋅ Winter Park Villas Condo SubDv. ⋅ 32792 Zip Code

Welcome to this Desirable Winter Park Villas Condo 2 Bedroom, 2 Bath, 1037 square feet, featuring Brand New Air Conditioning System and Brand New Carpet freshly installed! Excellent Location walking or bike riding distance to Full Sail University and easy access to UCF! Ideally located on first floor in rear of community with ample open parking. Your spacious Kitchen features ample counter space and abundant cabinetry, kitchen sink window with view of front door entry and parking area. Kitchen has a closet pantry and there is an opening to Dining Room with Bar Seating area. Dining Room has views to backyard and a Wet Bar with unique Sink Closet feature. Family Room has a fireplace and views of outside greenery. In hallway off entry is your Washer/Dryer closet. The Primary Bedroom is large with walk in closet and full bathroom with tub shower combo. The Secondary Bedroom features back yard views and built in closet and easy access to hallway full second bath. Outside you'll love the covered patio and lawn area for lounging outside. Off the patio is a storage closet for the Water Heater. Winter Park Villas amenities include community pool, fitness center and tennis courts. Seller is offering a One Year Assurant Home Warranty covering all the appliances included. Located in Winter Park School District and easy access to Orlando International Airport! Call for to see it today, priced under $200,000 location can't be beat! Property may be under audio/visual surveillance.

623 Grenadine Court Unit 623, Winter Park

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

Welcome to 1621 Chestnut Avenue, ideally situated in the heart of Winter Park's coveted "Tree Streets" neighborhood. Offered at $899,000, this single-story block home sits on a generous 50x150' lot and offers 2,022 square feet of living space with 3 bedrooms and 2.5 baths. Whether you envision a thoughtful remodel or a ground-up new build, this property presents outstanding potential in one of Winter Park's most desirable pockets, where similar transformations are already reshaping the streetscape. Inside, tile flooring flows through the main living areas, complementing a versatile layout that includes a formal living room, a combined kitchen and dining area, and a separate den with pocket doors perfect for a home office or media room. The oversized bedrooms offer generous space throughout, including a primary suite with a private en suite bath. Two additional guest bedrooms share a convenient Jack-and-Jill bathroom, ideal for family or guests. At the rear of the home, an enclosed sunroom provides a peaceful retreat overlooking the well-manicured backyard, a tranquil spot to relax and unwind. With its prime location, solid bones, and abundant possibilities, 1621 Chestnut Avenue is ready for its next owner to make it their own.

1621 Chestnut Avenue, Winter Park

4 Beds ⋅ 3 Baths ⋅ Golfside Sec 03 SubDv. ⋅ 32792 Zip Code

Welcome to this beautifully maintained four-bedroom, three-bathroom home offering over 2,000 square feet of thoughtfully designed living space in desirable Winter Park community. Overlooking the 9th fairway of Winter Park Pines Golf Course, this home offers a picturesque golf course setting and a peaceful backdrop for everyday living. The split-bedroom floor plan provides both privacy and versatility, while the formal living and dining rooms create inviting spaces for entertaining. Light-toned wood and tile flooring flow throughout, complemented by crown molding, recessed lighting, and a wood-burning fireplace that adds warmth and character. The contemporary kitchen features honey-oak cabinetry, granite countertops, stainless steel appliances, a breakfast nook, and a center island with seating for two. The spacious primary suite is privately positioned from the secondary bedrooms and offers a generous walk-in closet and an impressive ensuite bathroom featuring floor-to-ceiling slate tile, an espresso-colored contemporary double vanity with glass vessel sinks, and a walk-in slate tile shower. Ideal for family or guests, a convenient Jack and Jill bathroom serves two bedrooms while the hall bathroom is directly adjacent to the fourth bedroom. A dedicated laundry room/mud room with built in shelving includes the washer and dryer. French doors open to the spacious screened lanai, where the scenic 9th fairway views take center stage. New screening was installed in 2021, creating an ideal setting for morning coffee, al fresco dining, or relaxing while enjoying the beautifully maintained golf course landscape. The quarter-acre lot also features lemon and Japanese blueberry trees, while the two-car garage offers built-in shelving and an updated garage door and mechanicals. Beyond the property, enjoy convenient access to the Cady Way Trail, Cady Way pool, playground, and tennis/pickleball courts, as well as nearby UCF, Rollins College, Full Sail University, AdventHealth Winter Park, and Crosby Wellness Center. Orlando International Airport is approximately 20 minutes away. Zoned for top-rated Brookshire Elementary, Glenridge Middle School, and Winter Park High School, this exceptional home combines comfortable living, desirable amenities, and spectacular golf course views in a sought-after Winter Park location. ROOF - 2024 HVAC - 2024 ELECTRICAL - 2015

943 Fairway Drive, Winter Park

3 Beds ⋅ 3 Baths ⋅ Mc Intyre Place Condo SubDv. ⋅ 32789 Zip Code

Private, no-through-traffic street in one of Winter Park's most desirable locations. Just a short walk from downtown Winter Park and Park Avenue, this light-filled townhome offers the perfect combination of privacy, space, and convenience. Step inside to soaring ceilings, abundant natural light, and a spacious floor plan designed for comfortable everyday living and entertaining. The first floor features a generous living area, separate dining space, and an updated eat -in kitchen with plenty of cabinetry and workspace. Two private patios—one on each side of the townhome—extend the living space outdoors and provide wonderful spots for morning coffee, dining, entertaining, or simply relaxing. Upstairs, you'll find three generously sized bedrooms with excellent closet space. Thoughtfully designed closet organizers provide exceptional storage, while the spacious primary suite offers a comfortable and private retreat. High ceilings, large windows, abundant storage, and an inviting indoor-outdoor layout give this home a bright and open feel throughout. Meticulously cared for and updated this is an exceptional opportunity to enjoy low-maintenance townhome living without sacrificing space or privacy. Best of all is the location—enjoy the ability to walk to Park Avenue and experience the restaurants, shopping, cafés, parks, events, and charm that make downtown Winter Park one of Central Florida's most sought-after destinations. A rare combination of location, lifestyle, and livability!

565 Huntington Avenue Unit 565, Winter Park

1 Beds ⋅ 1 Baths ⋅ Parkview Village SubDv. ⋅ 32792 Zip Code

Beautifully renovated first-floor 1-bedroom, 1-bath condominium in the highly desirable Parkview Village community, conveniently located directly across from Full Sail University on Semoran Blvd. This move-in-ready home features a spacious open-concept layout, an oversized bedroom with a walk-in closet, a dedicated laundry closet with a washer and dryer, and a private screened-in patio overlooking a beautiful mature tree for added privacy and relaxation. The home has been extensively updated with a newer A/C system, a fully renovated kitchen and bathroom, and a complete suite of stainless steel appliances-including the refrigerator, range, microwave, dishwasher, washer, and dryer-all replaced in 2022. Modern features include a preinstalled Nest Wi-fi thermostat, Eufy doorbell/lock, and wall-mounted TV brackets in both the living room and bedroom. Residents enjoy resort-style amenities including a community pool, hot tub, picnic and BBQ area, and a newly built fenced dog park. The location has easy access to Lake Baldwin, Downtown Winter Park, the University of Central Florida, Downtown Orlando, and Orlando International Airport. Major roadways including SR 436, SR 408, and East Colonial Drive are just minutes away, making commuting throughout Central Florida quick and convenient. Whether you're looking for a comfortable primary residence or an investment property, this exceptional condominium is the perfect combination of location, modern updates, and everyday convenience.

3019 Antique Oaks Circle Unit 127, Winter Park

3 Beds ⋅ 3 Baths ⋅ Casa Jardin Condo SubDv. ⋅ 32789 Zip Code

In the heart of Winter Park’s coveted Virginia Heights neighborhood, just moments from the boutiques, dining, and charm of Park Avenue and the green spaces of Seven Oaks Park, this exceptional Mediterranean-inspired end-unit condominium offers an unparalleled blend of elegance, comfort and accessible convenience. Encompassing nearly 2,000 square feet, the residence features three bedrooms, two-and-a-half baths and a thoughtfully designed floor plan that lives like a private home. Bathed in natural light, the interiors are framed by expansive window walls and floor-to-ceiling glass doors that create a bright, airy ambiance throughout. Architectural details including graceful arched passageways, column-lined hallways, and a custom wrought-iron spiral staircase add timeless character and sophistication. Beautifully updated and meticulously maintained, every room reflects a sense of warmth and refinement. The spacious primary retreat is a sanctuary, featuring soaring cathedral ceilings, dual walk-in closets and a spa-inspired bath designed for relaxation. Two additional bedrooms offer versatility for guests, family or a home office. The open-concept living and dining areas are enhanced by travertine and luxury vinyl plank flooring, coffered ceilings, designer lighting, and a beautifully appointed chef’s kitchen complete with solid wood cabinetry, granite countertops, a center island and generous walk-in pantry. French doors open to a freshly painted screened courtyard, creating a private outdoor escape ideal for entertaining or quiet evenings at home. Above, the freshly painted rooftop terrace provides a spectacular setting for alfresco dining, sunset gatherings or simply enjoying Florida’s year-round sunshine. Additional features include a powder bath, plantation shutters, ceiling fans throughout, an oversized two-car garage, and a third-floor walk-in attic offering abundant storage and exciting future expansion possibilities. Residents of Casa Jardin enjoy a beautifully refreshed community, recently enhanced with a new roof, exterior paint and professional landscaping. Ownership also includes exclusive access to Lake Virginia and renowned Winter Park Chain of Lakes through College Point, featuring a private lakefront gathering area along with kayak and paddleboard storage. Ideally near Azalea Lane Recreation Center, the Winter Park Tennis Center, Orange Avenue’s popular restaurants and shops, and top-rated schools, this remarkable residence offers a rare opportunity to enjoy one of Central Florida’s desirable lifestyles.

1278 S Pennsylvania Avenue Unit 13, Winter Park

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

Designed to evoke the timeless architecture of Olde Winter Park, this exceptional modern Tudor home features character, craftsmanship, and presence rarely found in today's market. Perfectly positioned on an expansive 0.37-acre homesite in the highly coveted Park Grove neighborhood, the residence offers the rare privilege of walking to Park Avenue while still having immense privacy. A soaring 20-foot foyer creates an unforgettable first impression and immediately establishes the home's sense of grandeur. Beyond the entry, the expansive great room is defined by dramatic exposed wood beams, a sleek electric fireplace, and a custom-built entertainment wall accented with subtle LED underlighting. At the heart of the home, the chef's kitchen is equal parts statement and workspace. Custom cabinetry is paired with a full Thermador appliance suite, including a paneled built-in refrigerator, while striking Taj Mahal quartzite countertops complete the space. Just beyond, an oversized butler's pantry dramatically expands the kitchen's functionality. Outfitted with extensive cabinetry, generous prep space, a secondary refrigerator, sink, and dishwasher, it is designed to support everything from intimate dinners to large-scale entertaining. The adjacent dining room is equally refined, featuring a custom dry bar complete with a built-in wine refrigerator. One of the home's most exceptional attributes is its floor plan. Offering two luxurious primary suites, a rarity in Winter Park, the residence provides remarkable flexibility for multigenerational living or extended guests. Both suites feature custom Idelli closet systems and spa-inspired baths appointed with marble mosaic tile, expansive walk-in showers, freestanding soaking tubs, and dual vanities. Every additional bedroom is designed as a private ensuite with its own walk-in closet. Two guest suites are conveniently located on the main level, while upstairs you'll find a spacious game room, a dedicated study nook for kids, and a second laundry room to complement the main-level laundry. The outdoor living experience is equally impressive. An expansive backyard, rarely found in Winter Park, creates a private setting for everyday living and entertaining alike. A covered lanai with a fully equipped summer kitchen overlooks the resort-style pool and spa, while upgraded landscaping and generous green space complete the grounds. An oversized motor court and a three-car garage with soaring 12-foot ceilings provide an uncommon level of parking and storage for the car enthusiast. Positioned just moments from Park Avenue, Winter Park Village, and Hannibal Square, this is far more than another luxury home. It is a thoughtfully crafted masterpiece that captures the timeless character of Olde Winter Park while delivering the scale, amenities, and craftsmanship expected of a modern home. Opportunities to own a property of this caliber, in a location this desirable, are exceptionally rare. Don't miss out!

1417 Williams Drive, Winter Park

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

Very well maintained townhouse great location in Waterbridge on cul-de-sac near tennis courts. This 2 bedroom/den or 3 bedroom , 3 bathroom with primary upstairs and additional bedroom on main floor is renovated with hardwood floors downstairs, updated recessed lighting throughout, updated plumbing, volume ceilings, great ambient light and windows, barrel tile roof. Kitchen with updated appliances, cabinetry with undermount lighting and granite with courtyard for fountain feature or small table for morning coffee. Open dining living room combination with a fireplace. Primary bathroom has dual sinks, granite counters, bidet and custom tile. Primary Bedroom has gas fireplace. Outdoor living is perfect for entertaining with screened covered atrium with brick paver patio to enjoy Florida breezes. This townhouse has everything. Near restaurants, hospital, schools and downtown Winter Park Towncenter at Baldwin Park. Walk to Blue Jacket Park. Move in ready.

1256 Melissa Court, Winter Park

2 Beds ⋅ 2 Baths ⋅ Phillips Circle Rep SubDv. ⋅ 32789 Zip Code

Experience effortless Winter Park living in Whispering Waters, a premier 55+ lakefront community beautifully situated along the shores of Lake Osceola & just a short stroll from Park Avenue. Priced below appraised value, this rare third-floor mid-century modern condo offers exceptional value and a truly turnkey lifestyle. Filled with natural light, the thoughtfully designed floor plan features spacious living and dining areas overlooking tranquil waterfall ponds and lush, beautifully maintained grounds. A versatile bonus space provides the perfect setting for a home office, den, or creative retreat. The expansive owners suite is designed for relaxation, featuring a private sitting area, dual closets, direct access to the pool, and a spa-inspired bath complete with a jetted tub. The generously sized secondary bedroom offers a cozy reading nook and dual closets, providing comfort and flexibility for guests. Enjoy effortless, worry-free living with secure underground parking, a deeded parking space, and convenient elevator access. Even better, monthly association dues include electricity, air conditioning, heat, water, sewer, and trash—making everyday living remarkably simple. Step outside your door and enjoy everything that makes Winter Park so special, from the acclaimed shops and restaurants of Park Avenue to Rollins College and Winter Parks historic golf course. With its prime lakefront setting, exceptional location, and low-maintenance lifestyle, this is a rare opportunity to own a piece of one of Central Florida’s most desirable communities. Discover the best of Winter Park living at Whispering Waters—schedule your private showing today.

311 E Morse Boulevard Unit 4-5, Winter Park

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

Discover the ease of Winter Park living in the highly desirable gated community of Park West, ideally located just steps from Park Avenue. From this exceptional location, charming boutiques, sidewalk cafés, award-winning restaurants, and the popular weekly farmers market are all within easy reach—giving you the freedom to leave the car behind and enjoy everything Park Avenue has to offer. This beautifully remodeled second-floor corner residence offers the privacy, comfort, and convenience you've been looking for. The thoughtfully updated kitchen features wood cabinetry and granite countertops, while both bathrooms have been tastefully remodeled. Spacious bedrooms, generous storage, and a comfortable flow throughout the home provide plenty of room for everyday living or welcoming guests. Enjoy the simplicity of a well-maintained community with beautifully landscaped grounds, a sparkling swimming pool, and tennis courts. As a corner unit, this residence also offers enhanced privacy and convenient access into and out of the building—perfect for those seeking a low-maintenance lifestyle or an easy lock-and-leave retreat. With Rollins College and Full Sail University nearby and Park Avenue just moments away, this condo puts the best of Winter Park right at your doorstep. Whether you're looking for a full-time residence, a seasonal escape, or simply a home that allows you to spend less time on maintenance and more time enjoying life, Park West offers an exceptional combination of location, comfort, and convenience.

250 Carolina Avenue Unit 205, Winter Park

4 Beds ⋅ 2 Baths ⋅ Winter Park Estates SubDv. ⋅ 32792 Zip Code

Modern Ranch Gem on a Corner Lot | 4 Bed | 2 Bath | 2,126 Sq Ft | Screened Pool | No HOA | Winter Park, FL Welcome to this beautiful 4-bedroom, 2-bathroom ranch-style home in Winter Park Estates! Situated on a desirable corner lot with no HOA, this spacious 2,126-square-foot home offers flexibility, comfort, and plenty of room to enjoy Florida living. The inviting floor plan features a huge bonus room, perfect for a media room, home office, playroom, gym, or additional living space. The updated kitchen offers a fresh, modern feel while maintaining a practical layout. Step outside to your screened-in pool and spacious outdoor area, ideal for relaxing, entertaining, and enjoying the Florida sunshine year-round. With four bedrooms, two full bathrooms, a generous bonus room, a corner lot, and no HOA restrictions, this home offers an exceptional combination of space and convenience in Winter Park. You will be close to charming downtown shops, restaurants, parks, and easy access to Orlando amenities, all while enjoying a quiet residential setting. A must-see for buyers looking for a move-in-ready home with room to live, work, and entertain!

2641 Carvell Court, Winter Park

2 Beds ⋅ 2 Baths ⋅ Whisperwood Condo SubDv. ⋅ 32792 Zip Code

This charming 2-bedroom, 1.5-bath condo offers a desirable townhome-style layout with spacious living areas and thoughtful storage throughout. The community features deluxe vinyl fencing installed by the HOA, along with a clubhouse and a community pool, providing great amenities for residents to enjoy. Inside, you’ll find the convenience of an in-unit washer and dryer combo, ample storage under the stairs, and a large carport with an attached storage shed. The spacious primary bedroom opens directly to a generous private balcony—perfect for relaxing or unwinding after a long day. Ideally located just 15 minutes or less from UCF, Rollins College, Valencia East, and Full Sail University, and only 20 minutes from Orlando International Airport. Whether you’re a first-time homebuyer, student, investor, or looking to make your move into Winter Park, this home delivers affordability, convenience, and excellent potential.

7468 Canford Court Unit 24, Winter Park

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

LOCATION. LIFESTYLE. TIMELESS WINTER PARK CHARM. Discover an exceptional opportunity in Lake Knowles Terrace, where classic character, effortless comfort, and an enviable location come together beautifully. From the moment you arrive, the home makes an unforgettable first impression with charming curb appeal, elegant walkways, a brick-paver driveway, and a picturesque cobblestone brick road just off Palmer Avenue. Ideally positioned just one block from Lake Knowles and moments from Park Avenue, this residence offers the quintessential Winter Park lifestyle—peaceful, private, and exceptionally convenient. Step through the front door and into a light-filled, thoughtfully designed 2-bedroom, 1.5 bath residence offering approximately 1,100 square feet of comfortable living space. The inviting interior balances timeless charm with tasteful updates, creating a warm setting for both everyday living and entertaining. At the heart of the home, the beautifully updated kitchen features luxurious quartz countertops, stainless-steel appliances, abundant cabinetry, and generous storage, seamlessly opening to the family room. Sunlight pours through the windows, illuminating the space while a classic brick fireplace serves as a striking focal point, creating an inviting ambiance for cozy evenings and memorable gatherings. The home also offers a dedicated dining area and two comfortable bedrooms, complemented by a beautifully updated bathroom with stylish decorative finishes. Impeccably maintained throughout, the residence showcases wood flooring in the wet areas and an overall sense of care and refinement. The living experience continues outdoors, where the distinction between indoor and outdoor living nearly disappears. Step onto the newly constructed deck, pour a glass of wine, and unwind to the peaceful sounds of nature. The spacious homesite provides plenty of room for entertaining, outdoor games, a swing set, gardening, or simply enjoying the tranquility of your private surroundings. A versatile 16' x 11' detached laundry room, game room, or private retreat adds valuable flexibility and could easily serve as a home office, creative studio, fitness space, or ultimate man cave. Notable improvements include a new Trane HVAC system, interior and exterior units with air-duct cleaning, newer water heater, newer tile roof and decking (2021), updated electrical panel (2017), and beautifully maintained flooring. Surrounded by beautiful homes and nestled among tree-lined brick streets, this residence places you within easy reach of Park Avenue's celebrated dining, boutique shopping, cultural attractions, and vibrant charm. Enjoy a morning jog, leisurely bike ride, or golf-cart cruise to Park Avenue—all from a home tucked away in one of Winter Park's most desirable settings. A rare blend of character, comfort, and location—this is Winter Park living at its most inviting.

1409 Sunset Drive, Winter Park

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

Virtually Staged. Beautifully updated and thoughtfully designed, this four-bedroom, three-and-one-half-bath residence blends sophisticated interiors, inviting living spaces and an impressive outdoor setting. Gorgeous curb appeal and meticulously maintained landscaping create a welcoming first impression, while extensive recent improvements bring a fresh, refined feel throughout. Just off the entry, a stately office/den with a wood-burning fireplace offers a handsome, versatile space for a home office, library or sitting room, while a formal dining room provides an elegant setting for entertaining. At the heart of the home is the beautifully updated kitchen, featuring new cabinetry and hardware, marble countertops and an expansive center island with generous seating. Luxury appliances include a striking induction range, integrated refrigerator and convenient beverage refrigeration drawer, while a dedicated coffee bar adds function and style. A sunny breakfast nook provides casual dining space, and the kitchen opens seamlessly to the spacious great room, where French doors lead to the covered lanai and fill the interiors with natural light. A cleverly concealed doorway in the kitchen provides access to the garage and a large bonus room above, complete with a custom wet bar and under-counter beverage refrigerator, an exceptional space for entertaining, recreation or media. Privately on the first floor, the primary suite offers direct access to the covered lanai, an ample custom walk-in closet and spa-inspired bath with dual vanities, soaking tub and glass-enclosed shower. A laundry room with custom cabinetry and powder bath with outdoor access complete the main level. Upstairs, a bright and spacious family room accompanies three additional bedrooms. One features a private en-suite bath, while the remaining two share a Jack-and-Jill bath. All closets feature custom organizational systems. Outdoor living is equally impressive. Accessible from the great room and primary suite, the covered lanai overlooks the newly refinished heated saltwater pool and spa, surrounded by new non-slip pool deck pavers. Wi-Fi-enabled pool and spa equipment provides convenient app-based control. Redesigned by Signature Landscape, the backyard features a turf area for loungers, dedicated firepit space and new fence installed in 2023, creating a wonderful setting for outdoor entertaining. A professionally installed Mist and More mosquito misting system adds another level of comfort, while a gas line from the street supplies the pool and firepit. Extensive upgrades include three HVAC systems installed in 2024 and 2025, a new water heater, whole-home water filtration system and Ecobee smart thermostats. The interior and exterior were repainted in 2025, complemented by new flooring, baseboards and crown molding, custom window treatments, wallpaper and carefully selected designer finishes. Interiors by nationally recognized designer Jaime Garnet of WYC Designs create a polished, cohesive aesthetic throughout. Ideally just minutes from downtown Winter Park, the home offers convenient access to exceptional dining, shopping and cultural amenities, along with major roadways for easy connectivity throughout Central Florida. With extensive updates, flexible living spaces, sophisticated interiors and a beautifully redesigned outdoor setting, this exceptional residence is move-in ready.

948 Poinciana Lane, Winter Park

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

Under Construction. Located in the Kenilworth Shores neighborhood, this stunning new residence brings an elevated level of new construction to an increasingly desirable pocket of Winter Park. A sophisticated modern farmhouse façade creates an impressive first impression, framed by a sweeping double-entry curved driveway that gives the home a commanding yet welcoming presence. Inside, the open-concept design is both polished and remarkably livable. A dedicated home office sits just off the entry, while the expansive main living space is anchored by a statement entertainment wall with an electric fireplace. Pocketing sliders disappear to create a seamless connection to the covered lanai and backyard, extending the home’s entertaining spaces outdoors. At the center of it all, the chef’s kitchen features Taj Mahal countertops, an oversized island, custom cabinetry, and a complete suite of Stainless steel appliances. A generous dining area and large walk-in pantry add to the home’s effortless functionality. One of the floor plan’s greatest advantages is the inclusion of two bedrooms on the main level, a rarity in Winter Park. The primary suite is particularly impressive, offering a true sense of retreat with a spa-inspired bath featuring dual vanities, a freestanding soaking tub, an oversized walk-in shower, and an expansive custom closet with a center island. The additional downstairs bedroom provides flexibility for guests or multigenerational living. Upstairs, three additional generously sized bedrooms are served by two full baths and a dedicated laundry room, along with an air-conditioned bonus room that easily functions as a sixth bedroom, theater, game room, or fitness studio. In all, the home offers five bedrooms, four and a half baths, a private office, and a climate-controlled bonus space, giving families room to spread out without compromise. The backyard was designed to feel like a private resort. A covered lanai and dedicated cabana with a full summer kitchen overlook the large pool and spa, while generous lawn space provides something increasingly difficult to find in newer Winter Park construction. Located minutes from Park Avenue's shops, cafes, and restaurants and close to Advent Health Winter Park, Cady Way Park, and the YMCA, this home offers an exceptional location. For those seeking new construction without compromising on space, location, or lifestyle, this is a Winter Park home that checks the boxes that matter.

648 Worthington Drive, Winter Park

3 Beds ⋅ 2 Baths ⋅ Lake Bell Terrace SubDv. ⋅ 32789 Zip Code

Nestled in Winter Park's Lake Bell Terrace neighborhood, this 3 bedroom, 2 bathroom home is located close to everything that makes Winter Park special, Park Avenue's shops and restaurants, Winter Park Village, Mead Botanical Garden, the Winter Park golf course, and more. Inside, an open, light-filled living area flows effortlessly into the kitchen and dining room, with wood and tile flooring throughout. A large bonus room adds flexible space for a home office, playroom, or media room, while the spacious bedrooms and abundant storage make everyday living easy. Outside, a classic front porch invites cozy mornings with coffee, a screened patio provides year-round outdoor living, and the beautiful backyard with additional open patio is perfect for grilling and gathering. A dedicated laundry/utility room and attached 1 car garage complete this Winter Park gem.

1955 Eland Avenue, Winter Park

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

Rare Winter Park Opportunity | City-Approved 4,338 SF Buildable Area | R-2 Zoning | Detached Guest House Just a very short walk to Park Avenue, with restaurants, cafés, wine bars and boutiques within steps in virtually every direction, 950 S. Kentucky Avenue offers an exceptional combination of location, land, flexibility and future potential. Set on a 7,890-square-foot R-2 lot overlooking little Lake Midget and Park, the property allows for 4,338 square feet of buildable area, as approved by the City of Winter Park. The existing property is a charming mid-century residence on a brick-paved, tree-lined street. The block is distinguished by a mix of mature homes and beautiful new custom residences, including several striking modern homes that complement the neighborhood’s established character. The existing 2,155-square-foot home offers four bedrooms and three baths, including a detached one-bedroom, one-bath guest house with cabinetry already in place to complete a kitchenette. The detached guest house adds an unusual degree of versatility, whether used for guests, extended family, a private office or potential rental income. The current home can be enjoyed with some updating and improvements, allowing a new owner to take the time needed to create their ultimate vision. It features hardwood floors and distinctive historic crown molding salvaged from a Winter Park renovation. The kitchen overlooks the backyard and features a granite island and newer stainless appliances. A side entry from the tandem two-car carport leads into a practical mudroom with a tucked-away laundry closet. The spacious yard offers room for gardens, recreation, outdoor living and potentially a future pool. Recent improvements include a new roof in 2024, updated A/C in 2018, newer appliances and a transferable termite bond. Natural gas is available on-site. The location is truly special. Park Avenue and Central Park are a quick stroll away, while favorites including Croissant Gourmet, Ravenous Pig, Sushi Saint, Fiddler’s Green and Winter Park Playhouse are all within an easy walk. Rollins College, the Saturday Farmers Market, Hannibal Square and the many shops and restaurants of downtown Winter Park are also nearby. Families will also appreciate access to highly regarded Winter Park schools, including Audubon Park School (K–8) and Winter Park High School. Whether you choose to update and enjoy the existing home, use the guest house for additional flexibility or income, or ultimately create a new custom residence, 950 S. Kentucky Avenue offers a wonderful opportunity to live in the heart of Winter Park.

950 S Kentucky Avenue, Winter Park

4 Beds ⋅ 3 Baths ⋅ Winter Park Estates SubDv. ⋅ 32792 Zip Code

Welcome home to this beautifully presented 4-bedroom, 3-bath home located in Winter Park Estates. Offering a comfortable single-story layout and solid block construction, this home combines character, functionality, and inviting indoor and outdoor living spaces. Step inside to a spacious living area that flows naturally into the kitchen and adjoining living spaces, creating an excellent layout for everyday living and entertaining. One of the standout features is the private in-ground pool, creating a wonderful backyard setting for relaxing, entertaining, and enjoying Florida's year round outdoor lifestyle. The property also offers an attached garage, additional storage, and a functional layout designed to make the most of the home's space. Located in an established Winter Park neighborhood with no HOA, this property offers added flexibility without monthly association fees. The location provides convenient access to shopping, dining, parks, entertainment, and major roadways throughout Winter Park and the greater Orlando area. With its 4-bedroom, 3-bath layout, private pool, block construction, and desirable Winter Park location, this home offers a combination of space, convenience, and Florida living that is difficult to find.

2627 Ambergate Road, Winter Park

2 Beds ⋅ 2 Baths ⋅ Lake Knowles Terrace Add 02 SubDv. ⋅ 32789 Zip Code

Welcome to this beautifully maintained 1960s home nestled in one of Winter Park’s desirable neighborhoods, where classic charm meets thoughtful modern updates. Set along picturesque brick streets shaded by mature trees, this inviting home offers a warm, light-filled interior and a private backyard oasis. From the moment you enter, you’ll notice the abundance of natural light and the large windows that frame the living spaces. The spacious living room flows seamlessly into a bright, functional kitchen featuring newer appliances and a large window overlooking the front yard. Just off the kitchen, an indoor laundry room adds everyday convenience. A beautiful sunroom overlooks the private, landscaped backyard and offers a versatile space that could easily serve as a home office, reading room, or additional sitting area. Down the hallway, the spacious primary suite features an en-suite bathroom, ample closet space, and abundant natural light with peaceful views of the backyard. The second bedroom is generously sized and includes a walk-in closet. Step outside to discover a true gardener’s paradise. The lush, private backyard features a beautiful paved patio, winding paved pathway, mature landscaping, and plenty of space to relax, entertain, or enjoy the outdoors. The location is hard to beat, walking distance to the beautiful Lake Knowles and Lake Wilbar, just minutes from Park Avenue, the Winter Park YMCA, AdventHealth Winter Park, Rollins College, the Winter Park Chain of Lakes, golf courses, and an abundance of exceptional dining and shopping. The home also offers access to top-rated Orange County schools. Important updates include a complete remodel and added square footage (2009), a newer roof (2022), regularly maintained HVAC system (2020), hot water heater (2024), updated bathrooms (2025), kitchen appliance updates (2026), and a regularly maintained irrigation system. This special home offers the perfect blend of classic Winter Park character, modern updates, beautiful outdoor living, and an unbeatable location.

1431 Palm Avenue, Winter Park

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

Built in 2017 and thoughtfully enhanced with over $130K in recent improvements, this modern and sleek Winter Park residence is tucked along a quiet dead-end street, offering a functional, open floorplan in an exceptional location. Recent upgrades make this home feel wonderfully fresh and new, including a Mosquito Nix misting system for year-round outdoor pest control, Culligan whole-home water filtration system, fresh paint throughout the entire home, a beautifully remodeled spa-inspired Primary bathroom, renovated powder room, Lutron smart dimmer switches with upgraded LED lighting, a custom-built marble fireplace wall…and the list goes on! Offering 4 bedrooms and 3.5 bathrooms, with a dedicated office, upstairs loft area, and the potential for two laundry rooms, this home masterfully pairs modern design with comfortable everyday living. A soaring 20-foot foyer makes for an impressive introduction, with a private home office just off the entry. The open-concept living spaces center around a sleek chef’s kitchen with an oversized 8.5-foot island, quartz countertops, Thermador appliances, a 6-burner gas range with stainless steel hood, wine refrigerator, and large pantry. The adjoining dining and living areas enjoy views of the pool and spacious backyard, while a newly added electric fireplace with a custom marble wall creates a stunning focal point. The enormous 1st floor Primary Suite has undergone an extensive remodel, including new dual custom walk-in closets with a built-in wall safe, a new floating dual vanity with an anti-fog LED mirror, and an upgraded walk-in shower with a new privacy/glass combination wall, multiple shower heads, and a new freestanding soaking tub. Upstairs, a loft area offers tremendous versatility and connects 3 additional bedrooms, all with new modern LVP flooring (NO carpet) and walk-in closets. Two bedrooms share an updated hall bath with new marble flooring. The 4th bedroom is privately positioned on the opposite side of the home with an en-suite bath and French doors leading to a private balcony. The former upstairs utility space has been thoughtfully transformed into a kitchenette with custom cabinetry, new countertops, a utility sink, and a built-in microwave. This area is especially valuable for extended stays or a secondary living arrangement. A custom work/study area was also added to the rear bedroom for added flexibility. Outside, the fully fenced backyard is lined with a lush bamboo wall and majestic palms, creating a private retreat with a saltwater pool, covered lanai, and ample remaining space for pets or outdoor entertaining. The covered lanai and pool area provide convenient access to the powder bath, recently renovated with gorgeous, marbled floor-to-ceiling tile. The 2-car garage features wall-mounted shelving, multiple overhead storage racks, and durable flooring, plus glass doors for natural light and a sleek appearance. The sellers partnered with Terra Energy to install solar panels on the roof, providing significant savings on their electric bill. (This fantastic subscription service is $186/month with the solar panel company, and additional information will be provided!) With its contemporary architecture, flexible floorplan, substantial recent investments, and highly coveted location, 2343 Versailles Avenue offers the rare combination of newer construction and extensive upgrades in the heart of Winter Park.

2343 Versailles Avenue, Winter Park

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

This house comes with a REDUCED RATE through the seller's preferred lender. This is a lender-paid rate buydown that reduces the buyer's interest rate and monthly payment. Charming 1950 block bungalow in sought-after Orwin Manor! This inviting 3-bedroom, 2-bath home sits on a generous corner lot with a side-load driveway and garage, offering added breathing room, curb appeal, and convenience. A paver walkway leads to the covered front porch, setting the tone for the home’s classic character and welcoming appeal. Inside, original hardwood floors complement a renovated, generously sized kitchen—ideal for everyday living and entertaining. Recent improvements include a 2020 roof, 2021 HVAC system, plus new windows, doors, and added insulation. The dining room features French doors opening to a newly poured concrete patio and charming backyard offering loads of potential for gardening, play, pets, or creating your own private outdoor retreat. Previously utilized as an investment rental, this property presents an excellent opportunity for an owner-occupant or investor seeking a desirable Winter Park location with strong rental appeal. Enjoy close proximity to AdventHealth’s world-class Orlando campus, as well as the shopping, dining, and lifestyle destinations of Winter Park, Park Avenue, Mills 50, and downtown Orlando. A wonderful opportunity to own a character-filled home in one of the area’s most desirable central neighborhoods.

1652 Berkshire Avenue, Winter Park

6 Beds ⋅ 5 Baths ⋅ Timberlane Shores SubDv. ⋅ 32789 Zip Code

Under Construction. Beautifully composed from every angle, this extraordinary residence captures something increasingly rare in new construction: a genuine sense of character, permanence, and architectural identity. Designed by Gary Hancock and meticulously executed by Vimaro Homes, this home features extraordinary materials, bespoke details, and spaces that feel equally refined and inviting. Set on a large corner homesite in Timberlane Shores, the residence enjoys an uncommon sense of openness, complemented by beautiful lake views from its upper levels. Inside, a striking marble mosaic foyer introduces interiors where every finish has been carefully considered. The main living room is a showpiece, featuring illuminated tray ceilings, extensive custom millwork, a bespoke built-in feature wall, and a fireplace wrapped in Calacatta marble. Expansive pocketing sliders disappear to seamlessly connect the living space with the covered lanai, creating an effortless transition between indoor and outdoor entertaining. At the heart of the home is a chef's kitchen designed to be a true showpiece. Calacatta marble countertops, custom inset cabinetry, a statement ILVE range, paneled built-in refrigerator, and a full suite of Thermador appliances establish an exceptional level of finishes. Just beyond, a large secondary prep kitchen provides plenty of additional storage. A charming breakfast nook offers a more intimate setting for everyday dining, while the formal dining room has been designed for memorable evenings, complemented by a sophisticated bar and glass-enclosed wine display. The first-floor primary suite is a true retreat with direct access to the lanai, custom millwork, illuminated tray ceilings, and an impressive sense of scale. Its spa-inspired bath is finished with marble flooring, Perrin & Rowe fixtures, dual vanities, a freestanding soaking tub, and an oversized walk-in shower. Completing the suite are designated his-and-hers closets, providing an exceptional amount of storage and functionality. An additional main-level bedroom can be used as a guest suite, private office, or library. Upstairs, the home continues to impress with four additional bedrooms and a spacious second living area. Above, a third-floor bonus space provides yet another dimension of flexibility and can be transformed into a private gym, game room, media room, or secluded retreat. From the upper levels, glimpses of the nearby lake further reinforce the home's special setting. Outdoors, the residence was created to embrace the Central Florida lifestyle. The outdoor spaces were conceived as a true extension of the home, with a covered terrace that creates an inviting setting for everything from relaxed afternoons to evening gatherings. Retractable screens allow the space to be enjoyed throughout the year, while a beautifully appointed summer kitchen makes outdoor dining effortless. Beyond, the pool is framed by an oversized patio, manicured grounds, and thoughtfully layered landscaping. This home offers a location that is difficult to replicate. Tucked within the peaceful enclave of Timberlane Shores, the home is just minutes from Park Avenue's shopping and dining, while remaining within walking distance of Blue Jacket Park and the dining, shopping, and lifestyle of Baldwin Park. The property is also zoned for the highly desirable Audubon Park K-8 School. IF PURCHASED EARLY, THE INTERIOR OF THIS HOME CAN BE CUSTOMIZED TO THE NEW OWNERS PERSONAL TASTE. CALL FOR ADDITIONAL DETAILS.

620 Virginia Drive, Winter Park

4 Beds ⋅ 4 Baths ⋅ Lake Forest Park SubDv. ⋅ 32789 Zip Code

Under Construction. In a coveted Winter Park enclave, this masterful LUIH residence balances contemporary grandeur with effortless livability. Spanning 2,500 square feet of open-concept living space, the home features four bedrooms and three-and-a-half lavish bathrooms. Framed by hand-selected architectural stone, the elegant entryway reveals a luminous interior anchored by wide-plank light oak flooring that flows seamlessly across both levels. At the heart of the home, the chef’s kitchen boasts a premium Thermador appliance suite, custom Fabuwood shaker cabinetry, vein-matched quartz countertops, a custom pot-filler, and a wine refrigerator. The main-level primary suite offers a true private sanctuary, highlighted by a spa-inspired bath with a freestanding soaking tub, gold-brushed hardware, and a frameless glass walk-in shower. Dissolving the boundaries between indoors and out, the main living area opens to an expansive covered lanai complete with a summer kitchen and a built-in grill. This alfresco retreat overlooks a private, resort-style backyard centered around a saltwater pool, perfectly designed for relaxation or grand-scale entertaining. Zoned for Audubon K-8 and Winter Park High School, and located just minutes from Park Avenue, Trinity Prep, and Lake Highland, this residence presents an unparalleled opportunity for elevated luxury in one of Central Florida’s most exclusive locations.

2308 Mulbry Drive, Winter Park

2 Beds ⋅ 3 Baths ⋅ Temple Trail Village SubDv. ⋅ 32789 Zip Code

A rare opportunity in Winter Park’s coveted 32789! This stunning fee-simple townhome offers the feel of a private retreat with the architectural pedigree of Fugelberg Koch (FK Architecture), the freedom of NO HOA FEES, and an extraordinary setting overlooking the 80-acre Howell Creek Preserve. Tucked away in a highly desirable Winter Park location, this 2-story end-unit lives much larger than its 1,701 square feet and delivers a lifestyle that is truly hard to replicate. The heart of this home may just be its incredible outdoor living space. Step through the living area and onto the expansive deck, where a covered canopy creates a year-round outdoor room overlooking the lush Howell Creek Preserve. With a firepit, market lighting, and treetop views stretching across the native Florida landscape, this is the kind of space that begs you to linger—morning coffee surrounded by nature, afternoon cocktails with friends, or evenings gathered around the fire under the lights. The elevated vantage point places you virtually eye-level with the cypress canopy, creating a dreamy sense of privacy and connection to nature that is rarely found in townhome living. And perhaps best of all, this is a view that cannot be renovated into another home. Inside, soaring 14-foot ceilings and dramatic picture windows fill the living room with an abundance of natural light while framing beautiful views of the preserve. The open, airy design makes the home feel exceptionally spacious and brings the outdoors in. The stunning kitchen features gorgeous Spanish tile flooring, solid wood cabinetry, granite countertops, and a new backsplash. The dining room adds character with built-in cabinetry and French doors, while the spacious indoor laundry room provides exceptional everyday convenience. Upstairs, two generously sized bedrooms and two full bathrooms provide a comfortable private retreat. A convenient powder room is located downstairs for guests. The coveted end-unit location also offers additional outdoor space along the side of the home, beautifully enhanced with brick hardscaping and room for relaxing, grilling, entertaining, or overflow parking. Parking is another standout feature, with a one-car garage plus two designated parking spaces—a rare convenience in this setting. And then there is the location. Situated in the prestigious 32789 zip code, this home puts you in close proximity to the Winter Park Racquet Club, Winter Park Chain of Lakes, and surrounded by some of Central Florida’s most sought-after real estate. Enjoy the best of Winter Park while coming home to your own private perch above the trees. Fee-simple ownership. No HOA fees. Exceptional architecture. Preserve views. Incredible outdoor living. Coveted Winter Park location. This is far more than a townhome—it is a lifestyle.

2881 Temple Trail, Winter Park

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

Discover this exceptional custom-designed modern pool home, ideally situated in one of Winter Park's most sought-after neighborhoods. Located on a quiet street, this spacious residence offers 5 bedrooms, 4.5 bathrooms, and a large upstairs loft—providing the perfect blend of luxury, comfort, and functionality. From the moment you enter, you'll be captivated by the abundance of natural light and stunning hardwood floors that flow throughout the main level and continue upstairs into the loft and primary suite. The thoughtfully designed floor plan includes a downstairs bedroom and full bath, ideal for guests, in-laws, or a private home office. Designed with the entertainer in mind, the gourmet kitchen is a true showstopper—featuring quartz countertops, an oversized island, Jenn Air appliances including a double oven, and generous cabinet space. A large butler’s pantry with an additional sink offers even more storage and prep space. Seamlessly transition from indoor to outdoor living with the sliding glass doors that open to a covered lanai, private pool, and expansive fenced in backyard—perfect for relaxing or hosting gatherings year-round. Upstairs, the luxurious primary suite includes a walk-in closet and a spa-like bathroom with dual sinks, a soaking tub, and a separate walk-in shower. Three additional bedrooms, two full bathrooms, and a spacious laundry room with more storage complete the upper level. Additional features include a dedicated mudroom with built-in bench seating and storage, and an air-conditioned two-car garage with insulated doors and epoxy floors. All of this, just minutes from the Winter Park Racquet Club, Park Avenue’s boutique shopping and dining, and top-rated schools: Dommerich Elementary, Maitland Middle, and Winter Park High. Don’t miss this rare opportunity to own a one-of-a-kind home in one of Winter Park's premier neighborhoods.

2407 Lafayette Avenue, Winter Park

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

Under Construction. Designed to capture the timeless character of Olde Winter Park while delivering an extraordinary level of modern luxury, this is a truly one-of-a-kind residence by Vimaro Homes. Set within the highly sought-after Park Grove neighborhood and designed by renowned architect Gary Hancock, the home makes an unforgettable first impression with a stately front façade, manicured grounds, dual porte cochere’s, and a motor court leading to a two-car garage. Every element has been thoughtfully considered to create a residence that feels as though it has always belonged in Winter Park. Inside, exceptional craftsmanship takes center stage. A marble mosaic entry introduces interiors defined by chevron-pattern hardwood flooring, refined millwork, natural stone, and carefully curated finishes. The floor plan is equally impressive, balancing grand entertaining spaces with an effortless sense of livability. The main level features a dedicated library/home office, formal dining room, and expansive gathering room overlooking the private courtyard. At the heart of the home, the chef’s kitchen pairs Calacatta marble countertops with a full suite of Thermador appliances, a statement ILVE range, and an oversized butler’s pantry offering exceptional prep and storage space. The first-floor primary suite is a private retreat with direct access to the courtyard and an incredible spa-inspired bath finished in marble. Dual vanities, Perrin & Rowe fixtures, a freestanding soaking tub, walk-in shower, and an expansive dressing room elevate the suite to another level. Upstairs, four generously proportioned bedrooms each feature an ensuite bath and walk-in closet, surrounding a spacious central loft ideal for an additional living or entertaining space. Continuing to the third level, a fully finished attic space provides an unexpected bonus room perfectly suited for a private gym or a game room. The outdoor living experience is just as remarkable. At the center of the home is a spectacular courtyard-style pool, creating a private resort atmosphere framed by the residence and lush landscaping. An expansive covered cabana provides multiple areas for dining and lounging, complemented by a fireplace and full summer kitchen for year-round entertaining. Beyond the courtyard, ample yard space adds another layer of usability rarely found with such an intimate outdoor design. This home also offers the rare opportunity to enjoy one of Winter Park’s most desirable residential settings while remaining within walking distance of the boutiques, acclaimed restaurants, cafés, and vibrant atmosphere of Park Avenue. Hannibal Square and Winter Park Village are also just moments away, placing some of the city’s best dining, shopping, and entertainment within effortless reach. Timeless in its architecture and uncompromising in its execution, this home is destined to become one of Winter Park’s most distinguished residences. Renderings are artistic interpretations. Features and finishes may vary from final construction.

857 Brock Street, Winter Park

2 Beds ⋅ 2 Baths ⋅ Lancelot/Winter Park SubDv. ⋅ 32792 Zip Code

LOCATION! Welcome to this beautifully maintained 2-bedroom, 2-bathroom second -floor-unit condo in Winter Park, offering comfort, convenience, and peace of mind, with major updates completed in august 2026. A fully renovated with new flooring, updated fixtures. The kitchen has also been, stone countertops, and a full suite of stainless steel appliances. Located near the University of Central Florida, Full Sail University, and SR-417, this condo offers quick access to major commuting routes, shopping, dining, and everyday essentials. Whether you're looking for a primary residence or a long-term investment opportunity, this property combines location, functionality, and value in one of Orlando's most connected areas.

Winter Park

4 Beds ⋅ 3 Baths ⋅ Whisperwood Condo SubDv. ⋅ 32792 Zip Code

OWNER FINANCE may be available with down payment. Unique 4 Bedroom 3 bath unit. Perfect for investors looking to rent to college attendees at UCF and surrounding or for larger families needing 4th bedroom. Lots of upgrades including 2 new bathrooms, new laundry room, new flooring and lots of new paint. Brand new AC system installed in 2025 and hot water heater in 2022. Granite counters, stainless appliances, ceiling fans and tons of storage. Rear screened and covered lanai off living room, covered and open rear private yard/ garden off kitchen and private balcony off master bedroom. Minutes to UCF, lots of shopping and all major highways

7487 Canford Court Unit 5, Winter Park

5 Beds ⋅ 6 Baths ⋅ Kenilworth Shores Sec 01 SubDv. ⋅ 32792 Zip Code

Under Construction. Situated on a prominent corner lot in one of Winter Park's most desirable neighborhoods, this exceptional new construction residence makes an unforgettable first impression with its commanding architecture, refined craftsmanship, and remarkable attention to detail. Every element of the home has been designed to deliver a level of luxury rarely found at this price point, creating a residence that is both visually striking and exceptionally functional. A dramatic entry sets the tone from the moment you step inside, where a custom paneled feature wall and ceiling with integrated lighting create an architectural statement. Beyond the foyer, the expansive great room unfolds beneath soaring ceilings, anchored by a stunning entertainment wall featuring custom millwork, integrated LED lighting, and a sleek electric fireplace that serves as the centerpiece of the home's main gathering space. Oversized glass doors invite natural light throughout while seamlessly connecting the interior to the outdoor living areas. Designed for both everyday living and effortless entertaining, the chef's kitchen is as beautiful as it is functional. Custom cabinetry provides an abundance of storage, complemented by quartz countertops, an oversized center island, and a complete suite of premium Thermador appliances, including a built-in coffee system and paneled refrigerator. Just beyond, a spacious walk-in pantry offers extensive additional cabinetry, generous prep space, and a second dishwasher, making hosting on any scale effortless. The first-floor primary suite offers a private retreat with direct access to the backyard and resort-style pool. Its spa-inspired bath features dual vanities, an expansive walk-in shower, and a freestanding soaking tub, while the extraordinary custom closet by Hommes Design elevates everyday living with integrated LED lighting, a center island, and meticulously designed storage. A second downstairs bedroom, a highly sought-after feature rarely found in Winter Park, provides exceptional flexibility for guests, extended family, or a private home office. Upstairs, a spacious bonus room creates an additional living space complete with its own custom entertainment center, integrated LED lighting, and electric fireplace. A second primary suite, two additional generously sized bedrooms, and a private balcony complete the upper level, offering an ideal layout for large families and guests alike. The outdoor living experience is equally impressive. A covered lanai with a full summer kitchen overlooks a striking L-shaped pool with a raised spillover spa, while the oversized backyard and expansive side yard provide an exceptional amount of green space. The home also features a dedicated pool bath for functionality. Located just minutes from Cady Way Park, the Winter Park YMCA, and the boutiques and restaurants of Park Avenue, this residence also benefits from one of Winter Park's fastest-transforming corridors, where significant investment and redevelopment continue to enhance the area's long-term appeal. Combining exceptional architecture, thoughtful design, and an outstanding package of upgrades, this is a rare opportunity to own one of the most impressive new homes available in Winter Park today.

1901 Loch Berry Road, Winter Park

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

Experience a rare expression of design-forward lakefront living on Lake Sylvan in the heart of Old Winter Park. Fully remodeled through a comprehensive, down-to-the-studs transformation, virtually every major component is new—giving this approximately 2,400-square-foot residence the quality, systems and finishes of a modern custom home. Framed by mature live oaks and sweeping 180-degree water views, the home combines refined craftsmanship and extraordinary lakefront serenity with warm European Contemporary architecture influenced by Belgian design and Organic Modern principles. Expansive, minimalist-profile windows frame the water from nearly every principal living space, while a dramatic 12-foot sliding glass wall connects the open living area to approximately 1,500 square feet of additional outdoor living. Multiple terraces, an integrated outdoor kitchen and beautifully landscaped surroundings create an exceptional setting for waterfront entertaining or quiet mornings beneath the oak canopy. Inside, natural wood, matte black accents, architectural lighting and tactile materials establish a cohesive, warm and inviting aesthetic. Custom white oak wall panels made in Spain, hand-cut white oak beams and architectural transitions, a textured brick feature wall, built-in Sonos audio and a dedicated entertaining bar reflect the attention given to every detail. The European-inspired kitchen features full-height cabinetry incorporating materials imported from Portugal, extensive integrated pantry storage, a Thermador appliance suite with a 36-inch range and griddle, and a Miele steam oven. Positioned at the heart of the living area, the kitchen creates an effortless setting for everyday life and entertaining, always with the lake close at hand. Each of the home’s three bedrooms includes a private en-suite full bath, with an additional powder room serving the common areas. A flexible lake-view office—currently used as a fitness and sauna studio—offers an inspiring setting for work, wellness or creative pursuits. The primary suite opens through nearly eight feet of accordion-style glass doors to a private rooftop terrace, inviting morning coffee, yoga, sunbathing or evening movies beneath the sky. Beyond its architectural design, the comprehensive transformation includes a new roof and roof components, electrical wiring, plumbing and piping, four-zone HVAC system, windows, stucco, drywall, flooring, kitchen and bathrooms. The result combines the character, proportions and established setting of an Old Winter Park home with the quality, efficiency and peace of mind expected from a modern custom residence. Turnkey, distinctive and intimately connected to the water, this exceptional home brings together architectural vision, modern livability and the coveted Winter Park lifestyle on the shores of Lake Sylvan.

1420 Aloma Avenue, Winter Park

4 Beds ⋅ 4 Baths ⋅ Lakeview Terrace SubDv. ⋅ 32789 Zip Code

Welcome to modern luxury in the heart of Winter Park! This custom 2014-built estate rests on an expansive double lot in the highly sought-after Lakeview Terrace community. Offering nearly 3,800 sq. ft. of sophisticated yet comfortable living space, this 4-bedroom, 3.5-bath residence combines timeless architectural details—including soaring vaulted ceilings, crown molding, and dark hardwood floors—with the ultimate layout for functional living. An inviting foyer with volume ceilings and a large transom window fills the home with natural light, leading into a spacious family room anchored by a marble-wrapped electric fireplace with custom lighting and a media niche. The chef’s kitchen is open, bright, and ideal for entertaining, featuring 42-inch shaker double-stacked cabinetry, premium Bosch stainless steel appliances, granite countertops, a designer backsplash, a large pantry, and peninsula bar seating alongside an eat-in breakfast nook. Seamlessly connected, the formal dining room shines with a tray ceiling, custom wallpaper, and designer fixtures. Convenience continues in the oversized laundry room, equipped with a second refrigerator and secondary pantry. Designed for total flexibility, the main level features a dedicated executive office, a media room, a secondary guest suite, and a lavish primary retreat. The primary suite boasts custom built-ins, a massive walk-in closet, direct outdoor access, and a spa-inspired bath with double vanities, a soaking tub, and a large dual-head shower. Upstairs, you’ll find two additional spacious bedrooms, a full bath, and a versatile bonus loft. Outside, a private resort oasis awaits with an open-air lanai and covered porch for alfresco dining, surrounded by lush mature landscaping, pathways trimmed with turf grass, and professional landscape lighting. The heated pool and spa feature a sun shelf with a fountain feature and linear fire elements along the edge that transform the backyard at night. Completing the estate is a 3-car total garage layout, featuring an attached 2-car garage plus a separate detached structure with guest house, studio, or private office potential. Located just one mile from historic Park Avenue, zoned for top-rated schools (Lakemont Elementary, Glenridge Middle, Winter Park High), and walkable to Phelps Park, the YMCA, and local dining.

1840 Bryan Avenue, Winter Park

1 Beds ⋅ 1 Baths ⋅ Waterfall Cove At Winter Park Condominium D107 SubDv. ⋅ 32789 Zip Code

Don't miss out the great opportunity to own a unit in the heart of Winter Park Area. A perfect primary or secondary residence or investment home. Waterfall Cove is a great community with spacious pool, playground and lots of lush landscaping. Easy access to Major Highways a minute from I-4, bike away from Downtown Winter Park, close to major theme parks, major shopping area, restaurant, movie theater and a short drive to Cocoa Beach.

1695 Lee Road Unit D107, Winter Park

3 Beds ⋅ 3 Baths ⋅ Hidden Oaks Condo Ph 01 SubDv. ⋅ 32792 Zip Code

Welcome To This Beautifully 3 Bedroom, 2.5 Bathroom Condominium Located in the Desirable Hidden Oaks Community. Offering Updated Living Space, This Home Combines Comfort, Style, and an Unbeatable Location. Step Inside to a Spacious and Inviting Family Room Featuring Beautiful Laminate Flooring, Abundant Natural Light, and an Open, Welcoming Atmosphere. The Updated Kitchen Is Sure to Impress with Quartz Countertops, Stainless Steel Appliances, and A Sliding Glass Door That Opens to a Private Patio—Perfect for Relaxing or Entertaining. Upstairs, You'll Find All Three Bedrooms and Two Full Bathrooms, including a Generously Sized Primary Suite with a Walk-In Closet and Large Front-Facing Windows That Fill the Room with Natural Light. Residents of Hidden Oaks Enjoy a Peaceful Setting with Access to a Community Swimming Pool, Assigned Parking, And Plenty of Guest Parking. Ideally Located Just Minutes from Major Highways 408 And 417, This Home Is Only 4 Minutes from Full Sail University, Minutes from the University of Central Florida (UCF), Downtown Orlando, and Conveniently Close to Valencia College, Rollins College, Winter Park Shopping and Dining, Restaurants, and Everyday Conveniences. The Property Is Also Zoned for Highly Desirable Winter Park Schools, Making It an Excellent Choice for Homeowners and Investors Alike. Don't Miss This Move-In-Ready Opportunity in One of the Area's Most Convenient Locations!

7413 Belle River Court Unit 3, Winter Park

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

Brand new roof. Conveniently located between downtown Winter Park and College Park with easy access to shopping, restaurants and highways. Zoned for Audubon Park K-8 for elementary and middle school. All the amenities one could want in this luxurious townhome. Tall ceilings and doorways throughout home. Custom tile floors on the first floor with a gas fireplace in the great room. Two patios featured on the first floor, a pavered and covered rear and side patio perfect for BBQs or teatime. The kitchen is equipped with stainless and gas appliances for the chef in your family. Granite countertops throughout home. Wood stairs take you to the second floor with a generous primary bedroom, a light and bright guestroom and a bonus living space complete with a wet bar. Balcony from each suite. Washer and dryer conveniently located upstairs near the two bedrooms. There is no HOA and the home features a low maintenance yard. This townhome will not disappoint you.

1071 Aragon Avenue, Winter Park

3 Beds ⋅ 2 Baths ⋅ Lake Waunatta Wods SubDv. ⋅ 32792 Zip Code

MOVE IN READY! New roof, new bathrooms, new kitchen, new floors, new electrical panels and more. Located in the beautiful lake community of Lake Waunatta Woods. Large private lot on greenbelt. 3 bedroom, 2 bath POOL home with 2 masters and split floor plan. The second master has outside entrance for option to use as a mother-in-law suite or rental. Spacious living room/dining room, family room, laundry room and 2 car garage. Beautiful pool area with screened porch and two patios. Just minutes to UCF and Full Sail University. Easy access to 417 and 15 minutes to downtown Winter Park, walk to Publix and Target. Fast closing available. Don't miss this gem, pack your bags and live life in this mini retreat that you will call home!

4026 Tenita Drive, Winter Park

4 Beds ⋅ 3 Baths ⋅ Park Pointe Rep SubDv. ⋅ 32789 Zip Code

A MUST SEE BEAUTIFUL WELL MAINTAINED POOL HOME by ORIGINAL OWNERS in SOUGHT AFTER WINTER PARK ZIPCODE & SCHOOLS. PICTURES PROVIDE a GREAT PORTRAYAL of the FLOORPLAN but THERE ARE MANY FEATURES TO POINT OUT - THIS 2868 SQFT HOME has a 3-WAY SPLIT with 4 BEDROOMS, 3 FULL BATHROOMS, plus BONUS ROOM & OFFICE. YOU WILL NOT BELIEVE ALL THE STORAGE, STORAGE, STORAGE UNDER AIR! The BONUS ROOM (12.4 X 11.7) OFF PRIMARY BEDROOM COULD BE a NURSERY, OFFICE, EXERCISE ROOM, or OWNERS RETREAT. There is an ADDITIONAL OFFICE (13.6 X 11.6 ) with BUILT N DESK & STORAGE CABINETS MAKING a GREAT HOMESCHOOL ROOM, CRAFT AREA, or HOME OFFICE WHERE a PRIVATE EXTERIOR ENTRY DOOR is NEEDED. ONE BEDROOM could be USED as an IN-LAW SUITE with IT’S ENSUITE BATHROOM with SHOWER. The SPACIOUS GARAGE has NEW SHARK FLOORING (7/26), NEW PAINT, NEW ELECTRIC CAR CHARGING OUTLET (6/26), NEW INSULATED GARAGE DOOR & A MINI SPLIT AC – LOTS OF POSSIBILITIES! MANY FUN MEMORIES can be ENJOYED with FAMILY & FRIENDS AROUND the BEAUTIFUL SCREENED POOL & LARGE COVERED LANAI & DECK ( RESURFACED 9/25 ) The NEW OWNER of this LOVELY HOME will APPRECIATE all the UPDATES that have BEEN DONE over LAST FEW YEARS – NEW $29K LENOX UPGRADED AC (3/26), NEW FRONT DOOR (4/26), NEW GOOGLE NEST DOORBELL (3/26), NEW INSULATION in ATTIC & ON GARAGE DOOR (6/26), NEW PAVER DRIVEWAY (5/26 ) NEW UPGRADED FLASHING AROUND CHIMNEY (5/26), GAS TANKLESS WATER HEATER W RECIRCULATING FEATURE(2023), NEW DUCT WORK (2019) NEW WINDOWS (2020), WHOLE HOUSE REPLUMBED (2020), ROOF (2016), STAINLESS APPLIANCES (2019), WHOLE HOUSE WATER SOFTNER & DOUBLE OSMOSIS SYSTEM for DRINKING WATER, SELLER WILL CONSIDER CARPET ALLOWANCE WITH ACCEPTABLE OFFER. ****** THIS HOME IS WORTH SEEING ******

2667 Cochise Trail, Winter Park

3 Beds ⋅ 2 Baths ⋅ Stansbury Estates SubDv. ⋅ 32789 Zip Code

Tucked away on a quiet street just minutes from the heart of Winter Park, this beautifully updated bungalow offers the perfect blend of character, modern updates, and flexibility. The true standout is the detached 1-bedroom, 1-bath guest house, a rare feature that's ideal for visitors, a private home office, fitness studio, creative space, or even an income-producing opportunity. The main home features two spacious bedrooms and a beautifully renovated bathroom, while timeless charm is showcased throughout with original hardwood floors, crown molding, custom built-ins, and an open-concept living space. The thoughtfully designed kitchen combines butcher block and custom concrete countertops with quality appliances, while the adjacent laundry and utility room adds extra functionality. Step outside to a backyard designed for year-round Florida living. The covered patio, complete with café lighting and ceiling fans, overlooks a fully equipped outdoor kitchen with custom concrete countertops, creating the perfect setting for entertaining. Lush tropical landscaping, an outdoor shower, and abundant storage complete the private outdoor oasis. Beyond its charm, this home is packed with practical upgrades including a metal roof, whole-house natural gas generator, and an exterior security camera system, providing comfort and peace of mind through every season.

2007 Cornell Avenue, Winter Park

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

Under Construction. Perfectly positioned along one of Winter Park's most picturesque tree-lined cobblestone streets, this exceptional new construction residence offers a rare opportunity to own a home where timeless architecture, refined craftsmanship, and an unrivaled location come together. A striking marble mosaic foyer creates an unforgettable first impression, immediately setting the tone for the level of detail found throughout the residence. Just off the entry, a dedicated home office provides the ideal space for working remotely or enjoying a quiet retreat. Beyond, the thoughtfully designed floor plan unfolds into expansive living spaces filled with natural light and connected by effortless flow. The great room serves as the heart of the home, highlighted by a custom-built entertainment wall with integrated LED lighting, a sleek electric fireplace, and oversized sliding glass doors that blur the line between indoor and outdoor living. Designed for both everyday living and elegant entertaining, the chef's kitchen is a showpiece. Taj Mahal quartzite countertops are paired with an exceptional suite of Thermador appliances, including a paneled built-in refrigerator, while extensive custom cabinetry provides an abundance of storage without compromising the clean, sophisticated aesthetic. The adjoining dining room creates an inviting setting for gatherings and is complemented by a beautifully appointed dry bar complete with a wine refrigerator, making entertaining effortless. Privately situated on the main level, the primary suite is a true retreat with direct access to the lanai through expansive sliding glass doors. The spa-inspired bath showcases exquisite marble mosaic tile, dual vanities, a freestanding soaking tub, an oversized walk-in shower, and a generous custom walk-in closet, creating a space that feels both luxurious and serene. Upstairs, three spacious guest bedrooms are thoughtfully arranged alongside a comfortable secondary living area and an expansive bonus room, offering remarkable flexibility for a media room, game room, fitness studio, or additional gathering space. The outdoor living experience is equally impressive. A spacious covered lanai is designed for year-round enjoyment, featuring a fully equipped summer kitchen, generous space for alfresco dining and entertaining, a sparkling pool and spa, and ample green space for recreation or relaxation. While the home's finishes and craftsmanship are exceptional, it is the location that truly sets it apart. Enjoy the rare privilege of walking to the boutiques, award-winning restaurants, and vibrant atmosphere of Park Avenue, the campus of Rollins College, Virginia Park, and the acclaimed East End Market. Zoned for highly sought-after Audubon K-8 and surrounded by the charm and character of the Lake Sue District, this is more than a home; it's a statement of luxury Winter Park living.

361 E Kings Way, Winter Park

3 Beds ⋅ 2 Baths ⋅ Waterfall Cove SubDv. ⋅ 32789 Zip Code

Vacant! Great location! Must See! New paintinf interior, and new carpet. The best area at Winter Park, close to major shoppiing center,

1695 Lee Road Unit A101, Winter Park

4 Beds ⋅ 5 Baths ⋅ Villa View Park SubDv. ⋅ 32789 Zip Code

Custom-built Santa Barbara-style estate set on one of Winter Park's most coveted brick-paved streets, just moments from Park Avenue's boutiques, galleries and celebrated restaurants, Winter Park Golf Course, Winter Park Racquet Club, historic Rollins College and vibrant Winter Park Village. Built in 2010, this four-bedroom, 4.5-bath residence spans 3,661 square feet across two floors, with cathedral ceilings, a cozy fireplace and colonial windows and French doors, which frame the resort-style pool retreat. A gracious main-floor primary suite offers dual vanities and a large walk-in closet. The double-island chef's kitchen features a gas range and premium Thermador appliances, anchoring an open-plan living, dining and kitchen design, modeled for everyday ease and effortless entertaining. A flexible bonus space is ideal for a home office, formal dining or gym. Upstairs, three additional spacious bedrooms each offer their own en-suite bath and walk-in closet. The home wraps around a covered courtyard leading to the heated saltwater pool and spa, creating a private outdoor enclave. Parking is a breeze with an oversized two-car garage, additional golf cart parking, plus utility pad. Ample storage and workspace complete the rear of the property, which is also wired for a future whole-home generator. A rare offering in the heart of Winter Park, where timeless design meets an unmatched lifestyle.

645 Pansy Avenue, Winter Park

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

There are luxury homes, and then there are homes that redefine luxury altogether. Crafted by renowned luxury builder Vimaro Homes, this extraordinary residence is the product of meticulous vision, extraordinary craftsmanship, and an unwavering commitment to quality. Every space has been curated to create one of the most refined and meticulously executed homes to ever come to market in Winter Park. Situated on an expansive 15,000-square-foot homesite in the coveted Park Grove neighborhood, just moments from the boutiques and acclaimed dining of Park Avenue, the home immediately captivates with its striking architectural presence and a sweeping double-entry driveway. Beyond the front doors, a breathtaking foyer unfolds beneath soaring 22-foot ceilings, where an elegant, curved staircase, intricate marble mosaic flooring, oversized windows, and meticulous millwork establish a level of craftsmanship rarely found in today's market. Chevron-pattern engineered hardwood flooring extends throughout, complemented by exquisite natural marble and thoughtfully curated designer finishes at every turn. Designed to impress while remaining effortlessly livable, the grand living room features illuminated tray ceilings, a custom-built entertainment wall, and a sleek electric fireplace. The chef's kitchen is a true showpiece, anchored by dramatic Calacatta Viola marble countertops and backsplash, a complete Thermador appliance suite with paneled refrigerator and freezer, and a stunning ILVE range. An expansive butler's pantry with a second sink, double oven, warming drawer, dishwasher, and abundant preparation space elevates both entertaining and everyday functionality, while formal and casual dining spaces provide the perfect setting for gatherings of any scale. The primary suite is a private sanctuary designed for ultimate comfort, featuring its own coffee bar, an extraordinary custom dressing room. The primary also features a spa-caliber bath appointed with striking marble finishes, a dramatic illuminated walk-in shower, freestanding soaking tub, and Perrin & Rowe fixtures. A first-floor guest suite or dedicated office offers exceptional flexibility, while upstairs, three spacious en-suite bedrooms with walk-in closets are complemented by a hidden bonus room. Pocketing glass doors create a seamless transition to an exceptional outdoor retreat complete with a covered lanai featuring retractable screens, a fully equipped summer kitchen, resort-style pool and spa, expansive backyard, and professionally curated landscaping. Located just minutes from Park Avenue and surrounded by top-rated schools, this residence is more than a luxury home, it is a statement of artistry, craftsmanship, and timeless design that redefines what luxury new construction can be in Winter Park.

1525 Granville Drive, Winter Park

4 Beds ⋅ 4 Baths ⋅ Kenilworth Shores Sec 01 SubDv. ⋅ 32792 Zip Code

Thoughtfully designed with an uncompromising commitment to quality, craftsmanship, and detail, this exceptional new construction residence is an expression of luxury living. Defined by its striking architecture and refined contemporary design, the home makes an unforgettable first impression with a dramatic two-story foyer featuring soaring ceilings, a statement staircase with custom millwork, designer lighting, and LED accent illumination. Just beyond, a custom wine display with Dekton surfaces and integrated lighting, creates a sophisticated focal point while introducing the exceptional finishes found throughout the home. Designed for both everyday living and effortless entertaining, the expansive great room is anchored by a floor-to-ceiling custom millwork feature wall with integrated LED lighting and a sleek electric fireplace. Oversized sliding glass doors create a seamless connection to the outdoor living spaces, while the chef's kitchen serves as the heart of the home with custom cabinetry, quartz countertops, extensive under-cabinet LED lighting, a premium appliance package, and an oversized walk-in pantry. Located on the main level, the primary suite offers a peaceful retreat with direct access to the lanai and pool. The spa-inspired bath features dual vanities with backlit mirrors, a freestanding soaking tub, an expansive walk-in shower, and a custom walk-in closet. Upstairs, a spacious loft provides an ideal secondary gathering space complete with a stylish dry bar and built-in wine refrigerator. Three additional bedrooms offer generous accommodations for family and guests, each finished with the same exceptional attention to detail. Outdoor living is equally impressive with a massive covered lanai featuring a fully equipped summer kitchen, an additional electric fireplace, and generous space for dining and relaxation. Beyond, a resort-style pool with a spillover spa is complemented by an expansive backyard and side yard. Ideally located just minutes from Cady Way Park, AdventHealth Winter Park, and the shopping, dining, and charm of Park Avenue, this exceptional residence offers the perfect blend of luxury, convenience, and lifestyle. With craftsmanship and design rarely found at this price point, this is a home that is both timeless and unforgettable.

525 S Lakemont Avenue, Winter Park

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There are 250 homes for sale in Winter Park, Florida as of 2026-08-21, at a median list price of $757,000 and a median of 54 days on market. Every active Winter Park listing is above, newest first. What follows is what those listings add up to.

Winter Park market at a glance

Active listings	250
Median list price	$757,000
Median price per square foot	$421
Median size	1,936 square feet
Median year built	1974
Median days on market	54
On market 60+ days	116 (46.4%)
Priced below original asking	115 (46.0%)

Source: Stellar MLS via the Bridge RESO feed, pulled 2026-08-21. Updated weekly.

What the numbers say for Winter Park buyers

46.0% of Winter Park listings are asking less than they did on day one, and 46.4% have been on the market 60 days or longer. Those two figures are the practical case for making an offer here. A seller 54 days in who has already cut once is a different negotiation than a listing that went live last week.

The typical reduction so far has been 6.29% off the original asking price. That is the size of a first concession, not a final one.

Winter Park homes by price range

Under $250,000	49	19.6%
$250,000 to $400,000	16	6.4%
$400,000 to $600,000	36	14.4%
$600,000 and up	149	59.6%

Property types in Winter Park

Single Family Residence	163
Condominium	68
Townhouse	18
1/2 Duplex	1

Neighborhoods and subdivisions in Winter Park

Every Winter Park subdivision with at least 4 active listings, ranked by inventory. These 89 homes are 36% of the Winter Park market; the rest are in smaller subdivisions or on unplatted land.

Subdivision	Active	Median price	Median DOM	Price per sq ft
The Enclave Winter Park	10	$2,074,500	55	$543
Kenilworth Shores	9	$1,800,000	63	$571
Lake Knowles Terrace	7	$995,000	14	$532
Hidden Oaks Condo	6	$195,000	43	$179
Glencoe	5	$630,000	72	$295
Winter Park Village	5	$1,100,000	90	$543
Lawndale	5	$1,400,000	89	$442
Golfside Villas Condo	5	$138,000	53	$173
Winter Park Pines	5	$669,900	42	$331
Colonies	4	$149,500	101	$145
Winter Park Estates	4	$502,500	52	$300
Lakeside Manor Apts Condo	4	$192,400	70	$248
Chateaux Du Lac	4	$236,450	77	$232
Winter Park Woods Condo	4	$82,500	30	$78
Killarney Estates	4	$1,262,500	11	$837
Charmont	4	$2,749,000	26	$829
Whisperwood Condo	4	$199,000	106	$141

Subdivision names come from the MLS as agents entered them. Counts as of 2026-08-21.

About Winter Park

Winter Park is a city of 29,795 at the 2020 census, founded as a resort community by northern business magnates in the late nineteenth and early twentieth centuries. It is home to Rollins College, a private liberal arts college.

European settlement dates to 1858, when David Mizell Jr. bought an eight-acre homestead between Lakes Virginia, Mizell and Berry. The settlement around it was called Lake View, and it got its first post office in 1870.

It did not grow quickly until 1880, when the South Florida Railroad laid track between Orlando and Sanford a few miles west, and Loring Chase arrived from Chicago.

Winter Park zip codes

32789 (175 listings), 32792 (75 listings)

Winter Park homes by property type

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Frequently asked questions

How many homes are for sale in Winter Park, FL?

There were 250 active residential listings in Winter Park as of 2026-08-21, at a median list price of $757,000. That count comes from the Stellar MLS feed and is refreshed weekly.

What is the median home price in Winter Park, FL?

The median list price in Winter Park was $757,000 as of 2026-08-21, or about $421 per square foot. The median home on the market is 1,936 square feet and was built in 1974.

How long do homes take to sell in Winter Park?

Median days on market was 54 as of 2026-08-21. 116 listings, 46.4% of the Winter Park market, have been listed 60 days or longer, and that is where most of the negotiating room sits.

Are Winter Park sellers reducing their prices?

115 Winter Park listings, 46.0% of the market, are now asking less than they did originally, at a median reduction of 6.29%. That is the size of a typical first concession here, and it is usually not the last one.

What neighborhoods are in Winter Park, FL?

133 named subdivisions had at least one active listing in Winter Park as of 2026-08-21. 17 of them had 4 or more, and those are listed above with their own median price and days on market. The Enclave Winter Park led with 10 active listings at a median of $2,074,500.

What zip codes cover Winter Park, FL?

Winter Park listings sat in 2 zip codes as of 2026-08-21: 32789 with 175 active listings, 32792 with 75 active listings.

The Homes In Orlando Team at NextHome Neighborhood Realty covers Orange, Seminole, Lake and Volusia counties. Call or text 407-616-9019 to see any Winter Park listing on this page.