Location: Winter Springs
Keyword(s): Winter Springs High
Keyword(s) High School: Winter Springs High
Do Not Show Listings
1384 MILL STREAM LN, WINTER SPRINGS, FL 32708
$399,90032 Days on yellowkey MLS ID: TB8504740
REDUCED by $5,000 (1.2%) on 05/27/2026
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 1932 Built: 2015Monthly Fee: $233 Tax: $5,288 (2024)Community: Jesups LandingTownhouse
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$5,288
Elementary School: Layer Elementary
High School: Winter Springs High
Tax Year: 2024
Middle School: Indian Trails Middle
Remarks: One or more photo(s) has been virtually staged. Do not miss out on this opportunity for a spacious, tastefully updated, move-in ready townhome in the heart of Winter Springs! This is a low maintenance 3-bed, 3.5 bath end unit with quaint landscaping leading you up the stairs to your classy entry. The interior boasts recent vinyl flooring and no carpet anywhere, perfect for all season in FL. The kitchen and living room are on the main level creating a seamless relaxing or entertaining experience with the ability for residents and guests to have privacy in bedrooms. All modern stainless steel appliances convey! The spacious primary bed/bath is on the 3rd floor and provides a large walk-in closet and dual sinks. Enjoy paradise from your key west style balcony above the 2-car garage. The community amenities include a fitness center and pool overlooking the neighborhood pond. Enjoy quick and easy access to shopping, dining, outdoor activities and entertainment, many of these steps from your front door.
Listing is courtesy of: TAH FLORIDA LLC (844-874-2661)
Listing Agent: Joshua Nogowski (754-234-9626)
1513 BLACK BEAR CT, WINTER SPRINGS, FL 32708
$1,479,50092 Days on yellowkey MLS ID: O6385058
1 Days Off yellowkey (back on 5/27/2026)
REDUCED by $69,500 (4.5%) on 04/16/2026
Bed: 4 Bath: 5.0 Gar: 3 Liv Area Sq Ft: 6175 Built: 1989Monthly Fee: $142 Tax: $23,523 (2025)Community: Bear Creek EstatesSingle Family
Taxes:$23,523
Elementary School: Keeth Elementary
Tax Year: 2025
Remarks: Under contract-accepting backup offers. Welcome to this exceptional home in the exclusive gated community of Bear Creek Estates, set on over an acre of lush wooded greenbelt with beautiful landscaping and a circular driveway that creates outstanding curb appeal. The over 6,000 sq. ft. (includes 1 car garage/hobby room of approx. 280 sq.ft.) home features a new architectural tile roof (less than one year old) and 10-foot ceilings throughout the first floor, creating a bright and spacious feel. Inside, you’ll find elegant formal living and dining spaces, a private home office, and a comfortable family room overlooking the sparkling pool and lanai. The home offers oversized secondary bedrooms with seating areas, plus a large additional bedroom that can serve as an office, art studio or flex space. Entertainment is exceptional with two theater spaces, The main floor home theater is projector-ready, with acoustic panels, granite snack counter, an electronic masking screen and wiring for 7.1 sound. The upstairs primary bedroom is massive in size and the ideal retreat to unwind at end of the day! Complete with its sitting area and outdoor deck with stunning panoramic views of lush nature. The upstairs primary suite in this home also includes a projector drop-down screen and wiring for 5.1 sound. The private backyard retreat features a beautiful pool with LED lighting, waterfall feature, and updated pump and filter (2023), along with panoramic views of lush green space. Additional highlights include a smart audio system controlled by smartphone app, extensive network wiring, pre-wiring for security cameras, well-fed irrigation, and a backyard telescope pier with power and ethernet. In Winter Springs, this home offers peaceful luxury living while being close to shopping, dining and major commuting routes.
Listing is courtesy of: PREMIER SOTHEBYS INT'L REALTY (407-333-1900)
Listing Agent: Lynda Miller (407-620-2924)
451 HARBOR WINDS CT, WINTER SPRINGS, FL 32708
$357,50010 Days on yellowkey MLS ID: O6406257
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1914 Built: 2008Monthly Fee: $298 Tax: $3,832 (2025)Community: Harbor WindsSpa: NoTownhouse
Taxes:$3,832
Elementary School: Winter Springs Elementary
Middle School: South Seminole Middle
Remarks: One or more photo(s) has been virtually staged. Welcome to 451 Harbor Winds Court, located in the desirable Winter Springs’ gated community of Harbor Winds! This beautifully maintained and truly move-in ready two-story townhome offers 3 bedrooms, 2.5 bathrooms, and an attached 2-car garage with updates throughout. Major improvements have already been completed for peace of mind, including a new roof, gutters, A/C system, water heater, and stainless steel kitchen appliances—all installed in 2023. Step inside to discover an inviting floor plan featuring an upgraded kitchen with granite countertops, 42" wood cabinetry, stainless steel appliances, a walk-in pantry, breakfast bar, and a charming breakfast nook perfect for casual dining. The kitchen opens seamlessly to the spacious living area, where sliding glass doors lead to the rear lanai—ideal for relaxing or entertaining. Upstairs, the spacious primary suite easily accommodates a king-sized bedroom set and features a large walk-in closet along with a private ensuite bath complete with dual vanities, a soaking tub, and a separate glass-enclosed shower. The additional bedrooms provide plenty of space and flexibility for guests or a home office. Residents of Harbor Winds enjoy access to a resort-style community pool and well maintained neighborhood, all while being conveniently located near shopping, dining, and everyday conveniences. Centrally located with easy access to Orlando’s world-famous attractions, including Walt Disney World and Universal Studios, and less than an hour from the beautiful beaches of New Smyrna and Daytona. Schedule your private showing today, don't miss out!
Listing is courtesy of: KELLER WILLIAMS HERITAGE REALTY (407-862-9700)
Listing Agent: Jeff Singletary (407-383-1933)
1018 WEATHERED WOOD CIR, WINTER SPRINGS, FL 32708
$369,00016 Days on yellowkey MLS ID: O6408847
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1718 Built: 1978Monthly Fee: $107 Tax: $1,316 (2025)Community: Wedgewood Unit 2Single Family
Taxes:$1,316
Remarks: Welcome to refined, low-maintenance living in the highly sought-after Wedgewood Golf Villas within Tuscawilla. Perfectly positioned in one of Seminole County’s most established golf communities, this beautifully maintained residence offers the ideal blend of comfort, privacy, and convenience with golf cart-friendly streets, mature surroundings, and HOA-maintained lawn care for truly effortless ownership. Thoughtfully updated with a ROOF (2019), HVAC system (2017), and freshly painted exterior (2026), this move-in-ready 3-bedroom, 2-bath home showcases timeless appeal and functional design. Inside, abundant natural light, soaring vaulted ceilings, and a warm, inviting layout create an atmosphere that feels both spacious and intimate. The expansive great room, anchored by a charming fireplace, serves as the heart of the home — ideal for entertaining or quiet evenings in. A generously sized 315-square-foot screened lanai extends the living space outdoors, overlooking a large private fenced backyard with endless potential for a custom outdoor retreat, garden, or entertaining space. The first-floor primary suite offers a peaceful sanctuary with a spacious en-suite bath featuring a walk-in shower. Plush carpeting adds warmth throughout the living areas and bedrooms, while durable tile flooring enhances the kitchen and baths. Residents enjoy private access to scenic walking trails along the golf course, as well as close proximity to the private Tuscawilla Country Club, Trotwood Park, shopping, dining, nature trails, and top-rated Seminole County schools, with easy connectivity to SR 417 for commuting throughout Central Florida. Offering 1,713 square feet under air and 2,131 total square feet, this exceptional residence presents an outstanding opportunity for discerning buyers seeking comfort, community, and a lock-and-leave lifestyle in the heart of Tuscawilla.
Listing is courtesy of: HOME WISE REALTY GROUP, INC. (407-712-2000)
Listing Agent: Darryl Donkel (407-325-1234)
280 MOREE LOOP #2, WINTER SPRINGS, FL 32708
$150,00014 Days on yellowkey MLS ID: O6409577
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1187 Built: 1978Monthly Fee: $420 Tax: $2,656 (2025)Community: Baytree VillageCondo
Taxes:$2,656
Elementary School: Highlands Elementary
Remarks: One or more photo(s) has been virtually staged. Welcome home to this first-floor condo in the desirable Bay Village community of Winter Springs! Nestled among beautiful tree-lined streets, this spacious unit offers a fantastic opportunity to make it your own. The upgraded kitchen features stainless steel appliances, ample cabinetry, and plenty of workspace for cooking and entertaining. The open-concept living and dining area is filled with natural light thanks to the wall of sliders and windows along the living room. Laminate flooring runs throughout the home with no carpet anywhere for easy maintenance and a cohesive look. Residents of Bay Village enjoy access to the community pool and a prime location close to parks, shopping, dining, and top-rated schools. This home is move-in ready and waiting for its new owner to bring their vision, add some fresh updates, and give it the love and facelift to truly make it shine!
Listing Agent: Danielle Pensala (407-529-5752)
724 BARRINGTON CIR, WINTER SPRINGS, FL 32708
$399,900378 Days on yellowkey MLS ID: O6312092
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1450 Built: 1987Monthly Fee: $120 Tax: $1,771 (2024)Community: Georgetowne Unit 1Single Family
Taxes:$1,771
Remarks: Very well maintained home in Tuskawilla! Updated kitchen with Granite countertops, Elegant mirrored wall, Ceramic Tile throughout. Double sinks in beautiful master bathroom with garden shower tub! Owners have access to the neighborhood clubhouse and Community pool, HOA takes care of front yard lawn maintenance. Two parks and a nature trail are walking distance from the home. Walk to Trotwood Park and to Tuskawilla Country Club for a round of golf or tennis or to just socialize at the café and bar. This is a great opportunity to own an adorable low maintenance single-family home in the most affordable sought-after Country Club community in Seminole county. A rated school district! Short drive to Oviedo Marketplace and restaurants! Seller willing to contribute $2000 towards closing costs!! Don't miss this opportunity!! --
Listing is courtesy of: DIAMOND 2000 REALTY, INC (321-231-4195)
Listing Agent: Ramon Ortiz Cruz (321-231-4195)
276 SAN GABRIEL ST, WINTER SPRINGS, FL 32708
$285,00049 Days on yellowkey MLS ID: O6399623
REDUCED by $5,000 (1.7%) on 05/20/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1089 Built: 1994Monthly Fee: $127 Tax: $3,719 (2025)Community: Deersong 2Single Family
Taxes:$3,719
Remarks: Price Improvements. This 3-bedroom, 2-bathroom home in Deersong-2 is a fantastic opportunity for anyone looking for a move-in-ready property in Winter Springs. With its newly updated kitchen, Modern faucet, granite countertops, and indoor laundry. High ceilings at living room, the home feels both modern and spacious. The community offers excellent amenities, including a gated pool and tennis courts, all for a low HOA fee. It is zoned A+ Seminole county public schools, . Its prime location near top-rated Seminole County schools and the popular Torcaso Cove park makes it ideal for daily living. will not last long, Schedule your private showing today!!
Listing is courtesy of: KELLER WILLIAMS WINTER PARK (407-545-6430)
Listing Agent: Mariam Sherkawy (407-272-4234)
1020 TAPROOT DR, WINTER SPRINGS, FL 32708
$509,90016 Days on yellowkey MLS ID: O6409011
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 1905 Built: 2021 Tax: $4,953 (2024)Community: Oak Forest Unit 1Single Family
Taxes:$4,953
Remarks: Welcome to highly sought-after Oak Forest in Winter Springs! Built in 2021, this beautifully maintained 3-bedroom, 3-bathroom home offers modern style, energy efficiency, and a versatile floorplan designed for today’s lifestyle. With all major systems from 2021, this move-in ready home provides peace of mind and low-maintenance living throughout. Inside, you’ll find plank tile flooring, abundant natural light, and a spacious open-concept layout perfect for entertaining. A versatile bonus space offers endless possibilities and could easily serve as a 4th bedroom, home office, playroom, or media room. The bright, modern kitchen features shaker-style cabinetry, quartz countertops, stainless steel appliances, a large center island with bar seating, and a generous walk-in pantry. The spacious primary suite is thoughtfully designed with a large walk-in closet, dual vanities, a soaking tub, and a separate walk-in shower. One of the secondary bedrooms includes its own private en-suite bathroom, making it ideal for guests or multi-generational living. Step outside through elegant double French doors to enjoy the covered back porch overlooking the large vinyl-fenced backyard — perfect for relaxing, entertaining, or pets. Additional highlights include PAID-OFF solar panels, double-pane windows, overhead garage storage racks, and a pull-down attic ladder for extra storage convenience. Best of all, there is NO HOA, giving you added flexibility and freedom. Conveniently located near top-rated Seminole County schools, Trotwood Park, the Cross Seminole Trail, Winter Springs Town Center, and with easy access to Oviedo, University of Central Florida, Casselberry, and Winter Park, this home truly offers the best of Central Florida living!
Listing is courtesy of: RE/MAX TOWN & COUNTRY REALTY (407-695-2066)
Listing Agent: Dominick Florio (321-377-4045)
180 CONSTITUTION WAY, WINTER SPRINGS, FL 32708
$304,99915 Days on yellowkey MLS ID: O6408927
Bed: 2 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1275 Built: 2005Monthly Fee: $300 Tax: $4,266 (2025)Community: Heritage Park TwnhmsTownhouse
Taxes:$4,266
Remarks: Welcome to the highly sought-after gated community of Heritage Park Townhomes in Winter Springs! This tastefully remodeled 2-bedroom, 2.5-bathroom townhome is completely move-in ready and filled with stylish custom upgrades throughout. Step inside to find a warm and inviting living space featuring a custom-built wooden mantle over the electric fireplace, creating the perfect focal point for relaxing or entertaining. The dining area showcases a stunning custom 3D accent wall adding a modern designer touch to the home. The kitchen is beautifully upgraded with quartz countertops, stainless steel appliances, and a pantry providing additional storage space. Upstairs you’ll find both bedrooms thoughtfully laid out in a split floor plan for added privacy. The spacious primary suite features a walk-in closet and an ensuite bathroom complete with quartz countertops and a stand-alone shower. The laundry area is located upstairs in its own designated hallway closet for easy access. When you step outside to your back patio, you'll notice the owners added pavers creating the perfect cozy outdoor space for relaxing evenings or late-night movies under the stars. A/c is 2022! Enjoy low-maintenance living with an HOA fee of only $300/month which includes exterior grounds maintenance, gated community access, community pool, and a playground. This unit also offers a 1-car garage, private driveway parking, and additional guest parking spaces designated for visitors. Located near shopping, dining, parks, and major roadways, this beautifully updated townhome is ready for its next owner to call home!
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Jeavanna Lanza Pa (585-313-3408)
101 PARTRIDGE CIR, WINTER SPRINGS, FL 32708
$625,00022 Days on yellowkey MLS ID: O6407799
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2181 Built: 1974 Tax: $2,635 (2025)Community: Winter Springs Unit 4Spa: NoSingle Family
Taxes:$2,635
Remarks: Situated on a spacious 0.38-acre lot in the highly sought-after Tuscawilla community of Winter Springs, this beautifully updated pool home combines thoughtful upgrades, flexible living space, and inviting outdoor areas with the added benefit of NO HOA. Inside, the remodeled kitchen opens to the main living spaces and showcases updated cabinetry, stone countertops, tile backsplash, stainless steel appliances, recessed lighting, and a custom range hood. A newly added pantry and bar area complement the open kitchen design. The split-bedroom layout offers added privacy, with the primary suite tucked away on one side of the home and the secondary bedrooms positioned on the opposite side. The primary suite also features a walk-in closet and versatile bonus space ideal for a home office, nursery, gym, or sitting area. Multiple living and flex spaces provide endless options for entertaining, working from home, or creating additional lounge and dining areas. Major updates include new Luxury Vinyl Plank flooring throughout, fresh interior and exterior paint, upgraded bathrooms, full home replumb and complete rewire (2026), new roof (2024), HVAC (2019), and water heater (2018). Step outside to enjoy an oversized resurfaced and retiled screened pool, expansive lanai and deck space, fully fenced backyard, and a newly paved private front courtyard designed for relaxing and gathering outdoors. Located near Tuscawilla Country Club, Central Winds Park, shopping, dining, Publix, Winter Springs High School, and SR-417, this home offers the perfect balance of privacy, convenience, and the established charm Tuscawilla is known for.
Listing Agent: Belinda Gonzales (321-277-8994)
1513 GRACEFUL DOE LOOP, WINTER SPRINGS, FL 32708
$679,90021 Days on yellowkey MLS ID: O6408012
1 Days Off yellowkey (back on 5/23/2026)
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2995 Built: 2020Monthly Fee: $135 Tax: $6,580 (2025)Community: Tuskawilla Crossings 50'SSingle Family
Taxes:$6,580
Remarks: Under contract-accepting backup offers. From the moment you walk in, this beautifully appointed 2020 built home in Tuskawilla Crossings and backing up to wooded conservation, feels warm, inviting, and effortlessly functional. This expansive two-story residence offers 4 bedrooms, 2.5 bathrooms, a spacious loft, and the open-concept layout today’s buyers are hunting for. The heart of the home is a bright, beautifully connected living space where the family room, dining area, and kitchen flow effortlessly together—perfect for entertaining, holidays, or laid-back nights at home. The kitchen delivers serious style with 42” cabinetry, quartz countertops, slate appliances, and oversized prep space that makes everyday living feel elevated. Upstairs, the primary suite is oversized and calming with a spa-style bath featuring dual sinks, soaking tub, walk-in shower, and a massive walk-in closet, while the upstairs laundry room adds convenience exactly where you need it. This home includes a whole-house Brita Pro water filtration and softener system, transferable Taexx in-wall pest defense system through Home Team Security, Ring doorbell, security system, faux wood blinds, extended tile flooring, and washer & dryer. Outside, enjoy peaceful conservation views and no rear neighbors! The large backyard, covered lanai and recently added pavers create the perfect setup for cookouts, playtime, pets, or future outdoor dreams with the swing set included too. Located in one of Winter Springs’ most sought-after areas with a community pool, playground and quick access to shopping, dining and major roadways—this home checks boxes buyers didn’t even know they had. Homes this clean, this upgraded, and this move-in ready don’t stay quiet for long. Schedule your exclusive showing today!!
Listing is courtesy of: COLDWELL BANKER REALTY (407-333-8088)
Listing Agent: Miranda Earnest (321-624-0287)
702 GLASGOW CT, WINTER SPRINGS, FL 32708
$313,70063 Days on yellowkey MLS ID: O6394959
REDUCED by $4,000 (1.3%) on 05/23/2026
Bed: 4 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1878 Built: 1974Monthly Fee: $450 Tax: $3,285 (2024)Community: Highland Patio Homes Amended PlatSpa: YesCondo
Taxes:$3,285
Remarks: Welcome to a beautifully updated patio home tucked away on a quiet, tree-lined cul-de-sac in the desirable Pebble Creek community of The Highlands in Winter Springs. Enjoy Villa-style living with a two-story layout. Offering 4 bedrooms, 2.5 bathrooms, and a thoughtfully designed layout with the primary suite conveniently located on the first floor, this home blends comfort, functionality, and low-maintenance living. From the moment you arrive, you’ll appreciate the private courtyard entry—perfect for morning coffee or relaxing evenings, along with multiple outdoor spaces, including a screened-in porch and two fenced areas ideal for pets or gardening. Inside, the home features warm wood accents, soaring ceilings, and an abundance of natural light throughout. The updated kitchen is equipped with a gas double oven, modern appliances, pantry storage, and flows seamlessly into the main living areas. An interior laundry/utility room adds everyday convenience. Bathrooms have been tastefully renovated with updated vanities, tilework, and glass shower enclosures. Recent upgrades provide peace of mind, including re-piping, updated HVAC system, water heater, garage door, and energy-efficient windows and doors. Additional improvements include updated flooring, custom closet shelving, and enhanced finishes throughout the home. Located within The Highlands, residents enjoy a wide range of amenities, including a community pool, clubhouse, tennis courts, playgrounds, and miles of scenic walking trails and boardwalks. The HOA maintains exterior elements such as the roof, paint, and landscaping, allowing for easy, low-maintenance living
Listing is courtesy of: SHAWFIELD REALTY GROUP (407-963-7749)
Listing Agent: Carrie Sue Shawfield (407-963-7749)
429 SHEOAH BLVD #12, WINTER SPRINGS, FL 32708
$180,00098 Days on yellowkey MLS ID: O6386330
1 Days Off yellowkey (back on 5/22/2026)
REDUCED by $18,900 (9.5%) on 05/15/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1187 Built: 1978 Tax: $2,420 (2024)Community: Baytree VillageCondo
Taxes:$2,420
Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Welcome to this beautifully updated 3-bedroom, 2-bathroom condo offering the perfect blend of style, comfort, and convenience in the heart of Seminole County. Inside, you’ll find quartz countertops throughout, stainless steel appliances, and stylish brick-lay tile flooring that adds character and a modern touch to the main living areas. The thoughtfully designed layout includes an interior laundry room complete with a full-size GE washer and dryer for everyday ease. The living room features double sliding glass doors that flood the space with natural light and open to your private balcony — the perfect spot for morning coffee or winding down in the evening. Enjoy a low-maintenance lifestyle with an HOA that covers exterior maintenance, roof, and common areas. Community amenities include a junior Olympic-sized pool, pickleball and basketball courts, scenic lake views with a covered pavilion, picnic areas with grills, and beautiful nature trails for outdoor enjoyment. Ideally located with easy access to UCF, 417, 17-92, SR 434, the Cross Seminole Trail, shopping, dining, and more — all while being zoned for top-rated Seminole County schools. Whether you're a first-time buyer, investor, or looking to downsize without sacrificing style, this condo checks all the boxes!
130 SEVILLE CHASE DR, WINTER SPRINGS, FL 32708
$739,90015 Days on yellowkey MLS ID: O6409028
Bed: 4 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 2433 Built: 1999Monthly Fee: $187 Tax: $7,238 (2025)Community: Seville ChaseSpa: YesSingle Family
Taxes:$7,238
Elementary School: Sterling Park Elementary
Remarks: Discover the perfect blend of comfort, privacy, and luxury in the sought-after gated community of Seville Chase. Nestled on a large private fenced lot, this beautifully maintained 4-bedroom, 3-bathroom home offers a desirable 3-way split floor plan designed for both everyday living and entertaining with no rear neighbors. Step inside to find elegant upgrades throughout, including crown molding, upgraded baseboards, rounded corners, and upgraded interior doors that add a refined touch to every room. The spacious family room is the heart of the home, featuring a cozy fireplace and surround sound for the ultimate movie night or game day experience. The kitchen and living spaces flow seamlessly to your own outdoor oasis complete with a sparkling pool, relaxing spa, and patio surround sound system — perfect for entertaining or unwinding in total privacy. Additional recent improvements provide peace of mind and energy efficiency, including: new 2-stage variable AC with humidity control (2023), new water heater (2023), added blown-in insulation with plywood attic flooring (2023) and new wood-look tile flooring in the rear bedrooms With its thoughtful layout, premium upgrades, and resort-style backyard, this home offers the Florida lifestyle you’ve been waiting for in one of the area’s most desirable gated neighborhoods.
Listing is courtesy of: FLORIDA RE ANALYSTS, INC (407-702-8363)
Listing Agent: Drew Vandermay (407-221-7041)
965 PAPAYA LN, WINTER SPRINGS, FL 32708
$729,90020 Days on yellowkey MLS ID: OM724828
0 Days Off yellowkey (back on 5/22/2026)
Bed: 5 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 3514 Built: 1986Monthly Fee: $3 Tax: $3,805 (2025)Community: Oak Forest Unit 5Single Family
Taxes:$3,805
Remarks: Under contract-accepting backup offers. Nestled in the highly sought-after Oak Forest community of Winter Springs, this beautifully maintained and fully remodeled 5-bedroom, 4-bath pool home offers more than 3,500 square feet of versatile living space designed for luxury, comfort, and flexibility. The main residence features a spacious open-concept kitchen, living and dining area, plus a separate family room and dedicated office/gym space. Adding exceptional value and versatility, the property also includes an attached bonus home with a private entrance. The lower level offers a in-law one-bedroom floor plan with an open living, kitchen, and dining area along with its own patio, while the upstairs studio suite includes a kitchenette and full bath — creating incredible opportunities for multi-generational living, guest accommodations or a home office setup. Inside the main home, the updated kitchen showcases solid wood cabinetry, quartz countertops, high-end stainless steel appliances, and abundant natural light throughout. The luxurious primary suite has been thoughtfully remodeled with custom millwork, shiplap accents, built-in storage, recessed lighting, warm wood-grain tile flooring, designer finishes, and direct patio access for a true private retreat. Step outside and experience Florida living at its finest in the screened-in pool area overlooking a fully fenced backyard and peaceful wooded preserve. Designed for entertaining, the outdoor space features a fully equipped outdoor kitchen including concrete countertops, sink, and refrigerator, built-in fireplace, TV, pool, poolside entertaining areas, low-maintenance artificial turf, a gazebo seating area with TV and fans, and an additional storage shed. Additional highlights include a 2-car garage, abundant parking, solar energy panels, wood-grain tile flooring throughout the main living areas, and well-maintained systems. Ideally located near top-rated Seminole County schools, shopping, dining, parks, and major roadways, this exceptional move-in ready property perfectly combines style, functionality, and an unbeatable location.
Listing is courtesy of: REAL ESTATE RESOLUTIONS OF FLO (813-849-8918)
Listing Agent: Josh Mclennan (813-849-8918)
10 N FAIRFAX AVE, WINTER SPRINGS, FL 32708
$789,00031 Days on yellowkey MLS ID: O6404221
0 Days Off yellowkey (back on 5/20/2026)
Bed: 8 Bath: 0.0 Liv Area Sq Ft: 3636 Built: 1981 Tax: $6,129 (2025)Community: North OrlandoApartment
Taxes:$6,129
Remarks: Under contract-accepting backup offers. Turnkey FULLY RENOVATED quadplex in desirable Winter Springs. NO HOA!! Major updates (2019–2020) include ROOF, HVAC, PLUMBING, INTERIORS and ELECTRIC BREAKER PANERL & APPLIANCES—minimizing near-term maintenance and the property is fully fenced.SOLID CONCRETE BLOCK BUILDING! All FOUR UNITS are fully RENOVATED with MODERN finishes and strong RENTAL APPEAL. Each unit offers 2 bedrooms, 1 full bath, 1 half bath, a screened PRIVATE PORCH porch with storage, and NEWER SAMSUNG WASHER/DRYER IN EACH UNIT! Upgrades include STAINLESS STEEL appliances, GRANITE countertops, and engineered WOOD FLOORING. NO CARPET! Separate WATER & ELECTRIC METERS for each unit, plus security alarm in each unit. Ample FRONT PARKING. Estimated rents of ~$1,650 per unit provide SOLID INCOME potential. Located near Winter Springs Town Center, Central Winds Park, TOP Seminole County SCHOOLS, shopping, and dining. Easy access to SunRail via Longwood SunRail Station. Rent-ready with STRONG UPSIDE and NO additional work required. Call today!
Listing is courtesy of: JOHN SADRI & COMPANY (407-619-9999)
Listing Agent: John Sadri (407-619-9999)
1422 SPALDING RD, WINTER SPRINGS, FL 32708
$425,000372 Days on yellowkey MLS ID: O6313691
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1456 Built: 1983Monthly Fee: $95 Tax: $1,306 (2024)Community: Wedgewood Tennis VillasSpa: NoSingle Family
Taxes:$1,306
Remarks: PRICE REDUCTION!!!Ready to move into! Well maintained and updated 3-bedroom Tuskawilla villa, HOA maintains the lawn. This home boasts an open floor plan featuring beamed vaulted ceilings, a wood burning stone fireplace, an eat in kitchen and a spacious screened porch ROOF INSTALLED IN 2023, AC INSTALLED IN 2021, Resurfaced bath tub, shower and vanity countertops. Professional tennis courts and a clubhouse facility right across the street. Opportunity to join the Tuskawilla Country Club for golf, swimming, dining and more! NEW KITCHEN INSTALLED IN 2023! WITH UPDATED CABINETRY, QUARTZ COUNTERTOPS, STAINLESS STEEL APPLIANCES! CLOSET PANTRY & QUARTZ BREAKFAST BAR! Eat-in kitchen, vaulted ceilings with elegant wooden beams. Enjoy the living space outdoors in a large screened-in patio, enjoy your backyard, with 12 inch concrete tiles, vinyl fence for privacy, creating a relaxed setting for entertaining . Relax and enjoy the enclosed front porch with sliding door access to both bedrooms. Sliding door in the master bedroom with access to the ceramic tiled back screened porch. This home is near Trotwood Park, Cross Seminole Trail and Bear Creek Nature Trail. A short drive to Oviedo Mall, Winter Springs Town Center and the many parks in the area. The location is one of the best with quick access to the 417. The schools include some of the top-rated schools in all of Central Florida. Schedule your showing today, before it’s too late!
709 WINDWILLOW CIR, WINTER SPRINGS, FL 32708
$819,00045 Days on yellowkey MLS ID: O6399823
REDUCED by $20,000 (2.4%) on 05/09/2026
Bed: 5 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 3407 Built: 1988Monthly Fee: $20 Tax: $368 (2024)Community: Lake Tuskawilla Ph 1Spa: NoSingle Family
Taxes:$368
Remarks: Under contract-accepting backup offers. Located in a small, low-traffic community with minimal turnover, this beautifully updated corner-lot home offers an exceptional blend of space, privacy, and functionality. Featuring a highly desirable four-way split bedroom floor plan, the layout is perfect for large families, multi-generational living, or those who love to entertain. The private in-law suite includes a spacious bedroom, living area, walk-in closet, and full bath—ideal for guests or extended family. The home’s open yet flexible design allows for both comfortable everyday living and seamless entertaining. Step inside to vaulted ceilings, new flooring, updated lighting and fans, and a stunning living room with a shiplap feature wall and triple-panel sliding glass doors overlooking the pool. The family room features a wood-burning fireplace with a stone front and granite hearth, plus updated LED lighting and pool views. The fully renovated kitchen is a showstopper, featuring 42-inch farmhouse-style cabinets, quartz countertops, stainless steel appliances, a vent hood, built-in microwave, coffee bar/dry bar, double trash pull-outs, specialty cabinetry, and a massive 10x4 island with seating for six. Dual pantries—including a walk-in—provide ample storage. The primary suite is a true retreat with private patio access, a dressing room, walk-in closet with barn door, and a completely updated bath with vaulted ceilings, dual sinks, oversized walk-in shower, private water closet, and a French door leading to a secluded garden area. Enjoy Florida living at its finest with a screened-in pool featuring a fountain, two covered patios, a private pool bath, and a separate pool storage room—all within a fully fenced, private backyard. Additional highlights include a mudroom entry with built-in seating and storage, a large interior laundry room with utility sink and cabinetry, generous closet space throughout, new garage door with an opener, and attic storage access. Major updates include a 2020 roof, 2022 AC units, and recently renovated kitchen and bathrooms. Zoned for top-rated Seminole County schools. This move-in ready home truly has it all—space, style, and an unbeatable layout in a prime location.
Listing is courtesy of: COLDWELL BANKER REALTY (407-696-8000)
Listing Agent: Brad Merrell (407-920-7800)
224 HIGHLANDS GLEN CIR, WINTER SPRINGS, FL 32708
$295,00017 Days on yellowkey MLS ID: O6409042
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1185 Built: 1986Monthly Fee: $63 Tax: $3,265 (2025)Community: Highlands GlenVilla
Taxes:$3,265
Remarks: Welcome to 224 Highlands Glen Circle, a beautifully updated 3-bedroom, 2-bath villa with 1,185 sq. ft. of comfortable living space. This home features a modern kitchen with new countertops and appliances, along with fresh interior paint and new flooring throughout. Enjoy the ease of a move-in ready home with a 1-car garage. The community offers fantastic amenities, including a pool, tennis courts, playground, and park, perfect for active lifestyles and family fun. Ideally located in Winter Springs, this villa combines style, convenience, and comfort, schedule your showing today!
Listing is courtesy of: THE AGENCY FL (407-335-4119)
Listing Agent: Brian Hyser (407-951-2472)
65 S DEVON AVE, WINTER SPRINGS, FL 32708
$314,90025 Days on yellowkey MLS ID: O6404319
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1075 Built: 1960 Tax: $2,218 (2024)Community: North Orlando 2Nd AddSpa: NoSingle Family
Taxes:$2,218
Remarks: Welcome to 65 S Devon Avenue, a charming 3 bedroom, 2 bath block-construction home in the heart of Winter Springs—perfect for first-time homebuyers or anyone looking for a move-in-ready home in a highly rated school district. This well-maintained property features a large fully fenced yard, ideal for pets, play, and outdoor living. Enjoy Florida evenings on your screened and covered lanai,or take advantage of the concrete patio pad—a great spot for a firepit, grilling area, or weekend entertaining. A two-car driveway provides ample parking and convenience. No HOA Inside, the home offers a functional layout with natural light throughout, comfortable living spaces, and the solid peace of mind that comes with block construction. Located in the sought-after Winter Springs school district, zoned for: • Winter Springs Elementary • Indian Trails Middle School • Winter Springs High School You’ll love the central location—just minutes to shopping, dining, parks, SR-434, the 417 Expressway, and all the everyday conveniences that make Winter Springs one of Central Florida’s most desirable communities. Affordable, well-located, and full of potential—this home is a fantastic opportunity to own in Winter Springs.
Listing is courtesy of: RE/MAX PRIME PROPERTIES (407-347-4512)
Listing Agent: Tina Bircher (321-228-4267)
Please select an email frequency other than None since you have chosen for us to email you with changes that match your search.