Location: Winter Park , 32792
Do Not Show Listings
739 ROUGHBEARD RD, WINTER PARK, FL 32792
$800,00040 Days on yellowkey MLS ID: O6404545
Bed: 5 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2194 Built: 1968 Tax: $6,179 (2025)Community: Winter Park PinesSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$6,179
Elementary School: Aloma Elem
High School: Winter Park High
Tax Year: 2025
Middle School: Glenridge Middle
Remarks: Welcome to Winter Park Pines, one of Winter Park’s most desirable neighborhoods. This updated 5 bed, 3 bath pool home features a split floor plan, generous room sizes, and wood-plank tile flooring throughout most of the home. Inside, the formal living and dining rooms flow together and overlook the pool through French doors, while the large primary suite offers an en-suite bath, walk-in closet, and its own French doors to the huge covered, insulated patio. The light and bright kitchen includes a large breakfast bar, built-in pantry, and white cabinetry and appliances, and opens to the family room with a wood-burning fireplace and built-in desk. A separate bedroom wing provides four generous guest bedrooms and two full baths, including a Jack-and-Jill setup with walk-in closet, plus a true pool bath with access to the backyard and an inside utility/laundry room. Outdoor living is a highlight, with a fenced backyard, kidney-shaped pool, plenty of deck space, and ample yard beyond the pool so you’re not sacrificing green space. The large covered, insulated patio is ideal for year-round use. Major updates include a new roof (2022), new electric panel and updated outlets (2022), water lines re-piped to CPVC by a previous owner, new fence (2023), new dishwasher (2024), new water heater (2025), newer stove, washer, and dryer, new light fixtures throughout, and bathrooms updated with modern colors and fixtures. The exterior, garage, patio, and pool deck have all been freshly painted, giving the home a clean, move-in ready feel. This is a rare opportunity to own a well-maintained pool home in a prime Winter Park location—just steps from Cady Way Park and Trail and moments from Winter Park Pines Golf Course, with Winter Park High School and the nearby hospital campus within short distance and quick access to downtown Orlando, major highways, both airports, Disney, and Universal.
Listing is courtesy of: SERHANT (786-296-8626)
Listing Agent: John Harbuck (407-538-2841)
1515 WINTER GREEN BLVD, WINTER PARK, FL 32792
$300,000100 Days on yellowkey MLS ID: O6384755
1 Days Off yellowkey (back on 5/16/2026)
REDUCED by $15,000 (4.8%) on 04/28/2026
Bed: 3 Bath: 2.5 Liv Area Sq Ft: 1652 Built: 1984Monthly Fee: $188 Tax: $3,993 (2024)Community: Winter GreenTownhouse
Taxes:$3,993
Elementary School: English Estates Elementary
High School: Lake Howell High
Tax Year: 2024
Middle School: Tuskawilla Middle
Remarks: Under contract-accepting backup offers. Offering the comfort and feel of a single-family home with the convenience of townhome living, this beautifully maintained two-story residence features 3 bedrooms, 2.5 baths, and a private courtyard conveniently located in Winter Park. Sliding glass doors throughout the home fill the interior with natural light and create a seamless connection to your private outdoor courtyard. Inside, the spacious layout is complemented by low-maintenance tile flooring throughout and a cozy wood-burning fireplace, adding warmth and character to the main living area. The kitchen is well-appointed with granite countertops, stainless steel appliances, and a newer refrigerator, while the generously sized bedrooms provide comfortable retreats. The primary suite features two closets and an ensuite bath with dual sinks. Major system updates provide exceptional peace of mind, including a brand-new roof and HVAC system installed in January 2026, along with fresh exterior paint, newer gutters (approximately three years old), and a newer fence. The washer and dryer convey, making this home truly move-in ready. The community offers an exceptionally low HOA fee of under $200 per month, adding to the home’s overall value. Ideally located with easy access to Winter Park, Maitland, Full Sail University, UCF, Rollins College, and Valencia College, as well as nearby shopping, dining, and major roadways. With its spacious design, private outdoor space, and proven rental history, this property presents an outstanding opportunity as either a primary residence or investment. Reach out to schedule your private showing now!
Listing is courtesy of: KELLER WILLIAMS WINTER PARK (407-545-6430)
Listing Agent: Jill Healey (407-797-1420)
2401 ANTILLES DR, WINTER PARK, FL 32792
$320,000220 Days on yellowkey MLS ID: O6357934
0 Days Off yellowkey (back on 5/14/2026)
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1719 Built: 1977Monthly Fee: $95Community: Windward Square Sec 1Townhouse
Taxes:$0
Elementary School: Eastbrook Elementary
Remarks: Under contract-accepting backup offers. Fantastic end unit with enclosed Florida Room in the sought after Windward Square! This 3/2 features several updates including a, updated kitchen with 42" wood cabinets, granite counters and a center island! Most rooms have upgraded ceiling fans from Dan”s Fans with a lifetime guarantee. The home has newer A/C, high impact windows and the home has been re-piped for your peace of mind. This is a wonderful space and great to prep for a dinner party! Open floor concept with dining room and family room. Enclosed Florida room with high impact windows is great extra living space marking this home just over 1700sf. Master bedroom is a good size with walk in closet. Secondary rooms are spacious and full 2nd bath. You have a wonderful front fenced courtyard and a nice sized fenced back yard. End unit and 2 assigned car parking spaces. Community features low HOA and community pool, gated back entrance for easy access to Semoran, tennis courts and club house. Zoned for great Seminole County schools and minutes to shopping/dining, Altamonte Springs Mall, Downtown Winter Park, Full Sail University and to UCF. This is a great one level townhome with very reasonable HOA.
Listing is courtesy of: KELLER WILLIAMS REALTY AT THE PARKS (407-629-4420)
Listing Agent: George Freelove (407-408-5167)
3054 BLUEBROOK DR, WINTER PARK, FL 32792
$410,00062 Days on yellowkey MLS ID: O6398450
REDUCED by $17,500 (4.1%) on 05/15/2026
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1939 Built: 1973 Tax: $6,422 (2025)Community: Laurel SpgsSingle Family
Taxes:$6,422
Remarks: Just Reduced the Price! "Open the Doors to Your Dreams" of owning an Affordable Home with a pool in Winter Park. The home features a Spacious Kitchen with Upgraded Cabinets, and stone countertops; Primary bedroom suite is amazing. You will love the layout and upgraded primary bathroom; Beautiful Porcelain tile flooring throughout the home; Large family room with fireplace; Large screened back porch/LANAI. And here is an inground pool in the back yard. You will enjoy entertaining in this home featuring a gourmet kitchen with granite countertops, and stainless steel appliances. This property may qualify for Seller Financing (Vendee). If property was built prior to 1978, Lead Based Paint Potentially Exists. Come tour this home today. We expect this one not to be on the market long at this REDUCED price.
Listing is courtesy of: WEATHERSPOON REALTY INC (407-878-4468)
Listing Agent: Eugene Weatherspoon (407-878-4468)
205 LEWFIELD CIR #205, WINTER PARK, FL 32792
$220,000152 Days on yellowkey MLS ID: S5141588
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 927 Built: 1973 Tax: $796 (2024)Community: Stratford A Winter Park CondoCondo
Taxes:$796
Elementary School: None
High School: None
Middle School: None
Remarks: MOTIVATED SELLER! Wonderful! Exceptional Winter Park location! Amenities include 2 pools, lighted tennis courts, fitness center, car care facilities & clubhouse, enjoy the simple life in this 2 bedroom, 2 bath, ground floor unit. Sip your morning coffee while admiring the garden landscaping from your screen enclosed patio. Host a BBQ with family and friends at the community clubhouse or enjoy shopping at the many neighborhood retail and grocery outlets nearby. The quaint restaurants, coffee houses, golf courses, and farmers markets of Winter Park and Baldwin Park are within biking distance. There is always something to see and do at this prime location. Recent upgrades include: new electric panel (2024), new washer/dryer in unit (2024), new dishwasher (2023), refrigerator (2020).
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Eimi Moreno Carrera (321-945-6195)
814 DENSMORE DR, WINTER PARK, FL 32792
$425,00058 Days on yellowkey MLS ID: O6399773
2 Days Off yellowkey (back on 5/13/2026)
Bed: 4 Bath: 2.0 Liv Area Sq Ft: 1610 Built: 1960 Tax: $5,402 (2025)Community: Winter Park EstatesSingle Family
Taxes:$5,402
Elementary School: Lakemont Elem
Middle School: Maitland Middle
Remarks: Under contract-accepting backup offers. Welcome to this charming home situated on a spacious lot in a quiet, established neighborhood in Winter Park. From the moment you arrive, you’ll appreciate the inviting curb appeal, expansive front yard, and peaceful setting that make this property feel like home. Inside, the home offers a light and open layout with a seamless flow between the living, dining, and kitchen spaces—perfect for both everyday living and entertaining. The updated kitchen features modern cabinetry, granite countertops, stainless steel appliances, and a functional layout with bar seating, making it both stylish and practical. The bedrooms are comfortably sized with great natural light, offering flexibility for family, guests, or a home office. The bathrooms have been thoughtfully updated, including a beautifully renovated shower with modern tilework that adds a fresh, clean feel. The Florida room in the back creates a relaxing space for drinking coffee or curling up for a family movie night. Step outside to a generously sized backyard with endless potential—whether you envision creating an outdoor entertaining space, adding a pool, or simply enjoying the open green space. With plenty of room to spread out, this yard offers the kind of flexibility that’s hard to find. Conveniently located near local shopping, dining, and major roadways, this home offers both comfort and accessibility. Zoned for great Winter Park schools. Whether you’re a first-time buyer, investor, or looking to downsize, this property presents an incredible opportunity to own a home with room to make it your own.
Listing is courtesy of: ORANGE SLICE PROPERTIES (863-632-9765)
Listing Agent: Liz Jones (407-619-6345)
311 SCOTTSDALE SQ #311, WINTER PARK, FL 32792
$109,900231 Days on yellowkey MLS ID: O6355536
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 785 Built: 1974Monthly Fee: $2,097 Tax: $1,271 (2024)Community: Winter Park Woods CondoCondo
Taxes:$1,271
Remarks: This 1 bedroom, 1 bath condo at 311 Scottsdale Sq, Winter Park, FL 32792 is leased to a reliable long-term tenant paying $1,450 / month. Located on the first floor in the established Winter Park Woods community, this unit features an open-concept layout as soon as you walk in. The HOA includes water, access to two community pools, a playground, and tennis courts. Winter Park Woods is also zoned for highly rated schools in Florida, which helps with both property value and long-term rental demand. The location is a major plus. This condo sits in the heart of Winter Park / Winter Park Pines / Goldenrod area, close to Full Sail University, UCF, AdventHealth, Orlando International Airport, and main highways for easy commuting. You’re just minutes from shopping, grocery stores, restaurants, gyms, parks, and Winter Park’s retail corridors. You also have quick access to downtown Winter Park, Orlando, and major job centers, which keeps rental demand very strong in this area.
Listing is courtesy of: EMPIRE NETWORK REALTY (407-440-3798)
Listing Agent: Omar Rodriguez (321-442-2001)
2225 WINTER WOODS BLVD, WINTER PARK, FL 32792
$375,00061 Days on yellowkey MLS ID: O6398734
1 Days Off yellowkey (back on 5/12/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1473 Built: 1968Monthly Fee: $2 Tax: $3,236 (2024)Community: Winter Woods Unit 01Single Family
Taxes:$3,236
Remarks: Under contract-accepting backup offers. MULTIPLE OFFERS RECEIVED, PLEASE SUBMIT YOUR BEST OFFER BY 5PM EST ON MONDAY 5/11/2026. Welcome to this beautifully maintained three-bedroom, two-bathroom home offering nearly 1500 square feet of thoughtfully designed living space on an expansive pie-shaped lot. Featuring a desirable split floor plan, this move-in ready residence combines functional living spaces with tasteful updates throughout, all in a convenient location close to shopping, dining, major roadways, and some of Central Florida’s most sought-after destinations. Inside, fresh interior paint and updated wood-grain laminate and tile flooring create a warm and inviting atmosphere. Multiple living and gathering spaces include a comfortable sitting room, dedicated dining area, and a spacious layout ideal for both everyday living and entertaining. The laundry room offers exceptional storage space and a utility sink, with the washer and dryer included, for added convenience. The kitchen features honey-toned oak cabinetry, black appliances, a closet pantry, and ample workspace for meal preparation and hosting. Privately positioned away from the secondary bedrooms, the primary suite serves as a peaceful retreat with fresh paint, a walk-in closet, ceiling fan, and en-suite bathroom complete with a white single vanity and tiled shower. The updated hall bathroom, renovated in 2021, showcases a contemporary white vanity and tiled tub/shower combination. Step outside to enjoy the oversized fully fenced backyard offering endless opportunities for outdoor living, gardening, pets, or future enhancements. A screened lanai with brand-new screening installed in 2025 provides the perfect spot to relax year-round. Additional exterior improvements include an updated paver driveway and updated garage doors completed in 2024, enhancing both curb appeal and functionality. The two-car garage and mature landscaping complete the exterior package. Ideally located just minutes from everyday conveniences, this home is approximately 10 minutes from the dining, shopping, and charm of Park Avenue in Winter Park, 25 minutes from Orlando International Airport, and offers close proximity to UCF, Full Sail University, and Rollins College. Convenient access to major transportation routes, restaurants, retail stores, and entertainment makes this location as practical as it is desirable. ROOF - 2019 HVAC - 2021 PLUMBING - 2025 ELECTRICAL - 2025
Listing Agent: Amy Turner (407-803-3885)
1427 LAKE FLORENCE WAY, WINTER PARK, FL 32792
$639,000205 Days on yellowkey MLS ID: TB8449992
1 Days Off yellowkey (back on 5/11/2026)
REDUCED by $36,000 (5.3%) on 05/06/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2193 Built: 2019Monthly Fee: $186 Tax: $5,586 (2024)Community: Lake Florence PreserveSpa: YesSingle Family
Taxes:$5,586
Remarks: Welcome to this beautifully maintained, Stunning Better-Than-New 6-Year-Old Custom Home in Gated Lake Florence Preserve, one-owner custom home that truly has it all. From the moment you enter, you’ll appreciate the exceptional quality and craftsmanship, including upgraded 8' interior doors, 10-foot ceilings, crown molding, and elegant tray ceilings throughout—even in the primary suite. One of the home’s most impressive features is the expansive 16-foot pocket sliding glass door that creates a seamless indoor–outdoor connection, making your private backyard oasis feel like a natural extension of your living space. Step into the custom heated pool with built-in spa, finished in luxurious PebbleTec, and enjoy the tranquil waterfall cascading from the spa into the pool. The entire screened-in lanai is surrounded by lush landscaping and enhanced by a striking outdoor LED lighting system. The fully fenced backyard overlooks a generous greenspace that enhances privacy and creates an ideal setting for pets, entertaining, or unwinding. TV wall mounts are already installed inside and on the lanai, ideal for watching the game or unwinding by the pool. The upgraded kitchen is a chef’s dream, featuring premium finishes and a gas stove, while the open-concept living area offers an inviting space for everyday living and entertaining. All bedrooms feature recently upgraded flooring, and the primary suite includes a large walk-in closet and a spa-like bathroom with a luxurious rain shower head. The home is outfitted with numerous upgrades for comfort and convenience, including motorized blinds on the sliding glass doors, ceiling fans throughout, dimmer light switches, and a full security system. Fresh interior paint including all doors adds a crisp, updated feel to every room. Practical features include an interior storage room, a tankless water heater, and a full sprinkler system covering both the front and backyard. The home also comes prewired with plumbing, gas, and electric for a future outdoor kitchen, offering excellent potential for expanded outdoor living. The garage is exceptionally functional, featuring a 240V EV outlet, a dedicated golf cart parking space, added shelving, and attic storage for additional organization and convenience.
Listing is courtesy of: COMMUNITY REALTY ASSOCIATES (561-852-1341)
Listing Agent: Douglas Addeo (561-251-3408)
819 DENSMORE DR, WINTER PARK, FL 32792
$375,00037 Days on yellowkey MLS ID: O6405658
3 Days Off yellowkey (back on 5/11/2026)
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1300 Built: 1961 Tax: $5,225 (2025)Community: Winter Park Estates Sec 2Single Family
Taxes:$5,225
Remarks: Under contract-accepting backup offers. Welcome to 819 Densmore Drive, a beautifully refreshed concrete block ranch home in the heart of Winter Park Estates, one of Winter Park's most established neighborhoods with no HOA. This move-in ready home checks every box for buyers who want turn-key condition with an accessible price and a coveted Winter Park address. From the moment you pull up, the curb appeal speaks for itself. A crisp white exterior with fresh paint, an extra large driveway with RV, Boat, or trailer parking, and a lush green lawn, sit against the quiet, tree-lined street that makes this neighborhood so beloved. Step inside and you'll notice the brand-new Palmer Oak Rigid Core Luxury Vinyl Plank flooring running throughout the entire home, installed in 2026! It delivers the warmth of hardwood with the durability Florida living demands, and ties every room together beautifully. The interior was freshly painted top to bottom in 2026, giving every room a bright, clean feel that makes the home feel completely renewed. The layout is open and functional, with generous living areas, a dining room anchored by a chandelier that stays with the home, and bedrooms filled with natural light and ceiling fans throughout. The kitchen comes equipped with the refrigerator included, a functional breakfast bar, recessed lighting, and plenty of storage. Blinds, decorative framed bath mirrors, ceiling fans, and keypad entry all stay. Both bathrooms received new vanities and toilets in 2026, delivering a completely fresh, modern look. The big-ticket systems are solid. The roof was replaced in February 2022. The HVAC system is less than two years old. The plumbing was repiped to PEX in 2016, and the home connects to city sewer, public water, and public irrigation. No well, no septic, no solar obligations. Clean, uncomplicated ownership. The backyard is shaded by a mature tree with room to spread out, BBQ, add playgrounds, pools, or bounce houses, and the property sits high and dry away from flood zones. Zoned for Lakemont Elementary, Maitland Middle, and Winter Park High School, this home places you in one of Orange County's most sought-after school districts. Minutes to Park Avenue dining and boutique shopping, Advent Health Winter Park, Winter Park Pines Golf Course, the Cady Way Trail, and easy access to SR-436, Aloma Avenue, and the 408. Winter Park Estates is the kind of neighborhood where properties like this, genuinely updated and truly move-in ready in a community this well-established and well-located, don't sit long. Schedule your showing today.
Listing is courtesy of: DON HARKINS REALTY LLC (321-377-0341)
Listing Agent: Donald Harkins, Iii (321-377-0341)
3374 HAMLET LOOP, WINTER PARK, FL 32792
$370,00044 Days on yellowkey MLS ID: O6403488
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1397 Built: 1994Monthly Fee: $63 Tax: $5,326 (2024)Community: Villas Of Casselberry Ph 3Single Family
Taxes:$5,326
Remarks: Tucked inside a quiet Winter Park neighborhood, this three-bedroom, two-bath home offers a comfortable layout and a sense of privacy that’s hard to find. No rear neighbors and a tree-lined backyard create a peaceful setting you’ll appreciate every day. The main living area is open and versatile, allowing you to arrange the space in a way that truly fits your lifestyle. The living room and dining room flow into the kitchen, where you’ll find lots cabinet storage, eat in space, and a view out to the backyard. The primary suite is conveniently located on the main floor, featuring generous windows that bring in natural light, a walk-in closet, and an updated en suite bath. A half bath downstairs adds convenience for guests. Upstairs, two spacious bedrooms share a full bath, offering comfortable separation from the main living areas. The Villas of Casselberry community has a pool for you to enjoy. The location places you just minutes from Park Ave’s shops, dining, events and great parks. With easy access to major roads and a central location close to Rollins, UCF, Full Sail and downtown Orlando, this home offers both comfort and connectivity. If you’ve been looking for space, privacy, and a well located Winter Park address, this one is worth seeing in person. Schedule your showing today!
Listing is courtesy of: KELLER WILLIAMS ADVANTAGE REALTY (407-977-7600)
Listing Agent: Barrett Spray (407-927-3650)
5454 BRACKEN COURT, WINTER PARK, FL 32792
$199,00037 Days on yellowkey MLS ID: O6401099
0 Days Off yellowkey (back on 5/7/2026)
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1332 Built: 1984Monthly Fee: $110 Tax: $728 (2024)Community: Fernbrook TrailsTownhouse
Taxes:$728
Remarks: Charming two-story townhouse in Winter Park offering great potential for the right buyer! This 3-bedroom, 2-bath home features a cozy fireplace, a spacious layout, and a back porch overlooking a large, fenced backyard—perfect for outdoor enjoyment. The property does need some TLC, making it an excellent opportunity for investors or buyers looking to add their personal touch. Conveniently located near shopping, dining, parks, and major roadways, this home combines location with opportunity.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Mark Ramey (407-496-1766)
517 ROUGHBEARD RD, WINTER PARK, FL 32792
$565,00060 Days on yellowkey MLS ID: O6399029
1 Days Off yellowkey (back on 5/2/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1873 Built: 1971 Tax: $4,323 (2025)Community: Winter Park Pines Unit 17Single Family
Taxes:$4,323
Remarks: Under contract-accepting backup offers. Welcome home to the Winter Park Pines where the trees line the streets and the mailman delivers to your door. This beautifully maintained 3-bedroom, 2-bathroom home offering 1,873 square feet of comfortable living in the highly desirable and serene Winter Park Pines community. This light-filled residence features a thoughtfully designed split floor plan with high ceilings, fresh interior paint (2026), skylights, and laminate and tile flooring throughout, creating a bright and inviting atmosphere from the moment you enter. The open living and dining areas are anchored by a charming wood-burning brick fireplace, while crown molding, ceiling fans, and French doors add both style and functionality throughout the home. The well-appointed kitchen includes white and gray cabinetry, stainless steel appliances, and a convenient pantry closet, perfect for both everyday living and entertaining. It flows seamlessly into the main living areas, making it easy to gather with family and friends. The spacious primary suite offers a private retreat, thoughtfully separated from the secondary bedrooms, and features a walk-in closet with custom built-ins, ceiling fan, and French doors leading to the expansive and shaded backyard. The renovated en-suite bathroom showcases double vanities and a beautifully tiled shower with frameless glass enclosure. The secondary bedrooms are well-sized and versatile, with easy access to the renovated hall bathroom featuring a granite double vanity, navy cabinetry, and direct access to the backyard, ideal for indoor-outdoor living. Step outside to enjoy a fully fenced, landscaped backyard situated on a generous .22-acre lot. The expansive patio with terracotta tile flooring provides the perfect space for outdoor dining, entertaining, or simply relaxing in a private setting. Additional highlights include a two-car garage and a Ring home security and surveillance system for added peace of mind. Located just minutes from top-rated Winter Park schools, the Cady Way Trail, Winter Park Pines Golf Course, Advent Health Winter Park campus, Crosby Wellness Center and a variety of shopping and dining options, this home offers both tranquility and convenience. Residents also enjoy access to nearby community amenities including a pool, playground, beach volley ball courts and tennis/pickleball courts. With close proximity to major roadways, downtown Winter Park, and Orlando International Airport, this property truly combines comfort, location, and lifestyle. Don’t miss the opportunity to make this exceptional home yours in one of Winter Park’s most sought-after neighborhoods. Roof 2020, HVAC 2022, Plumbing 2014, Water Heater 2021.
2774 BRIGHT BIRD LN, WINTER PARK, FL 32792
$465,000540 Days on yellowkey MLS ID: O6266098
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1907 Built: 2024Monthly Fee: $375 Tax: $1,009 (2023)Community: Grayson SquareTownhouse
Taxes:$1,009
Tax Year: 2023
Remarks: Motivated seller! Brand new townhouse professionally decorated, and available today! Built in 2024, this property offers a great floorplan: with a lot of natural light and coziness. Fall in love with the modern and spacious house located in a prestigious area! Close to shops and markets this is an amazing opportunity for those looking for a quiet neighborhood but close to everything at the same time! Schedule a tour today!
Listing is courtesy of: FLORIDA CONNEXION PROPERTIES (407-574-2636)
Listing Agent: Priscila Triska (321-354-5459)
5331 OAK CT, WINTER PARK, FL 32792
$460,000332 Days on yellowkey MLS ID: S5130868
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1263 Built: 1976 Tax: $2,311 (2024)Community: Wrenwood Heights Unit 2Spa: NoSingle Family
Taxes:$2,311
Remarks: Welcome to Wrenwood Heights Community!! Very well Maintain Pool Home on CUL-DE-SAC LOT!! Great community with no HOA. House located on spacious large lot 0.31 Acre. House features Open Concept with 3 bedroom and 2 bathroom! New Roff 2024. Pool was resurfaced in 2025. Fully Fenced Backyard with upgraded Paver patio and mature landscaping and Fruit trees. Community located in Winter Park close to parks, shopping, dining and main highways. Seminole County schools! Call today to schedule your private showing!
Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)
Listing Agent: Nataliya Voroshylo Hylton (407-284-7247)
1131 WILDMEADOW RUN, WINTER PARK, FL 32792
$825,00081 Days on yellowkey MLS ID: O6392218
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2589 Built: 2020Monthly Fee: $165 Tax: $5,312 (2024)Community: Meadows At Hawks CrestSingle Family
Taxes:$5,312
Middle School: Sanford Middle
Remarks: Winter Park - Located in the gated community of Hawks Crest, this 4-bedroom, 3.5-bath home offers 2,589 square feet of well-designed living space on a premium pond-view lot. Built in 2020, the home features a downstairs primary suite, open-concept living area, and a versatile upstairs loft. Additional highlights include a tile roof, modern finishes, a screened-in patio for outdoor living, and access to community amenities. This home combines location, layout, and value in a beautiful Winter Park gated communities.
Listing is courtesy of: BECK REALTY LLC (407-256-6369)
Listing Agent: Joann Beck (407-256-6369)
2922 REEF KNOT PL, WINTER PARK, FL 32792
$1,149,000370 Days on yellowkey MLS ID: O6316445
0 Days Off yellowkey (back on 5/2/2026)
Bed: 4 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 3153 Built: 2019Monthly Fee: $186 Tax: $10,521 (2024)Community: Lake Florence PreserveSpa: YesSingle Family
Taxes:$10,521
Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Incredible Value!!! Major price reduction! Private Lakefront Living! Move-in Ready! Wake up to water views, quiet mornings and the kind of lifestyle that rarely becomes available in the Winter Park/Howell Branch area. Set along the shores of a private ski lake- Lake Florence, this single-level lakefront residence offers a serene retreat within an intimate gated enclave of just 28 homes. A setting that feels private and peaceful that is increasingly hard to find. Designed for both everyday comfort and effortless entertaining, the thoughtfully planned 4-bedroom, 3.5-bath layout includes a dedicated office, formal dining room and a desirable three-way split floor plan that provides flexibility and privacy for today’s lifestyle. At the heart of the home, the gourmet kitchen blends beauty and function with quartz countertops, a substantial center island, natural gas cooktop, 42" solid wood cabinetry, walk-in pantry, and a generous butler’s pantry—perfect for hosting or simply enjoying the flow of daily living. Rich wood flooring carries throughout the home connecting the kitchen seamlessly to the light-filled family room and casual dinette area. The primary suite is a true lakefront sanctuary featuring peaceful water views, two walk-in closets and a spa-inspired bath with dual sinks and an oversized shower with dual shower heads. Many upgrades are to be found through out this home such as an extra oversized storage closet, crown molding, custom mud room off of the laundry room, high ceilings, tray accents and abundant natural light to enhance the home’s relaxed, refined feel. Outdoors, the property transforms into a private lakefront escape. Enjoy sweeping water views, a sparkling pool and spa, custom rock waterfall, screened-in lanai and a fully fenced yard framed by tall privacy hedges and mature trees—ideal for quiet evenings or weekend gatherings. Direct lake frontage and access to a nearby community dock complete the lifestyle experience. A three-car garage with a separate AC wall unit offers added versatility—perfect for a workshop, home gym, or additional storage. Thoughtfully positioned, this home represents a rare opportunity to own a lakefront retreat that delivers serenity, lifestyle and value—all within close proximity to shopping, dining and top-rated schools in a prime location!
Listing Agent: Ellen Bessette (407-496-0076)
2627 AMBERGATE RD, WINTER PARK, FL 32792
$510,0001187 Days on yellowkey MLS ID: O6093816
Bed: 4 Bath: 3.0 Gar: 1 Liv Area Sq Ft: 1805 Built: 1959 Tax: $4,750 (2022)Community: Winter Park EstatesSingle Family
Taxes:$4,750
Tax Year: 2022
Remarks: Price Reduced !! This beautiful and remodeled home is turnkey and ready to move in! Investors -- You will love the cash flow upside with this property. Updated Roof, AC, Exterior Paint, Patio, Garage, Driveway, Fence, Sprinkler System, Lighting, Flooring, Kitchen, and much more. You will enjoy entertaining your guests with this large saltwater pool with cabana, as well as yard space for your pets. Save money with No HOA, in a nice mature community. Smart home comes a split floor plan, and kitchen has a large island with granite countertops. Home features an extended driveway with room for a Small boat, Jet ski or RV. *All information is intended to be accurate but is not guaranteed.
Listing is courtesy of: COLDWELL BANKER REALTY (407-647-1211)
Listing Agent: Ryan Minadie (407-765-9990)
7484 CANFORD CT #8, WINTER PARK, FL 32792
$250,00047 Days on yellowkey MLS ID: O6402492
Bed: 3 Bath: 2.5 Liv Area Sq Ft: 1578 Built: 1974 Tax: $2,121 (2025)Community: Whisperwood CondoCondo
Taxes:$2,121
Elementary School: Cheney Elem
Remarks: This three-bedroom, three-bath updated Winter Park townhome-style condo is located in a quiet complex, a perfect place to call home. It's just minutes away from the University of Central Florida, Full Sail University, & Valencia College. This location makes an excellent investment for a college (or parents of) student. The upgraded kitchen has granite countertops with a custom sink, newer stainless steel appliances, and a closet pantry. There is a separate dining room that opens onto a very private brick paver patio with a new privacy fence. This unique condo features a flexible layout, an inside utility, and includes the washer & dryer. Modern-design porcelain tile flooring. The home has a large screen porch, which is considered by many in Florida, to be extra living space. There is also a front courtyard that is perfect for a raised bed garden or ???. Highly desired Winter Park schools. A 2-car carport with an ample lockable storage closet. New roof in 2020 and an updated electric system. The complex has a private community pool
Listing Agent: Greg Harrison (407-276-6141)
1951 CANNY CV, WINTER PARK, FL 32792
$444,900182 Days on yellowkey MLS ID: O6367023
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1782 Built: 2023Monthly Fee: $375 Tax: $6,889 (2025)Community: Grayson SquareTownhouse
Taxes:$6,889
Remarks: Welcome to easy, light-filled living in this beautifully maintained 3-bedroom, 2.5-bath corner townhome in the gated Grayson Square community. Freshly painted and designed for comfort, the open living and dining spaces feel bright and inviting, flowing effortlessly to a covered lanai—perfect for relaxing evenings or casual gatherings. The kitchen offers a clean, modern look with stainless steel appliances, quartz countertops, and plenty of cabinet space for storage and organization. Upstairs, the owner’s suite provides a private retreat with a walk-in closet and a spacious ensuite bath featuring dual vanities and a glass-enclosed shower. A two-car garage with epoxy flooring and an in-unit washer and dryer add everyday convenience. Residents also enjoy access to a resort-style pool with cabana, along with high-speed fiber-optic internet and streaming services included. Located just minutes from downtown Winter Park, with easy access to major roadways, shopping, dining, and everyday essentials, this home offers a great balance of comfort, convenience, and low-maintenance living.HABLO ESPANOL
Listing Agent: Denise Del Castillo (321-960-3110)
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