Location: Winter Springs
Keyword(s): Winter Springs High
Keyword(s) High School: Winter Springs High
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214 CHESTNUT RIDGE ST, WINTER SPRINGS, FL 32708
$625,00098 Days on yellowkey MLS ID: O6372400
REDUCED by $19,900 (3.1%) on 05/17/2026
Bed: 4 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 2474 Built: 2001Monthly Fee: $42 Tax: $5,539 (2024)Community: Chestnut Ridge In TuscawillaSingle 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: Here is your future DREAM HOME! Best price DIRECT GOLF FRONT HOME IN ORLANDO! Did you ever dream of drinking your Coffee daily while looking at a pristine GOLF course and Conservation view? CUSTOM HOME that sits 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. 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. This property, fronting the 16th hole of the Tuscawilla Country Club, is not just a home—it's a lifestyle waiting for you at Chestnut Ridge. 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)
4901 PETRA CT, WINTER SPRINGS, FL 32708
$674,900Listed 05/29/2026 3:06PM MLS ID: O6412001
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2644 Built: 1986Monthly Fee: $40 Tax: $2,783 (2024)Community: TuskabaySingle Family
Taxes:$2,783
Elementary School: Keeth Elementary
Remarks: Make yourself at home in this spacious, beautifully undated residence located in one of the most desirable and sophisticated neighborhoods in Winter Springs, in the heart of Central Florida. This spacious four bedroom, two bath split-plan home offers comfort and versatility throughout . Features include a formal dining room; inviting Florida room, private den, and a generously sized master suite designed for relaxation. With a thoughtful layout and plenty of space, this home is perfect for both everyday living and entertaining. All kitchen appliances are included featuring 42" custom, cabinetry, carpet in the living room and all bedrooms. Bamboo flooring in the sunroom and office with ceramic tile in the kitchen, bathrooms and laundry room (with pull-down ironing board). The living room features an electric fireplace, built in bookshelves, vaulted ceiling, that creates a warm and inviting atmosphere in the heart of the home. Move in ready. Roof; 2016, AC/heat pump; 12/24, microwave; 2026, electric box; 1/2025, replumbed entire house; 2023.
Listing is courtesy of: FLORIDA HOME TEAM REALTY LLC (407-774-8100)
Listing Agent: Pat Long (407-406-6733)
1262 TARFLOWER DR, WINTER SPRINGS, FL 32708
$389,99017 Days on yellowkey MLS ID: O6407223
0 Days Off yellowkey (back on 5/29/2026)
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1678 Built: 2026Monthly Fee: $356 Tax: $1,457 (2025)Community: Hickory GroveTownhouse
Taxes:$1,457
Elementary School: Layer Elementary
Tax Year: 2025
Remarks: Under Construction. Welcome to the Catalina I, a thoughtfully designed townhome in the heart of Winter Springs, FL, where style, comfort, and functionality come together seamlessly. This modern residence features an open-concept layout that connects the gathering room, dining area, and kitchen—creating a bright, airy space perfect for both everyday living and effortless entertaining. Offering 3 spacious bedrooms, this home provides flexible options ideal for families, remote professionals, or those needing a dedicated home office. The versatile loft adds even more living space, perfect for a media room, play area, or additional workspace tailored to your lifestyle. Designed with livability in mind, the Catalina I delivers a balance of comfort and convenience in one of Central Florida’s most desirable suburban communities.
Listing is courtesy of: MATTAMY REAL ESTATE SERVICES (407-440-1760)
Listing Agent: Amanda Warren (321-662-0779)
600 NORTHERN WAY #1804, WINTER SPRINGS, FL 32708
$310,00013 Days on yellowkey MLS ID: O6402233
Bed: 4 Bath: 2.5 Liv Area Sq Ft: 1726 Built: 2007 Tax: $4,110 (2024)Community: Tuscany Place Ph 1Spa: NoCondo
Taxes:$4,110
Remarks: Welcome to Tuscany Place in the heart of sought after Tuscawilla! This well-maintained townhouse style condo offers a spacious floor plan with abundant natural light, generous living and dining areas, and a well-appointed kitchen perfect for everyday living and entertaining. Enjoy spacious bedrooms, ample storage and an outdoor patio ideal for relaxing after a long day. Located in a gated community with amenities including a community pool and beautifully maintained grounds. Conveniently situated near Trotwood Park, shopping, dining, schools, golf course and major roadways for an easy commute. A fantastic opportunity to enjoy the Winter Springs lifestyle!
Listing is courtesy of: BHHS FLORIDA REALTY (407-406-5300)
Listing Agent: Sandra Moshir (407-765-5272)
622 ANHINGA RD, WINTER SPRINGS, FL 32708
$384,900157 Days on yellowkey MLS ID: O6369225
REDUCED by $13,600 (3.4%) on 05/18/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1721 Built: 1988Monthly Fee: $106 Tax: $4,083 (2024)Community: GreenspointeSingle Family
Taxes:$4,083
Elementary School: Highlands Elementary
Middle School: South Seminole Middle
Remarks: NEW TILE ROOF INSTALLED APRIL 2026 + TRANSFERABLE 4-POINT INSPECTION + APPROXIMATELY 5-MINUTE WALK TO HIGHLANDS ELEMENTARY! Welcome to 622 Anhinga Road, a move-in-ready home located in the highly desirable Greenspointe community of Winter Springs. One of the most expensive updates a homeowner can face has already been completed with a BRAND-NEW TILE ROOF installed in April 2026, providing long-term value, durability, and peace of mind for years to come. To make the buying process even easier, the seller has already completed a transferable 4-Point Inspection available to the new owner. This beautiful 3-bedroom, 2.5-bathroom home offers over 1,700 square feet of living space and a highly desirable floor plan with the primary suite conveniently located on the first floor. The spacious owner's retreat features a large walk-in closet and a private bathroom with dual vanities, a soaking tub, separate shower, and private water closet. As you enter the home, you'll immediately notice the soaring ceilings, abundant natural light, and open-concept layout that creates a bright and welcoming atmosphere. The main living areas feature tile flooring throughout, while the kitchen offers granite countertops, stainless steel appliances, light cabinetry, a breakfast bar, and views of the living and dining areas—perfect for everyday living and entertaining. Sliding glass doors lead to a shaded backyard, creating the perfect space for relaxing, grilling, entertaining guests, or simply enjoying Florida evenings. Upstairs, you'll find a spacious loft that can easily serve as a home office, media room, playroom, gym, or second living area, along with two additional bedrooms and a full bathroom. Families will love the location within the highly rated Seminole County School District. Highlands Elementary School is just a short walk from the home, allowing many residents to enjoy the convenience of walking their little ones n to school in approximately 5 minutes. South Seminole Middle School and Winter Springs High School are also nearby. Residents enjoy access to The Highlands community amenities, including a community pool, tennis courts, pickleball courts, basketball courts, playgrounds, parks, clubhouse, walking trails, and recreational facilities designed for an active Florida lifestyle. Conveniently located near Winter Springs Town Center, UCF, Valencia College, shopping, dining, SR-417, SR-434, I-4, Downtown Orlando, and Central Florida attractions, this home offers both comfort and convenience in one of Seminole County's most sought-after communities. Vacant and easy to show. Major updates already completed, including a NEW TILE ROOF (April 2026), HVAC (2017–2018), WATER HEATER (2022), and a TRANSFERABLE 4-POINT INSPECTION. A rare opportunity to own a move-in-ready home in Winter Springs with top-rated schools, outstanding community amenities, and important updates already taken care of.
Listing is courtesy of: KELLER WILLIAMS ADVANTAGE 2 REALTY (407-393-5901)
Listing Agent: Alexa Monasterio Flores (786-915-9294)
1054 WINDING WATERS CIR, WINTER SPRINGS, FL 32708
$549,90045 Days on yellowkey MLS ID: O6398229
REDUCED by $10,000 (1.8%) on 05/29/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2321 Built: 1998Monthly Fee: $42 Tax: $4,167 (2025)Community: Winding HollowSpa: YesSingle Family
Taxes:$4,167
Remarks: This beautiful 4-bedroom, 3-bath, one-story pool home offers over 2,300 sqft of living space on a premium conservation lot with no rear neighbors, providing privacy and a peaceful setting. Major updates already completed: roof 2019, AC updated 2020–2021, pool resurfaced 2022, and kitchen updated 2022. Solar panels will be paid off at closing, giving the new owner added value and energy efficiency. The home features a spacious split floor plan with high ceilings and abundant natural light. Formal living and dining areas flow into a large family room with a wood-burning fireplace, connecting seamlessly to the kitchen and outdoor space. The kitchen offers ample cabinet space, updated finishes, and includes stainless steel appliances: range, refrigerator, dishwasher, and microwave. Washer and dryer are also included. The primary suite is oversized with a large en-suite bathroom featuring dual sinks, soaking tub, separate shower, and a spacious walk-in closet. Secondary bathrooms are well maintained with potential for future personalization. Flooring includes tile, laminate/engineered flooring, and carpet in select areas. Additional features include an indoor laundry room and a 2-car garage with extra storage. Step outside to a screened-in pool and covered patio, ideal for Florida living year-round. The backyard backs to conservation, offering privacy and no rear neighbors. Situated on one of the larger lots in the neighborhood and directly across from a park and schools, this is a prime location close to shopping, dining, and major highways. Approximately 25–30 minutes to Downtown Orlando, 20–25 minutes to UCF, and about 45–60 minutes to the beaches. Zoned for top-rated Seminole County schools. Homes in this area with similar features and updates have sold in higher ranges, making this a strong opportunity.
161 BEAR SPRINGS DR, WINTER SPRINGS, FL 32708
$484,99087 Days on yellowkey MLS ID: O6386458
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1704 Built: 2026Monthly Fee: $356 Tax: $1,457 (2025)Community: Hickory GroveTownhouse
Remarks: Under Construction. A standout feature of this end-unit home is the owner’s suite, conveniently located on the first floor, providing privacy and ease of access. This inviting retreat includes abundant natural light, a generous walk-in closet, and a well-appointed private bath. The open-concept main floor features expansive living and dining areas that flow seamlessly into a thoughtfully designed kitchen—complete with stainless steel appliances, including a refrigerator, a walk-in pantry, and a spacious breakfast bar—ideal for entertaining or everyday living. Laundry room, complete with washer and dryer is conveniently located on the main floor. Upstairs, you’ll find two additional bedrooms, a versatile loft perfect for a home office or media space, along with ample storage and a dedicated laundry area. A rear-loading 2-car garage adds both functionality and curb appeal. Located in desirable Winter Springs near the vibrant Town Center, residents enjoy a highly sought-after lifestyle with walkable access to shopping, dining, and community events. Known for its top-rated schools, scenic parks, and extensive trail system, Winter Springs offers a perfect balance of small-town charm and modern convenience—just a short drive from Orlando. Discover low-maintenance townhome living in one of Central Florida’s most connected and livable communities.
173 BEAR SPRINGS DR, WINTER SPRINGS, FL 32708
$484,99087 Days on yellowkey MLS ID: O6386437
Remarks: Under Construction. With an open concept ground floor and spacious living areas, the Sofia is ideal for entertaining and everyday life. Dedicated as an end unit, this floorplan features 3 bedrooms, 2.5 bathrooms and a rear-loading 2-car garage. The 2nd floor features a loft, abundant storage, and laundry space. Located on the 1st floor, the owner's suite that has it all - a spacious walk-in closet, great natural light, and private bath. Stainless steel appliances, a walk-in pantry and a breakfast bar are all featured in this floorplan's thoughtfully designed kitchen.
189 BEAR SPRINGS DR, WINTER SPRINGS, FL 32708
$491,990141 Days on yellowkey MLS ID: O6372546
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1704 Built: 2025Monthly Fee: $356 Tax: $1,457 (2025)Community: Hickory GroveTownhouse
Remarks: Experience luxurious living in the Sofia floorplan, where the spotlight shines on the exquisite first-floor owner's suite that exudes sophistication with a spacious walk-in closet, abundant natural light, and a private bath. This end unit boasts an open-concept ground floor, perfect for entertaining and daily life. With 3 bedrooms, 2.5 bathrooms, and a rear-loading 2-car garage, this residence offers both style and functionality. Enjoy the convenience of first-floor laundry, while the 2nd floor features a loft and two generous-sized bedrooms. The thoughtfully designed kitchen showcases stainless steel appliances, a walk-in pantry, and a breakfast bar for a truly elevated living experience. Located in desirable Winter Springs near the vibrant Town Center, residents enjoy a highly sought-after lifestyle with walkable access to shopping, dining, and community events. Known for its top-rated schools, scenic parks, and extensive trail system, Winter Springs offers a perfect balance of small-town charm and modern convenience—just a short drive from Orlando. Discover low-maintenance townhome living in one of Central Florida’s most connected and livable communities.
986 TURKEY HOLLOW CIR, WINTER SPRINGS, FL 32708
$498,900134 Days on yellowkey MLS ID: O6374288
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1864 Built: 1985Monthly Fee: $3 Tax: $3,119 (2024)Community: Oak Forest Unit 4Spa: YesSingle Family
Taxes:$3,119
Remarks: 986 Turkey Hollow Circle—where comfort, style, and Florida living come together beautifully. Nestled in one of Winter Springs’ most desirable neighborhoods, this 4-bedroom, 2-bath pool home offers the perfect blend of warmth, functionality, and thoughtful updates—just minutes from Tuskawilla Road, SR-434, shopping, dining, and top-rated schools. Step inside to an open, light-filled great room where the kitchen, dining, and living spaces flow effortlessly—ideal for both everyday living and entertaining. The heart of the home is the kitchen, featuring rich cabinetry, custom backsplash, farmhouse sink, and a spacious island with cooktop and bar seating—perfect for gathering and connection. Just beyond, the inviting living room showcases vaulted ceilings, recessed lighting, tile flooring, and a stunning brick fireplace, creating a cozy yet open atmosphere. Sliding glass doors lead to your private outdoor retreat. Enjoy true Florida living outdoors with a sparkling pool, heated spa, and expansive covered lanai (10’ x 48’)—perfect for relaxing evenings, entertaining guests, or weekend poolside fun. Wood-tone decking, a fire pit area, gazebo dining space, and dedicated grill area complete this backyard oasis. The primary suite is a peaceful escape, offering private lanai access, a spacious bath, and walk-in closet. A split floor plan provides three additional bedrooms and an updated guest bath with convenient pool access—ideal for family or guests. Recent updates include: • POOL & DECK RESURFACED (2024) + new heater & pump • ROOF (2020) • Updated bedroom WINDOWS (2024) • Renovated GUEST BATH (2024) • New recessed lighting (2024) • New stainless steel refrigerator (2023) • Lanai flooring, spa lighting, gazebo & paver grill area Warm, welcoming, and move-in ready—this is the kind of home where memories are made. (All information intended to be accurate, but not guaranteed.)
Listing is courtesy of: CALL IT CLOSED INTL REALTY (407-338-3339)
Listing Agent: Christopher Dunlop (321-223-0407)
984 TURKEY HOLLOW CIR, WINTER SPRINGS, FL 32708
$410,0003 Days on yellowkey MLS ID: O6410083
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: One or more photo(s) has been 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)
120 E BAHAMA RD, WINTER SPRINGS, FL 32708
$1,249,000116 Days on yellowkey MLS ID: O6379165
REDUCED by $50,900 (3.9%) on 05/29/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 4464 Built: 1989 Tax: $12,488 (2025)Community: Bahama RanchesSpa: NoSingle Family
Taxes:$12,488
Elementary School: Winter Springs Elementary
Remarks: Mid Century Modern Paradise!! A Beautiful, well-designed home with spectacular architecture offering privacy, space, and long-term versatility on a rare 2.22-acre lot with RV/Toy parking—delivering exceptional value in this area. A separate in-law or guest suite features its own exterior entrance and full bathroom, ideal for multigenerational living, a private office, studio, or extended stays. The main living areas are sprawling, thoughtfully arranged with strong natural light and a functional flow for everyday living and a large Loft for entertaining, office or hobbies. The large primary suite includes a spacious en-suite bath and walk-in closet. Bedrooms two and three are oversized, each with walk-in closets; one includes a hidden play loft/ adventure nook accessible through the Narnia style closet access. The expansive property also includes a detached casita in the backyard, currently used as a workshop, with clear potential to be converted into a guest home, rental unit, or Airbnb. Located on a quiet street in an established Winter Springs neighborhood, with convenient access to top-rated schools, shopping, dining, and major commuter routes. Concessions considered with the right scenario. Buyer and buyer’s agent to verify all information. Both owners are licensed real estate agents.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Alma Merrill (801-613-8090)
1270 TARFLOWER DR, WINTER SPRINGS, FL 32708
$409,99017 Days on yellowkey MLS ID: O6407275
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1678 Built: 2026Monthly Fee: $356 Tax: $1,457 (2025)Community: Hickory GroveTownhouse
Remarks: Under Construction. The Catalina II offers a spacious and modern open-concept design on the main level, creating the perfect setting for entertaining, everyday living, and gathering with family and friends. This thoughtfully designed townhome features 4 bedrooms, 2.5 bathrooms, and a rear-loading 2-car garage, blending functionality with contemporary style in desirable Winter Springs, FL. The owner’s suite serves as a private retreat, complete with a well-appointed ensuite bathroom and a generous walk-in closet. The chef-inspired kitchen is designed for both beauty and performance, showcasing stainless steel appliances, a walk-in pantry, and a convenient breakfast bar ideal for casual dining and hosting.
1219 SWAN ST, WINTER SPRINGS, FL 32708
$350,00075 Days on yellowkey MLS ID: O6391011
0 Days Off yellowkey (back on 3/21/2026)
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1848 Built: 1978 Tax: $2,327 (2024)Community: Winter Spgs Unit 4Single Family
Taxes:$2,327
Remarks: Under contract-accepting backup offers. Build your dream home on this rare 0.47 acre corner lot located at 1219 Swan Street in the highly desirable Tuscawilla area of Winter Springs. This spacious homesite offers plenty of room to design a custom residence while enjoying the charm and established beauty of one of Seminole County’s most loved communities. The property is zoned for single family residential use, allowing for the construction of a custom single family home that fits your vision and lifestyle. Located in an optional HOA section of Tuscawilla, homeowners enjoy flexibility while still benefiting from the surrounding community amenities and pride of ownership. Just a short walk away is the Tuscawilla Country Club, a private club offering a full golf course with Diamond Zoysia greens surrounded by majestic Live Oak trees draped in Spanish moss. Members enjoy a well stocked Golf Pro Shop, fitness center, and The Oaks Restaurant which serves lunch, dinner, and brunch in a welcoming setting. The club also features six Har Tru clay tennis courts with LED lighting and a Jr Olympic sized swimming pool at the Aquatics Center along with numerous social activities throughout the year for both adults and children. Beyond the club, the Tuscawilla community is known for its beautiful parks, playgrounds, and scenic walking and biking trails that wind through the neighborhood, creating a peaceful and active outdoor lifestyle. With its large size, corner location, and unbeatable proximity to golf, tennis, dining, and recreation, this lot presents an exceptional opportunity to build a custom home in one of Winter Springs’ most sought after communities. Close to 417 highway which connects easily to I-4 to take you anywhere from Downtown Orlando, to Tampa or Daytona beach! Zoned for Keeth Elementary, Indian Trails Middle School, and Winter Springs High School in highly rated Seminole County Public Schools. Cash or hard-money only please.
Listing is courtesy of: RE/MAX TOWN & COUNTRY REALTY (407-695-2066)
Listing Agent: Kristine Mckinley (407-415-2412)
167 CONSTITUTION WAY, WINTER SPRINGS, FL 32708
$295,00096 Days on yellowkey MLS ID: O6383981
REDUCED by $4,000 (1.3%) on 05/29/2026
Bed: 2 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1275 Built: 2005Monthly Fee: $300 Tax: $2,666 (2025)Community: Heritage Park TwnhmsTownhouse
Taxes:$2,666
Remarks: One or more photo(s) has been virtually staged. ROOF & ELECTRICAL UPDATED (2023) – this well-maintained townhome in the gated Heritage Park community of Winter Springs offers peace of mind along with stylish, LOW MAINTENANCE LIVING in one of Seminole County’s most convenient locations! Thoughtfully designed with TILE & LUXURY VINYL PLANK FLOORING throughout, this home feels light, bright, and MOVE-IN READY from the moment you step inside. The OPEN CONCEPT main floor is ideal for everyday comfort and easy entertaining, featuring a comfortable living area that flows seamlessly into the kitchen. The home chef will appreciate the long breakfast bar for casual dining, STAINLESS STEEL APPLIANCES, rich cabinetry, and generous prep space, while a convenient half bath downstairs adds functionality for guests. Sliding glass doors open to a SCREENED LANAI finished with wood look tile, where mature landscaping and tranquil POND VIEWS create a peaceful outdoor retreat – perfect for morning coffee or unwinding at the end of a long day. Upstairs, both bedrooms offer private en-suite full baths, creating an ideal layout for homeowners, guests, or roommates. The PRIMARY SUITE includes a large WALK-IN CLOSET and relaxing water views, while the overall layout provides comfort and privacy for everyday living. Perfectly positioned across from the COMMUNITY POOL while enjoying serene views out back, this home delivers the best of both worlds. Heritage Park is a GATED COMMUNITY in the heart of Winter Springs, ideally located just off SR-434 and directly across from Central Winds Park, with access to walking trails, lakes, and endless outdoor space to explore. Spend weekends biking the Cross Seminole Trail, boating on Lake Jesup, or checking out the many nearby parks and recreation areas. Residents enjoy access to a community pool, park, and playground, all just minutes from shopping, dining, and major roadways for an easy commute throughout Central Florida. Whether you are searching for your first home, a low-maintenance lifestyle, or a strong rental opportunity, this Constitution Way townhome checks all the boxes with location and lifestyle appeal! Call today to schedule your tour!
Listing is courtesy of: WEMERT GROUP REALTY LLC (407-743-8356)
Listing Agent: Jenny Wemert (407-809-1193)
140 N. FAIRFAX, WINTER SPRINGS, FL 32708
$325,000178 Days on yellowkey MLS ID: O6364352
REDUCED by $6,000 (1.8%) on 04/24/2026
Bed: 3 Bath: 1.0 Liv Area Sq Ft: 1188 Built: 1959 Tax: $2,426 (2024)Community: North OrlandoSingle Family
Taxes:$2,426
Remarks: Fully Renovated Winter Springs Home with No HOA – Move-In Ready in Seminole County Welcome to 140 N. Fairfax Avenue in Winter Springs, Florida, a beautifully renovated home that blends classic Florida charm with modern upgrades in one of Seminole County’s most desirable and convenient locations. This extensively updated 3-bedroom, 1-bath home sits on a generous 8,900-square-foot lot and offers a turnkey opportunity for first-time buyers, downsizers, or investors seeking a move-in ready property in the Orlando metro area. Inside, the home has been thoughtfully remodeled from top to bottom. The interior features new flooring, fresh paint, modern lighting, and a completely updated kitchen and bathroom, along with new appliances and updated mechanical systems. A brand-new HVAC system installed in late 2025 and new energy-efficient windows add comfort and efficiency, allowing the next owner to enjoy years of low-maintenance living. The open and functional layout provides comfortable everyday living while maximizing natural light throughout the home. Outside, the spacious yard offers plenty of room to create your ideal outdoor living space. With no HOA restrictions, homeowners have the flexibility to add a garage or workshop, store a boat or trailer, or design additional outdoor entertaining areas. The property’s generous lot size offers rare freedom and versatility that is increasingly hard to find in Central Florida. For outdoor recreation, the home is located just a short walk to Torcaso Park, featuring a playground, splash pad, soccer fields, and a fishing pier. Residents also enjoy close proximity to Lake Jesup, Spring Hammock Preserve, and the Cross Seminole Trail, one of the region’s most popular trails for biking, jogging, and scenic walks. Families benefit from access to highly regarded Seminole County Public Schools, including Highlands Elementary School, Indian Trails Middle School, and Winter Springs High School, all located within a short drive of the home. Convenience is another major highlight of this location. The home is just minutes from Winter Springs Town Center, Oviedo on the Park, and Winter Park, providing easy access to shopping, dining, entertainment, and everyday services. Healthcare facilities such as Orlando Health South Seminole Hospital and AdventHealth Altamonte Springs are also nearby, offering quick access to medical care. Public transportation options are available throughout the area via the LYNX regional bus system, which serves Seminole County and connects residents to destinations across the greater Orlando area. Commuters can also access nearby SunRail stations in Longwood and Altamonte Springs for convenient rail service into downtown Orlando and surrounding employment centers. Safety and emergency services are close by as well, including Seminole County Fire Department stations serving the Winter Springs area, providing quick response coverage for local residents. Winter Springs itself is consistently recognized as one of the best places to live in Central Florida, known for its community feel, parks, trails, and easy access to major employers throughout Orlando, Lake Mary, and the Seminole County tech corridor. Whether you’re searching for a move-in ready home, an investment property, or an affordable Central Florida residence close to parks, schools, and commuter routes, 140 N. Fairfax Avenue delivers comfort, flexibility, and location in one exceptional package.
Listing is courtesy of: ERA GRIZZARD REAL ESTATE (407-203-5800)
Listing Agent: Shawn Mccormick (321-439-4277)
126 SEVILLE CHASE DR, WINTER SPRINGS, FL 32708
$769,00058 Days on yellowkey MLS ID: O6392873
REDUCED by $16,000 (2.0%) on 04/15/2026
Bed: 5 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 3205 Built: 2000Monthly Fee: $184 Tax: $9,320 (2024)Community: Seville ChaseSingle Family
Taxes:$9,320
Elementary School: Sterling Park Elementary
Remarks: **Price Improvement** and a $20,000.00 SELLER CONCESSION towards buyer's closing costs ** Welcome to Seville Chase, a quiet gated neighborhood in Winter Springs with tree-lined streets and access to great schools like South Seminole Middle and Winter Springs High Schools.This 5-bedroom, 4-bath home sits on a large 0.41-acre lot and offers over 3,000 square feet of living space, mostly on one level, with a practical 3-way split floor plan that gives everyone their own space.As you walk in through the double front doors, you’ll notice the natural light, high ceilings, and nice touches like crown molding and archways. There’s a formal living and dining area up front, and a big family room that opens right into the kitchen—great for everyday living and hanging out.The kitchen has plenty of counter space, an island with bar seating, and a bright breakfast nook that looks out over the backyard and trees.Out back, you’ve got a covered lanai and a big yard with tons of potential. It’s already set up with electric, gas, and plumbing hookups—making it easy to add a pool or build out your dream outdoor space.The primary suite is set off to one side of the home for privacy and includes two walk-in closets, a spacious bathroom, and an attached flex room that works well as an office, nursery, or quiet retreat.On the other side of the home, there are three more bedrooms and two bathrooms, giving plenty of room for family or guests. Upstairs, there’s a fifth bedroom with its own bathroom plus an air-conditioned bonus/storage room—perfect for a game room, gym, or hobby space.The home has been well taken care of, with regular A/C duct and carpet cleanings, updated lighting, fresh exterior paint, and a painted garage floor. The extra-long, wide driveway gives you plenty of parking and leads to your three car garage.You’re also in a great location—close to shopping, restaurants, Oviedo Mall and the Winter Springs Town Center, with easy access to major roads and nearby employers like University of Central Florida.If you’re looking for space, a solid layout, and the chance to make a backyard your own, this home is definitely worth a look. Come check it out and see if it feels like home. Not local? No worries, please click on the two attached links,one being a video walk through and the other is your own personal 360 degree tour of the whole house, walk through it like you are in the home! Looking forward to seeing you!
Listing is courtesy of: KELLER WILLIAMS ADVANTAGE REALTY (407-977-7600)
Listing Agent: Robert Johnson (407-920-4920)
328 SAN MIGUEL ST #328, WINTER SPRINGS, FL 32708
$224,900130 Days on yellowkey MLS ID: O6375171
1 Days Off yellowkey (back on 4/29/2026)
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1032 Built: 1980Monthly Fee: $135 Tax: $2,102 (2025)Community: Indian RidgeCondo
Taxes:$2,102
Remarks: Under contract-accepting backup offers. Welcome home to this charming 3-bedroom, 2-bathroom home, which offers 1,032 square feet of beautifully updated living space. This property features a newly painted interior and a fully remodeled eat-in kitchen equipped with brand-new stainless steel appliances, shaker cabinets with modern hardware, a trendy backsplash, and granite countertops. The home is designed with a functional split-floor plan for added privacy. The master suite includes a private bathroom with a new vanity, lighted mirror, and updated lighting. On the opposite side of the home, you will find two additional bedrooms and a second bathroom, which also features a new vanity and modern lighting fixtures. The layout includes separate living and dining rooms, with brand-new ceiling fans installed in the living area and all bedrooms. Major high-ticket maintenance items have been recently addressed, including a new roof installed in 2025, a new hot water heater in 2023, and an HVAC system from 2018 with air ducts replaced in 2020. Exterior features include a private patio with a storage shed, and residents can enjoy a low monthly HOA fee that provides access to a community pool and tennis courts. Located conveniently near schools, major highways, medical centers, and prime shopping and dining, this home is an ideal choice for a growing family or a strategic investment opportunity.
Listing is courtesy of: REALTY TECH INC (407-332-9757)
Listing Agent: Carmen Vazquez (407-617-9045)
877 BENCHWOOD DR, WINTER SPRINGS, FL 32708
$460,0001 Day on yellowkey MLS ID: O6410431
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)
268 TAVESTOCK LOOP, WINTER SPRINGS, FL 32708
$569,90016 Days on yellowkey MLS ID: O6407307
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
Remarks: PHOTOS COMING SOON**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)
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