Location: Winter Park , 32792
Do Not Show Listings
2052 LEANNE CT, WINTER PARK, FL 32792
$456,00062 Days on yellowkey MLS ID: O6379323
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2264 Built: 1969 Tax: $1,581 (2024)Community: Eastbrook Sub Unit 15Single Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$1,581
Elementary School: None
High School: None
Tax Year: 2024
Middle School: None
Remarks: Welcome to 2052 Leanne Ct, a home that exudes warmth and elegance. The living room is graced with a cozy fireplace, perfect for those chilly evenings. The kitchen is a chef's dream, boasting all stainless steel appliances for a sleek, modern look. The primary bedroom is a haven of comfort with double closets for ample storage. The primary bathroom is a sanctuary with double sinks, providing ample space for your morning routine. The fenced-in backyard provides a private outdoor space for relaxation and entertainment. The home has been recently updated with fresh interior and exterior paint, giving it a clean, refreshed look. New flooring throughout the home adds a touch of sophistication and durability. The new appliances ensure efficiency and convenience. Included 100-Day Home Warranty with buyer activation
Listing is courtesy of: OPENDOOR BROKERAGE LLC (480-462-5392)
Listing Agent: Karen Albright (480-462-5392)
2501 TAHOE CIR, WINTER PARK, FL 32792
$259,90067 Days on yellowkey MLS ID: O6378209
REDUCED by $10,000 (3.7%) on 04/05/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1495 Built: 1981 Tax: $3,757 (2025)Community: Cedarwood Village 1Condo
Taxes:$3,757
Elementary School: English Estates Elementary
High School: Lake Howell High
Tax Year: 2025
Middle School: Tuskawilla Middle
Remarks: Recently Improved to $259,900 - One of the BEST Values in Winter Park !! Welcome home to this spacious two-story Winter Park condo located in the sought-after Cedarwood Village community. Tucked away among mature landscaping yet close to everything, this residence offers a comfortable blend of privacy, architectural character, and convenience in a prime Central Florida location. The main living area features soaring 16.5-foot vaulted ceilings, a wood-burning fireplace, and sliding glass doors that lead to a screened rear porch, creating a seamless indoor-outdoor connection. Two skylights and a second-story loft overlooking the living room add architectural interest and flexible space ideal for a home office, reading nook, or guest retreat. The thoughtfully designed split floor plan enhances functionality and privacy. Additional highlights include a spacious kitchen with breakfast bar and island, a primary suite on the main level, and a screened back porch perfect for relaxing or entertaining. Community amenities include a swimming pool and tennis courts, supporting a low-maintenance, active lifestyle. Located just minutes from Rollins College, with convenient access to local retail shopping, dining, and everyday conveniences, this home is also a short drive to downtown Orlando, offering easy access to museums, theaters, and a variety of local events—combining the charm of Winter Park with excellent city connectivity. All measurements and information should be verified.
Listing is courtesy of: COLDWELL BANKER REALTY (407-647-1211)
Listing Agent: Mya Adloo (678-923-9460)
2401 ANTILLES DR, WINTER PARK, FL 32792
$320,000152 Days on yellowkey MLS ID: O6357934
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: 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)
3463 ARNEL DR, WINTER PARK, FL 32792
$479,90020 Days on yellowkey MLS ID: O6390301
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1770 Built: 1967 Tax: $4,648 (2024)Community: Eastbrook Sub Unit 11Single Family
Taxes:$4,648
Remarks: Your pool home in Winter Park. This home offers three bedrooms plus a versatile bonus room, approximately 1,770 sq ft of living space, built in 1967, along with a two-car garage and extended driveway for additional parking. Located in the established Eastbrook community with no HOA. Key updates include a roof replaced in 2018, solar panels installed in 2020 (fully paid off), water heater replaced in 2019, and AC replaced in July 2013. A comprehensive home warranty through First American Home Warranty is included, covering major systems for added peace of mind. Inside, you’ll find a bright and functional layout with comfortable living and dining areas that flow naturally, along with an updated kitchen featuring granite countertops and modern cabinetry. Both bathrooms have been updated with clean, modern finishes. The bonus room offers flexibility for a home office, gym, nursery, or additional living space. Step outside to a fully fenced backyard featuring a private pool, creating the perfect space for relaxing, entertaining, and enjoying Florida living year-round, with a great balance of pool deck and green space. Conveniently located near Downtown Winter Park, Park Avenue, Rollins College, Full Sail University, UCF, major highways, and zoned for top-rated Seminole County schools.
Listing is courtesy of: KELLER WILLIAMS ADVANTAGE 2 REALTY (407-393-5901)
Listing Agent: Alexa Monasterio Flores (786-915-9294)
4872 ORANGE AVE, WINTER PARK, FL 32792
$375,00060 Days on yellowkey MLS ID: O6380333
1 Days Off yellowkey (back on 4/5/2026)
Bed: 3 Bath: 2.5 Liv Area Sq Ft: 1881 Built: 1960 Tax: $4,494 (2024)Community: Suburban Homes First AddSingle Family
Taxes:$4,494
Elementary School: Lakemont Elem
Middle School: Maitland Middle
Remarks: 3 bedroom 3 bathroom pool home. Enjoy the large backyard. Schedule your showing today!
Listing is courtesy of: ALFA REAL ESTATE LLC (407-545-9562)
Listing Agent: Thai Nguyen (407-545-9562)
2175 MARSH SEDGE LN, WINTER PARK, FL 32792
$845,00012 Days on yellowkey MLS ID: O6393503
1 Days Off yellowkey (back on 4/4/2026)
Bed: 5 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3188 Built: 2019Monthly Fee: $236 Tax: $9,100 (2025)Community: Hawks CrestSingle Family
Taxes:$9,100
Remarks: Under contract-accepting backup offers. Beautifully designed and impeccably maintained, this light-filled home offers the perfect blend of modern comfort and timeless style. Featuring an open and airy layout, the home is highlighted by abundant natural light, neutral designer finishes, and thoughtfully curated living spaces throughout. The bright and inviting living area flows seamlessly, creating the ideal space for both everyday living and effortless entertaining, while a spacious loft provides additional flexibility for a media room, lounge, or family retreat. The serene primary suite offers a true retreat-like atmosphere with soft neutral tones and abundant natural light, complemented by a well-appointed primary bath featuring dual vanities, expansive counter space, and a clean, modern design. The master bedroom is on the first floor. Additional bedrooms are upstairs, comfortable, and versatile, each filled with natural light and designed to accommodate guests, family, or personalized use. A charming flex space is also upstairs and offers endless possibilities as a playroom, creative studio, or additional living area. Secondary bathrooms are well-maintained with modern finishes and timeless appeal, enhancing both style and convenience throughout the home. Step outside to an expansive screened lanai that creates a private outdoor oasis, ideal for dining, lounging, or entertaining while enjoying tranquil views. An additional outdoor seating area further enhances the home’s indoor-outdoor lifestyle, offering the perfect setting for relaxing or gathering with guests. Move-in ready and thoughtfully styled, this home combines comfort, versatility, and elevated design in every detail, making it an exceptional opportunity for a wide range of buyers. The neighborhood also offers a plethora of amenities including a dog park, pool, clubhouse, gym, and walking trails. You are also in close proximity to dining, schools, and entertainment. Come see this home today!
Listing is courtesy of: ORANGE SLICE PROPERTIES (863-632-9765)
Listing Agent: Liz Jones (407-619-6345)
7445 BETTY ST, WINTER PARK, FL 32792
$435,0005 Days on yellowkey MLS ID: OM721366
0 Days Off yellowkey (back on 4/4/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1576 Built: 1983 Tax: $3,769 (2025)Community: Wrenwood Unit 3 4Th AddSingle Family
Taxes:$3,769
Remarks: Under contract-accepting backup offers. Newly remodeled ranch in a prime location! Situated in a great neighborhood with easy access to everything, this move-in ready home checks all the boxes. Featuring a desirable split floor plan, this home offers both functionality and privacy. Inside, you’ll find brand new windows, beautiful new wood flooring, and new carpet in the guest bedrooms, along with fresh interior paint, new baseboards and door trim, and updated ceiling fans and light fixtures throughout. The fully renovated kitchen showcases new cabinets with soft-close features and quartz countertops, creating a clean, modern feel. Bathrooms have been refreshed with new toilets, and every detail has been thoughtfully updated. Enjoy the outdoors with a screened porch featuring new outdoor carpet and a new irrigation system to keep your yard looking its best. The home also features a newly painted exterior and a roof replaced in 2022 for added peace of mind. This is a truly turnkey home with quality upgrades throughout—ready for its next owner to move in and enjoy.
Listing is courtesy of: LISTY, LLC (561-309-9240)
Listing Agent: Nicholas Macy (561-309-9240)
1183 WILDMEADOW RUN, WINTER PARK, FL 32792
$830,00045 Days on yellowkey MLS ID: O6379772
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3020 Built: 2020Monthly Fee: $150 Tax: $5,682 (2024)Community: Meadows At Hawks CrestSingle Family
Taxes:$5,682
Remarks: Welcome to this original-owner residence in The Meadows at Hawk’s Crest, where thoughtful design and exceptional privacy come together—featuring two true primary suites, one on the first floor and one on the second. Set on an oversized fenced homesite along a quiet non-thru street with no neighbor to the east, this beautifully maintained 4-bedroom, 3.5-bath home offers over 3,020 sq.ft. of living space and approximately $80,000 in luxury upgrades throughout, along with both a seller-provided home warranty and remaining builder warranty for added peace of mind. • PRIMARY SUITES—The first-floor primary suite offers a private main-level retreat with split vanities, a walk-in shower, and a spacious closet, while the second-floor primary suite features dual walk-in closets, a double-sink vanity, and walk-in shower, providing exceptional flexibility for extended stays or multigenerational living. • LIVING SPACES—The open-concept main level seamlessly connects the kitchen, dining, and family room, enhanced by quartz countertops, stainless steel appliances, an externally vented kitchen hood, luxury vinyl plank flooring throughout the first floor, and recessed lighting across the entire home, including both primary bedrooms; a dedicated first-floor office adds valuable versatility, while upstairs a generous loft and oversized game/media room create a true second living zone alongside two additional bedrooms and a full bath. • TECHNOLOGY & FEATURES—Cat5 wiring with a central hub supports modern connectivity, with the home pre-wired for security and enhanced by a Ring doorbell, exterior cameras, and smart-ready infrastructure, while storage is abundant with multiple walk-in closets, hall and linen storage, pull-down attic access, and garage ceiling storage racks. • OUTDOOR LIVING—Exterior landscape lighting, a mounted outdoor TV, and a widened paver driveway complement a private backyard with ample space for a future pool or custom outdoor oasis. • COMMUNITY & LOCATION—Lawn care is included within The Meadows, and residents enjoy resort-style amenities including a community pool, splash pad, fitness clubhouse, and virtual-guard gated entry, all conveniently located near shopping, dining, major roadways, and Winter Park attractions with quick access to Lake Howell Branch Park, the Cross Seminole Trail, and the Cady Way Trail—offering a rare combination of dual primary suites, privacy, and value priced below comparable plans currently offered in Hawk’s Crest.
Listing is courtesy of: COLDWELL BANKER REALTY (407-696-8000)
Listing Agent: Kara Lushear (321-663-5550)
676 DUNBLANE DR, WINTER PARK, FL 32792
$750,000122 Days on yellowkey MLS ID: O6365557
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1827 Built: 1962 Tax: $5,584 (2024)Community: Kenilworth Shores Sec 04Single Family
Taxes:$5,584
Elementary School: Brookshire Elem
High School: Winter Park High
Middle School: Glenridge Middle
Remarks: This meticulously maintained POOL HOME located in the highly desirable Kenilworth Shores community could be YOURS! 3 Beds | 2 Baths | Bonus Room | This classic ranch-style residence offers a spacious and functional layout with three well-appointed bedrooms, two full bathrooms, a formal living room, dining area, and a bright breakfast nook. An additional bonus room provides flexible use — ideal as a home office, creative studio, workout space or playroom — all with tranquil views of the pool and backyard. The property features a beautifully landscaped, fully fenced yard and a private pool area, perfect for entertaining, relaxing, or enjoying the Florida lifestyle. Originally updated in 2012, the home benefits from a well-balanced and comfortable floorplan, complemented by key mechanical upgrades including a newer HVAC system and roof, and a brand-new water heater installed in 2024. With these major updates already completed, the property is truly move-in ready — offering peace of mind and lasting value. Don’t miss your opportunity to own a beautifully maintained home in a location that continues to deliver on both lifestyle and convenience. Zoned for Brookshire Elementary, Glenridge Middle, and Winter Park High, the location also offers close proximity to top institutions and amenities, including Rollins College (2.3 miles), Full Sail University (2.4 miles), AdventHealth Winter Park (0.9 miles), and the VA Medical Center (1.3 miles). Outdoor enthusiasts will appreciate the nearby Cady Way Trail, Blue Jacket Park, and Lake Baldwin, all within a short drive, offering walking paths, open green space, and recreational opportunities. ASSUMABLE VA LOAN at 2.25% Interest Incredible opportunity to assume the seller’s VA mortgage at just 2.25% interest. Just minutes from the vibrant centers of Baldwin Park and Park Avenue, this property provides convenient access to an array of restaurants, boutique shops, cafés, and year-round events. 676 Dunblane Drive is a rare opportunity to own a well-located, move-in-ready home in one of Winter Park’s most established and sought-after neighborhoods. Book your private showing TODAY!
Listing is courtesy of: BALDWIN PARK REALTY LLC (407-986-9800)
Listing Agent: Emma Kaplan (407-942-7542)
3019 ANTIQUE OAKS CIR #124, WINTER PARK, FL 32792
$154,000227 Days on yellowkey MLS ID: O6337083
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 749 Built: 1984Monthly Fee: $300 Tax: $2,050 (2024)Community: Parkview VillageCondo
Taxes:$2,050
Elementary School: Aloma Elem
Remarks: The Ultimate Winter Park is your every desire. Investment Potential, Student Sanctuary or just a long-awaited Life. Centrally located at your fingertips. Location, Lifestyle, Luxurious Zip Code, Friends, Culture and Community. Discover an unparalleled opportunity to own a piece of prime real estate in the heart of Winter Park, Florida. This beautifully appointed condo apartment is located within a vibrant, amenity-rich HOA community offering a perfect blend of convenience and value. Whether you're a first-time buyer, a savvy investor seeking strong rental return, or a student prioritizing location and community, this unit checks every box, all at an exceptional, reasonable price point. The very best luxury boutiques, fine dining, sidewalk cafes, and vibrant art festivals. Instant access to top tier schools and hospitals. A very short commute to Rollins College, Full Sail University, UCF, Valencia College and major medical centers like AdventHealth and Orlando Health facilities, making it ideal for any resident, and or faculty. Transportation is easily accessible to Downtown Orlando where the famous Lake Eola Park is, Winter Springs, Oviedo, The Orlando International Airport, Cady Way Trail, Biking, Hiking, Swimming, Volleyball, Pickleball, Tennis and Painting at The Crealde School Of Art. There's just so much within reach. Explore local gatherings, social events and community connections. For all investors, strong rental income potential and appreciation value. There's low maintenance and worry-free ownership opportunities. Let's build a portfolio together. Don't walk...run!
Listing Agent: Cassandra Kelly Flores (347-723-4649)
1923 LINDEN RD, WINTER PARK, FL 32792
$499,9997 Days on yellowkey MLS ID: O6393643
Bed: 4 Bath: 3.0 Liv Area Sq Ft: 2117 Built: 1955 Tax: $340 (2024)Community: Tanglewood Sec 4Single Family
Taxes:$340
Remarks: ***WINTER PARK **** 4 BEDROOMS ****3 BATHROOM **** PAID OFF SOLAR ***** WILL HELP BUYER****METAL ROOF ***1/3 ACRE*** Welcome to 1923 Linden Rd, Winter Park—a well-maintained single-story residence offering space, character, and an exceptional location. Built in 1955, this solid masonry and concrete block home features 4 bedrooms, 3 full bathrooms, and approximately 2,117 heated square feet, with 2,281 total building square feet. Located in the highly desirable area of Winter Park, the home provides convenient access to shopping, dining, parks, and top-rated schools, as well as nearby Park Avenue and downtown Orlando. The interior offers a functional layout with multiple living areas, ideal for both everyday living and entertaining. Original character elements such as plaster interior walls and two fireplaces add warmth and timeless appeal. The centrally located kitchen provides ample workspace and flows seamlessly into the main living areas. Situated on a generous 0.315-acre lot (13,717 sq ft) with approximately 117 feet of frontage and 114 feet of depth, the property offers plenty of room for outdoor enjoyment, future enhancements, or expansion. Additional features include Metal Roof that allows for 20 degrees cool, continuous footing foundation, and package cooling system. A strong opportunity for buyers seeking a well-built home with character, space, and long-term value in a prime location.
Listing Agent: Milton James (407-572-4458)
643 DUNBLANE DR, WINTER PARK, FL 32792
$699,80038 Days on yellowkey MLS ID: O6386136
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1575 Built: 1962 Tax: $4,598 (2024)Community: Kenilworth Shores Section Four Y/71 Lot 21 Blk BSingle Family
Taxes:$4,598
Remarks: PRICED TO SELL! Charming, quaint, and character-filled 3-bedroom, 2-bath home in the heart of Winter Park. From the moment you enter, you’re welcomed by warm original cognac hardwood floors that flow throughout the main living areas, creating a timeless and inviting atmosphere. The home offers a comfortable and functional layout with open yet cozy living and dining spaces, ideal for everyday living and entertaining. The remodeled kitchen blends classic charm with modern convenience and connects seamlessly to both indoor and outdoor living. The primary bedroom and bathroom offer a cozy, intimate setting, with excellent potential for future expansion or customization to suit your needs. While there are no walk-in closets, all closets have been custom-designed by California Closets, maximizing storage and organization throughout the home. Step outside to a private backyard retreat designed for Florida living. The saltwater pool, fully equipped outdoor kitchen with built-in bar, and tranquil pond with waterfall create a serene, zen-like setting perfect for relaxing or entertaining. Additional features include a tiled 2-car garage with abundant storage space, roof (2023), AC (2023), ductwork (2022), and a hybrid energy-efficient water heater (2020). Ideally located near top-rated schools, shopping, dining, and parks, this home offers a rare blend of charm, lifestyle, and opportunity in a prime Winter Park location.
Listing is courtesy of: ZEN LIVING HOMES LLC (407-800-2717)
Listing Agent: Nydia Marrero (407-620-6221)
639 FRIAR RD, WINTER PARK, FL 32792
$795,0004 Days on yellowkey MLS ID: O6395715
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 1950 Built: 1967 Tax: $3,415 (2025)Community: Winter Park PinesSingle Family
Taxes:$3,415
Remarks: Welcome to 639 Friar Road, ideally situated on a quiet street in the highly desirable Winter Park Pines neighborhood. This extensively updated residence offers the character of a classic 1960s home with the quality and feel of a 2026 renovation. Major improvements include a new roof, new HVAC system with new ductwork, new panel box, and thoughtfully curated high-end kitchen, bath, and lighting design elements. Original terrazzo flooring has been meticulously restored and polished throughout, preserving the home’s timeless appeal. Featuring four bedrooms, three full baths, the home offers a functional open-concept layout with a desirable split floor plan. Two primary suites, each with private en-suite baths, provide flexibility for multi-generational living or guest accommodations. The property showcases strong curb appeal and continues to impress outdoors with a spacious backyard and an oversized lanai designed for entertaining. Zoned for highly rated Winter Park schools, this home delivers an exceptional blend of style, comfort, and indoor-outdoor living in one of Winter Park’s most established neighborhoods.
Listing is courtesy of: FLORIDA REALTY INVESTMENTS (407-207-2220)
Listing Agent: Dianne Moore (407-494-7575)
731 BONGART RD, WINTER PARK, FL 32792
$499,99994 Days on yellowkey MLS ID: S5140952
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 1826 Built: 1961 Tax: $5,910 (2025)Community: Winter Park EstatesSingle Family
Taxes:$5,910
Remarks: Experience luxury living in this stunning, fully remodeled single-family home located in the heart of Winter Park, where modern sophistication meets exceptional functionality. This spectacular residence features a total of 4 spacious bedrooms and 3 modern bathrooms, boasting sleek laminate flooring throughout and a chef-inspired kitchen fully equipped with premium stainless steel appliances. A standout feature of this property is its versatile layout: one bedroom and one bathroom are completely separate from the main living area, offering the perfect solution for guest privacy, a multi-generational suite, or an opportunity to generate additional rental income. Outside, the massive backyard and sparkling pool provide an ideal setting for family gatherings and outdoor entertainment, all while being nestled in a prime location just minutes from the iconic Park Avenue shopping district, the Winter Park Farmer’s Market, and convenient access to the 436. This home is the ultimate choice for those seeking the perfect blend of suburban tranquility and urban convenience in the very best of Central Florida living.
Listing is courtesy of: MY REALTY GROUP, LLC. (786-847-7421)
Listing Agent: Maria Gomez Arevalo, Pa (407-705-7203)
2015 SUMMERFIELD RD, WINTER PARK, FL 32792
$1,375,000151 Days on yellowkey MLS ID: O6357615
Bed: 4 Bath: 4.0 Gar: 1 Liv Area Sq Ft: 3024 Built: 1957 Tax: $7,243 (2025)Community: Kenilworth Shores Sec 07Single Family
Taxes:$7,243
Remarks: Experience refined Winter Park living in Kenilworth Shores, a highly sought after neighborhood near Baldwin Park, Lake Baldwin trails, and the dining and boutiques of Park Avenue. This location places you close to Rollins College, Winter Park High, and the cultural center of Winter Park FL. Inside, natural light moves through open living spaces finished with wide porcelain tile floors. The kitchen stands as a sophisticated gathering space with a large quartz island, custom cabinetry, Bosch appliances, and a walk in pantry. The primary suite offers a peaceful retreat with direct access to the pool and a spa inspired bath. A second ensuite bedroom, dedicated office, and generous flex room provide versatility for daily living. The backyard feels like a private resort with a covered outdoor kitchen and a sparkling pool framed by thoughtful landscaping. This property may qualify for a seller funded permanent rate buydown with a participating lender. Equal Housing Opportunity.
Listing is courtesy of: REAL BROKER, LLC (855-450-0442)
Listing Agent: Christina Fata (407-917-8946)
1507 GOLFSIDE DR, WINTER PARK, FL 32792
$975,0004 Days on yellowkey MLS ID: O6395355
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2003 Built: 1981 Tax: $2,783 (2025)Community: Greenview At Winter PinesSingle Family
Taxes:$2,783
Remarks: One or more photo(s) has been virtually staged. OUTSTANDING RENOVATION in a FANTASTIC LOCATION! Peace, Quiet & GOLF COURSE LIVING! This rare opportunity places you along the 13TH tee & offers tranquil backyard views of the 16TH fairway of the Winter Park Pines Golf Course (WP18)! Tree-lined street welcomes you to this completely renovated Floor to Ceiling ONE STORY beauty offers Serendipity LW Wood & porcelain tile flooring throughout. Updates include (but definitely not limited to) BRAND new kitchen with Stainless Steel Appliances, new cabinets & quartz countertops. Formal living & dining rooms PLUS Family room with vaulted ceilings featuring a new electric fireplace for amazing ambiance and sliding doors inviting you to new brick pavered 31x 11 screened porch overlooking newly refinished sparkling pool & golf course (no rear or side neighbors!!) Bedroom wing of home offers a large inside laundry room, beautiful guest/pool bath with dual sinks & shower/tub and 2 fresh guest bedrooms. THE PRIMARY SUITE has been thoughtfully remodeled with sliding doors to pool, AMAZING primary bath with oversized work-of-art shower with dual shower heads, dual vanity, separate water closet & HUGE walk-in closet! Extras include: NEW double paned windows & 3 sliding doors to pool/patio, crown molding, NEW roof November 2024, oversized 2 car garage, NEW landscaping, all NEW ceiling fans & light fixtures, NO HOA!! Zoned for Brookshire Elementary, Glenridge Middle & Winter Park High. WELCOME HOME!
Listing is courtesy of: FANNIE HILLMAN & ASSOCIATES (407-644-1234)
Listing Agent: Catherine D'Amico (407-252-3210)
1174 WILDMEADOW RUN, WINTER PARK, FL 32792
$669,9006 Days on yellowkey MLS ID: O6394974
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1770 Built: 2021Monthly Fee: $150 Tax: $6,672 (2025)Community: Hawks CrestSingle Family
Taxes:$6,672
Remarks: Welcome to 1174 Wildmeadow Run in Winter Park’s gated Hawk’s Crest community. Located on a quiet, non-thru street, this SINGLE-STORY residence offers modern construction, refined finishes, and a comfortable, well-designed layout in the heart of Winter Park. Built in 2021, the home was thoughtfully planned for everyday living and easy entertaining. The open-concept design feels light and welcoming, featuring WOOD-LOOK TILE FLOORING, crown molding, recessed lighting, CUSTOM PLANTATION SHUTTERS, and ENERGY-EFFICIENT DOUBLE-PANE WINDOWS throughout the main living areas. At the center of the home, the kitchen is both functional and inviting, offering quartz countertops, stainless steel appliances, white cabinetry with crown molding, a custom backsplash, a PREP ISLAND, and a SECOND LARGE ISLAND WITH SEATING that naturally draws people together in the living and dining spaces. Just off the main living area, a FRENCH-DOOR FLEX ROOM provides a quiet, flexible space that works beautifully as a formal dining room, home office, or additional living area. The primary suite is positioned for privacy and offers a relaxing retreat with a TRAY CEILING, generous walk-in closet, and a well-appointed en-suite bath featuring a dual-sink quartz vanity, upgraded cabinetry, and a GLASS-ENCLOSED WALK-IN SHOWER. Two additional bedrooms are well positioned in this split plan and share a FULL BATHROOM WITH A TUB AND SHOWER COMBINATION and a QUARTZ VANITY, while a SEPARATE HALF BATH WITH PEDESTAL SINK is conveniently located for guest use. A TRIPLE SLIDING GLASS DOOR opens from the main living area to a COVERED REAR LANAI overlooking a FULLY FENCED BACKYARD with room to accommodate a FUTURE POOL, creating an easy indoor-outdoor connection that’s ideal for morning coffee, relaxed evenings, or casual gatherings. Additional features include a two-car garage with built-in storage, BRICK PAVER DRIVEWAY, TERRACOTTA TILE ROOF, GUTTERS, smart-home and security pre-wiring, and an HVAC SYSTEM WITH AN UPGRADED IONIZATION FEATURE DESIGNED TO HELP PURIFY THE AIR. Hawk’s Crest is a gated community known for its RESORT-STYLE AMENITIES, including a lakeside pool, fitness center, clubhouse, splash pad, playgrounds, walking trails, BBQ areas, and SCENIC COMMUNITY DOCKS AND BOARDWALKS. Lawn care and landscaping are included. Ideally located near Winter Park dining, shopping, and everyday conveniences. AVAILABLE FOR PRIVATE SHOWINGS.
1090 WILDMEADOW RUN, WINTER PARK, FL 32792
$845,00010 Days on yellowkey MLS ID: O6394208
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2589 Built: 2021Monthly Fee: $243 Tax: $6,258 (2024)Community: Hawks CrestSingle Family
Taxes:$6,258
Remarks: One or more photo(s) has been virtually staged. This luxurious Modern Style home epitomizes maintenance-free living, featuring a premium solar system you own outright, paying for your electricity. (Ask to see the bill.) Imagine relaxing on your private, expanded lanai, soaking in the breathtaking sunsets. Your spacious 4-bedroom, 3.5-bathroom home offers premium views of nature, and is just steps away from the community resort clubhouse. With gated access, Hawks Crest Residence enjoy an abundance of amenities, including a resort pool and fitness center, sidewalks and playgrounds throughout. And for those seeking adventure, enjoy dock access to Lake Howell, complete with a canoe/kayak launch. Daily, residents can relax and unwind while the management association takes care of all landscaping around the home, ensuring that residents can enjoy true maintenance-free living. The state-of-the-art off-grid solar system is equipped with battery backup with a 30-year warranty transferable to new owners. And this home is pre-wired for electric vehicles with room to expand. Excess power produced is sold back to the power company through the “Net Metering” program. Additionally, upgrades include heavy-duty commercial luxurious vinyl wide-plank flooring, two power monitoring systems, a whole-house water softener & filter system, along with 8-foot doors all designed for comfort, convenience and a peaceful home where you can relax. Nestled in this spacious home, you’ll find 20-foot-high ceilings and breathtaking views of the illuminated fountain from various rooms, creating a serene and relaxing atmosphere you’ll enjoy, even from the kitchen sink. And with a smart-winch lift, your chandelier maintenance is a breeze. (Rated up to 200lbs) Uniquely designed, this home was built to withstand extreme weather conditions, featuring concrete/granite tile roof, along with a steel reinforced, concrete-filled block walls and slab, all anchoring to the foundation that uniquely ties everything together, ensuring the utmost strength and safety for your family. Owners have meticulously maintained this home and comes with floor plans, a complete set of blueprints, along with photos of the home during the building process, and even includes documents for all equipment and appliances. The premium solar system comes with a 30-year warranty, including scheduled updates like the new power panel, installing April 2026. And yes, the warranty is transferable to new owners. This home features a split floor plan, with a primary bedroom on the first floor and a second primary bedroom upstairs. Spanning 2,589 square feet, the home also includes an additional 540 square feet of screened-in lanai (18x30), providing a private outdoor space to enjoy sunsets while overlooking the resort water features and landscaping. Schedule a showing for your buyers today!
Listing is courtesy of: BHHS FLORIDA REALTY (352-729-7325)
Listing Agent: Rod Chevalier (352-729-1818)
200 SAINT ANDREWS BLVD #315, WINTER PARK, FL 32792
$169,00052 Days on yellowkey MLS ID: V4947283
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 793 Built: 1970Monthly Fee: $451 Tax: $873 (2024)Community: Four Seasons CondoCondo
Taxes:$873
Remarks: One or more photo(s) has been virtually staged. Experience elevated living in this beautifully appointed 1-bedroom, 1-bath residence located on the second floor in the heart of Winter Park, Florida. The home showcases elegant wood-look tile flooring throughout, creating a seamless, upscale aesthetic with both style and durability. The primary bedroom is enhanced with classic plantation shutters, offering timeless sophistication, privacy, and beautiful natural light control. Step onto your private balcony overlooking the resort-style pool, providing a serene backdrop for morning coffee or evening relaxation. Designed for modern convenience, the residence includes a private in-unit washer and dryer, elevating everyday comfort. Perfectly positioned just minutes from Park Avenue, enjoy immediate access to Winter Park’s renowned cafés, fine dining, boutique shopping, and cultural attractions, as well as close proximity to Rollins College. This refined condo seamlessly blends luxury, lifestyle, and location, making it an exceptional opportunity in one of Central Florida’s most desirable neighborhoods.
Listing is courtesy of: RE/MAX ADVANTAGE (386-846-1515)
Listing Agent: Eric Zimmerman (386-846-1515)
5473 BRACKEN CT, WINTER PARK, FL 32792
$295,000101 Days on yellowkey MLS ID: O6368415
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1178 Built: 1986Monthly Fee: $101 Tax: $2,205 (2024)Community: Fernbrook TrailsTownhouse
Taxes:$2,205
Remarks: One or more photo(s) has been virtually staged. Move-in ready 3-bedroom, 2-bath townhome in desirable Winter Park featuring recent exterior paint and a clean, modern presentation throughout. BRAND NEW water heater, A/C replaced in 2021, and NEW ROOF (2026). The spacious family room sits beneath dramatic two-story vaulted ceilings highlighted by tongue-and-groove ceiling planks, creating an open and architectural focal point. The functional layout includes a large bedroom and full bath on the main level—ideal for guests, a home office, or multi-generational living. Upstairs, two additional bedrooms share a Jack-and-Jill style bath, offering privacy and efficiency. The kitchen opens to the dining and living areas, making the space well-suited for everyday living and entertaining. Sliding doors lead to a screened-in patio and a private, white PVC-fenced yard—low maintenance and perfect for relaxing or pets. Additional features include wood-look flooring in main living areas, neutral finishes, and abundant natural light. Conveniently located near Winter Park shopping, dining, parks, and major roadways. A strong option for buyers seeking space, location, and low-maintenance townhome living.
Listing is courtesy of: KELLER WILLIAMS ADVANTAGE III (407-207-0825)
Listing Agent: David Fraser (407-920-9749)
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