Location: Winter Springs
Keyword(s): Winter Springs High
Keyword(s) High School: Winter Springs High
Do Not Show Listings
661 ANDOVER CIR, WINTER SPRINGS, FL 32708
$435,0009 Days on yellowkey MLS ID: O6417072
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1735 Built: 1994Monthly Fee: $125 Tax: $5,042 (2025)Community: Georgetowne Unit 3Spa: NoSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$5,042
Elementary School: Keeth Elementary
High School: Winter Springs High
Tax Year: 2025
Middle School: Indian Trails Middle
Remarks: Welcome to 661 Andover Circle, a beautifully updated home in the sought-after Tuscawilla community of Winter Springs. This move-in ready residence features ceramic tile flooring, fresh interior paint, and a spacious split-bedroom floor plan designed for comfortable living. The updated kitchen offers granite countertops, newly painted cabinetry, a brand-new range, ample storage, and a functional layout perfect for everyday living and entertaining. The spacious primary suite provides a private retreat, while a brand-new HVAC system offers peace of mind for years to come. Enjoy Florida living year-round from the screened rear patio, perfect for relaxing with your morning coffee or entertaining family and friends. Conveniently located near Trotwood Park, you'll have easy access to pickleball and tennis courts, playgrounds, sports fields, covered pavilions, and more. Just around the corner, Tuscawilla Country Club features tennis facilities and a beautiful 18-hole golf course for those who enjoy an active lifestyle. The HOA covers front lawn maintenance, providing low-maintenance living. Located near top-rated Seminole County schools, shopping, dining, the Seminole Trail, and SR-417, this home offers the perfect combination of comfort, convenience, and community. Don't miss your opportunity to own this beautifully updated Tuscawilla home. Schedule your private showing today! Please note that the home does not have a backyard sprinkler system. All information pertaining to the property is deemed reliable, but not guaranteed. Information to be verified by the Buyer. Be advised that cameras may exist recording audio and video inside/outside the property, such as ring doorbells. Photos are digitally enhanced and could be altered, please verify.
Listing is courtesy of: DJ & LINDSEY REAL ESTATE (904-643-6199)
Listing Agent: Christopher Anuszewski (407-230-7921)
947 GLEN ABBEY CIR, WINTER SPRINGS, FL 32708
$525,0004 Days on yellowkey MLS ID: O6418792
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2416 Built: 1997Monthly Fee: $126 Tax: $2,980 (2025)Community: Greenbriar Sub Ph 2Spa: NoSingle Family
Taxes:$2,980
Elementary School: Rainbow Elementary
Remarks: Welcome to 947 Glen Abbey Circle in the sought-after Greenbriar Country Club and Golf Course community of Winter Springs. This impeccably maintained 4-bedroom, 3-bathroom home with a spacious loft offers thoughtfully designed living space with beautiful conservation views and a flexible floor plan perfect for everyday living and entertaining. The bright and open layout features soaring ceilings in the formal living and dining areas, creating an impressive first impression. The spacious kitchen is equipped with wood cabinetry, ceramic tile flooring, and overlooks the family room, where sliding glass doors lead to a screened porch overlooking the peaceful conservation area. The first-floor primary suite provides a private retreat with a large walk-in closet, garden tub, separate shower, and dual vanity. An interior laundry room and convenient half bath complete the main level. Upstairs, you'll find three additional bedrooms, a full bathroom, and a versatile loft that overlooks the living and dining areas below, enhancing the home's open and airy feel. Whether used as a game room, home office, media space, or play area, the loft adds flexibility to meet a variety of lifestyle needs. Recent updates and meticulous care throughout make this property truly move-in ready. Enjoy the lifestyle that Greenbriar offers, with access to golf, country club amenities, top-rated Seminole County schools, shopping, dining, and major roadways just minutes away. This is a rare opportunity to own a beautifully maintained home in one of Winter Springs' most desirable communities. Schedule your private showing today.
Listing is courtesy of: RE/MAX TOWN & COUNTRY REALTY (407-695-2066)
Listing Agent: Denise Mckinley (407-625-0635)
4967 COURTLAND LOOP, WINTER SPRINGS, FL 32708
$790,000Listed 06/26/2026 7:48AM MLS ID: O6419028
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2339 Built: 1989Monthly Fee: $40 Tax: $6,933 (2025)Community: TuskabaySingle Family
Taxes:$6,933
Remarks: Welcome to this beautifully upgraded 4 bedroom, 3 bath pool home in the desirable Tuskabay community located in Winter Springs. Designed for both comfortable living and effortless entertaining, this light-filled home features an open living area, inviting floor plan with abundant natural light and crown molding throughout. The spacious family room features a cozy fireplace creating the perfect ambiance. The heart of the home is the impressive chef's kitchen, boasting extensive 42" cabinetry, ample counter space, premium finishes and a built in wine refrigerator that adds a touch of sophistication. The luxurious primary ensuite bathroom features dual sinks, an exquisite shower and walk-in closet. The spacious living areas flow seamlessly to the oversized covered lanai, ideal for morning coffee, outdoor dining, or relaxing while overlooking the sparkling pool and spa. The expansive fenced in backyard with plenty of room to play, garden or simply enjoy the extra space creating the perfect indoor-outdoor Florida lifestyle. With generous bedrooms, three full baths, laundry/mud room and exceptional outdoor living spaces, this Tuskabay gem offers the perfect combination of style, comfort, and functionality. Don't miss the opportunity to make this exceptional home yours! Schedule your tour today.
Listing is courtesy of: FANNIE HILLMAN & ASSOCIATES (407-644-1234)
Listing Agent: Lou Diberardino (315-569-6900)
4901 PETRA CT, WINTER SPRINGS, FL 32708
$674,90028 Days on yellowkey 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
Tax Year: 2024
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)
622 ANHINGA RD, WINTER SPRINGS, FL 32708
$374,900184 Days on yellowkey MLS ID: O6369225
REDUCED by $10,000 (2.6%) on 06/26/2026
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: $374,900 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)
476 CLUB DR, WINTER SPRINGS, FL 32708
$275,00094 Days on yellowkey MLS ID: O6392856
REDUCED by $10,000 (3.5%) on 04/22/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1460 Built: 1995Monthly Fee: $520 Tax: $1,765 (2025)Community: Cypress ClubTownhouse
Taxes:$1,765
Remarks: Welcome to 476 Club Drive, a beautifully cared-for townhome nestled in the highly sought-after Cypress Club section of The Highlands in Winter Springs—a community known for its incredible amenities and natural surroundings. This spacious 3-bedroom, 2-bath residence blends comfort, functionality, and peace of mind with key updates already completed. Enjoy the benefits of a new roof 2026, new water heater 2026, 2020 A/C system, a full repipe completed in 2016, and a 2016 whole home water softener. Inside, you’ll find an inviting layout with knockdown ceilings throughout the main level and an open living and dining area tucked toward the rear of the home for added privacy. Updated recessed lighting enhances the space, creating a warm and welcoming atmosphere. Just beyond, a step-down enclosed patio offers a serene retreat overlooking wooded views—perfect for relaxing or entertaining. The flexible floor plan includes a downstairs bedroom with an adjacent full bath, ideal for guests, a home office, or multi-generational living. Upstairs, two generously sized bedrooms feature soaring ceilings and abundant natural light. The primary suite offers ample closet space and tranquil views of the surrounding greenery, along with a spacious en-suite bath complete with a Jacuzzi tub and separate shower—perfect for unwinding after a long day. Cypress Club stands out as the only neighborhood within The Highlands with its own private pool, in addition to access to the community’s extensive amenities. Residents enjoy multiple pools, tennis courts, scenic walking trails, parks, pavilions, BBQ areas, a clubhouse, as well as volleyball and basketball courts—delivering a true Florida lifestyle right outside your door. Don’t miss this opportunity to own a move-in-ready home in one of Winter Springs’ most desirable communities!
Listing is courtesy of: KELLER WILLIAMS HERITAGE REALTY (407-862-9700)
Listing Agent: Jeff Singletary (407-383-1933)
280 MOREE LOOP #2, WINTER SPRINGS, FL 32708
$150,00035 Days on yellowkey MLS ID: O6409577
2 Days Off yellowkey (back on 6/26/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1187 Built: 1978Monthly Fee: $425 Tax: $2,656 (2025)Community: Baytree VillageCondo
Taxes:$2,656
Remarks: Under contract-accepting backup offers. Virtually Staged. Welcome home to this first-floor condo in the desirable Bay Village community of Winter Springs! Nestled among beautiful tree-lined streets, this spacious unit offers a fantastic opportunity to make it your own. The upgraded kitchen features stainless steel appliances, ample cabinetry, and plenty of workspace for cooking and entertaining. The open-concept living and dining area is filled with natural light thanks to the wall of sliders and windows along the living room. Laminate flooring runs throughout the home with no carpet anywhere for easy maintenance and a cohesive look. Residents of Bay Village enjoy access to the community pool and a prime location close to parks, shopping, dining, and top-rated schools. This home is move-in ready and waiting for its new owner to bring their vision, add some fresh updates, and give it the love and facelift to truly make it shine!
Listing Agent: Danielle Pensala (407-529-5752)
1035 N ELK CT, WINTER SPRINGS, FL 32708
$900,00018 Days on yellowkey MLS ID: O6414324
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3360 Built: 1978 Tax: $10,432 (2025)Community: Winter Spgs Unit 2Spa: YesSingle Family
Taxes:$10,432
Remarks: Seller may consider buyer concessions if made in an offer ~ Over 1.3 PRIVATE ACRES, a DREAM BACKYARD, and a home filled with character – this is the kind of property that rarely comes to market in the heart of Winter Springs! Set on a secluded 1.32 ACRE CUL-DE-SAC LOT with an optional HOA, this beautifully UPDATED SINGLE STORY POOL HOME offers more than 3,000 square feet of versatile living space with 4 bedrooms, 3.5 baths, a dedicated FLEX/DEN, BONUS ROOM, and a flowing floor plan designed for everyday living and unforgettable entertaining. Major updates include A/C systems updated (2022/2023), septic service in (2022), and a 2016 roof, giving peace of mind for years to come. The GATED COURTYARD ENTRY welcomes you home, while the circular driveway provides abundant parking for family and guests. Inside, you will find no carpet – just WOOD LOOK TILE, wood laminate flooring, and new SLATE TILE in the chef's kitchen. Thoughtfully updated with rich cabinetry topped with crown molding, sleek stone countertops, a striking herringbone backsplash, breakfast bar seating, upgraded STAINLESS STEEL APPLIANCES including a built-in wall oven, and a layout that opens seamlessly to the living spaces, this kitchen was made for gathering. Crown molding, custom accent details, a cozy WOOD BURNING FIREPLACE, updated bathrooms, and charming architectural touches throughout give this home a warmth, style, and personality you simply can't recreate. Designed to embrace Florida living, three sets of FRENCH DOORS and windows from the main living areas and oversized sliding glass doors from the PRIMARY SUITE open to an incredible COVERED LANAI featuring a beautiful WOOD SLAT CEILING, generous spaces for outdoor dining and relaxing, and views of the SCREENED HEATED POOL and separate SPA with a PERGOLA/BAR. Beyond the lanai, discover your own private retreat complete with mature trees, winding garden paths, a FIRE PIT, fenced dog run, lush landscaping, and endless green space that feels worlds away from the city. Located in one of Winter Springs' most desirable areas with TOP-RATED SCHOOLS and easy access to Tuskawilla Road, Red Bug Lake Road, SR 417, shopping, dining, parks, golf, the Tuscawilla Country Club, Trotwood Park, Bear Creek Nature Trail, the Oviedo Mall and a variety of everyday conveniences, this is a rare opportunity to enjoy unmatched privacy, space, and timeless charm without sacrificing location. Homes offering this much land, versatility, and outdoor living in the heart of Winter Springs are few and far between – schedule your private showing today and fall in love with this exceptional property!
Listing is courtesy of: WEMERT GROUP REALTY LLC (407-743-8356)
Listing Agent: Jenny Wemert (407-809-1193)
161 BEAR SPRINGS DR, WINTER SPRINGS, FL 32708
$444,990114 Days on yellowkey MLS ID: O6386458
5 Days Off yellowkey (back on 6/23/2026)
REDUCED by $40,000 (8.2%) on 06/01/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1704 Built: 2026Monthly Fee: $356 Tax: $1,457 (2025)Community: Hickory GroveTownhouse
Taxes:$1,457
Elementary School: Layer Elementary
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.
Listing is courtesy of: MATTAMY REAL ESTATE SERVICES (407-440-1760)
Listing Agent: Amanda Warren (321-662-0779)
986 TURKEY HOLLOW CIR, WINTER SPRINGS, FL 32708
$494,000161 Days on yellowkey MLS ID: O6374288
REDUCED by $4,900 (1.0%) on 06/24/2026
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)
1406 BLUMBERG BLVD, WINTER SPRINGS, FL 32708
$420,00039 Days on yellowkey MLS ID: O6408695
REDUCED by $5,000 (1.2%) on 06/19/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1476 Built: 2024Monthly Fee: $356 Tax: $6,076 (2025)Community: Hickory Grove TwnhmsTownhouse
Taxes:$6,076
Remarks: Welcome to this almost-new townhome in beautiful Winter Springs! Located in the desirable Hickory Grove community, where you will find a maintenance free living, relaxing pool and cabana, playground for the little ones and a dog park for your furry friend, all just a few steps away and NO CDD to pay. The monthly HOA dues also include: landscaping, irrigation, weed control, exterior paint, roof, 1GB of high speed internet and cable premium package. This stunning residence has been tastefully decorated and offers the perfect blend of modern style, comfort, and convenience. Your front door opens up to the serene parks, fountains and walkways just across the street from your favorite stores and restaurants. Enjoy an open-concept layout with plenty of natural light, a modern kitchen with state of the art SS appliances, quartz counters and a beautiful island to entertain your guests. 3 bedrooms, 2.5 bathrooms, and a 2-car garage, and much more. This home is move-in ready and designed for easy living. Upstairs, the generous primary suite offers a private retreat with an en-suite bath and ample closet space. Built with today’s lifestyle in mind, this home also includes the peace of mind of a builder warranty, this is a fantastic opportunity to own a like-new home in one of Central Florida’s most sought-after areas with top-rated schools.
Listing is courtesy of: RALISTO, LLC (407-493-6032)
Listing Agent: Kalex Espinosa (407-493-6032)
1357 MILL STREAM LN, WINTER SPRINGS, FL 32708
$399,9009 Days on yellowkey MLS ID: O6417015
REDUCED by $100 (0.0%) on 06/25/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1606 Built: 2015Monthly Fee: $230 Tax: $4,811 (2025)Community: Jesups LandingTownhouse
Taxes:$4,811
Remarks: Welcome to this beautifully updated 3-bedroom, 2.5-bath end-unit townhome in the desirable Jesups Landing community of Winter Springs! Recent updates include new flooring, new exterior paint and a new roof creating a fresh, modern feel. The thoughtfully designed layout features generous living and dining areas that flow seamlessly into the kitchen, making entertaining easy. Upstairs, you'll find all three bedrooms, the laundry area, and a gorgeous patio, in addition to a spacious primary suite that offers a relaxing retreat with ample closet space and an en-suite bath. One of the home's most attractive features is its unbeatable location adjacent to Central Winds Park, where residents can enjoy pickleball courts, a baseball diamond, basketball court, a fishing pier, nature trail, picnic facilities and pavilion, a soccer field, playground, volleyball cours, NEW PICKLEBALL COURTS AND A GREAT DOG PARK in additiona to year-round community events. Families will also appreciate the proximity to highly rated Seminole County schools, shopping, dining, and major commuter routes. Whether you're a first-time homebuyer, downsizing, or seeking a low-maintenance lifestyle in one of Winter Springs' most desirable locations, this beautifully maintained townhome is a must-see!
Listing is courtesy of: KELLER WILLIAMS CLASSIC (407-292-5400)
Listing Agent: Michelle Richardson (321-299-8490)
101 PARTRIDGE CIR, WINTER SPRINGS, FL 32708
$625,00043 Days on yellowkey MLS ID: O6407799
1 Days Off yellowkey (back on 6/25/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2181 Built: 1974 Tax: $2,635 (2025)Community: Winter Springs Unit 4Spa: NoSingle Family
Taxes:$2,635
Remarks: Under contract-accepting backup offers. Situated on a spacious 0.38-acre lot in the highly sought-after Tuscawilla community of Winter Springs, this beautifully updated pool home combines thoughtful upgrades, flexible living space, and inviting outdoor areas with the added benefit of NO HOA. Inside, the remodeled kitchen opens to the main living spaces and showcases updated cabinetry, stone countertops, tile backsplash, stainless steel appliances, recessed lighting, and a custom range hood. A newly added pantry and bar area complement the open kitchen design. The split-bedroom layout offers added privacy, with the primary suite tucked away on one side of the home and the secondary bedrooms positioned on the opposite side. The primary suite also features a walk-in closet and versatile bonus space ideal for a home office, nursery, gym, or sitting area. Multiple living and flex spaces provide endless options for entertaining, working from home, or creating additional lounge and dining areas. Major updates include new Luxury Vinyl Plank flooring throughout, fresh interior and exterior paint, upgraded bathrooms, full home replumb and complete rewire (2026), new roof (2024), HVAC (2019), and water heater (2018). Step outside to enjoy an oversized resurfaced and retiled screened pool, expansive lanai and deck space, fully fenced backyard, and a newly paved private front courtyard designed for relaxing and gathering outdoors. Located near Tuscawilla Country Club, Central Winds Park, shopping, dining, Publix, Winter Springs High School, and SR-417, this home offers the perfect balance of privacy, convenience, and the established charm Tuscawilla is known for.
Listing Agent: Belinda Gonzales (321-277-8994)
498 GREEN SPRING CIR, WINTER SPRINGS, FL 32708
$249,0007 Days on yellowkey MLS ID: O6418425
Bed: 2 Bath: 1.5 Liv Area Sq Ft: 1363 Built: 1987Monthly Fee: $190 Tax: $1,639 (2025)Community: Mount Greenwood Unit 4 OfTownhouse
Taxes:$1,639
Elementary School: Winter Springs Elementary
Remarks: Welcome to 498 Green Spring Circle in the desirable Mount Greenwood community of Winter Springs! This beautifully maintained 2 bedroom, 1.5 bath end-unit townhome offers peaceful pond views, low-maintenance living, and access to top-rated Seminole County schools. Step inside to an open and inviting floor plan featuring ceramic tile flooring throughout the main living areas and fresh interior paint. The spacious living and dining areas flow seamlessly to the oversized screened patio with paver flooring, creating the perfect space to relax, entertain, or enjoy your morning coffee while overlooking the tranquil water and mature trees. The kitchen opens to the main living space, creating a bright and functional layout ideal for everyday living. Upstairs, you'll find two generously sized bedrooms with large closets and ample storage. An additional exterior storage closet off the patio provides even more convenience. Residents of Mount Greenwood enjoy a low HOA and outstanding community amenities, including a sparkling pool, tennis courts, playground, and scenic walking and biking trails. Ideally located just off SR 434 and minutes from Winter Springs Town Center, shopping, dining, parks, and major commuter routes. Whether you're a first-time homebuyer, downsizing, or searching for the perfect Florida retreat, this move-in-ready townhome offers comfort, convenience, and beautiful waterfront views. Don't miss this opportunity to enjoy the Florida lifestyle in one of Winter Springs' most desirable locations. Schedule your private showing today!
Listing is courtesy of: SUNDIAL REAL ESTATE LLC (407-601-2200)
Listing Agent: Nicole Van Treese (407-462-9050)
270 SAN GABRIEL ST, WINTER SPRINGS, FL 32708
$249,900226 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
Remarks: 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)
600 NORTHERN WAY #1608, WINTER SPRINGS, FL 32708
$272,000126 Days on yellowkey MLS ID: G5108558
REDUCED by $2,900 (1.1%) on 06/25/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1425 Built: 1981Monthly Fee: $373 Tax: $2,582 (2025)Community: Tuscany PlaceCondo
Taxes:$2,582
Remarks: Very motivated sellers! Condo in Tuskawilla’s Tuscany Place •Discover comfort and convenience in Winter Springs’ Tuskawilla neighborhood. Tuscany Place is a gated community with a private pool, near Trotwood Park, Cross Seminole Trail, and top-rated schools. •Double Balcony (length of condo) •Corner unit with pool view •Updated kitchen w/stainless steel appliances •New water heater (2023) •New roof (2023) •New AC (2016) •Washer/dryer (2026) •Primary bedroom with walk-in closet, en-suite, and balcony access •Split floor plan for privacy. Seize this opportunity to own a beautifully updated condo in a prime location! FHA Approved Condo complex.
Listing is courtesy of: WORTH CLARK REALTY (352-988-7777)
Listing Agent: Kelly Boulton (407-906-8348)
577 WALDEN CT, WINTER SPRINGS, FL 32708
$399,00018 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
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)
149 CHERRY CREEK CIR, WINTER SPRINGS, FL 32708
$1,130,0002 Days on yellowkey MLS ID: O6414847
Bed: 5 Bath: 5.0 Gar: 3 Liv Area Sq Ft: 4001 Built: 1996Monthly Fee: $123 Tax: $12,825 (2025)Community: Reserve At Tuscawilla Ph 1 TheSpa: YesSingle Family
Taxes:$12,825
Remarks: Virtually Staged. Privately set within the exclusive gated community of Tuscawilla Reserve, this stunning custom estate delivers over 4,000 square feet of light-filled, designer-inspired living centered around a spectacular kitchen and family room that truly defines the home. With 5 bedrooms, 5 full baths, plus a private office/bonus room, this residence offers exceptional versatility for today’s lifestyle. Sleek wood flooring flows seamlessly throughout the main living areas, complementing the home’s open, modern design. The impressive kitchen and family room feature soaring two-story ceilings and expansive windows, framing views of the outdoors and pool area while filling the space with natural light—creating an inviting setting for both everyday living and elevated entertaining.The chef’s kitchen is a true centerpiece, anchored by JennAir appliances, including double ovens, convection oven, and microwave combo, along with a massive granite-topped island—all coming together to create a stunning focal point that anchors the kitchen and family room. Custom details further enhance the design, including a built-in buffet with integrated wine refrigerator and an oversized walk-in pantry. The thoughtfully designed floor plan offers incredible flexibility, including an upstairs retreat featuring an additional bedroom, full bath, and expansive flex space that can easily function as a media room, playroom, or second private office.Step outside to your private backyard oasis featuring a sparkling pool and spa with a new heater, surrounded by mature landscaping and a fully fenced yard, offering both openness and privacy. Additional highlights include a 3-car side-entry garage, whole house water softener and expansive living areas that support a variety of lifestyle needs. Ideally located near the Seminole Trail and just minutes from Tuscawilla Country Club, residents enjoy golf, tennis, swimming, and vibrant social amenities. Zoned for highly regarded Seminole County schools, this home offers both lifestyle and long-term value. Golf carts are a popular mode of transportation within the community, adding to the charm and convenience. A seamless blend of modern design, natural light, and elevated living—this is Tuscawilla Reserve at its finest. Schedule your private showing today and experience this exceptional home in person.
Listing is courtesy of: COLDWELL BANKER REALTY (407-696-8000)
Listing Agent: Susan Williams (407-696-8000)
1107 WINTER SPRINGS BLVD, WINTER SPRINGS, FL 32708
$570,0009 Days on yellowkey MLS ID: O6417844
0 Days Off yellowkey (back on 6/24/2026)
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: Under contract-accepting backup offers. 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 Agent: Laura Leigh Wood (407-310-4908)
1055 CHESTERFIELD CIR, WINTER SPRINGS, FL 32708
$499,90022 Days on yellowkey MLS ID: O6413841
REDUCED by $10,100 (2.0%) on 06/23/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1665 Built: 1984Monthly Fee: $25 Tax: $5,048 (2025)Community: AmherstSpa: NoSingle Family
Taxes:$5,048
Remarks: Beautiful pool home located in the highly desirable Amherst community of Winter Springs! Situated on an oversized .34-acre lot, this well-maintained 3-bedroom, 2-bath home offers a spacious split-bedroom floor plan with vaulted ceilings, abundant natural light, and a cozy wood-burning fireplace in the oversized family room. Updated bathrooms and ceramic wood looking flooring in main living areas. The screened with an large pool and covered lanai create the perfect setting for year-round outdoor living and entertaining, and no rear neighbors for privacy. The primary suite features a walk-in closet and spacious bath with dual sinks newly remodeled. Additional highlights include a 2-car garage, irrigation system, rain gutters, public utilities, and low annual HOA dues. New Roof (2025), New Water Heater & A/C (2024). Conveniently located near top-rated Seminole County schools, parks, shopping, dining, major roadways, and the 417.
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Brittany Zapitz (321-230-4445)
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