Location: Winter Springs
Do Not Show Listings
717 ADIDAS RD, WINTER SPRINGS, FL 32708
$439,90012 Days on yellowkey MLS ID: V4949727
REDUCED by $5,100 (1.1%) on 06/24/2026
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1812 Built: 1986Monthly Fee: $95 Tax: $5,844 (2025)Community: Wedgewood Tennis VillasSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$5,844
Elementary School: None
High School: None
Tax Year: 2025
Middle School: None
Remarks: Virtually Staged. Welcome home to this absolutely charming and move-in-ready 2-bedroom, 2-bathroom home nestled in one of the most desirable areas of Winter Springs! From the moment you arrive, you'll appreciate the countless updates, beautiful wood beams and inviting curb appeal that make this home truly special. Major improvements provide peace of mind, including a 4-year-old roof, brand-new water heater, new flooring throughout, fresh interior and exterior paint, new appliances, and all-new light fixtures and ceiling fans. The beautifully updated kitchen offers modern style and functionality, while both bathrooms have been thoughtfully remodeled with today's buyer in mind. The spacious and light-filled bonus room overlooks the picturesque backyard and tranquil pond, creating the perfect space for a home office, reading room, playroom, or additional living area. Step outside and enjoy your backyard retreat featuring stunning water views and majestic oak trees that provide natural shade and beauty year-round while enjoying your morning coffee and watching the family of ducks swim by daily to greet you. Located in a great walking neighborhood, you'll love being just minutes from Tuscawilla Country Club and its renowned golf course, with olympic size pool and dining. Near top-rated schools and parks. Conveniently close to everything you need such as shopping, restaurants, medical facilities and your only a short drive to Florida's famous Theme Parks and about a 45 min drive to the best Beaches around. This adorable home offers the perfect blend of comfort, style, and location. Completely move-in ready and waiting for its new owners to fall in love—don't miss this incredible opportunity to own a piece of Winter Springs paradise!
Listing is courtesy of: COLDWELL BANKER REALTY (407-696-8000)
Listing Agent: Tracy Phillips, Llc (386-747-4914)
568 BUCKHORN DR, WINTER SPRINGS, FL 32708
$475,00023 Days on yellowkey MLS ID: O6413584
0 Days Off yellowkey (back on 6/24/2026)
REDUCED by $10,000 (2.1%) on 06/22/2026
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2076 Built: 2012Monthly Fee: $167 Tax: $3,280 (2025)Community: Winter Spgs Village Ph 1Single Family
Taxes:$3,280
Remarks: Under contract-accepting backup offers. This is one of the few 4 bedroom Bungalows built in sought after Winter Springs Village and it is situated on a premium lot with a manicured greenspace in front and a pond view with a lighted fountain in the rear. Enjoy sitting on the front porch in this quiet and serene setting with no through traffic. Recently painted interior and trim along with brand new carpet upstairs. This turn key property has lower utility bills due to many energy efficient features & design with Low E Vinyl dual pane double tint windows, foam insulated attic, energy star appliances & AC replaced in 2019. This 4 bedroom floor plan has a spacious loft area & 2.5 bathrooms, separate dining room, living room that is open to the kitchen & a full 2 car garage with extra ceiling racks for additional storage. The HOA includes lawn & irrigation maintenance, community pool/clubhouse, playground & secure mailboxes. In walking distance to the Seminole Trail, Winter Springs Town Center, restaurants & Publix. Easy access to 417 for a commute downtown, University of Central Florida, Orlando International Airport or the beaches. Highly rated Seminole County Schools. Bring your most discriminating buyers as this home will not disappoint!
Listing is courtesy of: KELLER WILLIAMS ADVANTAGE REALTY (407-977-7600)
Listing Agent: P. Darlene Brown, Pa (407-719-4420)
440 BUCKSKIN CT, WINTER SPRINGS, FL 32708
$525,00096 Days on yellowkey MLS ID: O6394274
REDUCED by $9,900 (1.9%) on 06/24/2026
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1922 Built: 1986Monthly Fee: $30 Tax: $5,731 (2025)Community: Deer Run Unit 20Single Family
Taxes:$5,731
Elementary School: Red Bug Elementary
High School: Lake Howell High
Middle School: Tuskawilla Middle
Remarks: **This house comes with a REDUCED RATE through the seller's preferred lender. This is a lender-paid rate buydown that reduces the buyer's interest rate and monthly payment.** PAID-OFF 15kW SOLAR + 10Gb whole-home Ethernet — corner lot in the heart of Winter Springs! This 4BR/2.5BA Deer Run home blends colonial charm and fresh curb appeal with smart upgrades new construction can't touch. Whole-home fiber terminal & wired Ethernet in every room. Smart thermostat w/ 3 remote sensors (app-enabled). New master shower & custom closet w/ multiple bars & abundant shelving. Re-piped 6-zone irrigation w/ modular manifold & smart rain/soil-aware controller. Hardwired smoke detectors, GFIs in all wet areas & shower vent fans throughout. Open floor plan, engineered hardwood & wood-burning fireplace. Outside, enjoy fresh landscaping, a brand-new fence & a corner lot your neighbors will envy — all minutes from the 417, Red Bug Lake Rd, Tuskawilla Rd, top-rated Seminole County schools, parks & shopping. Updated the right way — come see it today!
Listing is courtesy of: KELLER WILLIAMS REALTY AT THE PARKS (407-629-4420)
Listing Agent: Thomas Nickley, Jr (407-629-4420)
109 CHERRY CREEK CIR, WINTER SPRINGS, FL 32708
$1,090,00057 Days on yellowkey MLS ID: O6404923
0 Days Off yellowkey (back on 6/23/2026)
REDUCED by $60,000 (5.2%) on 05/28/2026
Bed: 5 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 3440 Built: 1996Monthly Fee: $123 Tax: $7,388 (2024)Community: Reserve At Tuscawilla Ph 1 TheSpa: YesSingle Family
Taxes:$7,388
Elementary School: Keeth Elementary
High School: Winter Springs High
Tax Year: 2024
Middle School: Indian Trails Middle
Remarks: Under contract-accepting backup offers. Virtually Staged. Welcome to 109 Cherry Creek Circle, a custom Von Jacobs-built residence located in the gated Reserve at Tuscawilla. Set on a beautifully landscaped 0.59-acre homesite, this 5-bedroom, 4-bath pool home offers the space, craftsmanship, and outdoor lifestyle that are increasingly hard to find in Winter Springs. Designed with the character and quality of a custom-built estate, the home features generous room sizes, volume ceilings, wood flooring, crown molding, detailed millwork, a gas fireplace, and a thoughtful floor plan that offers both comfortable everyday living and excellent entertaining space. The main-level primary suite provides privacy and convenience, while the additional bedrooms offer flexibility for guests, office space, fitness, hobbies, or multigenerational needs. The heart of the home is the outdoor living area. A screened, heated pool and spa, covered lanai, summer kitchen with Viking grill and Texas smoker, and a fire pit lounge accented with Tennessee River Rock create a true resort-style setting for relaxing, gathering, and enjoying the Florida lifestyle year-round. This home has been lovingly maintained and offers an incredible opportunity for a buyer who appreciates custom construction, a premier gated Tuscawilla location, and the chance to make thoughtful cosmetic updates over time. With over half an acre, a 3-car side-entry garage, mature landscaping, and a private outdoor retreat, 109 Cherry Creek Circle delivers the foundation, setting, and lifestyle buyers are searching for. Conveniently located near Tuscawilla Country Club, parks, trails, shopping, dining, Seminole County schools, and major Central Florida roadways, this property combines privacy, space, and everyday convenience in one of Winter Springs’ most established communities.
Listing Agent: Kara Lushear (321-663-5550)
339 INGLENOOK CIR, WINTER SPRINGS, FL 32708
$359,90033 Days on yellowkey MLS ID: O6411718
1 Days Off yellowkey (back on 6/5/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1437 Built: 1992Monthly Fee: $22 Tax: $4,816 (2025)Community: Mount Greenwood Unit 1Single Family
Taxes:$4,816
Remarks: Under contract-accepting backup offers. ACCEPTING BACK-UP OFFERS! New Roof Being Installed 06/24/26! Welcome to this fantastic opportunity in the heart of Winter Springs! This 3-bedroom, 2-bathroom single-family home features a highly desirable split-floor plan, providing the perfect layout for privacy and everyday living. Priced to sell, this property serves as a wonderful blank canvas ready for your personal design touch and imagination. The main living area features open sightlines to the kitchen, making the space feel connected and absolutely great for entertaining. From the main living area, sliding glass doors lead you right out to a spacious, covered and screened-in lanai—ideal for enjoying the beautiful Florida weather. Situated on a wonderful, private lot, the backyard offers plenty of space for pets, play, or creating your own outdoor oasis. Complete with a 2-car garage and great curb appeal on a quiet circle, this home checks all the major boxes and is just waiting for you to make it your own. Excellent location with easy access to local dining, shopping, and major roadways. Schedule your private tour today!
Listing is courtesy of: HOMESMART (407-476-0451)
Listing Agent: Christine Bouchard (904-907-5440)
1530 BRAEWICK ST, WINTER SPRINGS, FL 32708
$449,90016 Days on yellowkey MLS ID: TB8518340
0 Days Off yellowkey (back on 6/19/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1889 Built: 1999Monthly Fee: $115 Tax: $2,255 (2025)Community: Fox Glen At Chelsea Parc TuscawillaSingle Family
Taxes:$2,255
Remarks: Located in Winter Springs, FL, this beautifully updated single-story home offers 3 bedrooms and 2 bathrooms with a long list of brand-new upgrades that make it truly move-in ready. Major systems have been replaced — including a new AC and water heater — while fresh interior paint, new carpet, and new LVP flooring give the home a clean, modern feel throughout. The kitchen shines with new quartz countertops and all-new appliances, including a range, microwave, and dishwasher, and the bathrooms have been refreshed for a polished, updated look. New light fixtures tie it all together, creating a bright, cohesive space that's ready for its next owner. Schedule your showing today.
Listing is courtesy of: OFFERPAD BROKERAGE FL, LLC (813-534-6326)
Listing Agent: Rob Jones (844-448-0749)
662 SARANAC DR, WINTER SPRINGS, FL 32708
$643,10026 Days on yellowkey MLS ID: O6413437
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2180 Built: 1986Monthly Fee: $6 Tax: $3,686 (2025)Community: Tuscawilla Unit 14ASingle Family
Taxes:$3,686
Remarks: Under contract-accepting backup offers. Welcome to this beautiful 4-bedroom, 2-bath pool home nestled in the highly sought-after Tuscawilla community of Winter Springs. Situated on an oversized .34-acre lot, this well-maintained residence offers more than 2,180 square feet of comfortable living space with a spacious, open floor plan designed for both everyday living and entertaining. Enjoy cozy evenings by the fireplace, relax by the private pool, and appreciate the convenience of a two-car garage. The property is surrounded by mature trees and lush landscaping, creating a peaceful and inviting setting. Ideally located near top-rated Seminole County schools, parks, shopping, dining, and major roadways, this home also offers close proximity to Trotwood Park and Tuscawilla Country Club, with easy access to Oviedo, Winter Park, and downtown Orlando.
Listing is courtesy of: WATSON REALTY CORP (407-332-6000)
Listing Agent: Jim Ruddy (407-718-0984)
240 N DEVON AVE, WINTER SPRINGS, FL 32708
$375,00019 Days on yellowkey MLS ID: O6416300
REDUCED by $9,900 (2.6%) on 06/23/2026
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1238 Built: 1958 Tax: $476 (2025)Community: North OrlandoSingle Family
Taxes:$476
Elementary School: Highlands Elementary
Remarks: Welcome to 240 N Devon Avenue, a fully updated three-bedroom, two-bath home in the heart of Winter Springs, where the renovation has been done for you and the only thing left to do is move in. Inside, the open-concept main living area is anchored by a stunning stone fireplace with built-in shelving and crown molding throughout. The kitchen has been beautifully upgraded with custom wood cabinetry, quartz countertops, tile backsplash, and stainless steel appliances. Both bathrooms are finished with custom tile showers and the same level of detail you'll find throughout the home. Light, bright, and timeless. Beyond the finishes, the major systems have all been addressed: metal roof installed 2024, full HVAC replacement in 2022 (inside and outside units), whole-home repipe in 2022, updated electrical, and a gas tankless water heater. Nothing left to update or worry about! A 16x16 sunroom with AC extends the living space year-round, opening to a backyard built for play and entertaining. A putting green, paver patio, and pergola sit behind an eight-foot privacy fence, surrounded by low-maintenance xeriscaping that means weekends free from mowing. A detached 20x20 garage and workshop offers serious storage, project space, or whatever your hobby calls for. Ample off-street parking handles guests, trailers, RVs, or boats. Step out the front door and you are one block from the community park with its ocean-inspired playground, splash pad, pond, and walking trails. The Cross Seminole Trail is also nearby, putting miles of paved trail at your fingertips. Quick access to both I-4 and the 417 makes commuting a breeze, and you are surrounded by top-rated Seminole County schools. 240 N Devon is a rare combination of move-in-ready renovation, generous outdoor living, freedom from HOA restrictions, and a central Winter Springs location with parks and trails just steps from your door. Call today for your private showing!
Listing is courtesy of: REAL BROKER, LLC (855-450-0442)
Listing Agent: Lindsey Hudson (865-712-8452)
1335 SAN FELIPE CT, WINTER SPRINGS, FL 32708
$450,00014 Days on yellowkey MLS ID: O6417601
1 Days Off yellowkey (back on 6/23/2026)
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1571 Built: 1987 Tax: $5,051 (2025)Community: Sunrise Village Unit 6Spa: YesSingle Family
Taxes:$5,051
Remarks: Under contract-accepting backup offers. Welcome home to this move-in-ready 4-bedroom, 2-bathroom pool home with a 2-car garage, situated on a quiet cul-de-sac with no through traffic. This solid-block-construction home offers an open floor plan and exceptional curb appeal, featuring fresh exterior paint, updated stucco, professional landscaping, and a brand-new roof installed in June 2026. Inside, you'll find fresh interior paint, updated lighting and ceiling fans throughout, and a beautifully renovated kitchen and bathrooms. The spacious kitchen opens to the main living areas and features new stainless steel appliances, making it ideal for both everyday living and entertaining. The living room is anchored by a stunning fireplace that has been transformed with a custom stucco finish, elegant marble accents, and a floating mantel. Major mechanical updates include a 2022 AC system, a brand-new 2026 water heater, and updated plumbing with the home fully repiped, providing added value and peace of mind for years to come. Step outside to enjoy your private screened pool area and fully fenced backyard with no rear neighbors, offering exceptional privacy and the perfect space for relaxation, pets, and outdoor gatherings. With block construction, a brand-new roof, and a location outside of a flood zone, this home offers the potential for lower insurance costs and added peace of mind. For additional buyer confidence, a 4-Point Inspection, Wind Mitigation Report, Wood Destroying Organism (WDO) Report, and Energy Report are attached to the MLS for review. Conveniently located with a low HOA of just $345 per year, this home combines style, comfort, and value in one complete package.
Listing is courtesy of: NEXTDWELL (855-432-1123)
Listing Agent: Austin Cummings (407-242-8891)
629 RYAN CT, WINTER SPRINGS, FL 32708
$475,00054 Days on yellowkey MLS ID: O6396980
REDUCED by $4,000 (0.8%) on 06/23/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1857 Built: 2004Monthly Fee: $35 Tax: $1,899 (2024)Community: The Highlands Sections Seven & EightSingle Family
Taxes:$1,899
Remarks: Beautifully maintained 3-bedroom, 2-bathroom home located in the highly sought-after Highlands community in Winter Springs, FL. Real hardwood floors flow through the main living areas, adding warmth and timeless appeal. The spacious kitchen features elegant stone countertops, ample cabinetry, and plenty of room for cooking and entertaining. The primary suite serves as a relaxing retreat with an en suite bathroom that includes a dual sink vanity, a large soaking tub, and a walk-in closet. The split-bedroom layout offers added privacy, while the two additional bedrooms provide flexibility for guests, family, or a home office. Step outside to enjoy the oversized lot, offering plenty of space for outdoor living and activities. The screened-in lanai is perfect for enjoying Florida’s weather year-round, whether you're relaxing or hosting guests. A 2-car garage adds convenience and extra storage. Residents also enjoy access to a community pool, as well as tennis courts, pickleball courts, and scenic nature trails, perfect for an active and social lifestyle. Ideally located in Winter Springs, this home is close to top-rated Seminole County schools, beautiful parks and trails, shopping and dining options, and provides easy access to major roadways for commuting to Orlando and surrounding areas. Enjoy a balance of peaceful suburban living with everyday conveniences just minutes away.
Listing is courtesy of: SOTERA LIVING (407-725-9660)
Listing Agent: Lisa D'Orazio Llc (813-493-5383)
268 TAVESTOCK LOOP, WINTER SPRINGS, FL 32708
$557,90048 Days on yellowkey MLS ID: O6407307
REDUCED by $12,000 (2.1%) on 06/22/2026
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2415 Built: 2001Monthly Fee: $150 Tax: $4,293 (2025)Community: ParkstoneSingle Family
Taxes:$4,293
Elementary School: Layer Elementary
Remarks: New Price **268 Tavestock Loop, Winter Springs, FL 32708** Perfectly situated in the heart of Winter Springs, this stunning 4-bedroom, 2.5-bathroom home offers the ideal location with easy access to shopping, dining, theme parks, major roads, and the airport. Nestled within a desirable gated community, you'll enjoy peace of mind along with fantastic amenities including a community Lake Jess Up, pool, park, and 2 playground walking path, community benches. Step inside this beautiful two-story home and immediately notice the high ceilings that create a bright, open atmosphere throughout. Hard flooring runs seamlessly from room to room, giving the entire 2,883 square feet a clean, modern feel that is both stylish and easy to maintain. The kitchen is equipped with sleek stainless steel appliances, making it the perfect space to prepare meals and gather with family and friends. With four spacious bedrooms, there is plenty of room for everyone. The primary bedroom offers a comfortable retreat after a long day, while the additional bedrooms provide flexible space for family, guests, or a home office. Two full and half bathroom ensure convenience for the entire household. This move-in ready home means no waiting and no hassle. Simply unpack and start enjoying everything this wonderful property and community have for you. Whether you are relaxing by the community pool, taking the family to the playground, walking trails, Lake Jess Up or exploring all that Central Florida has in store, this home puts it all within reach. Don't miss your chance to make 268 Tavestock Loop your new home. Schedule your private showing today!
Listing is courtesy of: FUSILIER REALTY GROUP (407-476-0476)
Listing Agent: Zep Bholai-Lawrence (321-689-3467)
984 TURKEY HOLLOW CIR, WINTER SPRINGS, FL 32708
$410,00035 Days on yellowkey MLS ID: O6410083
0 Days Off yellowkey (back on 6/21/2026)
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1821 Built: 1985Monthly Fee: $3 Tax: $3,100 (2025)Community: Oak Forest Unit 4Single Family
Taxes:$3,100
Remarks: Under contract-accepting backup offers. Virtually Staged. A spacious 3-bedroom, 2-bathroom home located in the highly sought-after community of Oak Forest in Winter Springs. Known for its beautiful tree-lined streets, mature oak trees, and quiet suburban charm, this family-friendly neighborhood also offers access to top-rated schools and is conveniently located near popular restaurants, shopping, and everyday conveniences. Inside, this home features a versatile and functional floor plan with a spacious family room, separate living room, dining room, large kitchen, dedicated office space, and an indoor laundry room. The detached shed provides the perfect opportunity for extra storage, a workshop, or hobby space. Step outside to enjoy the private backyard complete with a fire pit — ideal for relaxing or entertaining guests. The garage has been split into an office and storage space but can be converted back into a two car garage. Major upgrades and improvements include an updated roof (2018), gutters(2018), HVAC system(2022), windows(2020), garage door(2020), hot water heater(2021), electrical panels(2023), and added insulation(2019). Additional features include an indoor electric fireplace (2022), and numerous updates throughout, offering peace of mind and move-in-ready convenience. Call today to schedule your private tour!
Listing is courtesy of: ALL REAL ESTATE & INVESTMENTS (407-917-8206)
Listing Agent: Kelsey Payton (407-718-2967)
214 CHESTNUT RIDGE ST, WINTER SPRINGS, FL 32708
$590,000130 Days on yellowkey MLS ID: O6372400
REDUCED by $10,000 (1.7%) on 06/19/2026
Bed: 4 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 2474 Built: 2001Monthly Fee: $42 Tax: $5,539 (2024)Community: Chestnut Ridge In TuscawillaSpa: NoSingle Family
Taxes:$5,539
Elementary School: Rainbow Elementary
Remarks: Under contract-accepting backup offers. WOW, BEST PRICE IN Winter Springs! Executive TUSCAWILLA Golf Course and Country Club living! Incredible opportunity. Here is your future DREAM HOME! Best price DIRECT GOLF FRONT HOME IN ORLANDO! Why wait to build on a 50 ft lot when you can live in a custom home Did you ever dream of drinking your Coffee daily while looking at a pristine GOLF course and Conservation view? Maintenance free yard that is DIRECTLY on the 16th hole of the Tuscawilla Golf Course. Builder of this neighborhood built this One of a kind home for himself and it has a one of a kind view. VIEW VIDEO WALK THROUGH TOUR. Energy Efficient SOLAR that is PAID FOR! Chestnut Ridge is a serene Winter Springs community in Seminole County This exquisite property, situated on .24 acres of loads of landscaping, with amazing azaleas with many colors, is the epitome of luxury living, perfect for executive families seeking a harmonious blend of comfort and elegance. Boasting an impressive 4 bedrooms and 3 bathrooms, this custom-built home offers a spacious upstairs private en suite featuring 1 bedroom and 1 bath, ideal for guests, playroom or a secluded home office. A true Gardeners Paradise. The interior is nothing short of breathtaking with soaring 10’ ceilings and solid red oak flooring that greets you in the foyer and extends through the kitchen and breakfast nook. The heart of the home, a chef's kitchen, is adorned with quality chestnut wood cabinets, sleek granite countertops, and a wet bar island, perfect for entertaining. Hallway complete with bright skylights that lead to bedroom 2 and 3 that actually both have access to the hall Jack n Jill bath. Three way split floor-plan offers loads of lifestyle options. Attention to detail is evident with 5 1/4” baseboards, recessed lighting, and a luxurious custom built-in entertainment center. Cozy up by the gas-burning fireplace or enjoy the oversized 860 SF 3-car garage/workshop, equipped with an insulated ceiling and reinforced garage doors, offering ample space for vehicles and projects alike. Custom Built pergola off the garage offers additional charm. So Many options. Complete with a direct wire for a generator access. The master suite is a sanctuary with a generous 8' x 12' walk-in closet featuring custom solid walnut cabinets. Bask in the Florida sunshine on your awning-covered rear deck with a view of the golf course and conservation area. Built in 2001 with a new roof in 2020, this move-in ready home benefits from top-of-the-line “Low E” windows, R-30 attic insulation. Yard is LOW MAINTENANCE! Location is paramount, with proximity to quality schools, shopping, dining, and major employment hubs.You are upgrading your LIFESTYLE in this neighborhood. HIGHLIGHTED EXTRAS Throughout. Along with the purchase this home comes with 20 solar panels, that are PAID FOR, which can provide 7.8 kWh are connected with the Duke power grid. The electric bill reflects how much power you use and how much you push back to the grid. You are credited equally for power pushed back in the final monthly amount due. Additionally, there is a backup battery which in the event of power outage will provide 6 dedicated circuits for the house with standby power during brief power outages."A" Rated schools, all three! A MUST SEE!
Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)
Listing Agent: Laurie Cain (407-484-9944)
877 BENCHWOOD DR, WINTER SPRINGS, FL 32708
$450,00034 Days on yellowkey MLS ID: O6410431
REDUCED by $10,000 (2.2%) on 06/18/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1612 Built: 1983Monthly Fee: $3 Tax: $3,127 (2024)Community: Oak Forest Unit 3Single Family
Taxes:$3,127
Remarks: Inviting curb appeal welcomes you into this beautifully maintained Winter Springs pool home tucked within the peaceful established subdivision of Oak Forest. Step inside to an open floor plan with immediate views of the backyard oasis, creating a light and airy feel perfect for everyday living and entertaining. The spacious kitchen opens seamlessly to the living and dining areas and features granite countertops, stainless steel appliances and a breakfast bar ideal for gathering with family and friends. The floor plan offers comfortable living spaces, while sliding doors lead out to the screened porch overlooking the private backyard retreat. Enjoy Florida living year-round with the screened patio, resurfaced pool featuring a PebbleTec finish completed in 2020, a fully fenced yard and plenty of room to relax or entertain outdoors. Major updates provide peace of mind, including the roof, AC, and water heater all replaced in 2015. Additional improvements include gutters added in 2020, pool pump replaced in 2016, new garage door opener in 2025, and updated microwave, dishwasher, and garbage disposal in 2026. This home sits on a spacious lot in a quiet, established neighborhood. Conveniently located near SR-417, shopping, dining, and top-rated Seminole County schools - walking distance to both the elementary and middle school. This home is also just minutes from Trotwood Park and Central Winds Park which features pickleball courts, sports fields, playgrounds, walking trails, and community events.
Listing is courtesy of: COMPASS FLORIDA LLC (407-203-9441)
Listing Agent: Melissa Condrey (407-505-9339)
200 BLUE CREEK DR, WINTER SPRINGS, FL 32708
$625,00014 Days on yellowkey MLS ID: O6416327
Bed: 4 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 2344 Built: 1997Monthly Fee: $70 Tax: $3,467 (2025)Community: Chestnut Estates Ph 2Single Family
Taxes:$3,467
Elementary School: Lawton Elementary
High School: Oviedo High
Remarks: Under contract-accepting backup offers. Virtually Staged. Meticulously maintained and beautifully positioned with peaceful conservation and pond views, this 4-bedroom, 3-bathroom home in Chestnut Estates offers 2,344 square feet of spacious single-story living in the desirable Tuscawilla area. Set on an oversized 0.26-acre lot with no rear or side neighbors, this property combines a versatile floorplan, generous living spaces and inviting indoor-outdoor living. Inside, high ceilings and tons of natural light create a bright, open feel throughout the heart of the home. The layout includes a formal dining room with tray ceiling, a front living/flex room with French doors, a spacious family room and an open kitchen with granite countertops, stainless steel appliances, breakfast bar, pantry, and a sunny breakfast nook overlooking the backyard and conservation. The thoughtfully designed split-bedroom floorplan offers both privacy and flexibility. The tucked away primary suite features direct access to the screened rear porch, a large walk-in closet, dual vanities, a garden tub, and a separate shower. Two secondary bedrooms share a spacious Jack-and-Jill style bathroom with an oversized vanity and abundant storage, while the fourth bedroom is positioned near the third full bathroom, which features a walk-in shower and direct porch access. Outdoor living truly shines with a covered screened porch, custom paver patio and firepit area, mature landscaping, aluminum fencing, and peaceful pond and conservation views. The larger lot and natural backdrop create a peaceful setting for relaxing or entertaining. Pride of ownership is evident throughout, with major improvements including a new roof in 2024, Goodman HVAC system in 2021, updated outdoor living spaces, enhanced landscaping and drainage improvements, and consistent preventative maintenance over the years. Conveniently located near Tuscawilla Country Club, parks, shopping, dining, major roadways, and Seminole County schools, this well-cared-for home offers space, privacy, and an exceptional opportunity to enjoy comfortable living in a beautifully maintained home with a setting that’s becoming increasingly difficult to find. Schedule your showing today!
Listing is courtesy of: KELLER WILLIAMS ADVANTAGE 2 REALTY (407-393-5901)
Listing Agent: Amanda Meyer (201-406-2900)
995 DYSON DR, WINTER SPRINGS, FL 32708
$750,00012 Days on yellowkey MLS ID: O6418233
0 Days Off yellowkey (back on 6/20/2026)
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2855 Built: 1979 Tax: $9,147 (2025)Community: Winter Spgs Unit 3Single Family
Taxes:$9,147
Remarks: Tucked behind dual steel security gates on more than 1.6 wooded acres in sought after Tuscawilla, this one of a kind gated estate offers exceptional privacy just three blocks from the Tuscawilla Country Club and golf course. Surrounded by mature trees and natural beauty, the property feels like a private park while remaining minutes from shopping, parks, top rated Seminole County schools, major highways, dining, golf, swimming, and tennis. This custom-built California contemporary home features 3 bedrooms, 2.5 baths, and a loft. The dramatic great room showcases soaring two story vaulted ceilings, expansive windows with tranquil wooded views, a polished granite fireplace with gas logs, built-in bookcases, and a wine rack. The adjoining dining and entertaining area includes granite countertops, a wet bar, and a built-in wine cabinet. The kitchen is designed for both everyday living and entertaining, offering cherry cabinetry, solid surface countertops with an integrated sink, an oversized breakfast nook, and a large walk-in pantry. An artistic steel staircase leads to the loft, an ideal space for a home office, studio, or flex room with elevated views of the surrounding landscape. The spacious primary suite features a large walk-in closet and a spa-inspired bath finished in slate with a built-in Jacuzzi tub and waterfall feature, a walk-in shower with fixed glass enclosure, bidet, and updated dual vanity. Additional upgrades include a tankless water heater, updated HVAC system, upgraded plumbing, a large interior laundry room, oversized two car garage, and a separate workshop. The Florida friendly landscape requires minimal maintenance, and the expansive grounds provide ample room for a future pool, tennis court, guest house, or additional outdoor amenities. New septic 2025, part of roof replaced 2025. A rare opportunity to own a private estate property in the heart of Tuscawilla with unmatched natural surroundings and modern conveniences close at hand. Zoned PUD!
Listing is courtesy of: RE/MAX TOWN & COUNTRY REALTY (407-695-2066)
Listing Agent: Denise Mckinley (407-625-0635)
1160 CITRUS OAKS RUN, WINTER SPRINGS, FL 32708
$825,00044 Days on yellowkey MLS ID: O6408959
0 Days Off yellowkey (back on 6/12/2026)
REDUCED by $25,000 (2.9%) on 06/04/2026
Bed: 5 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3118 Built: 2001Monthly Fee: $127 Tax: $8,339 (2025)Community: Citrus OaksSingle Family
Taxes:$8,339
Remarks: Under contract-accepting backup offers. Exceptional luxury living awaits in this beautifully reimagined 5-bedroom, 3.5-bath residence located within an exclusive gated community. Offering over 3,100 square feet of refined living space, this impressive home showcases luxury finishes and thoughtful upgrades throughout, including elegant travertine flooring, rich oil-rubbed plank floors, and a stunning updated kitchen appointed with stainless steel appliances. Designed for both elevated entertaining and everyday comfort, the floorplan of his home is designed to be a “forever home” and serve you through all stages of life. The 5th bedroom/flex space is conveniently located adjacent to the Primary Bathroom, making it the perfect spot for a nursery or a home office. There are 2 bedrooms connected by a “Jack and Jill” bathroom on the opposite side of the residence, and a spacious, secluded guest suite tucked away on the back of the home; providing guests with a quiet space away from the hustle and bustle of daily life. The spacious interior flows seamlessly to a private screen-enclosed pool retreat featuring a resurfaced finish, travertine pavers, and a fully fenced backyard oasis. The luxurious primary and guest baths have been tastefully updated, while major improvements such as a 2019 roof, hurricane impact slider doors, and fresh exterior paint provide peace of mind and timeless appeal. Perfectly positioned near top-rated schools, upscale shopping, dining, and convenient 417 access, this exceptional residence delivers the ideal blend of luxury, comfort, and location.
Listing is courtesy of: JULIAN PROPERTIES, INC. (407-291-4900)
Listing Agent: Bo Julian (407-694-5843)
1385 SAN DIEGO CT, WINTER SPRINGS, FL 32708
$320,00083 Days on yellowkey MLS ID: O6397680
REDUCED by $29,000 (8.3%) on 06/17/2026
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1518 Built: 1983Monthly Fee: $29 Tax: $1,283 (2025)Community: Sunrise Village Unit 1Spa: NoSingle Family
Taxes:$1,283
Remarks: HUGE PRICE REDUCTION! LOWEST PRICED HOME IN SUNRISE VILLAGE! 2/2 UPDATED HOME! PLUS A BONUS ROOM PERFECT FOR OFFICE, NURSERY, PLAYROOM, HOBBY ROOM, FLORIDA ROOM OR JUST ADDITIONAL LIVING SPACE! OPEN FLOOR PLAN! KITCHEN FEATURES TILE FLOORS, EAT IN KITCHEN AND LIGHT WOOD CABINETRY! ROOF 2022, A/C 2023, WATER HEATER 2025! MAIN BATH UPDATED WITH DECORATIVE TILE, GRANITE COUNTER, TILE FLOOR! DOUBLE PANED WINDOWS! WIDE BLINDS! KNOCKDOWN CEILINGS! NO CARPETING THRU OUT! LARGE SCREENED PATIO WITH TILE FLOOR! LOTS OF NATURAL LIGHT! FANS! LAUNDRY IN GARAGE! GREAT LOCATION, HIGHLY RATED SCHOOLS, LOW HOA DUES ($345 YEAR), COMMUNITY BASKETBALL, TENNIS AND PLAYGROUND!. CONVENIENT TO ALL AREAS OF TOWN! PLEASE NOTE: SOLAR PANELS ON ROOF ARE LEASED, AND LEASE IS TRANSFERABLE! APPROX $80 MONTH! SELLER NOTES WITH POWER COMPANY CREDITS, BILL HAS BEEN APPROX. $30 MONTH!
Listing is courtesy of: COLDWELL BANKER REALTY (407-647-1211)
Listing Agent: Diane Fuller (407-923-2090)
1208 CHEETAH TRL, WINTER SPRINGS, FL 32708
$669,90012 Days on yellowkey MLS ID: O6416652
Bed: 5 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2837 Built: 1979 Tax: $3,887 (2025)Community: Tuscawilla Unit 06Single Family
Taxes:$3,887
Remarks: Under contract-accepting backup offers. Come fall in love with this versatile 5 bedroom 3 bath home on over 1/2 acre beautifully landscaped property with lush trees and gardens....your very own private oasis in the heart of Tuscawilla! With two large master suites, two spacious guest bedrooms plus a fifth bedroom/ home office with exterior door, the opportunities are endless! In addition, most of the home is very tastefully handicapped accessible. Tinker in your oversized 2 car garage, take a stroll to the neighborhood park or the country club, or sit on your covered back porch watching nature dance in your gorgeous and private backyard. Perhaps you could just float in your recently resurfaced screened, solar heated pool with artful brick paver deck and outdoor shower. Rest easy with a newer roof (2025) two new AC systems (2026 and 2024) updated plumbing, complete window replacement and gorgeous new sliding doors. Your parents, guests or special needs family member will enjoy the massive secondary primary suite with tasteful and versatile handicapped accesible bathroom with roll in shower,double sink vanity, and large accessible walk in closet. Tons of storage is found throughout the home including in the oversized laundry room with utility sink, and cabinets galore. Hey, imagine peace and quiet in a potentially chaotic household…. The main primary bedroom is completely separate from all of the others and includes a walk-in closet and a space large enough for all your dressers, nightstands and even a quiet sitting area to enjoy your favorite book. The ensuite Primary bath has Double doors, updated double vessel sinks and other delightful upgrades. As a bonus, you can open your sliding doors in your bedroom to the pool for a moonlight dip! Newer wood ceilings adorn the rear covered porch for daydreaming or making entertaining special. Guests, family and friends will appreciate the additional parking on the expansive driveway (we just know you're going to have a lot of company). Trotwood Park is a fun place to experience the farmer's market and your kiddos can get to school without accessing the major roads!! Tuscawilla isn't just a place to live.....it's a place to call home. This is truly a once in a lifetime opportunity at a very reasonable price. Hurry to see it now before someone else snatches it up!
Listing Agent: Colleen Kahl (407-630-0027)
724 BARRINGTON CIR, WINTER SPRINGS, FL 32708
$399,900404 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 Tuscawilla! Updated kitchen with Granite countertops, Elegant mirrored wall, Ceramic Tile throughout. Double sinks in beautiful master bathroom with garden shower tub! Owners. Replace all new appliance, 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 Tuscawilla 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)
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