Location: Winter Springs
Do Not Show Listings
1055 CHESTERFIELD CIR, WINTER SPRINGS, FL 32708
$499,90019 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
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$5,048
Elementary School: Rainbow Elementary
High School: Winter Springs High
Tax Year: 2025
Middle School: Indian Trails Middle
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)
510 SONATA CT, WINTER SPRINGS, FL 32708
$799,90056 Days on yellowkey MLS ID: O6402358
REDUCED by $25,000 (3.0%) on 06/23/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2381 Built: 1999Monthly Fee: $184 Tax: $6,415 (2024)Community: Seville ChaseSingle Family
Taxes:$6,415
Elementary School: Sterling Park Elementary
Tax Year: 2024
Middle School: South Seminole Middle
Remarks: SELLER MOTIVATED!! Make OFFER! Freshly Painted Exterior and Interior! Walk in and feel instantly at home! This beautifully renovated 4-bedroom, 3-bathroom triple-split pool home sits on nearly half an acre in the gated community of Seville Chase and is completely move-in ready. Step inside to soaring ceilings and a thoughtfully designed open layout that still offers comfortable separation of space. You’ll immediately notice the stunning porcelain tile floors and a high-end, fully updated kitchen featuring custom cabinetry, pull-out shelving, soft-close drawers and doors, and sleek quartz countertops—perfect for both everyday living and entertaining. Recent upgrades provide peace of mind, including: New tile roof (2025) with a 50-year warranty AC replaced in 2022 Water softener (2022) New pool pump Out back, enjoy your own private retreat with a screened pool overlooking a serene conservation area with a lake—ideal for relaxing or even bass fishing. The expansive yard also features mature fruit trees, including avocado, mango, lemon, and a cherry bush. All of this is conveniently located near Winter Springs, major highways (417 & 434), UCF, Seminole State College, and major employers like Lockheed Martin and Siemens. This home truly has it all—style, space, and location. Schedule your private showing today before it’s gone!
Listing is courtesy of: VOSS REALTY INC (407-456-0777)
Listing Agent: Lindsay Kaye Voss (407-456-0777)
662 SARANAC DR, WINTER SPRINGS, FL 32708
$643,10018 Days on yellowkey MLS ID: O6413437
0 Days Off yellowkey (back on 6/23/2026)
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2180 Built: 1986Monthly Fee: $6 Tax: $3,686 (2025)Community: Tuscawilla Unit 14ASingle Family
Taxes:$3,686
Elementary School: None
High School: None
Middle School: None
Remarks: Under contract-accepting backup offers. Welcome to this beautiful 4-bedroom, 2-bath pool home nestled in the highly sought-after Tuscawilla community of Winter Springs. Situated on an oversized .34-acre lot, this well-maintained residence offers more than 2,180 square feet of comfortable living space with a spacious, open floor plan designed for both everyday living and entertaining. Enjoy cozy evenings by the fireplace, relax by the private pool, and appreciate the convenience of a two-car garage. The property is surrounded by mature trees and lush landscaping, creating a peaceful and inviting setting. Ideally located near top-rated Seminole County schools, parks, shopping, dining, and major roadways, this home also offers close proximity to Trotwood Park and Tuscawilla Country Club, with easy access to Oviedo, Winter Park, and downtown Orlando.
Listing is courtesy of: WATSON REALTY CORP (407-332-6000)
Listing Agent: Jim Ruddy (407-718-0984)
1389 PONCE DE LEON BLVD, WINTER SPRINGS, FL 32708
$535,000Listed 06/23/2026 1:20PM MLS ID: O6413725
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2056 Built: 1980Monthly Fee: $32 Tax: $2,474 (2025)Community: Sunrise Unit 2-ASpa: NoSingle Family
Taxes:$2,474
High School: Oviedo High
Remarks: LOCATION, LOCATION, LOCATION! Beautifully remodeled home in the heart of Winter Springs, conveniently located near shopping, dining, banking, fresh market , Publix, Oviedo Mall, YMCA, and major roadways (417 & 408). This spacious residence features 4 bedrooms, 2 full bathrooms, 2 car garage and an open functional floor plan ideal for family living and entertaining, two large separate rooms :a dining room and a living room Recent updates include a water heater (2026)new porch (2026), A/C (2017), and roof (2017). The oversized backyard is shaded by magnificent historic oak trees and includes a utility/workshop, building gym, offering endless possibilities. The community features a playground, basketball court, and park, with an additional neighborhood park conveniently located right next door and the HOA fee is paid anually and is exceptionally affordable.
Listing is courtesy of: LA ROSA REALTY PREMIER LLC (407-401-9076)
Listing Agent: Gloria Florez (407-561-3046)
240 N DEVON AVE, WINTER SPRINGS, FL 32708
$375,00011 Days on yellowkey MLS ID: O6416300
REDUCED by $9,900 (2.6%) on 06/23/2026
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1238 Built: 1958 Tax: $476 (2025)Community: North OrlandoSingle Family
Taxes:$476
Elementary School: Highlands Elementary
Remarks: Welcome to 240 N Devon Avenue, a fully updated three-bedroom, two-bath home in the heart of Winter Springs, where the renovation has been done for you and the only thing left to do is move in. Inside, the open-concept main living area is anchored by a stunning stone fireplace with built-in shelving and crown molding throughout. The kitchen has been beautifully upgraded with custom wood cabinetry, quartz countertops, tile backsplash, and stainless steel appliances. Both bathrooms are finished with custom tile showers and the same level of detail you'll find throughout the home. Light, bright, and timeless. Beyond the finishes, the major systems have all been addressed: metal roof installed 2024, full HVAC replacement in 2022 (inside and outside units), whole-home repipe in 2022, updated electrical, and a gas tankless water heater. Nothing left to update or worry about! A 16x16 sunroom with AC extends the living space year-round, opening to a backyard built for play and entertaining. A putting green, paver patio, and pergola sit behind an eight-foot privacy fence, surrounded by low-maintenance xeriscaping that means weekends free from mowing. A detached 20x20 garage and workshop offers serious storage, project space, or whatever your hobby calls for. Ample off-street parking handles guests, trailers, RVs, or boats. Step out the front door and you are one block from the community park with its ocean-inspired playground, splash pad, pond, and walking trails. The Cross Seminole Trail is also nearby, putting miles of paved trail at your fingertips. Quick access to both I-4 and the 417 makes commuting a breeze, and you are surrounded by top-rated Seminole County schools. 240 N Devon is a rare combination of move-in-ready renovation, generous outdoor living, freedom from HOA restrictions, and a central Winter Springs location with parks and trails just steps from your door. Call today for your private showing!
Listing is courtesy of: REAL BROKER, LLC (855-450-0442)
Listing Agent: Lindsey Hudson (865-712-8452)
1335 SAN FELIPE CT, WINTER SPRINGS, FL 32708
$450,0006 Days on yellowkey MLS ID: O6417601
1 Days Off yellowkey (back on 6/23/2026)
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1571 Built: 1987 Tax: $5,051 (2025)Community: Sunrise Village Unit 6Spa: YesSingle Family
Taxes:$5,051
Remarks: Under contract-accepting backup offers. Welcome home to this move-in-ready 4-bedroom, 2-bathroom pool home with a 2-car garage, situated on a quiet cul-de-sac with no through traffic. This solid-block-construction home offers an open floor plan and exceptional curb appeal, featuring fresh exterior paint, updated stucco, professional landscaping, and a brand-new roof installed in June 2026. Inside, you'll find fresh interior paint, updated lighting and ceiling fans throughout, and a beautifully renovated kitchen and bathrooms. The spacious kitchen opens to the main living areas and features new stainless steel appliances, making it ideal for both everyday living and entertaining. The living room is anchored by a stunning fireplace that has been transformed with a custom stucco finish, elegant marble accents, and a floating mantel. Major mechanical updates include a 2022 AC system, a brand-new 2026 water heater, and updated plumbing with the home fully repiped, providing added value and peace of mind for years to come. Step outside to enjoy your private screened pool area and fully fenced backyard with no rear neighbors, offering exceptional privacy and the perfect space for relaxation, pets, and outdoor gatherings. With block construction, a brand-new roof, and a location outside of a flood zone, this home offers the potential for lower insurance costs and added peace of mind. For additional buyer confidence, a 4-Point Inspection, Wind Mitigation Report, Wood Destroying Organism (WDO) Report, and Energy Report are attached to the MLS for review. Conveniently located with a low HOA of just $345 per year, this home combines style, comfort, and value in one complete package.
Listing is courtesy of: NEXTDWELL (855-432-1123)
Listing Agent: Austin Cummings (407-242-8891)
749 WILLOW RUN LN, WINTER SPRINGS, FL 32708
$620,00040 Days on yellowkey MLS ID: O6407791
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2456 Built: 1986Monthly Fee: $17 Tax: $5,752 (2025)Community: Willow RunSpa: NoSingle Family
Taxes:$5,752
Elementary School: Red Bug Elementary
High School: Lake Howell High
Middle School: Tuskawilla Middle
Remarks: Spacious and well-maintained 4-bedroom, 3-bath home in a highly sought after neighborhood! The owner's suite includes a walk-in closet and granite vanity, while the additional bedrooms are bright and comfortable. The family room has soaring ceilings, a gorgeous brick wood-burning fireplace and sliding glass doors overlooking the private back yard. The kitchen features granite countertops and an eating area with easy access to the living spaces. Relax in the sparkling HEATED pool while you overlook the fenced-in back yard with plenty of room for outdoor activities and pavers that leads to a built-in fire pit- a perfect place to gather family and friends! Centrally located in Tuskawilla/Redbug area with "A" rated Seminole County Schools, restaurants, Marketplace Mall and close to 417 toll road. Minutes to Orlando International Airport & downtown. Note from the owners - We have truly loved living in this neighborhood and being part of such a warm, welcoming community. The neighbors are friendly, caring, and always look out for one another. Some of our favorite memories include trick-or-treating together on Halloween, the beautiful luminaries at Christmas, and the many neighborhood parties and gatherings throughout the year. It’s a special neighborhood filled with connection and wonderful neighbors . ROOF 2024 POOL PUMP 2025
Listing is courtesy of: COLDWELL BANKER REALTY (407-647-1211)
Listing Agent: Tasha Blomenkamp (407-403-3316)
629 RYAN CT, WINTER SPRINGS, FL 32708
$475,00046 Days on yellowkey MLS ID: O6396980
REDUCED by $4,000 (0.8%) on 06/23/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1857 Built: 2004Monthly Fee: $35 Tax: $1,899 (2024)Community: The Highlands Sections Seven & EightSingle Family
Taxes:$1,899
Remarks: Beautifully maintained 3-bedroom, 2-bathroom home located in the highly sought-after Highlands community in Winter Springs, FL. Real hardwood floors flow through the main living areas, adding warmth and timeless appeal. The spacious kitchen features elegant stone countertops, ample cabinetry, and plenty of room for cooking and entertaining. The primary suite serves as a relaxing retreat with an en suite bathroom that includes a dual sink vanity, a large soaking tub, and a walk-in closet. The split-bedroom layout offers added privacy, while the two additional bedrooms provide flexibility for guests, family, or a home office. Step outside to enjoy the oversized lot, offering plenty of space for outdoor living and activities. The screened-in lanai is perfect for enjoying Florida’s weather year-round, whether you're relaxing or hosting guests. A 2-car garage adds convenience and extra storage. Residents also enjoy access to a community pool, as well as tennis courts, pickleball courts, and scenic nature trails, perfect for an active and social lifestyle. Ideally located in Winter Springs, this home is close to top-rated Seminole County schools, beautiful parks and trails, shopping and dining options, and provides easy access to major roadways for commuting to Orlando and surrounding areas. Enjoy a balance of peaceful suburban living with everyday conveniences just minutes away.
Listing is courtesy of: SOTERA LIVING (407-725-9660)
Listing Agent: Lisa D'Orazio Llc (813-493-5383)
363 TWELVE OAKS DR, WINTER SPRINGS, FL 32708
$537,00087 Days on yellowkey MLS ID: O6394390
REDUCED by $42,000 (7.3%) on 06/23/2026
Bed: 5 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 3408 Built: 2000Monthly Fee: $48 Tax: $4,927 (2025)Community: Winding HollowSingle Family
Taxes:$4,927
Remarks: Outstanding 5-bedroom, 3-bathroom home with a Screened Pool and a beautiful Water view. New roof installed on 10/5/2018.Whole house exterior was repainted (including pool deck) in February/March 2020.Open concept, 2 story with a lot of natural light. Large kitchen overlooks the Spacious Family room. Spacious Great room, Living & Dining combo! Plus a Grand-sized Bonus room upstairs for the family to all enjoy! Tall Ceilings. 3-car garage! Ready for quick occupancy! Great Schools! Hurry! Won't Last!
Listing is courtesy of: KELLER WILLIAMS HERITAGE REALTY (407-862-9700)
Listing Agent: Caroline Moffitt Lawton (407-670-9797)
947 GLEN ABBEY CIR, WINTER SPRINGS, FL 32708
$525,000Listed 06/22/2026 4:04PM MLS ID: O6418792
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2416 Built: 1997Monthly Fee: $128 Tax: $2,980 (2025)Community: Greenbriar Sub Ph 2Spa: NoSingle Family
Taxes:$2,980
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)
143 HAYES RD, WINTER SPRINGS, FL 32708
$479,00039 Days on yellowkey MLS ID: O6407546
REDUCED by $10,000 (2.0%) on 05/27/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1649 Built: 1983 Tax: $1,782 (2024)Community: North Orlando Ranches Sec 02ASingle Family
Taxes:$1,782
Remarks: Welcome to 143 Hayes Rd, Winter Springs a rare opportunity to own a beautifully renovated home in one of the area’s most exclusive and sought-after locations. Situated on a huge corner lot surrounded by mature trees, this property offers privacy, space, and the freedom of no HOA with low property taxes. This home has been recently updated and is truly move-in ready, featuring a 2017 roof, brand-new AC system, fresh interior and exterior paint, new carpet, and a newly finished driveway. Every detail has been thoughtfully refreshed to provide comfort and peace of mind for the next owner. Step outside and imagine yourself enjoying your own private pool while being surrounded by peaceful natural scenery — the perfect setting for relaxing weekends, entertaining guests, or simply enjoying Florida living at its best. Conveniently located near top-rated schools, shopping, dining, and major highways while still offering the tranquility of a private retreat. Homes like this in Winter Springs rarely hit the market!
Listing is courtesy of: EMPIRE NETWORK REALTY (407-440-3798)
Listing Agent: Karla De La Cruz (407-775-0268)
71 TARPON CIR, WINTER SPRINGS, FL 32708
$525,0003 Days on yellowkey MLS ID: O6418735
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2637 Built: 1973Monthly Fee: $3 Tax: $2,415 (2025)Community: Winter Spgs Unit 4Single Family
Taxes:$2,415
Elementary School: Keeth Elementary
Remarks: Welcome to this stunning 4-bedroom executive residence nestled in the highly sought-after Tuscawilla Country Club golf community, where charm, comfort, and convenience come together with NO HOA restrictions. Showcasing a distinctive Mediterranean-inspired design, this home features elegant wrought iron accents and a welcoming private courtyard that creates exceptional curb appeal. Inside, you’ll find spacious living areas and generously sized bedrooms throughout. The expansive owner’s suite serves as a relaxing retreat, complete with a walk-in closet and an updated en-suite bath. An inside laundry room adds everyday convenience, while the thoughtful floor plan provides plenty of room for both entertaining and daily living. Step outside to your own backyard oasis featuring a large sparkling pool, perfect for enjoying Florida’s year-round sunshine, hosting gatherings, or simply unwinding in a private setting. Ideally located in Winter Springs, this home offers easy access to the University of Central Florida, Central Winds Park, Oviedo Mall, top-rated shopping and dining, and major roadways including SR 434 and SR 417. Enjoy the tranquility of a golf community setting while remaining close to everything Central Florida has to explore. Don’t miss this rare opportunity to own a beautiful pool home in one of Winter Springs’ most desirable communities!
Listing is courtesy of: CHERRY'S FOCUSED IN REALTY LLC (386-205-9438)
Listing Agent: Patrick Cherry (386-205-9438)
170 WOODED VINE DR, WINTER SPRINGS, FL 32708
$649,9005 Days on yellowkey MLS ID: O6418077
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2470 Built: 2019Monthly Fee: $137 Tax: $8,571 (2025)Community: Tuskawilla Crossings Ph 1Single Family
Taxes:$8,571
Remarks: Built in 2019, this thoughtfully designed floor plan is ideal for multigenerational living, extended stays for guests, remote professionals, or anyone seeking additional privacy and versatility. The main residence encompasses 3 bedrooms, 2.5 bathrooms, and a dedicated office/flex room, while a separate 1 bedroom, 1 bath suite above the garage creates a private retreat complete with its own entrance. The main level showcases an open concept design where the family room flows seamlessly into the spacious eat in kitchen. The kitchen is beautifully appointed with 42" cabinetry, quartz countertops, upgraded stainless steel appliances, and a generous walk in pantry. A versatile office/flex room offers endless possibilities as a home office, playroom, fitness area, study space, or hobby room. Upstairs, the primary bedroom serves as a comfortable escape, featuring a walk-in closet, French doors that lead to a private balcony and a spacious en suite bath with dual vanities, a garden tub, and separate walk-in shower. Two additional bedrooms and a full bath with dual sinks complete the second floor of the main residence. One of the home's most desirable and unique features is the private in-law suite above the garage. Measuring approximately 19' x 16', this separate living space includes its own full bathroom, dedicated HVAC system, built-in cabinetry and private entrance, making it ideal for in-laws, guests, college aged children, a home business, or additional flex space. The remainder of the home highlights a front porch, a covered rear porch, a brick paved driveway, oversized parking area, two car garage, whole home Gigabit Wi Fi, fiber internet, smart locks, smart lighting and a 60 amp outlet ready for electric vehicle charging. Residents of Tuskawilla Crossings enjoy resort style amenities including a community pool with cabanas, playground, walking trails, multiple dog parks, and direct access to the Seminole County Trail. Ideally located just minutes from Winter Springs Town Center, shopping, dining, top rated Seminole County schools, and SR 417.
Listing is courtesy of: DIBS REALTY, LLC (407-537-2232)
Listing Agent: Ashley Swindell (407-687-5481)
568 BUCKHORN DR, WINTER SPRINGS, FL 32708
$475,00015 Days on yellowkey MLS ID: O6413584
REDUCED by $10,000 (2.1%) on 06/22/2026
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2076 Built: 2012Monthly Fee: $167 Tax: $3,280 (2025)Community: Winter Spgs Village Ph 1Single Family
Taxes:$3,280
Remarks: This is one of the few 4 bedroom Bungalows built in sought after Winter Springs Village and it is situated on a premium lot with a manicured greenspace in front and a pond view with a lighted fountain in the rear. Enjoy sitting on the front porch in this quiet and serene setting with no through traffic. Recently painted interior and trim along with brand new carpet upstairs. This turn key property has lower utility bills due to many energy efficient features & design with Low E Vinyl dual pane double tint windows, foam insulated attic, energy star appliances & AC replaced in 2019. This 4 bedroom floor plan has a spacious loft area & 2.5 bathrooms, separate dining room, living room that is open to the kitchen & a full 2 car garage with extra ceiling racks for additional storage. The HOA includes lawn & irrigation maintenance, community pool/clubhouse, playground & secure mailboxes. In walking distance to the Seminole Trail, Winter Springs Town Center, restaurants & Publix. Easy access to 417 for a commute downtown, University of Central Florida, Orlando International Airport or the beaches. Highly rated Seminole County Schools. Bring your most discriminating buyers as this home will not disappoint!
Listing is courtesy of: KELLER WILLIAMS ADVANTAGE REALTY (407-977-7600)
Listing Agent: P. Darlene Brown, Pa (407-719-4420)
109 CHERRY CREEK CIR, WINTER SPRINGS, FL 32708
$1,090,00049 Days on yellowkey MLS ID: O6404923
REDUCED by $60,000 (5.2%) on 05/28/2026
Bed: 5 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 3440 Built: 1996Monthly Fee: $123 Tax: $7,388 (2024)Community: Reserve At Tuscawilla Ph 1 TheSpa: YesSingle Family
Taxes:$7,388
Remarks: Virtually Staged. Welcome to 109 Cherry Creek Circle, a custom Von Jacobs-built residence located in the gated Reserve at Tuscawilla. Set on a beautifully landscaped 0.59-acre homesite, this 5-bedroom, 4-bath pool home offers the space, craftsmanship, and outdoor lifestyle that are increasingly hard to find in Winter Springs. Designed with the character and quality of a custom-built estate, the home features generous room sizes, volume ceilings, wood flooring, crown molding, detailed millwork, a gas fireplace, and a thoughtful floor plan that offers both comfortable everyday living and excellent entertaining space. The main-level primary suite provides privacy and convenience, while the additional bedrooms offer flexibility for guests, office space, fitness, hobbies, or multigenerational needs. The heart of the home is the outdoor living area. A screened, heated pool and spa, covered lanai, summer kitchen with Viking grill and Texas smoker, and a fire pit lounge accented with Tennessee River Rock create a true resort-style setting for relaxing, gathering, and enjoying the Florida lifestyle year-round. This home has been lovingly maintained and offers an incredible opportunity for a buyer who appreciates custom construction, a premier gated Tuscawilla location, and the chance to make thoughtful cosmetic updates over time. With over half an acre, a 3-car side-entry garage, mature landscaping, and a private outdoor retreat, 109 Cherry Creek Circle delivers the foundation, setting, and lifestyle buyers are searching for. Conveniently located near Tuscawilla Country Club, parks, trails, shopping, dining, Seminole County schools, and major Central Florida roadways, this property combines privacy, space, and everyday convenience in one of Winter Springs’ most established communities.
Listing is courtesy of: COLDWELL BANKER REALTY (407-696-8000)
Listing Agent: Kara Lushear (321-663-5550)
314 SAN GABRIEL ST, WINTER SPRINGS, FL 32708
$279,990256 Days on yellowkey MLS ID: O6350799
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1091 Built: 1992Monthly Fee: $127 Tax: $2,209 (2024)Community: DeersongSpa: NoSingle Family
Taxes:$2,209
Remarks: **BUYER INCENTIVE AVAILABLE!! Preferred Lender is offering a COMPLIMENTARY TEMPORARY RATE BUY DOWN for qualified buyers on new loan locks completed on or before 6/30/26!!** Seller offering $2,500.00 toward Buyers Closing costs with an acceptable offer. Welcome to your dream home, perfectly positioned for easy commuting in Central Florida. This 3 bedroom, 2 full baths, split bedroom plan and screen enclosed side porch home boasts upgrades that make it shine brighter than most — capturing attention with these enhancements: Water Heater (Installed 03/2026), Roof (installed 2021) replaced in recent years for added peace of mind, insurance savings, and easier loan approval, Air Conditioning (2022) allowing you to stay comfortable year-round with a modern, energy-efficient system,Total Re-piping (2021) ensures smooth water flow and reduces future maintenance needs, Dishwasher (2021) for easy clean up. Stove & Refrigerator (2022) updated appliances for a sleek, functional kitchen, ready for your culinary adventures, Extra Kitchen Cabinets (2022) for extra space for all your kitchen storage needs, Luxury Vinyl in Bedrooms 2 & 3 provide a stylish, durable flooring that’s easy to maintain, Interior Paint (2021) fresh and neutral color walls throughout the home, Water-softener allows you to enjoy softer water for bathing, reduced hard water scale buildup, extended appliance life, and easier cleaning. This home is ideal for efficient daily living. Recent improvements mean less upkeep and more relaxation for you as well as the low HOA fees cover front and right side mowing, maintenance on the fence and shed, and a sparkling community pool — giving you more time to enjoy life! Newer systems and structural elements help lower insurance premiums and provide added security of your home. Close to local parks, Seminole County "A" Rated Schools, main shopping areas, major roadways for easy commuting. and exciting attractions and destinations for all ages. Perfect for every kind of buyer: seasonal residents can enjoy locking up and leaving, not having to worry about maintenance, collegiate students, checks all the boxes for first time home-buyers, empty-nesters downsizing, or anyone looking for comfortable carefree living.
Listing is courtesy of: WEICHERT REALTORS HALLMARK PRO (407-585-0500)
Listing Agent: Linda Bain (407-474-5269)
934 TORREY PINE DR, WINTER SPRINGS, FL 32708
$499,000261 Days on yellowkey MLS ID: O6349893
REDUCED by $15,000 (2.9%) on 06/10/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1678 Built: 2000Monthly Fee: $126 Tax: $2,280 (2024)Community: Greenbriar Sub Ph 2Single Family
Taxes:$2,280
Remarks: Virtually Staged. Beautifully remodeled golf course home in the highly desirable Tuscawilla community! This move-in ready residence has been extensively updated with a fresh modern design throughout, including all new flooring, new interior paint, new granite countertops, custom designer backsplash, stainless steel appliances, and an updated interior lighting package. The spacious primary suite features a fully renovated bath with a new granite vanity, updated hardware and lighting, and a completely redesigned custom glass-enclosed walk-in shower. The guest bath has also been tastefully updated with a new vanity. Enjoy peaceful golf course living with scenic surroundings and a spacious screened patio perfect for relaxing or entertaining. The roof has been recently inspected and is reported to be in fantastic condition, providing added peace of mind for the next owner. Conveniently located near top-rated Seminole County schools, parks, shopping, dining, and major roadways, this is an exceptional opportunity to own a beautifully updated home in one of Tuscawilla’s most sought-after golf course communities.
Listing is courtesy of: CENTURY 21 ALTON CLARK (407-636-4637)
Listing Agent: James Clark (407-575-7011)
1447 BIRD RD, WINTER SPRINGS, FL 32708
$2,625,000109 Days on yellowkey MLS ID: O6388126
REDUCED by $174,000 (6.2%) on 06/03/2026
Bed: 6 Bath: 5.0 Gar: 3 Liv Area Sq Ft: 6132 Built: 2026 Tax: $2,989 (2024)Community: Talis CrossingSingle Family
Taxes:$2,989
Remarks: Discover the pinnacle of secluded luxury in this brand-new, 8,000 SF estate, nestled in picturesque Winter Springs. From the moment you arrive, the custom glass French entry doors hint at the artistry within. Stepping into the grand foyer, you are greeted by statement marble and mosaic flooring that sets a tone of elegance, a design narrative that flows seamlessly throughout the home. Designed for both grand-scale entertaining and intimate daily life, the main living spaces are simply breathtaking. The great room soars with 16-foot ceilings and celestial windows, anchored by a stunning custom fireplace and bookcase display. A bank of 18-foot sliding glass doors dissolves the line between indoors and out, opening to a sprawling 1,125 SF covered patio. The chef’s kitchen is a masterpiece of form and function, featuring a 13-foot island, floor-to-ceiling cabinetry, a pet-feeding station, electric vehicle garage hookup, and a full suite of WiFi-enabled GE Cafe appliances, including a double wall oven and a 48-inch refrigerator. The home offers a versatile and luxurious layout for multi-generational living or visiting guests, highlighted by two distinct primary suites. One wing is dedicated to a private retreat with two walk-in closets, separate vanities, and a spa-inspired wet room with a freestanding tub and a four-port shower system. On the opposite side of the home, a second primary suite offers equal luxury with a massive walk-in closet and its own spa-like wet room, ensuring complete privacy for all. Beyond the main living areas, discover a wealth of flexible spaces tailored to a modern lifestyle. A dedicated movie theater or fitness center is pre-wired for the ultimate audio-visual experience, while two separate offices with storefront glass windows provide inspiring workspaces. A butler’s pantry/kitchen, wet bar with a beverage fridge, and a flexible flex room with a half-bath complete the impeccably designed interior. Outside, your private paradise awaits upon the spacious 1-acre parcel. The pavered pool deck surrounds a white quartz pool with a sun shelf and bubbler, all secured by a sleek black metal fence. Every detail has been considered, from the 150-gallon propane tank servicing the future summer kitchen and pool heater to the 4-zone HVAC, a commercial grade 50-year life-span TPO roof and two tankless water heaters for ultimate comfort. This is more than a home; it is a fully realized vision of eloquent Florida living.
Listing is courtesy of: MAVREALTY (727-314-3942)
Listing Agent: Robert Kirkwood, Iv (321-297-6489)
268 TAVESTOCK LOOP, WINTER SPRINGS, FL 32708
$557,90040 Days on yellowkey MLS ID: O6407307
REDUCED by $12,000 (2.1%) on 06/22/2026
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2415 Built: 2001Monthly Fee: $150 Tax: $4,293 (2025)Community: ParkstoneSingle Family
Taxes:$4,293
Elementary School: Layer Elementary
Remarks: New Price **268 Tavestock Loop, Winter Springs, FL 32708** Perfectly situated in the heart of Winter Springs, this stunning 4-bedroom, 2.5-bathroom home offers the ideal location with easy access to shopping, dining, theme parks, major roads, and the airport. Nestled within a desirable gated community, you'll enjoy peace of mind along with fantastic amenities including a community Lake Jess Up, pool, park, and 2 playground walking path, community benches. Step inside this beautiful two-story home and immediately notice the high ceilings that create a bright, open atmosphere throughout. Hard flooring runs seamlessly from room to room, giving the entire 2,883 square feet a clean, modern feel that is both stylish and easy to maintain. The kitchen is equipped with sleek stainless steel appliances, making it the perfect space to prepare meals and gather with family and friends. With four spacious bedrooms, there is plenty of room for everyone. The primary bedroom offers a comfortable retreat after a long day, while the additional bedrooms provide flexible space for family, guests, or a home office. Two full and half bathroom ensure convenience for the entire household. This move-in ready home means no waiting and no hassle. Simply unpack and start enjoying everything this wonderful property and community have for you. Whether you are relaxing by the community pool, taking the family to the playground, walking trails, Lake Jess Up or exploring all that Central Florida has in store, this home puts it all within reach. Don't miss your chance to make 268 Tavestock Loop your new home. Schedule your private showing today!
Listing is courtesy of: FUSILIER REALTY GROUP (407-476-0476)
Listing Agent: Zep Bholai-Lawrence (321-689-3467)
984 TURKEY HOLLOW CIR, WINTER SPRINGS, FL 32708
$410,00027 Days on yellowkey MLS ID: O6410083
0 Days Off yellowkey (back on 6/21/2026)
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1821 Built: 1985Monthly Fee: $3 Tax: $3,100 (2025)Community: Oak Forest Unit 4Single Family
Taxes:$3,100
Remarks: Under contract-accepting backup offers. Virtually Staged. A spacious 3-bedroom, 2-bathroom home located in the highly sought-after community of Oak Forest in Winter Springs. Known for its beautiful tree-lined streets, mature oak trees, and quiet suburban charm, this family-friendly neighborhood also offers access to top-rated schools and is conveniently located near popular restaurants, shopping, and everyday conveniences. Inside, this home features a versatile and functional floor plan with a spacious family room, separate living room, dining room, large kitchen, dedicated office space, and an indoor laundry room. The detached shed provides the perfect opportunity for extra storage, a workshop, or hobby space. Step outside to enjoy the private backyard complete with a fire pit — ideal for relaxing or entertaining guests. The garage has been split into an office and storage space but can be converted back into a two car garage. Major upgrades and improvements include an updated roof (2018), gutters(2018), HVAC system(2022), windows(2020), garage door(2020), hot water heater(2021), electrical panels(2023), and added insulation(2019). Additional features include an indoor electric fireplace (2022), and numerous updates throughout, offering peace of mind and move-in-ready convenience. Call today to schedule your private tour!
Listing is courtesy of: ALL REAL ESTATE & INVESTMENTS (407-917-8206)
Listing Agent: Kelsey Payton (407-718-2967)
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