Location: Winter Springs
Do Not Show Listings
214 CHESTNUT RIDGE ST, WINTER SPRINGS, FL 32708
$590,000122 Days on yellowkey MLS ID: O6372400
0 Days Off yellowkey (back on 6/21/2026)
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
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$5,539
Elementary School: Rainbow Elementary
High School: Winter Springs High
Tax Year: 2024
Middle School: Indian Trails Middle
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
$450,00026 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
Elementary School: Keeth Elementary
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)
819 DUNDEE DR, WINTER SPRINGS, FL 32708
$419,00020 Days on yellowkey MLS ID: O6412585
REDUCED by $10,000 (2.3%) on 06/16/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1701 Built: 1978Monthly Fee: $40 Tax: $1,558 (2025)Community: Highlands Sec 1Single Family
Taxes:$1,558
Elementary School: Highlands Elementary
Tax Year: 2025
Middle School: South Seminole Middle
Remarks: Welcome home to this charming 4-bedroom, 2-bath residence nestled on a spacious corner lot in the highly desirable Highlands community of Winter Springs. From the moment you arrive, you'll appreciate the inviting curb appeal, mature surroundings, and move-in ready condition that make this home truly special. Inside, vaulted ceilings and abundant natural light create an open and airy atmosphere, while updated flooring adds a fresh, modern touch throughout. The heart of the home features a cozy wood-burning fireplace, perfect for gathering with family and friends. The kitchen is both stylish and functional, offering beautiful wood cabinetry, granite countertops, and stainless steel appliances. The thoughtfully updated bathrooms provide comfort and convenience, while sliding glass doors from the living room lead to an expansive covered and screened patio—an ideal space for morning coffee, weekend barbecues, or simply relaxing and enjoying Florida's beautiful weather. The partially fenced backyard offers plenty of outdoor space, complete with a storage shed for tools, hobbies, or seasonal items. Located within The Highlands, residents enjoy access to exceptional community amenities including a swimming pool, playground, and tennis courts. Conveniently situated near shopping, dining, parks, and major highways, this home offers the perfect blend of comfort, convenience, and community. Don't miss your opportunity to make this wonderful Winter Springs home your own!
Listing is courtesy of: KGV REALTY GROUP (407-474-0844)
Listing Agent: Kristin Vogt Pllc (407-417-7206)
140 SEVILLE CHASE DR, WINTER SPRINGS, FL 32708
$769,90082 Days on yellowkey MLS ID: O6395594
REDUCED by $10,000 (1.3%) on 06/10/2026
Bed: 5 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3129 Built: 1999Monthly Fee: $184 Tax: $5,857 (2024)Community: Seville ChaseSingle Family
Taxes:$5,857
Elementary School: Sterling Park Elementary
Remarks: Welcome to a residence that truly embodies the phrase "NEIGHBOR'S ENVY, OWNER'S PRIDE" - an exceptional opportunity to own a showpiece home in the gated enclave of Seville Chase where smart living meets timeless elegance. This impeccably maintained, Solar-Powered SMART home offers an unparalleled blend of luxury, comfort, and sustainability. With Fully Paid Solar Panels keeping monthly electric cost under $45. The property greets you with commanding curb appeal, an extra-wide driveway, and an oversized side-entry garage, setting the tone for what lies within. Step inside to discover a designer-inspired interior adorned with gleaming cherry hardwood floors, elegant French doors, soaring tray ceiling, gracefully rounded architectural walls, and refined crown molding- each detail curated for those with a taste for elevated living. The heart of the home, a chef's kitchen, showcases Granite countertops, luxurious 42" cherry cabinetry with crown molding, a built-in desk, ample storage, and sleek stainless-steel appliances-perfectly blending form and function. A thoughtful 3-way split floor plan ensures privacy and space for all, with the primary suite offering a serene retreat complete with his and her walk-in closet and shared linen cabinetry. The fifth bedroom, with its custom-built-in shelving, is ideally suited for a nursery, personal library, or a quiet study. At the Rear, a True Showstopper awaits - an Expansive 1,000+ sq ft screened and paved lanai, fully outfitted with a complete outdoor kitchen, with ADDITIONALD NEW FULL SIZE REFRIGERATOR, Gas hook-up with Range, Microwave, etc. ready to host unforgettable evenings under the stars. Surrounded by Fresh landscaping, New Sod, and vibrant plantings with a gazebo this home has been lovingly updated with a new roof in 2016, solar in 2021, and two high-efficiency A/C systems (5-ton in 2016 and 3-ton in 2014). Ideally located in the highly acclaimed Seminole County School District, and just minutes from premium shopping and places to worship, this is more than a home, it's a lifestyle. Experience the beauty, serenity, and elegance this exceptional property has to provide. Your home awaits. DO NOT FORGET TO CLICK THE LINK TO SEE THE VIDEO WALK-THROUGH.
Listing is courtesy of: WEICHERT REALTORS HALLMARK PROPERTIES (407-644-5385)
Listing Agent: Joji Jacob (407-747-3681)
200 BLUE CREEK DR, WINTER SPRINGS, FL 32708
$625,0006 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)
1530 BRAEWICK ST, WINTER SPRINGS, FL 32708
$449,9008 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
Elementary School: None
High School: None
Middle School: None
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)
1105 CLINGING VINE PL, WINTER SPRINGS, FL 32708
$500,0003 Days on yellowkey MLS ID: O6416115
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2044 Built: 1993Monthly Fee: $53 Tax: $2,249 (2025)Community: Eagles LandingSingle Family
Taxes:$2,249
Remarks: Virtually Staged. Eagles Landing is calling and this one has the pool to prove it. Set on a lush quarter-acre lot in one of Winter Springs' most established neighborhoods, this 3-bed, 2-bath stunner checks every box: soaring vaulted ceilings, separate formal living and dining, a kitchen that opens to the family room, and a screened pool with spa just steps from your back door. The primary suite has a walk-in closet, dual vanity, soaking tub, separate shower, and marble finishes that make it feel like a true retreat. Big secondary bedrooms. Full laundry room. Washer and dryer stay. The big stuff is done: brand-new AC (2025), 5-year-old water heater, newer pool pump, solar + propane pool heater (both owned no leases). Swim year-round without the utility sticker shock. Tile flooring throughout the main living areas. Low HOA at just $158/quarter. Zoned for Seminole County schools. Minutes to SR 434, the 417, shopping, dining, and everything Central Florida has to offer. Calling all investors and savvy buyers with vision! This home has incredible bones, a layout that buyers love, and a backyard that sells itself. Add your cosmetic touches and watch the value follow. This is the kind of home people drive through a neighborhood hoping to find. Come see it before someone else does.
Listing is courtesy of: KELLER WILLIAMS ADVANTAGE REALTY (407-977-7600)
Listing Agent: Heather Pryor (321-303-5393)
1107 WINTER SPRINGS BLVD, WINTER SPRINGS, FL 32708
$570,0006 Days on yellowkey MLS ID: O6417844
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2345 Built: 1973Monthly Fee: $3 Tax: $2,525 (2025)Community: Winter Spgs Unit 4Single Family
Taxes:$2,525
Remarks: Welcome to this beautifully maintained, freshly painted 4-bedroom, 3-bathroom home situated on a picturesque wooded lot in the heart of Tuscawilla, one of Winter Springs' most sought-after communities. Built with quality craftsmanship and designed for comfortable living, this spacious residence features brand-new engineered wood flooring, generously sized bedrooms, multiple living areas, and a layout ideal for both everyday life and entertaining. For added peace of mind, the roof was replaced in August 2021. The expansive backyard provides endless opportunities to enjoy the Florida lifestyle. Whether you dream of creating a garden, playing ball with family and friends, hosting outdoor gatherings, or simply relaxing beneath the shade of mature trees, you'll appreciate the privacy and space this property offers. Located within the highly rated Seminole County School District, this home is also part of Tuscawilla's unique golf cart-friendly community. Enjoy the convenience of taking your golf cart to Tuscawilla Country Club for golf, tennis, dining, and social events. The club is also home to the renowned Tiger Sharks Swim Team, one of the area's most respected youth swim programs and a source of pride for the community. Outdoor enthusiasts will love being just moments from the Cross Seminole Trail, offering miles of scenic pathways for biking, walking, jogging, and enjoying the natural beauty of Central Florida. Conveniently located near SR 417, this home provides easy access to Orlando, area employers, shopping, dining, healthcare, Florida's beautiful beaches, and world-famous attractions. Restaurants, retail centers, and everyday conveniences are all just minutes away. If you're searching for a spacious home on a beautiful wooded lot with top-rated schools, outstanding recreational amenities, and the unmatched lifestyle that Tuscawilla offers, this is an opportunity you won't want to miss.
Listing is courtesy of: RE/MAX TOWN & COUNTRY REALTY (407-695-2066)
Listing Agent: Laura Leigh Wood (407-310-4908)
995 DYSON DR, WINTER SPRINGS, FL 32708
$750,0004 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 Agent: Denise Mckinley (407-625-0635)
1160 CITRUS OAKS RUN, WINTER SPRINGS, FL 32708
$825,00036 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)
577 WALDEN CT, WINTER SPRINGS, FL 32708
$399,00015 Days on yellowkey MLS ID: V4949540
REDUCED by $6,000 (1.5%) on 06/20/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1560 Built: 1974 Tax: $3,414 (2025)Community: Walden TerraceSingle Family
Taxes:$3,414
Elementary School: Winter Springs Elementary
Middle School: Tuskawilla Middle
Remarks: Back on MARKET! NO HOA Corner Lot Single Family Home features 4 beds, 2 baths. Open layout design home with tons of upgrades: Windows replaced back in 2020, ROOF replaced in 2022, Water Heater replaced 2025, Luxury Vinyl floors installed 2026. BRAND NEW INTERIOR PAINT gives a clean look. The kitchen is the focal point of the house. It features subway tiles EXHAUST FAN, STAINLESS STEEL APPLIANCES and cabinets. GRANITE COUNTER TOP installed in 2019 and a brand new fridge 2026. Bathroom with brand new glass doors and brand new bath tub. AC unit installed 2017. A fully fenced yard provides privacy with expansive open space ready for outdoor entertaining and dining space, gardening, play area, fire pit area and also has a chicken coop and chicken run area. All outdoor furniture plus the BBQ grill are included with the sale. 2 car garage and metal husky shelves for storage. Zoned for Seminole County top A rated schools. The property is located in a minimal flood risk area (Zone X). Schedule your viewing today.
Listing is courtesy of: RISE REALTY OF FLORIDA LLC (386-804-4114)
Listing Agent: Nicole Garcia Lozada (787-235-4293)
1385 SAN DIEGO CT, WINTER SPRINGS, FL 32708
$320,00075 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
$669,9004 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)
1201 WOLVERINE TRL, WINTER SPRINGS, FL 32708
$500,000156 Days on yellowkey MLS ID: O6374676
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1979 Built: 1977 Tax: $5,709 (2024)Community: Winter Spgs Unit 4Single Family
Taxes:$5,709
Remarks: Welcome to this charming 4-bedroom, 2-bath home tucked away in a quiet, tree-lined neighborhood in desirable Winter Springs. Surrounded by mature trees, this property offers a peaceful atmosphere and a spacious backyard, ideal for entertaining, relaxing, or enjoying Florida outdoor living. Inside, you’ll find a warm and inviting layout highlighted by an original masonry fireplace, adding timeless character and charm. Skylights in the living room and hallway flood the home with natural light, creating a bright and airy feel throughout the main living spaces. Conveniently located near schools, parks, shopping, dining, and major roadways, this home offers the perfect blend of tranquility and accessibility in an established community.
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Nairobi Rondon (786-935-0365)
724 BARRINGTON CIR, WINTER SPRINGS, FL 32708
$399,900396 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)
221 SHERRY AVE, WINTER SPRINGS, FL 32708
$359,90047 Days on yellowkey MLS ID: O6404854
REDUCED by $7,000 (1.9%) on 06/17/2026
Bed: 4 Bath: 2.0 Liv Area Sq Ft: 1700 Built: 1971 Tax: $523 (2025)Community: North Orlando Townsite Fourth Add ReplatSingle Family
Taxes:$523
Remarks: Beautiful fully renovated property featuring 4 spacious bedrooms, 2 modern bathrooms, and an additional room perfect for an office or play room. The home has been completely updated, including a new roof and new windows, providing improved energy efficiency and peace of mind. Open layout with excellent natural light and modern finishes throughout. Move-in ready, ideal for a family home or investment opportunity. Conveniently located with easy access to schools, shopping, and major roads.
Listing is courtesy of: LA ROSA REALTY ORLANDO LLC (407-288-8201)
Listing Agent: Rodrigo Chavez (407-652-8430)
809 BIG BUCK CIR, WINTER SPRINGS, FL 32708
$549,0009 Days on yellowkey MLS ID: O6416554
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2250 Built: 1984Monthly Fee: $3 Tax: $6,018 (2025)Community: Oak Forest Unit 3Single Family
Taxes:$6,018
Remarks: Welcome home to this beautifully renovated 4-bedroom, 2-bath residence offering approximately 2,250 square feet of thoughtfully designed living space in the highly desirable Oak Forest subdivision. From the moment you arrive, you'll appreciate the exceptional care and attention to detail that make this home truly move-in ready. The open-concept floor plan creates a bright and inviting atmosphere, perfect for both everyday living and entertaining. Luxury vinyl and tile flooring flow throughout the home, providing style, durability, and easy maintenance with no carpet to worry about. At the heart of the home is a stunning, fully renovated kitchen featuring quartz countertops, soft-close cabinetry, convenient pull-out drawers, and high-quality appliances that will delight any home chef. The spacious living and dining areas seamlessly connect to the Family Room, where vaulted ceilings, abundant windows, and natural light create a warm and welcoming gathering space. A wet bar complete with a bar refrigerator makes entertaining family and friends effortless. The spacious primary suite offers a beautifully updated bathroom with quartz countertops and a luxurious walk-in shower featuring a rainfall shower head. The secondary bedrooms are generously sized, and the guest bathroom has also been tastefully renovated with quality finishes. Step outside to your backyard retreat, thoughtfully designed for relaxation and entertaining while the cozy fire pit creates the perfect setting for enjoying cool Florida evenings. Major updates provide peace of mind for years to come, including a new roof installed in 2026, new soffits and gutters, new windows, a new water heater, complete repiping, and a new electrical breaker panel, AC installed in 2020. The garage floor has been freshly coated, adding to the home's clean and polished appearance. Ideally located near shopping, restaurants, medical facilities, and major roadways including SR 436, SR 434, and SR 417, this home offers exceptional convenience for commuting and daily living. Residents will also appreciate access to highly regarded schools. This meticulously maintained home combines modern upgrades, quality craftsmanship, exceptional outdoor living space, and an unbeatable location—making it a rare opportunity in Oak Forest.
Listing is courtesy of: COLDWELL BANKER REALTY (407-696-8000)
Listing Agent: Cheri Brandi (321-303-9456)
717 ADIDAS RD, WINTER SPRINGS, FL 32708
$445,0004 Days on yellowkey MLS ID: V4949727
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
Taxes:$5,844
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 Agent: Tracy Phillips, Llc (386-747-4914)
203 SWEETGUM, WINTER SPRINGS, FL 32708
$420,0004 Days on yellowkey MLS ID: O6417974
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1218 Built: 1973 Tax: $925 (2025)Community: North Orlando Terrace Unit 2 Sec 8Spa: NoSingle Family
Taxes:$925
Remarks: This meticulously maintained home offers an impressive combination of recent upgrades, thoughtful features, and exceptional outdoor living. The curb appeal is enhanced by professional landscape lighting, while 10-foot access gates on both sides of the property provide convenience and flexibility. A three-zone irrigation system helps maintain the beautifully landscaped grounds year-round. The backyard is designed for relaxation and enjoyment, featuring a sparkling pool with a removable safety fence, a LED pool light replaced in 2025, and a new pool pump and filter installed in 2026. For additional storage, workshop space, or hobby use, the property also includes a substantial 12’ x 20’ steel accessory building. No HOA, so bring your toys, Rv, camper etc! Inside, the garage has been refreshed with newly painted floors and walls and is illuminated by six custom LED light fixtures, creating a bright and functional space. Major system updates provide peace of mind, including a new roof installed in March 2026, a new central air conditioning system installed in March 2025, and a new hot water heater installed in May 2026. Additional recent improvements include a refrigerator replaced in 2024, a dishwasher installed in 2024, a garbage disposal added in 2025, a Google Nest smart thermostat installed in 2026, and an updated master bathroom toilet. With extensive recent improvements, modern conveniences, and pride of ownership evident throughout, this move-in-ready home offers outstanding value and is ready for its next owner to enjoy.
Listing is courtesy of: CENTURY 21 ALTON CLARK (407-636-4637)
Listing Agent: Joseph Connolly (631-365-6085)
270 SAN GABRIEL ST, WINTER SPRINGS, FL 32708
$249,900223 Days on yellowkey MLS ID: O6359666
REDUCED by $9,100 (3.5%) on 06/16/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1089 Built: 1994Monthly Fee: $121 Tax: $327 (2024)Community: Deersong 2Spa: NoSingle Family
Taxes:$327
Elementary School: Layer Elementary
Remarks: Price Improvement to $259,000 * Quick Closing Available. Welcome to 270 San Gabriel Street in Winter Springs—now offered at an updated price and ready for its next owner. This well-maintained, single-story home features vaulted ceilings and a bright, open layout that creates a comfortable and inviting living space. With neutral finishes and ceramic tile flooring throughout, the home is truly move-in ready. All appliances are included for added convenience. Enjoy morning coffee or unwind in the evening on the oversized screened patio, offering a private outdoor retreat. Additional exterior storage provides practical space for bikes, tools, and seasonal items. Located just minutes from the scenic Cross Seminole Trail, the Deersong community also offers access to a pool and cabana for residents to enjoy. Nearby parks, shopping, dining, and top-rated Seminole County schools add to the home’s appeal. Considering making a move to downsize? First-time homebuyer? investor? or seeking a low-maintenance second home in Central Florida? Schedule your private showing today. With a newly reduced price and quick closing available, this is an excellent opportunity to own a well-cared-for home in a desirable location..
Listing is courtesy of: MAINFRAME REAL ESTATE (407-513-4257)
Listing Agent: Alie Gattis (407-760-1488)
Please select an email frequency other than None since you have chosen for us to email you with changes that match your search.