Location: Winter Park
Do Not Show Listings
2521 GALLIANO CIR, WINTER PARK, FL 32792
$350,00035 Days on yellowkey MLS ID: O6419329
REDUCED by $10,000 (2.8%) on 07/22/2026
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1682 Built: 2003Monthly Fee: $175 Tax: $4,532 (2025)Community: Vistas At Lake HowellTownhouse
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$4,532
Elementary School: Sterling Park Elementary
High School: Lake Howell High
Tax Year: 2025
Middle School: Tuskawilla Middle
Remarks: Welcome to this beautifully maintained townhome located in the heart of Winter Park, Florida. From the moment you arrive, the charming exterior draws you in with its classic stucco finish, attached one-car garage, manicured landscaping, and a welcoming shaded entry framing the front door. Step inside to an inviting foyer featuring high ceilings, modern lighting, and a striking staircase that sets a stylish tone for the rest of the home. The main level transitions into an expansive, light-filled open concept floor plan seamlessly connecting the living room, dining area, and kitchen. Rich wood-look LVP flooring runs throughout the entire lower level, perfectly complementing the crisp neutral walls and providing a cohesive, contemporary aesthetic. The spacious living and dining areas offer an exceptional layout for both daily living and effortless entertaining. Large sliding glass doors at the rear of the home flood the living space with natural light and open directly to a private, screened-in back patio, making it easy to enjoy the Florida breeze. Overlooking the dining area is a spacious kitchen, which features a half-wall cutout that keeps the chef connected to the conversation. Equipped with plenty of warm wood cabinetry, neutral countertops, a deep double sink, and a suite of white appliances, this kitchen is as ample as it is welcoming. A convenient guest half-bathroom with a pedestal sink completes the well-designed ground floor layout. Head upstairs to discover the private living quarters, where the beautiful wood-look flooring continues through the hallway and into each spacious bedroom. The expansive primary suite serves as a true retreat, boasting high vaulted ceilings, an elegant modern ceiling fan, a massive walk-in closet with built-in wire shelving, and a trio of large windows that fill the space with cheerful morning light. This main bedroom easily accommodates king-sized furniture and offers the luxury of an attached en-suite bathroom with dual sinks. The additional bedrooms are equally impressive, each featuring soaring vaulted ceilings, updated stylish ceiling fans, and generous closet space near the dedicated upper-level laundry closet, which comes equipped with a washer and dryer. The outdoor and utility spaces add tremendous value and convenience to this efficient property. The attached garage features an open, clean layout perfect for secure parking, extra storage, or a small home workshop area. At the back of the home, the deep screened-in patio is an ideal spot for outdoor dining, grilling, or relaxing in the shade. The patio steps out onto a beautiful community green belt with pristine lawns and mature shade trees, offering a peaceful residential backdrop. Nestled in a premium, tree-lined enclave, the community boasts pristine, winding roads, manicured privacy hedges, and a scenic retention pond complete with a flowing water fountain feature. This idyllic neighborhood setting perfectly balances the tranquility of nature with outstanding proximity to nearby lakes, parks, major roadways, and local shopping centers. Don't miss the opportunity to own this pristine, move-in ready retreat in one of Central Florida's most highly sought-after locations.
Listing is courtesy of: LPT REALTY LLC (386-388-7877)
Listing Agent: Daniel Lennon (954-483-9760)
40 PALMER AVE, WINTER PARK, FL 32789
$7,250,000170 Days on yellowkey MLS ID: O6380444
INCREASED by $300,000 (4.3%) on 07/09/2026
Bed: 5 Bath: 5.5 Gar: 4 Liv Area Sq Ft: 5905 Built: 2026 Tax: $12,774 (2024)Community: Robert Dhu Macdonald ParkSpa: YesSingle Family
Taxes:$12,774
Elementary School: Lakemont Elem
High School: Winter Park High
Tax Year: 2024
Middle School: Maitland Middle
Remarks: Under Construction. Opportunities like this rarely present themself, just a eight-minute walk from the iconic shops, restaurants, and cafés of Park Avenue, 40 Palmer represents a rare convergence of architectural significance, uncompromising craftsmanship, and premier Winter Park location. Built by Vimaro Homes, this extraordinary new construction estate is a statement piece that redefines what luxury living looks like in the heart of Winter Park. The exterior architecture is refined yet commanding, with classical influences interpreted through a modern lens, setting the tone for the exceptional level of design and finishes found inside. One of the most remarkable features, and an offering rarely found in Winter Park, is the underground four-car garage. Designed to discreetly accommodate an impressive vehicle collection, the garage is complemented by a striking spiral staircase that rises from the basement through the main living level and continues to the second floor. The family room is nothing short of breathtaking, featuring bespoke millwork with integrated shelving, soft architectural lighting, and a dramatic fireplace wrapped entirely in marble. The kitchen is a culinary showpiece designed for those who expect nothing less than perfection. Calcutta marble countertops cascade across the space, paired with stunning custom cabinetry, and a professional-grade Thermador appliance suite. A dedicated dirty kitchen allows for discreet preparation, while an expansive walk-in pantry ensures effortless hosting and immaculate presentation. The primary bedroom wing features a spa-inspired bathroom finished in rich marble, featuring dual vanities, a freestanding soaking tub and an enormous walk-in closet with a separate washer and dryer. Upstairs, a dedicated laundry room and a spacious secondary living area provide flexibility for family living, guests, or relaxation. The lower level extends the home’s versatility, offering a workshop, dedicated holiday and seasonal storage, and seamless elevator access to the main level of the home. Outdoor living is equally impressive. A large covered exterior lanai with a pool bath and full summer kitchen creates a seamless indoor-outdoor lifestyle, ideal for entertaining year-round. The backyard is truly resort-inspired, featuring a large swimming pool, sunken fire pit, and spa, all set within a private, beautifully secluded outdoor setting. What ultimately sets 40 Palmer apart is not just its design or finishes, but its unmatched combination of luxury and location. Just minutes from Park Ave shopping and restaurants, moments from the famous Winter Park Golf Course, yet privately tucked away, this home offers a lifestyle that is both vibrant and exclusive. A truly rare opportunity to own a part of the exceptional standard of living delivered by Vimaro Homes.
Listing is courtesy of: ONE LUXURY INTERNATIONAL LLC (407-312-8003)
Listing Agent: Julie Christensen (407-592-2055)
2033 CANNY CV, WINTER PARK, FL 32792
$399,0008 Days on yellowkey MLS ID: O6426457
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1907 Built: 2023Monthly Fee: $375 Tax: $6,887 (2025)Community: Grayson SquareTownhouse
Taxes:$6,887
Elementary School: None
High School: None
Middle School: None
Remarks: Step into this beautifully designed townhome featuring an open-concept kitchen, dining, and living area—perfect for everyday living and entertaining. The modern kitchen boasts stainless steel appliances, gray cabinetry, and quartz countertops. Upstairs, the spacious primary suite offers a walk-in closet and a private in-suite bath with dual quartz vanities, while two additional bedrooms, a full bath, and a convenient laundry closet complete the second floor. Relax on the covered lanai and enjoy the privacy of this home's cul-de-sac location. The HOA includes landscaping, exterior maintenance and repairs, high-speed internet, and access to the gated community, providing low-maintenance living. With no CDD, this home is an excellent option for both homeowners and investors. Ideally located in highly desirable Winter Park, Grayson Square is just minutes from SR-436, SR-434, and SR-417, with Publix, Starbucks, shopping, dining, and top-rated Seminole County schools nearby. Park Avenue is only a short drive away, making this home the perfect combination of convenience, comfort, and value.
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Monica Puche (407-545-0692)
2831 MULFORD AVE, WINTER PARK, FL 32789
$675,00052 Days on yellowkey MLS ID: O6414319
REDUCED by $20,000 (2.9%) on 07/21/2026
Bed: 4 Bath: 2.5 Liv Area Sq Ft: 1647 Built: 1952 Tax: $3,192 (2025)Community: Orangewood ParkSpa: NoSingle Family
Taxes:$3,192
Remarks: Just Reduced by $20,000! This is your chance to own a beautifully updated Winter Park home at an even better value. Come see it before it’s gone! Rare opportunity to own on one of the most desirable streets in Audubon Park with a coveted Winter Park address. Just a few blocks from East End Market and surrounded by many of Orlando’s Michelin-recognized restaurants, this location offers an unbeatable combination of walkability, lifestyle, and top-rated schools. Zoned for Audubon Park K-8 and Winter Park High School, you’ll enjoy the best of both worlds: the character and community of Audubon Park with the prestige and convenience of Winter Park. This thoughtfully updated home features a 2024 roof, tankless water heater, new carpet, fresh interior and exterior paint, newer insulation, solid-core interior doors, Rain Bird irrigation with well, Vivint security system with cameras, and an Ecobee smart thermostat. The sunken living room creates a unique space for entertaining (it can provide stadium seating or be a conversation pit), while the detached mother-in-law suite adds flexibility for guests, multigenerational living, or rental income. Tucked away from the noise of Corrine Drive yet only blocks from East End Market, neighborhood parks, coffee shops, and dining, this is a rare chance to own in one of Orlando’s most sought-after neighborhoods. Front door does not convey and will be replaced with a similar refinished wood door prior to closing.
Listing is courtesy of: UNITED REAL ESTATE PREFERRED (407-243-8840)
Listing Agent: Patrick Arenson (305-951-6054)
2500 LEE RD #208, WINTER PARK, FL 32789
$175,000474 Days on yellowkey MLS ID: O6297570
0 Days Off yellowkey (back on 7/21/2026)
REDUCED by $5,000 (2.8%) on 05/14/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 956 Built: 1969Monthly Fee: $432 Tax: $1,519 (2025)Community: Lakeside Manor Apts CondoCondo
Taxes:$1,519
Elementary School: Killarney Elem
High School: Edgewater High
Middle School: College Park Middle
Remarks: Under contract-accepting backup offers. This charming two-bedroom, two-bathroom 2nd floor condo offers the perfect blend of comfort and convenience. Featuring tile and luxury vinyl plank flooring throughout, this home provides durability and style for modern living. The HVAC was replaced in 2020 and water, cable and internet are included in the monthly COA fee. Located in a picturesque community ON THE SHORES OF A SKI LAKE, residents will enjoy access to boat slips (based on availability, charge is $30/month), a boat ramp, a sparkling pool, a welcoming clubhouse, and mature landscaping that enhances the serene environment. Outdoor enthusiasts will appreciate the multiple barbeque grills and tables, ideal for courtyard or lakeside dining. Additional amenities include two on-site laundry rooms, on-site storage, and convenient proximity to key destinations. COA approval is required. The application fee is $85.00. Situated in Winter Park, the community is less than 10 minutes from Winter Park Village, Maitland, and Downtown Winter Park, about 10 minutes from College Park, and approximately 15 minutes from Downtown Orlando and Lake Mary. This prime location ensures easy access to shopping, dining, entertainment, and the vibrant city lifestyle.
Listing is courtesy of: KELLER WILLIAMS REALTY AT THE PARKS (407-629-4420)
Listing Agent: Debbie Jones (407-619-1850)
1610 GLADIOLAS DR, WINTER PARK, FL 32792
$410,00032 Days on yellowkey MLS ID: O6420292
REDUCED by $20,000 (4.7%) on 07/21/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1808 Built: 1979 Tax: $1,442 (2025)Community: Garden Lake Estates Unit 1Single Family
Taxes:$1,442
Elementary School: Red Bug Elementary
Remarks: PRICE IMPROVEMENT! This 4-bedroom, 2-bath pool home in the heart of Winter Park is priced to sell and offers an incredible opportunity to make it your own. While the property could use some TLC, it features solid major updates and endless potential to add value. Situated on an oversized lot with NO HOA, this home features a spacious enclosed lanai, perfect for enjoying Florida living year-round. The thoughtfully designed split floor plan offers added privacy, with the primary suite separated from the secondary bedrooms. The recently updated kitchen serves as the heart of the home, while major improvements including a 2023 HVAC system, 2019 water heater, and newer roof, to provide peace of mind for years to come. Whether you're an investor or a buyer looking to personalize a home in one of Central Florida's most desirable locations, this property offers exceptional potential and a rare opportunity in Winter Park.
Listing is courtesy of: LIFESTYLE INTERNATIONAL REALTY (305-809-8085)
Listing Agent: Jasmin Cabral (305-699-8099)
2006 CORNELL AVE, WINTER PARK, FL 32789
$328,00057 Days on yellowkey MLS ID: O6412789
REDUCED by $10,000 (3.0%) on 07/21/2026
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 797 Built: 1940 Tax: $4,795 (2025)Community: Stansbury EstatesSingle Family
Taxes:$4,795
Elementary School: Princeton Elem
Remarks: Welcome home to this charming and fully remodeled 2-bedroom, 1-bathroom gem nestled in the heart of Winter Park AND College Park. 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 hardwood 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.
Listing is courtesy of: FLORIDA HOME TEAM REALTY LLC (407-774-8100)
Listing Agent: Stacia Stephenson (407-415-5700)
241 W LAKE SUE AVE, WINTER PARK, FL 32789
$995,00062 Days on yellowkey MLS ID: O6411621
REDUCED by $4,000 (0.4%) on 07/21/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2304 Built: 1950 Tax: $14,823 (2025)Community: Virginia HeightsSingle Family
Taxes:$14,823
Elementary School: Audubon Park K8
Middle School: Audubon Park K-8
Remarks: Seller is offering a generous $25,000 credit toward price or closing costs, giving the next owner an incredible opportunity to personalize this Winter Park residence to their own taste. While the home could benefit from cosmetic updates, the fundamentals are already in place! A/C system and ductwork (2023), roof (2021), replumb (2026). For the right buyer, this is a rare chance to secure a premier location at a value that’s increasingly hard to find. Welcome to 241 W. Lake Sue Avenue, an exceptional offering in Virginia Heights, one of Winter Park’s most cherished and established neighborhoods. Nestled along a picturesque oak-canopied brick street and surrounded by multimillion-dollar estates, this beautifully updated pool home sits on an oversized 12,000-square-foot lot and delivers the lifestyle that defines Olde Winter Park living. Designed for effortless indoor-outdoor enjoyment, the home features sunlit interiors, soaring ceilings, architectural wood-beam accents, travertine flooring, and inviting gathering spaces that overlook a private backyard retreat. The chef’s kitchen anchors the residence, connecting seamlessly to the living and dining areas while offering serene views of the pool, spa, and lush outdoor living spaces. The spacious primary suite provides a calming escape with vaulted ceilings, a spa-inspired bath, and a generous walk-in closet. What truly sets this property apart is its location within Virginia Heights, where residents enjoy deeded access to a private Lake Virginia waterfront park. Just a short stroll away, homeowners have exclusive use of a private dock, canoe and kayak storage, open green space, and sweeping lakefront views across from Rollins College, an amenity rarely found in Winter Park. Moments from Park Avenue’s boutiques and dining, nearby parks, cultural venues, and top-rated schools, this home blends timeless charm with modern comfort in one of the city’s most coveted enclaves. Opportunities to purchase in Virginia Heights are limited; opportunities with private lake access, an oversized lot, and a resort-style backyard are even rarer. Priced below market value due to cosmetic updates needed, this property invites you to enhance the existing residence or build a new home from the ground up. Either path securing a legacy-worthy homesite in one of Winter Park’s most desirable locations!
Listing is courtesy of: COLDWELL BANKER REALTY (407-647-1211)
Listing Agent: Ken Dalton (407-928-8587)
1841 LAKE SPIER DRIVE, WINTER PARK, FL 32789
$1,595,00063 Days on yellowkey MLS ID: O6407841
REDUCED by $55,000 (3.3%) on 07/02/2026
Bed: 3 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 2467 Built: 1964 Tax: $4,844 (2025)Community: South Lakemont ShoresSpa: NoSingle Family
Taxes:$4,844
Elementary School: Baldwin Park Elementary
Middle School: Glenridge Middle
Remarks: Winter Park lakefront home! A rare opportunity to own a thoughtfully renovated mid century lakefront residence in Winter Park. This three bedroom four bath home offers stunning views, high ceilings and abundant natural light. The open layout flows effortlessly for everyday living and gatherings with friends and family. As you walk through the front door, you will be drawn to the large living area and a wall of windows and doors leading to the lake. The island kitchen is a cook's dream with abundant workspace and welcoming island seating. Imagine waking up every morning to yet another amazing view- The primary suite is spacious and private with newer bath and large walk- in closet. Nicely appointed secondary bedrooms and updated baths. In addition to the main living area, there is a separate oversized family room with a full bath adjacent. This home was completely renovated and expanded in 2013 creating a perfect blend of timeless architecture and carefully designed updates. Other features include two car garage with "glass" overhead doors and mini-split HVAC, metal roof, generous closets & storage throughout and recently installed sod. What makes this house truly special is the setting on Lake Spier- a ski lake tucked away in a secluded part of Old Winter Park . There are no homes across the lake- so spending time on the patio and dock offers an expansive view of water and trees and a remarkable sense of privacy. Inside and out, every space feels connected to the natural beauty. Great location to enjoy Winter Park living. Ideally situated near top rated schools - Baldwin Park, Glenridge and Winter Park High School. Enjoy close proximity to walking trails, restaurants and shopping. This home is truly special!
Listing is courtesy of: FANNIE HILLMAN & ASSOCIATES (407-644-1234)
Listing Agent: Nicole Seybold (407-808-9374)
1113 VIA DEL MAR, WINTER PARK, FL 32789
$1,595,000175 Days on yellowkey MLS ID: O6379697
1 Days Off yellowkey (back on 7/21/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2012 Built: 1957 Tax: $13,924 (2024)Community: Tuscany TerraceSpa: NoSingle Family
Taxes:$13,924
Elementary School: Dommerich Elem
Remarks: Exceptional opportunity in the heart of Winter Park — a truly premier and irreplaceable homesite offering rare scale, privacy, and extraordinary future build potential. The primary value is in the land, presenting an unparalleled canvas for a custom luxury residence, with virtually no comparable vacant land available in the immediate vicinity. Set on a tranquil small lake that provides remarkable serenity and picturesque water views, this property combines peaceful natural surroundings with unbeatable walkability. Ideally positioned just steps from the Racquet Club, moments to Park Avenue’s renowned dining, boutiques, and cultural venues, and within easy reach of the Winter Park Chain of Lakes. The location also offers the distinct prestige of residing within the coveted “Vias” of Winter Park, a collection of streets long regarded as one of the city’s most established and desirable residential enclaves. The existing residence is perfectly livable and has benefited from numerous upgrades, offering flexibility for immediate occupancy while planning a future custom build. The home also presents excellent rental potential. Please note the interior is currently being utilized for storage and does not reflect its full presentation potential, providing an opportunity for cosmetic refresh or personalization. Whether envisioned as a modern architectural statement or an elegant estate home, this site delivers the location, setting, and versatility sought by discerning builders, investors, and end¦users alike — a rare chance to secure one of Winter Park’s most desirable land offerings in a highly established neighborhood.
Listing is courtesy of: BAY HILL REALTY LLC (407-790-9810)
Listing Agent: David Barany (407-790-9810)
1823 SUNSET DR, WINTER PARK, FL 32789
$2,549,00022 Days on yellowkey MLS ID: O6421690
Bed: 5 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 3479 Built: 2026 Tax: $3,358 (2025)Community: Lake Knowles Terrace Add 02Spa: YesSingle Family
Taxes:$3,358
Remarks: Under Construction. Nestled along a quiet street in Winter Park’s coveted Tree Streets, this stunning coastal farmhouse new build delivers the perfect combination of timeless architecture, luxury finishes, and an unbeatable location. From the moment you arrive, the home captivates with its warm and inviting facade, charming architectural details, and exceptional curb appeal. Step inside to an impressive open layout where natural light, designer finishes, and meticulous craftsmanship set the tone. The spacious living room serves as the heart of the home, showcasing a sleek electric fireplace, custom built-in bookshelves with LED accent lighting, and expansive pocketed glass sliding doors that create a seamless connection to the outdoor living space. The chef’s kitchen is a true centerpiece, beautifully appointed with Taj Mahal countertops, custom cabinetry with LED underlighting, a premium Thermador appliance package, and a hidden walk-in pantry that blends functionality with luxury. Flowing effortlessly from the kitchen, the dining area offers the perfect setting for hosting, complete with a custom dry bar, additional cabinetry, and a dedicated wine fridge. Designed with a highly desirable layout rarely found in Winter Park, the first-floor features both the primary suite and an additional guest suite. The primary retreat offers generous proportions, beautiful natural light, and private sliders opening directly to its own lanai. The spa-inspired bathroom provides a true escape with marble mosaic flooring, dual vanities, and an elegant wet room featuring a spacious walk-in shower and freestanding soaking tub. Completing the suite is an expansive walk-in closet with its own stackable washer and dryer for ultimate convenience. Upstairs, a spacious loft creates an additional living area accompanied by a full laundry room and three generously sized bedrooms, providing flexibility for family, guests, or additional workspace. Step outside and experience Florida living at its finest. The covered lanai is designed for year-round enjoyment with a fully equipped summer kitchen overlooking the sparkling pool and spa, along with additional green space perfect for relaxing or entertaining. Located in the heart of Winter Park’s iconic Tree Streets, this residence offers one of the area’s most desirable lifestyles. Enjoy the ability to walk to Phelps Park while being just minutes from the Winter Park YMCA, Park Avenue’s renowned shopping and dining, and everything that makes this community one of Central Florida’s most sought-after destinations. Don’t miss this rare opportunity to own a brand-new construction residence in Winter Park’s highly coveted Tree Streets!
Listing Agent: Christopher Christensen (407-312-8003)
938 GOLFSIDE DR, WINTER PARK, FL 32792
$820,00013 Days on yellowkey MLS ID: O6425467
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2366 Built: 1968 Tax: $5,917 (2025)Community: Golfside Sec 2Spa: NoSingle Family
Taxes:$5,917
Elementary School: Brookshire Elem
Remarks: Under contract-accepting backup offers. **Due to the interest in the property, offers need to be in by Monday evening (7/20). ** Perfectly positioned on the 6th tee and 8th hole of the Winter Park Pines Golf Course, this home sits on an oversized quarter-acre lot and offers a rare opportunity to create your dream home while enjoying breathtaking golf course views. **The current floor plan features three bedrooms, as the original fourth bedroom has been converted into an expansive walk-in closet for the primary suite, and the flexible layout also offers the potential for a fifth bedroom.** While the interior offers an exciting opportunity to update, the sellers have already completed nearly $190,000 in major infrastructure and system improvements. One of the home's most valuable features is the fully paid-off solar panel system, which generates excess electricity that is returned to the utility company, resulting in an average monthly electric bill over 12 months is approximately $90. Additional capital improvements include a newer roof (2021), a new high-efficiency, variable-speed Lennox HVAC system (2025), a new energy-efficient, heat-pump water heater (2025), complete home repipe (2020), restoration of the cast-iron sewer system (2022) and plumbing stacks, upgraded attic insulation for enhanced energy efficiency (2023), a newer pool heater and pump (2024), added French drains (2025), new gutters with leaf guards, a deep irrigation well, an expanded circular paver driveway for ample parking space, and much more. Inside, the flexible floor plan offers endless possibilities. Beyond the spacious, front-facing living/dining room, the kitchen opens to a comfortable family room with a wood-burning fireplace. The kitchen window and pocket sliding glass doors frame beautiful views of the expansive covered lanai, screened pool, and rolling fairways beyond. The current 3-bedroom/2-bath layout on the left side can easily be reconfigured to restore the original 4th bedroom, which now serves as an oversized walk-in closet for the primary suite. The corner bedroom functions as both a guest room and home office, featuring a custom Murphy bed concealed behind a built-in bookcase, providing exceptional flexibility. On the opposite side of the home, an enormous bonus room with a full bath, offers direct pool access, and sweeping golf course views. Whether envisioned as a private guest suite or 5th bedroom, recreation room, home office, fitness studio, media room, or multigenerational living space, the bonus room has endless possibilities. Located just a few doors from the Cady Way Trail on one of the neighborhood's most picturesque oak-canopied streets, the setting is truly exceptional. This is a rare opportunity to purchase a home set directly on one of Winter Park's premier golf courses, where major mechanical system upgrades and costly infrastructure improvements have already been completed, creating the perfect opportunity to transform the interior into your own custom vision. Move in today, enjoy the exceptional location, and renovate at your own pace! Be sure to request a complete list of improvements, along with the floor plan, to fully appreciate the incredible potential this home presents.
Listing Agent: Marystuart Day (407-620-8683)
528 SAINT DUNSTAN WAY, WINTER PARK, FL 32792
$524,99049 Days on yellowkey MLS ID: O6414677
REDUCED by $10,010 (1.9%) on 07/11/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1656 Built: 1964 Tax: $6,000 (2025)Community: Winter Park PinesSingle Family
Taxes:$6,000
Remarks: Under contract-accepting backup offers. Welcome to Winter Park Pines, one of Winter Park's most desirable and established neighborhoods! Situated on nearly a quarter-acre lot, this beautifully maintained home with fresh interior paint combines modern updates, everyday comfort, and an unbeatable location. The stunning recently updated kitchen serves as the heart of the home, featuring stylish finishes and an inviting space for cooking, entertaining, and gathering. Throughout the home, you'll find attractive flooring with no carpet, offering both a clean, modern look and easy maintenance. Major improvements provide peace of mind, including a new roof and complete re-plumbing completed in 2023. The spacious lot offers plenty of room to enjoy outdoor living, gardening, pets, or future possibilities. Location is everything, and this home delivers. Just steps from Cady Way Pool and the popular Cady Way Trail, you'll enjoy easy access to recreation, fitness, and outdoor activities. Residents also love the convenient proximity to restaurants, shopping, parks, golf, and the charm of Downtown Winter Park. Best of all, there is no HOA, providing added flexibility and freedom. With significant recent updates, a generous lot, and a prime location in highly sought-after Winter Park Pines, this move-in-ready home is a wonderful opportunity to enjoy the very best of Winter Park living.
Listing is courtesy of: KELLER WILLIAMS WINTER PARK (407-545-6430)
Listing Agent: Jonathan Cole (407-928-9516)
840 W CANTON AVE, WINTER PARK, FL 32789
$649,90058 Days on yellowkey MLS ID: O6412754
REDUCED by $25,100 (3.7%) on 07/21/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1370 Built: 1952 Tax: $5,722 (2025)Community: N/ASingle Family
Taxes:$5,722
Remarks: Fully renovated 2 bedroom and 2 bathroom home with a bonus room, ideally located in the heart of Winter Park. Every detail has been updated, including new mechanical systems, electrical, plumbing, custom doors and windows, gutters, stucco finishes, fixtures, fresh landscaping, and new sod. Inside, you'll find an open-concept floor plan with professionally installed luxury vinyl plank flooring (2026) backed by a transferable 10-year warranty. The designer kitchen features butcher block countertops, a farmhouse sink, tile backsplash, and premium stainless steel appliances, including a ZLINE 36" six-burner gas range, ZLINE dishwasher, and KitchenAid refrigerator. A spacious bonus room with vaulted ceilings offers flexible living space for a home office, gym, media room, or playroom. The primary suite includes a spa-inspired bath with floor-to-ceiling porcelain tile, quartz vanity, touch-free LED mirror, and custom doors. Additional upgrades include copper plumbing already installed for a future tankless water heater. Step outside to a fully fenced backyard with gates on both sides and a private patio perfect for entertaining. Located just minutes from Winter Park Village, Park Avenue, Central Park, shopping, dining, entertainment, and Downtown Orlando, this low-maintenance Winter Park home offers exceptional rentability and walkability, and is situated in one of the area's most sought-after locations. Schedule your private showing today.
Listing is courtesy of: REAL BROKER, LLC (855-450-0442)
Listing Agent: Ken Pozek (407-813-2773)
262 LEWFIELD CIR #262, WINTER PARK, FL 32792
$149,50083 Days on yellowkey MLS ID: C7525448
REDUCED by $3,400 (2.2%) on 07/21/2026
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 678 Built: 1973 Tax: $1,278 (2024)Community: Stratford A Winter Park CondoSpa: NoCondo
Taxes:$1,278
Remarks: Walk into this freshly painted, pool view unit. Updates include new vinyl plank flooring throughout, new lighting, window coverings and a new tub/shower fixtures in the bathroom! Residents enjoy access to two pools, lighted tennis courts, fitness center, car care facilities and a clubhouse. The clubhouse can be rented for hosted gatherings. There is a free on-site laundry facility. Location is everything and this one delivers. Just minutes from downtown Winter Park, grocery stores, shopping and dining with access to I-4, 408,417, Semoran Blvd and State Road 50. Only 10 minutes to Full Sail, 20 minutes to UCF and close to Rollins College.
Listing is courtesy of: KELLER WILLIAMS REALTY FT MYER (239-236-4350)
Listing Agent: Andrew Bishop (863-381-1870)
2240 VENETIAN WAY, WINTER PARK, FL 32789
$3,500,00054 Days on yellowkey MLS ID: O6413398
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 4036 Built: 2011 Tax: $26,300 (2025)Community: Maitland Shores 1St AddSpa: NoSingle Family
Taxes:$26,300
Remarks: Virtually Staged. Positioned on a quiet canal, this exceptional property features a covered boat dock with lift, offering effortless access to the renowned Winter Park Chain of Lakes. This home, built by Liberty Development, with 4-bedrooms plus two bonus rooms blends elegance with comfortable everyday living. The main level offers a dedicated office area, formal dining room, and an inviting gathering room with gas fireplace, all flowing seamlessly into the stunning chef’s kitchen. Designed for entertaining, the kitchen features two large islands, exotic granite countertops, under-cabinet lighting, and premium Thermador appliances including a 6-burner gas range with griddle. The walk-in butler’s pantry has a beverage cooler and ice maker adds both style and functionality. The adjoining breakfast area is framed by grand windows overlooking the pool, cabana, and canal. The luxurious downstairs primary suite enjoys tranquil water views and a spa-inspired bath with travertine stone floors, marble counters, custom cabinetry, soaking tub, walk-in shower with steam and generous closet space. Upstairs you’ll find three additional bedrooms and a spacious bonus room, while a separate bonus suite above the garage provides future space for a media room, gym or guest retreat. The interior of the home is highlighted by hardwood floors, plantation shutters, decorative moldings and designer lighting throughout. The outdoor living area is equally impressive. French doors open to a covered porch with classic Old Winter Park brick, leading to a travertine-surrounded pool and private cabana with a wood-burning fireplace. Exterior highlights include a metal roof, durable cement board siding and wooden shutters. Don’t miss this limited opportunity to have immediate and easy access to the coveted Winter Park Chain of Lakes. *Some photos have been virtually staged*
Listing Agent: Johnny Hurlburt (407-579-3168)
2412 CHANTILLY AVE, WINTER PARK, FL 32789
$2,394,500168 Days on yellowkey MLS ID: O6381552
0 Days Off yellowkey (back on 5/26/2026)
REDUCED by $500 (0.0%) on 04/20/2026
Bed: 5 Bath: 6.5 Gar: 3 Liv Area Sq Ft: 4506 Built: 2026 Tax: $4,779 (2025)Community: Winter Park VillageSingle Family
Taxes:$4,779
Remarks: Exceptional design meets refined luxury in this brand-new architectural masterpiece by DaVinci. This 5 bedroom, 6.5 bath home offers over 4,500 square feet of bright, open living space designed for both comfort and functionality. Enter through your custom glass front door into the foyer leading to your main living area featuring a fireplace and sliding glass walls for indoor-outdoor living. This flows effortlessly into a gorgeous gourmet kitchen with high-end appliances featuring a Wolf range, Sub-Zero refrigerator, Euro-style cabinetry, oversized island, and walk-in pantry. The downstairs primary suite overlooks the pool and includes a spa-like bath with soaking tub and rain showers. An additional ensuite bedroom on the first floor works perfectly as a guest room or office. Upstairs you’ll find a large loft and media area with private balcony, along with three ensuite bedrooms including walk-in closets. Step outside and enjoy year-round living under the covered lanai featuring a summer kitchen overlooking the saltwater pool surrounded by mature landscaping. An outdoor bath adds extra convenience, and the oversized lot provides abundant space to relax, entertain or dine al fresco. This home comes complete with a spacious three-car garage with EV charging. Minutes to Interlachen Country Club, Winter Park Racquet Club, and Park Ave shopping. Don’t miss this beautiful custom modern home in one of Winter Park’s most sought-after neighborhoods! Ask about the new landscaping package, and driveway installation.
Listing Agent: Tab Bish Llc (855-450-0442)
1500 GAY RD #3C, WINTER PARK, FL 32789
$244,90041 Days on yellowkey MLS ID: O6417533
REDUCED by $3,100 (1.3%) on 07/21/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1026 Built: 1972Monthly Fee: $425 Tax: $3,244 (2025)Community: Chateaux Du LacCondo
Taxes:$3,244
Remarks: New Price/Seller Motivated! WINTER PARK LOCATION ALERT with AMAZING WALKABILITY to SO MANY shopping and dining options! Across from the newly renovated WP Shopping Village that includes top-rated restaurants, a movie theater, boutiques, grocery store and more! This 2bedroom/2 bathroom attractive second-story unit offers an updated kitchen and bathrooms with solid countertops. All solid flooring throughout - tile and laminate for easy care...no carpet. Enjoy the dining space that opens to the large great room and balcony where you'll love sitting in the evenings to relax. SPACIOUS BEDROOMS - Primary bedroom has an attached full bathroom and bedroom 2 has a LARGE walk-in closet. The 2nd Full Bathroom is accessed via a common hallway. The Chateaux Du Luc LAKEFRONT COMMUNITY offers FABULOUS AMENITIES that include an oversized heated pool, clubhouse, community deck, BBQ grill, 2 on-site saunas, updated on-site laundry facilities, and a resident-only boat ramp on skiable Lake Killarney. There's even storage for your Kayak or paddleboard! Roof 2025. Reach out today for your personal showing!!
Listing Agent: Heather Frazee (321-689-9465)
1870 WALKER AVE, WINTER PARK, FL 32789
$1,225,000138 Days on yellowkey MLS ID: O6390504
REDUCED by $74,000 (5.7%) on 07/07/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2046 Built: 2026 Tax: $3,981 (2025)Community: Osceola HeightsSingle Family
Taxes:$3,981
Remarks: This new residence, thoughtfully designed by Michael Wenrich, captures the timeless elegance and refined simplicity reminiscent of the iconic coastal architecture of Alys Beach. Clean architectural lines, graceful curves, and abundant natural light combine to create a home that feels sophisticated and inviting. Inside, gorgeous chevron-patterned wood floors flow throughout the main living areas, setting a warm and elegant tone. The open-concept floor plan is designed for everyday living and effortless entertaining, with expansive windows allowing natural sunlight to pour into every space. At the heart of the home is a beautifully designed kitchen that blends classic style with modern functionality. A stunning quartz waterfall island anchors the space, complemented by custom cabinetry and a suite of high-end appliances including an ILVE induction range with six elements and Café French door refrigerator, dishwasher and microwave. Designer-grade lighting and refined finishes elevate the kitchen into a centerpiece of the home. The dining room is filled with light and character, featuring three sets of French doors that open to a charming private front and side courtyard, an ideal setting for morning coffee or intimate outdoor dining. In the living room, a dramatic wall of sliding glass doors connects the interior to the brick patio and backyard, creating a seamless indoor-outdoor lifestyle. The first-floor primary suite offers a peaceful retreat, complete with a spacious walk-in closet and a spa-inspired bath featuring a large glass-enclosed shower, separate soaking tub and dual vanities. Additional conveniences on the main level include a beautifully appointed powder bath, a dedicated laundry room and a generous storage room tucked neatly beneath the staircase. Upstairs, a versatile loft provides additional living space ideal for a media area, office or lounge. Two additional bedrooms are also on the second floor, each featuring custom built-in closets, beautiful designer lighting and abundant natural light. Built with quality and efficiency in mind, the home includes numerous upgrades such as a slate roof, Trane air-conditioning system, Rheem tankless water heater and a two-car attached garage. Ideally just minutes from the renowned shopping and dining of Park Avenue and charm of downtown Winter Park, this exceptional home also offers convenient access to major roadways, Orlando International Airport, leading hospitals, and top-rated public and private schools, bringing together style, comfort and location in one remarkable new construction opportunity.
Listing is courtesy of: PREMIER SOTHEBY'S INTL. REALTY (407-644-3295)
Listing Agent: Mick Night (407-629-4446)
281 BREWER AVE, WINTER PARK, FL 32789
$1,800,0009 Days on yellowkey MLS ID: O6424364
Bed: 5 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 4029 Built: 2022 Tax: $26,908 (2025)Community: Osceola Shores Sec 02Single Family
Taxes:$26,908
Remarks: Short Sale. Welcome to this luxury, home in the heart of Winter Park. Less than a mile away from Park Ave. Winter Park that offers entertainment, restaurants, farmers market and so much more. A beautiful contemporary style home with modern interior finishes. Featuring an open floor plan, 5 bedrooms, 4.5 baths, a loft/flex space, media room, 2 study areas, front porch, back patio, lanai and so much more. Corner lot and privacy. Engineered hard wood floors through out the house and tile in utility rooms. 2 laundry rooms for convenience, located on 1st and 2nd floor of the home. Private backyard setting, a very large pool, an outdoor entertainment area featuring a kitchen and a fireplace and a screened in lanai. Metal Roof with Solar panels. A gas stove with large island and lots of space for entertainment. This home has a lot to offer in the most desirable location. Schedule your showing today.
Listing is courtesy of: HENTHORN REAL ESTATE (321-228-3188)
Listing Agent: John Henthorn (321-228-3188)
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