Location: Winter Park
Do Not Show Listings
508 DUNRAVEN DR, WINTER PARK, FL 32792
$595,000Listed 06/02/2026 10:15AM MLS ID: O6412363
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1370 Built: 1958 Tax: $2,281 (2025)Community: Kenilworth Shores Sec 03Single Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$2,281
Elementary School: Brookshire Elem
High School: Winter Park High
Tax Year: 2025
Middle School: Glenridge Middle
Remarks: Welcome to this stylishly renovated ranch-style pool home in Kenilworth Terrace, a special Winter Park neighborhood known for its connected community, central location, and easy access to everything people love about Winter Park. This beautifully renovated 3-bedroom, 2-bath home sits on nearly a quarter-acre lot and offers the perfect blend of style, comfort, and outdoor living. Step inside and you'll immediately feel the warmth of the home. The renovated kitchen is truly the heart of the space, beautifully designed with stylish tile backsplash, stainless steel appliances, mission style cabinetry, bar seating, and an additional coffee or wine bar area that makes the space feel both functional and elevated. Open to the living room, the kitchen creates an easy flow for everyday living and entertaining. The home has been thoughtfully updated throughout with new flooring, plantation shutters, renovated bathrooms, and designer touches that give the home a fresh, modern feel while still keeping all the charm of a classic Winter Park ranch. A dining room along the back of the home offers views of the yard and access to the covered lanai and custom pergola overlooking the pool. This is truly a backyard retreat! The sparkling pool is surrounded by pavers, lush landscaping, bamboo for privacy, and a fully fenced yard. The covered lanai and custom pergola create the perfect setting for morning coffee, quiet evenings, or hosting friends by the pool. This is the kind of backyard that makes Florida living feel easy. A large storage area and laundry room provide extra space for bikes and yard tools just off the carport. The bedrooms are tucked together along the hall, with the primary bedroom positioned on the back of the home for privacy, with an additional bathroom featuring an updated vanity and shower and a door to the pool area. The additional bedrooms share the hall bathroom with stylish modern updates including all new tile, a frameless glass shower, vanity, and fixtures. The thoughtfully designed spaces feel modern while also remaining timeless and classic. Additional features include a metal roof and newer windows and doors. Other notable additions over the years include irrigation, lush landscaping, and a refinished pool with tile surround. The 2-car carport provides plenty of covered parking for rainy days! Located in the City of Winter Park, this home offers incredible access to Park Avenue shopping and dining, Audubon Park with Michelin-star restaurants and local favorites, Sprouts Market, Lake Baldwin Dog Park, nearby parks, coffee shops, boutiques, and more. Zoned for Brookshire Elementary, Glenridge Middle, and Winter Park High. Cady Way Park is nearby with a community pool, baseball fields, a playground, pickleball courts, and miles of recreational and bike trails. Style, location, privacy, sparkling pool! This Winter Park home checks all the boxes. Schedule your private showing today!
Listing is courtesy of: KELLER WILLIAMS REALTY AT THE PARKS (407-629-4420)
Listing Agent: Kathryn Stelljes (407-982-7240)
7117 SWALLOW RUN #G1, WINTER PARK, FL 32792
$236,80096 Days on yellowkey MLS ID: O6385942
REDUCED by $13,000 (5.2%) on 04/23/2026
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1565 Built: 2011Monthly Fee: $385 Tax: $3,776 (2024)Community: Village/WhisperwoodCondo
Taxes:$3,776
Elementary School: None
High School: None
Tax Year: 2024
Middle School: None
Remarks: Welcome home! You've found it, a spacious end unit townhome style condo with private 1 car garage with extra storage space. Open floorplan first floor, when you walk in the front door you walk into a huge living room/dining room combination room with views out the back of your private screened patio overlooking a pond. The kitchen features lots of counter space, breakfast bar on the kitchen island and all appliances included! upstairs you will find a HUGE master suite with walk-in closet and ensuite bathroom with dual vanities, separate water closet and shower. Down the hall you have your indoor laundry closet, as well as two additional bedrooms with view of the pond. Easy commute to Downtown, Baldwin Park, Winter Park with quick access to the 408 and 417!
Listing is courtesy of: COMPLETE FLORIDA REALTY LLC (407-222-7281)
Listing Agent: Greg Traub (407-222-7281)
1914 BONANZA CT, WINTER PARK, FL 32792
$429,99918 Days on yellowkey MLS ID: O6408461
0 Days Off yellowkey (back on 6/2/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1727 Built: 1968 Tax: $4,497 (2025)Community: Eastbrook Sub Unit 13Single Family
Taxes:$4,497
Elementary School: Eastbrook Elementary
High School: Lake Howell High
Middle School: Tuskawilla Middle
Remarks: Welcome to your winter Park retreat! Step into this beautifully renovated 3 bedroom, 2 bathroom home where modern meets timeless comfort. Designed with an open floor plan, the living space flows seamlessly, making it perfect for both entertaining and everyday living. The brand new kitchen shines with contemporary finishes, while the new flooring throughout the home adds warmth and style. Both bathrooms have been thoughtfully renovated, offering a clean and modern feel. The Florida room, wrapped in huge windows. floods the home with natural light, creating a bright and inviting space you'll love year round. Step outside to enjoy a covered patio, ideal for morning coffee or relaxing evenings with friends and family. With its prime location, this home is a blend of convenience, charm, and modern living ready for you to make it your own. Call and schedule your showing today!
Listing is courtesy of: KELLER WILLIAMS WINTER PARK (407-545-6430)
Listing Agent: Judy Julien, Pa (407-234-4051)
2383 SUN VALLEY CIR #2383, WINTER PARK, FL 32792
$259,00043 Days on yellowkey MLS ID: O6400674
REDUCED by $10,000 (3.7%) on 05/24/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1295 Built: 1985Monthly Fee: $499 Tax: $2,560 (2024)Community: Cedarwood Village 1Condo
Taxes:$2,560
Elementary School: English Estates Elementary
Remarks: Nestled in a peaceful setting within the serene Cedarwood Village community, this charming one-story Winter Park condo offers a quiet retreat away from traffic noise, with a rear wooden fence for no visible neighbors for added privacy. The spacious 27-foot tiled and enclosed lanai creates the perfect place to relax and enjoy the tranquil surroundings. Cedarwood Village also offers low-maintenance living, with lawn care included in the HOA, along with amenities such as rebuilt tennis courts, a recently remodeled pool, a clubhouse, dog-walking areas, and newly paved roads. Conveniently located in a highly rated school district and close to shopping, dining, and entertainment, the property is also just minutes from Full Sail University, Valencia College, and UCF. Inside, the condo is beautifully updated and shows the care of meticulous owners. The modern kitchen features granite countertops, matching cabinetry, and an eat-in area with sliding doors leading to the private patio, while the bathrooms and dining room wet bar are finished with the same stylish cabinets and granite. The split floor plan includes tile flooring throughout the main living areas and wood floors in the bedrooms. The large living and dining spaces feature vaulted ceilings with skylights for abundant natural light, along with a cozy wood-burning fireplace. French doors from the living room open to the enclosed lanai, while the primary suite also has direct lanai access, ample closet space, and a private bath with both a tub and shower. Additional features include an interior laundry closet adjacent to the kitchen, updated plumbing, a roof replaced in 2018, and new ductwork installed in 2023. AC 2008. Seller providing a $4,500 Buyer credit at closing toward a new AC. Two assigned parking spaces are located directly in front of the unit.
Listing is courtesy of: WEICHERT REALTORS HALLMARK PROPERTIES (407-644-5385)
Listing Agent: Jeff Stewart (407-247-9762)
126 SCOTTSDALE SQ #126, WINTER PARK, FL 32792
$150,000165 Days on yellowkey MLS ID: S5140472
Bed: 2 Bath: 1.5 Liv Area Sq Ft: 1085 Built: 1974Monthly Fee: $950 Tax: $1,660 (2024)Community: Winter Park Woods CondoCondo
Taxes:$1,660
Remarks: Excellent opportunity to own this second-floor, 2-bedroom, 1/1-bath condo in a Conveniently location close to healthy centers, excellent schools, restaurants and shopping with easy access to Costco, Walmart, and various dining options. Only 4 miles from Winter Park SunRail Train Station and 20 minutes from Orlando International Airport. This unit offers a cozy living/dining area with sliding doors leading to a private balcony that includes extra storage.
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Maria Batista (321-208-4649)
2054 EASTBROOK BLVD, WINTER PARK, FL 32792
$500,000Listed 06/02/2026 11:16AM MLS ID: V4949389
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2031 Built: 1966 Tax: $5,054 (2025)Community: Eastbrook Sub Unit 8Single Family
Taxes:$5,054
Remarks: Check out this private pool home in lovely Winter Park. Offers 4 bedrooms, 3 baths and a 2 car garage. Huge kitchen overlooking family room. Inside laundry room. Fenced backyard. Zoned for Lake Howell High School.
Listing Agent: Melissa Stalzer (386-405-3457)
2006 CORNELL AVE, WINTER PARK, FL 32789
$338,000Listed 06/02/2026 7:07AM MLS ID: O6412789
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
High School: Edgewater High
Middle School: College Park Middle
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)
2503 TAHOE CIR #2503, WINTER PARK, FL 32792
$250,00061 Days on yellowkey MLS ID: O6395130
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1173 Built: 1981 Tax: $506 (2025)Community: Cedarwood Village 1Condo
Taxes:$506
Remarks: This charming one story condo is located in the desirable Cedarwood Village. This unique home boasts an open layout that is different from many others in the community. The home showcases engineered hardwood floors, skylights and wonderful natural light. The kitchen provides ample cabinet space, granite counters, built-in wine rack and beautiful custom tile work. The kitchen overlooks the dining and living room combo. The living room has 2 skylights and flows right into the delightful Florida room. The Florida room boasts wonderful built-in shelving and a glass door giving access to the backyard. The primary bedroom showcases wonderful built-in cabinets, 2 closets and an ensuite bathroom with a granite counter vanity. The primary bedroom also looks into the Florida room but can be shut off for privacy with a sliding door. The second bedroom is at the front of the home and has access to the guest bathroom with a granite counter vanity. Two assigned parking spaces are directly in front of the home. To top it all off, this home is in close proximity to several restaurants and shops and is an easy drive to downtown Winter Park.
Listing Agent: Beth Logullo (772-633-0670)
2261 MULBRY DRIVE, WINTER PARK, FL 32789
$1,995,0004 Days on yellowkey MLS ID: O6410979
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 3696 Built: 2020 Tax: $11,789 (2025)Community: Lake Forest ParkSpa: YesSingle Family
Taxes:$11,789
Elementary School: Audubon Park K8
Middle School: Audubon Park K-8
Remarks: Welcome to this extraordinary, better-than-new residence in the heart of Winter Park, a thoughtfully designed and impeccably upgraded custom, one-owner home built in 2020 that effortlessly blends timeless elegance with today’s most sought-after luxury features. Situated on a wonderfully deep, private lot with no HOA, this remarkable two-story home was crafted for elevated everyday living, unforgettable entertaining and seamless indoor-outdoor enjoyment. Offering 3,696 square feet, the flexible floor plan features four bedrooms, three full baths, a loft and a bonus room with a coffee/cocktail bar adjacent to accommodate a variety of lifestyles. The expansive first-floor primary suite is a true retreat, featuring a spa-inspired bath with heated floors, a soothing tub, an oversized walk-in shower and two large walk-in closets. The downstairs office with an en suite bath can easily function as a private guest suite or fourth bedroom. Quality craftsmanship shines throughout with detailed ceilings, engineered oak hardwood flooring, crown molding and baseboards, designer doors and hardware and plantation shutters throughout, creating a sophisticated yet inviting atmosphere. A rare combination of warmth and sophistication, this home beautifully balances luxury and functionality for modern living. The exceptional chef’s kitchen features a 60-inch Wolf gas range with a large griddle and double ovens, an expansive center island, a Sub-Zero refrigerator, a dining area and an adjacent butler’s pantry with an additional dishwasher and sink and a laundry room. Spacious gathering areas flow effortlessly into the spectacular outdoor retreat, complete with a covered lanai with remote screens, summer kitchen, outdoor fireplace, sparkling saltwater pool, separate heated spa and incredible privacy. Additional highlights include a Sonos sound system, high-definition security cameras, natural gas, a full-house generator, a separate air-conditioned workshop and a two-car garage. This exceptional Winter Park home offers the rare opportunity to enjoy newer construction elevated far beyond builder standards. Check out the 3D walk through tour! Call today to schedule your private showing.
Listing is courtesy of: PREMIER SOTHEBY'S INTL. REALTY (407-644-3295)
Listing Agent: Jo Ann Lamar (321-231-0052)
649 N PARK AVE, WINTER PARK, FL 32789
$3,500,000Listed 06/02/2026 10:18AM MLS ID: O6411141
Bed: 3 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 3180 Built: 2019Monthly Fee: $948 Tax: $22,599 (2025)Community: Park HillTownhouse
Taxes:$22,599
Elementary School: Lakemont Elem
Middle School: Maitland Middle
Remarks: Park Hill is one of Winter Park's most coveted addresses; a distinguished collection of luxury brownstones situated at the northern end of Park Avenue, steps from the city's finest boutiques, restaurants, cultural landmarks and the historic Winter Park Golf Course. Within this exclusive enclave, residence 649 occupies one of the community's most private settings. Beyond the stately brick courtyard and gas lantern-adorned entrance, this three-story home with private elevator is thoughtfully scaled for refined living. Not oversized, but extraordinarily well-appointed. Ten-foot ceilings, intricate millwork and moldings, and generous windows establish an ambiance of quiet elegance, while hardwood floors and designer fixtures carry that standard throughout. The open-concept main living area is built for effortless entertaining. The chef's kitchen features Wolf and Sub-Zero appliances, custom wood cabinetry, marble accents, a center island with bar seating, and a wet bar with beverage refrigerator and ice maker. The space opens directly to a private courtyard with a summer kitchen and dedicated alfresco dining area, creating a genuinely tranquil retreat that feels removed from the energy of the avenue. Upstairs, two guest suites each offer walk-in closets and en-suite baths. A dedicated laundry room and a covered terrace with fireplace, wet bar and half bath complete the level. The third-floor primary suite provides a true sense of retreat, with two custom walk-in closets, a private balcony, and a spa bath filled with natural light from windows and skylights. Dual vanities, a glass-enclosed steam shower and soaking tub are finished throughout in premium materials. Constructed of Old Carolina brick with three-story block construction, precast exterior trim and a slate mansard roof, the residence features a two-car air-conditioned garage, ample storage and soundproof hollow core floors. With exterior maintenance managed by the association, the lifestyle here is genuinely lock-and-leave. This is a rare opportunity to own in one of Central Florida's most prestigious communities, in a location that simply cannot be replicated.
Listing Agent: Drew Henner (407-406-0662)
7794 COUNTRY PL #2, WINTER PARK, FL 32792
$232,00046 Days on yellowkey MLS ID: O6397587
REDUCED by $5,000 (2.1%) on 06/02/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1068 Built: 1988Monthly Fee: $296 Tax: $2,620 (2024)Community: Goldenrod Villas CondoSpa: NoCondo
Taxes:$2,620
Remarks: Winter Park Clean, UPDATED and in Move In Condition - The newest condo's year built are located on the last street in the complex where this unit is located which features a more contemporary open floor plan. Enjoy the One story living with no steps. No apartment living with noisy neighbors. Another BONUS is *** NO condo neighbors across the street from you - PRIVATE!** Located second to the end of a Quiet Dead End Street. Step into a bright and airy condo featuring laminate and tile floors. Newer painted pastel colors throughout. The updated contemporary kitchen has NEWER Pecan colored cabinets and NEWER granite counter tops with stylish designer tile back splash. Both bathrooms have NEWER vanities and granite counter tops. The second bath features a granite top designer Pedestal vanity. The split bedroom floor plan that provides privacy, both bedrooms have spacious Walk-In closets. *** Open living area shines with natural sun light and is open to a screened porch, providing access to the private, fenced back courtyard. New (December 2024) High efficiency RHEEM 15.3 SEER AC unit keeps utility costs lower. New Roof (2021) New 6 panel Front entry door January (2025) New carpet in both bedrooms installed January (2025) Replumbed with New PEX plumbing pipes, New Refrigerator (2025) New light fixtures throughout. As a resident, you'll have access to the community pool and the convenience of being close to Winter Park - Park Avenue, the Cross Seminole Trail and Cady Way Trail, Winter Park Village, UCF and Full Sail. The location offers easy access to major roadways, shopping, and dining and is served by the reputable Seminole County Schools. Complete with fenced back courtyard! Community has swimming pool & bathrooms. ** Exterior of the building is scheduled to be painted. ** Professionally cleaned for new owners. Never smoked in. Compare to others needing all these upgrades.
Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)
Listing Agent: Tom Bercini (407-925-4760)
2702 PARKLAND DR, WINTER PARK, FL 32789
$1,139,75053 Days on yellowkey MLS ID: O6397997
REDUCED by $35,250 (3.0%) on 05/18/2026
Bed: 5 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2656 Built: 1949 Tax: $5,269 (2025)Community: ParklandoSingle Family
Taxes:$5,269
Remarks: Welcome to this beautifully updated Winter Park home, perfectly positioned on a desirable corner lot and zoned for Audubon Park K-8 and Winter Park High School. With 5 bedrooms and 3 full baths, this spacious residence offers the ideal blend of functionality and style for modern living. Step inside to an open, light filled floor plan featuring luxury vinyl floors and a cozy wood burning fireplace that anchors the main living space. The renovated kitchen is thoughtfully designed with both everyday living and entertaining in mind, flowing seamlessly into the dining and living areas. A dedicated office provides the perfect work from home setup or quiet retreat, while the flexible layout offers plenty of room for guests, growing families, or multi generational living. Outside, enjoy a private backyard with a charming fire pit and rock gathering are deal for relaxing evenings or hosting friends. The oversized lot also offers ample space to add a pool and create your own backyard oasis. Additional highlights include a 2-car garage, roof replaced in 2018, home repiped in 2019, and updated AC for peace of mind. This is a rare opportunity to own a move-in ready home in one of Winter Park’s most sought after neighborhoods, walking distance to the Audubon Park Garden District with amazing dining, and shopping.
Listing is courtesy of: NORDQUIST & COMPANY INC (407-694-0996)
Listing Agent: Elizabeth Nordquist (407-694-0996)
1077 MINNESOTA AVE, WINTER PARK, FL 32789
$1,395,0005 Days on yellowkey MLS ID: O6411722
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 3046 Built: 2025 Tax: $1,383 (2025)Community: NaSingle Family
Taxes:$1,383
Remarks: Location. Design. Lifestyle. Newly built in 2025 by Nautilus Homes and lightly lived in, this exceptional custom residence offers the perfect blend of modern construction, elevated design, and an unbeatable Winter Park location. Ideally positioned between Orlando Avenue and Orange Avenue, just moments from Park Avenue, Mead Botanical Garden, acclaimed dining, boutique shopping, and cultural attractions, this is a rare opportunity to enjoy the very best of Winter Park living. Framed by mature landscaping and featuring dual front porch seating areas, the home encompasses over 3,000 square feet of thoughtfully designed living space and more than 4,000 square feet under roof, with four bedrooms, four full baths, and a dedicated first-floor office. More than $100,000 in post-construction enhancements further elevate the home's style, functionality, and everyday comfort. Inside, wide-plank Crème Brûlée hardwood flooring flows throughout, creating a warm and sophisticated backdrop. Custom closet systems in every bedroom, plantation shutters, and designer Arhaus lighting add a refined touch throughout the home. The spacious great room is anchored by a custom-built entertainment wall featuring a sleek vapor fireplace and integrated LED accent lighting, creating a striking focal point for both relaxing and entertaining. The chef’s kitchen seamlessly combines beauty and function with ceiling-height custom cabinetry, a handcrafted wood range hood, premium finishes, and an elegant butler’s pantry accented by designer Kit Kat tile. A built-in wine and coffee bar enhances the home's entertaining appeal while providing everyday convenience. Designed for flexibility and privacy, the floor plan offers a first-floor guest suite and office, while three additional en-suite bedrooms are located upstairs. The luxurious primary suite serves as a private retreat, featuring a spa-inspired bath with a soaking tub, oversized nine-foot walk-in shower, dual shower systems, frameless glass enclosure, and linear drain detailing. Outdoor spaces have been thoughtfully curated for effortless living. Professional landscaping, mature trees, full gutter systems, artificial turf, and decorative rock accents create a private, low-maintenance backyard sanctuary. The oversized 24' x 22' garage is equally impressive, featuring custom cabinetry, a dedicated tool wall, overhead storage systems, and Shark Coating epoxy flooring. Zoned for highly regarded Audubon Park K-8 and Winter Park High School, and located just minutes from Park Avenue and Winter Park’s vibrant dining and entertainment district, this move-in-ready residence delivers luxury, convenience, and timeless design in one of Central Florida’s most sought-after neighborhoods. This property may be under audio/visual surveillance.
Listing is courtesy of: COLDWELL BANKER REALTY (407-333-8088)
Listing Agent: Frank Benevento (407-492-5153)
2808 BRIGHT BIRD LN, WINTER PARK, FL 32792
$399,0003 Days on yellowkey MLS ID: O6410294
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1907 Built: 2024Monthly Fee: $375 Tax: $6,126 (2025)Community: Grayson SquareTownhouse
Taxes:$6,126
Remarks: Impeccable 2-story townhome, newly built in 2024 and located in Grayson Square, a Gated Luxury Townhouse Community in enchanting Winter Park, with modern, sophisticated architecture and landscaping. The interior features the high-end Lux Fresh package, complemented by owner upgrades including light dimmers, ceiling fans, and a custom kitchen island. The chef’s kitchen is equipped with new stainless-steel appliances and expansive white stone countertops. Alabaster cabinetry with ceramic tile plus smooth stone counters adds a touch of elegance throughout. Shaw LVP floors on the main level and 2nd level bathrooms. Owner's suite with an oversized walk-in closet and a dual-sink ensuite. Spacious second and third bedrooms. 9' ceilings throughout. The first floor features a stunning open-concept living area with vinyl wood-plank flooring. Laundry closet on 2nd level. Kohler raised commodes on the 2nd level. Private patio area surrounded by lush greenery. Attached garage with 2 extra off-street parking spaces. The home includes a Ring doorbell and a rear security camera. Eeros internet modem and Extender for boosted device connectivity. includes a resort-style pool oasis with a cabana, with a view of the community lake. Competitive HOA fees cover roof replacement, Spectrum internet and TV, and general property upkeep. Situated in a manicured community with a sparkling pool, this home is close to fine dining, shopping, and entertainment, with easy access to downtown Orlando and local theme parks. It is highly rated for its proximity to quality Seminole County public schools and its convenience to daily necessities like Publix and Starbucks, as well as the shopping and dining of Park Avenue. Exclusions: Water Filtration System TV Mounts Window coverings (rods can stay) Kitchen island is negotiable. Washer/Dryer is negotiable Owner has priced to sell, don't miss this opportunity!
Listing Agent: Sean Flatley (609-208-8204)
1813 HARLAND PARK DR, WINTER PARK, FL 32789
$1,875,00032 Days on yellowkey MLS ID: O6403483
REDUCED by $120,000 (6.0%) on 05/28/2026
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3551 Built: 2013Monthly Fee: $268 Tax: $23,539 (2025)Community: Windsong - Knowles PlaceSpa: YesSingle Family
Taxes:$23,539
Remarks: Nestled within the highly sought-after Windsong community in Winter Park, this thoughtfully designed residence presents the perfect balance of functionality, comfort, and elevated indoor-outdoor living. This move-in ready home is sure to check all the boxes with 2 NEW HVAC units (2025), a downstairs Primary Suite, a convenient 1st floor private office/flex room, 2nd floor loft & bonus room, plus a private backyard oasis complete with a full summer kitchen, covered rear lanai, and saltwater pool with a heated spa. The large, covered front porch welcomes guests into a foyer that opens to a spacious and well-orchestrated floorplan. Just off the entry sits a versatile office/flex space, providing the perfect setting for a private workspace or playroom, while a conveniently located powder bath serves visitors with ease. The foyer unfolds with effortless flow into the heart of the home, where an expansive living room is designed for both everyday living and entertaining. The open-concept kitchen is both functional and refined, featuring a natural gas cooktop, built-in double ovens, and adjacent sunny dinette that overlooks the backyard and pool, creating a casual dining space filled with natural light. On the opposite end of the kitchen, a large walk-in pantry offers tons of storage, and a butler’s pantry/dry bar seamlessly adjoins the large dining room—ideal for hosting gatherings with a polished, intentional flow. At the rear of the living space, expansive stacking glass sliders open to the rear covered lanai, extending the living space outdoors. Enjoy space for dining, lounging, and entertaining with a full summer kitchen that includes a large gas grill, double gas burners, a sink, beverage fridge, and storage cabinets. The backyard beyond creates a true retreat that embodies the Florida lifestyle, where a heated spa overflows into a beautifully designed saltwater pool complete with a sun shelf, all wrapped in travertine decking, tropical landscaping, and a masonry wall for enhanced privacy. Situated at the rear of the home, the well-appointed primary suite offers a quiet escape with generous proportions, dual walk-in closets, and a sensible primary bath with split vanities, a soaking tub, separate shower, and private water closet. The main level continues with exceptional functionality, including a spacious laundry room lined with built-in cabinets for storage, and a 2-car garage with direct access to the side yard and overhead racks for additional storage capacity. Upstairs, a thoughtfully designed 2nd level provides incredible flexibility, featuring a central loft for a reading or study area, a large bonus room that's perfect for a game room or secondary living area, three additional bedrooms - each with walk-in closets, two full bathrooms, and a linen closet, plus an additional storage/media closet. This home is not just a residence—it’s a lifestyle. Windsong residents enjoy access to premier amenities, including multiple community pools, a splash pad, playgrounds, a clubhouse, and 2 community docks providing access to the Winter Park Chain of Lakes via Lake Berry & Lake Mizell. Ideally located just minutes from Park Avenue, Baldwin Park, and the vibrant Corrine Drive corridor, this property offers tranquility and convenience in one of Winter Park’s most desirable neighborhoods.
Listing is courtesy of: FANNIE HILLMAN & ASSOCIATES (407-644-1234)
Listing Agent: Marystuart Day (407-620-8683)
1850 ASTER DR, WINTER PARK, FL 32792
$500,000Listed 06/02/2026 8:55AM MLS ID: TB8513990
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1656 Built: 1978 Tax: $1,584 (2025)Community: Garden Lake Estates Unit 1Single Family
Taxes:$1,584
Remarks: Welcome to the heart of Winter Park. This beautifully maintained 4-bedroom, 2.5-bath pool home offers the perfect blend of warmth, functionality, and charm. From the moment you arrive, the curb appeal is unforgettable. Lush landscaping, mature greenery, and peaceful natural surroundings create a private and inviting setting that immediately feels like home. Inside you'll find an open and welcoming floor plan designed with both everyday living and entertaining in mind. The updated kitchen features stainless steel appliances, a spacious island, abundant cabinet storage, and seamless flow into the main living areas. A formal living area adds flexibility, offering the perfect space for a cozy sitting room, playroom, home office, or additional entertaining area. Natural light throughout the home creates a bright and airy atmosphere. Upstairs, you’ll find all four bedrooms and two full bathrooms, providing privacy and functionality for growing families. The screened-in porch overlooks a stunning backyard retreat complete with a sparkling pool, beautiful landscaping, and no rear neighbors for added privacy. Peaceful, quiet, and surrounded by nature and wildlife, this outdoor space makes it perfect for summer pool days, evening dinners outside, and making lifelong memories.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Brianna Lalumiere (727-641-3957)
7001 JACKMAN BLVD, WINTER PARK, FL 32792
$450,00018 Days on yellowkey MLS ID: O6408371
5 Days Off yellowkey (back on 6/2/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1482 Built: 1977 Tax: $4,421 (2025)Community: Howell Branch WoodsSingle Family
Taxes:$4,421
Remarks: Under contract-accepting backup offers. MUST SEE! Fully Renovated Pool Home with Major Upgrades in Winter Park! Welcome to this beautifully remodeled Winter Park pool home offering modern finishes, major system upgrades, and true move-in-ready convenience. Every detail has been thoughtfully updated to combine style, comfort, and long-term peace of mind. This fully renovated interior and exterior home features a stunning brand-new kitchen with elegant quartz countertops, all-new stainless steel appliances, modern cabinetry, and a clean open layout perfect for entertaining and everyday living. Throughout the home, you’ll find durable porcelain tile flooring that creates a seamless contemporary look while being ideal for Florida living. The fully remodeled bathrooms showcase stylish modern finishes, upgraded fixtures, and a fresh luxury feel. The home also includes a brand-new roof and new double-pane energy-efficient windows designed to improve comfort, efficiency, and long-term value. Step outside into your private backyard oasis featuring a recently resurfaced swimming pool along with a brand-new pool pump and filter system, creating the perfect space for relaxing, entertaining, and enjoying Florida living year-round. Additional features include updated lighting and modern finishes throughout, a bright open floor plan, spacious living areas, and a large backyard ideal for gatherings and outdoor enjoyment. Conveniently located near Downtown Winter Park, Park Avenue, UCF, Full Sail University, shopping, dining, parks, and major highways, this completely move-in-ready home combines luxury upgrades with an excellent location.
Listing is courtesy of: COLDWELL BANKER REALTY (407-647-1211)
Listing Agent: Habib Fahs (321-806-5196)
7517 LAUREL SPRINGS DR, WINTER PARK, FL 32792
$399,9905 Days on yellowkey MLS ID: O6411247
1 Days Off yellowkey (back on 6/2/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1678 Built: 1972 Tax: $6,116 (2025)Community: Laurel SpringsSpa: YesSingle Family
Taxes:$6,116
Elementary School: Aloma Elem
Remarks: Under contract-accepting backup offers. *MULTIPLE OFFERS! FINAL AND BEST OFFERS BY 10 PM 06/01/26* Welcome home to this beautifully maintained 3-bedroom, 2-bath *POOL* home in desirable Winter Park! Offering 1,678 square feet of single-story living, this home features an open floor plan with a spacious kitchen/family room combination. The open kitchen features 36” oak cabinetry, upgraded SS appliances, a garden window, and a kitchen island overlooking the dinette and family room. You’ll find laminate and tile flooring throughout the home, updated bedroom light fixtures (2026), and a converted 2-car garage offering flexible bonus space if you desire. Owners can escape to their primary suite with a walk-in closet, en-suite bathroom, and private French doors leading out to the HEATED SALTWATER POOL. Step outside to your own private backyard featuring an oversized covered patio with screened-in pool and a built-in spa, plenty of yard space to enjoy, a backyard shed for additional storage, a swing set, and a playhouse perfect for outdoor fun. With NO HOA, you’ll have the freedom to truly make this space your own! Major updates provide peace of mind, including a NEW water heater (2026), electrical panel replacement (2023), salinator replacement (2023), pool heater replacement (2024), roof (2019), and AC (2025). Conveniently located near shopping, dining, parks, and top-rated Seminole County schools, this move-in-ready home is the perfect blend of comfort, functionality, and Florida living!
Listing is courtesy of: KELLER WILLIAMS ADVANTAGE REALTY (407-977-7600)
Listing Agent: Jadel Patterson, Llc (407-922-5936)
1448 LAKE FLORENCE WAY, WINTER PARK, FL 32792
$1,199,0006 Days on yellowkey MLS ID: O6411164
Bed: 5 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 3652 Built: 2018Monthly Fee: $186 Tax: $7,277 (2025)Community: Lake Florence PreserveSpa: NoSingle Family
Taxes:$7,277
Remarks: Located within an intimate gated community of just 28 homes and only a short drive to Downtown Winter Park, this exceptional former model home by K. Hovnanian Homes showcases over $200,000 in builder and custom upgrades with luxury finishes and thoughtful design throughout. Residents enjoy access to a private community dock, perfect for launching a canoe or paddleboard or simply relaxing while enjoying sunset views over the water. This stunning Michelson floorplan offers the perfect blend of elegance, comfort, and functionality with spacious living areas designed for both everyday living and entertaining. Upon entry, you’re welcomed by a private office, formal dining room with custom accent features, recessed lighting throughout, beautiful wood-look tile flooring, and designer details at every turn. The open-concept family room features built-in speakers that continue throughout the main living spaces, upstairs, and outdoor lanai area, creating a seamless entertainment experience throughout the home. The gourmet kitchen is beautifully appointed with quartz countertops, 42” cabinetry, stainless steel appliances, gas cooktop, oversized island, modern backsplash, butler’s pantry with wine fridge, and an incredible walk-in pantry with custom built-in shelving. Massive 12-foot triple sliding glass doors open to the resort-style backyard featuring a beautiful open pool, custom fire pit, pergola seating area, pre-wire for a gas grill, and a backyard perfect for relaxing or entertaining. The first floor also includes a guest suite with a full bath and direct pool access, a mudroom, a coat closet, a convenient half bath, and an oversized three-car tandem garage with overhead storage. Upstairs, a beautiful wood tread staircase leads to an expansive loft and bonus room area along with spacious secondary bedrooms, all featuring walk-in closets. A Jack-and-Jill bathroom with dual sinks, additional full bath, oversized linen closets, and a large laundry room with sink and extensive cabinetry provide exceptional functionality and storage. The luxurious owner’s retreat is a true sanctuary featuring tray ceilings, built-in speakers, a stunning accent wall, coffee bar area, spa-inspired bath with an oversized walk-in shower, abundant storage, and an enormous walk-in closet with multiple sections. Additional highlights include a brand-new A/C unit and countless high-end finishes throughout. Ideally located near top-rated schools, shopping, dining, and major roadways, this meticulously maintained home offers elevated Florida living in one of the area’s most desirable gated communities.
Listing is courtesy of: RE/MAX 200 REALTY (407-629-6330)
Listing Agent: Abby Nelson (407-571-1445)
715 S RANGER BLVD, WINTER PARK, FL 32792
$695,0007 Days on yellowkey MLS ID: O6410899
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2312 Built: 1967Monthly Fee: $4 Tax: $2,773 (2025)Community: Winter Park PinesSingle Family
Taxes:$2,773
Remarks: Welcome to your dream home in the highly sought-after community of Winter Park Pines! This beautifully maintained 4-bedroom, 3-bathroom residence offers 2,312 square feet of comfortable and stylish living space ideally designed for modern and multigenerational lifestyles. The recently remodeled primary suite is a true retreat, featuring new carpeting and tile flooring, dual granite vanities, an oversized walk-in shower with modern, upgraded fixtures, a new water closet, and thoughtful contemporary finishes throughout. Inside, you’ll find timeless architectural charm which includes a formal dining room, three spacious living areas, plantation style shutters, and elegant hardwood flooring. One of the living spaces is highlighted by a stunning brick fireplace overlooking the beautiful private pool area and fully fenced backyard — creating the perfect setting for entertaining, family gatherings, or simply unwinding in your own backyard oasis. In addition, this spectacular residence also boasts tasteful landscaping touches for exceptional curb appeal, a large two-car garage with electric opener, a newer shingle roof replaced in late 2023, and fresh interior paint throughout the home. Ideally located near Winter Park Pines Golf Club, Cady Way Trail, Ward Park, Showalter Field, tennis and pickleball courts, top-rated schools, and the many shopping and dining destinations of Park Avenue and historic downtown Winter Park. Don’t miss this rare opportunity to own a true Winter Park gem — schedule your private showing today!
Listing is courtesy of: DAHLIA REALTY GROUP (689-777-4111)
Listing Agent: Chuck Tolfa (407-782-3518)
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