Location: Winter Springs
Keyword(s): Indian Trails Middle
Keyword(s) Middle School: Indian Trails Middle
Do Not Show Listings
975 DYSON DR, WINTER SPRINGS, FL 32708
$879,000Listed 06/17/2026 12:39AM MLS ID: O6417467
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2191 Built: 1980 Tax: $6,089 (2025)Community: Winter Spgs Unit 3Single Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$6,089
Elementary School: Rainbow Elementary
High School: Winter Springs High
Tax Year: 2025
Middle School: Indian Trails Middle
Remarks: Nestled on nearly two private acres in coveted Old Tuskawilla, this one-of-a-kind custom estate offers a rare opportunity to enjoy space, privacy, and timeless character in one of Seminole County's most sought-after communities. Surrounded by majestic oak trees, the property feels like a private retreat while remaining just minutes from top-rated schools, parks, golf, dining, and shopping. A private driveway leads to the home's side-entry two-car garage and picturesque setting. Inside, 2,191 square feet of living space blends warmth and functionality. Solid cherry hardwood flooring flows throughout the main level, where you'll find the formal dining room, a spacious family room, two fireplaces, a breakfast nook, and a generously sized primary suite conveniently located on the first floor. Also on the main level is a flexible office space that could easily serve as a fourth bedroom with minimal modifications, offering added versatility for growing families or guests. Upstairs, two bedrooms feature large closets and share a renovated Jack-and-Jill bathroom. The second floor has been updated with luxury vinyl plank flooring. The screened porch provides the perfect place to enjoy morning coffee while overlooking the expansive backyard, offering endless possibilities for a custom pool, guest house, workshop, or simply enjoying the natural beauty of the property. Nature lovers will appreciate the trail located directly behind the property, providing access for walking, jogging, and exploring the outdoors. Major updates provide peace of mind, including a whole-house repipe (2022), a 10' x 12' storage shed added in 2025, a new roof (2026), and fresh exterior paint (2026). While the kitchen and primary suite present opportunities for cosmetic updates and personalization, the home's solid construction, exceptional lot, and desirable location create an incredible foundation for your vision. Properties with this much land, character, and potential rarely become available in Tuskawilla. Whether you're seeking room to spread out, a private estate setting, or the chance to create your forever home, this exceptional property offers a truly unique opportunity.
Listing is courtesy of: VAN DEN BERG REAL ESTATE GROUP (407-739-9970)
Listing Agent: Caroline Van Den Berg (407-739-9970)
1204 SWAN ST, WINTER SPRINGS, FL 32708
$624,0001 Day on yellowkey MLS ID: O6417440
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 3334 Built: 1973 Tax: $3,677 (2024)Community: Winter Spgs Unit 4Spa: YesSingle Family
Taxes:$3,677
Elementary School: Keeth Elementary
Tax Year: 2024
Remarks: Rare opportunity in the heart of Winter Springs! Situated on an expansive 0.72-acre lot with NO HOA, this unique 4-bedroom, 2.5-bath pool home offers endless potential for the buyer seeking space, privacy, and the chance to create something truly special. The property features a recently resurfaced pool, a fully fenced backyard, and an incredible outdoor setting designed for entertaining and enjoying Florida living. One of the standout features is the detached pizza kitchen gazebo, perfect for hosting family and friends, along with an additional outbuilding complete with A/C, power, and plumbing—ideal for a workshop, studio, home office, hobby space, or future guest accommodations. Mature landscaping and abundant outdoor space provide room for recreation, gardening, boats, RVs, and more. Inside, the home offers a functional layout with tremendous upside. While cosmetic updates could enhance the property's full potential, the major features, lot size, and unique amenities make this a rare find in Winter Springs. Whether you're looking for a personal residence, multi-generational living setup, or an investment opportunity, this property is ready for your vision.
Listing is courtesy of: EXIT REALTY PREMIER LEGACY (407-801-8219)
Listing Agent: Chandler Williams (407-702-3815)
114 STONE GABLE CIR, WINTER SPRINGS, FL 32708
$485,9001 Day on yellowkey MLS ID: O6417280
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1814 Built: 1998Monthly Fee: $50 Tax: $4,263 (2025)Community: Stone GableSingle Family
Taxes:$4,263
Elementary School: Layer Elementary
Remarks: Welcome to the desirable city of Winter Springs, where 114 Stone Gable Cir sits on a beautiful corner lot with peaceful pond views to the rear and side of the home. Just minutes from shopping, restaurants, theme parks, major roads, and the airport, this move-in ready residence puts convenience right at your fingertips. Inside, 1,814 square feet of bright living space welcomes you with high ceilings and an open floor plan that flows naturally from room to room. Hard flooring runs throughout, keeping upkeep easy while adding a clean, modern look. The kitchen is ready for everything from casual breakfasts to weekend gatherings, featuring sleek granite countertops and stainless steel appliances. This thoughtfully designed home offers three comfortable bedrooms and two full bathrooms. The smart split layout tucks the primary bedroom away on its own side for added privacy, creating a quiet retreat at the end of the day, while two additional bedrooms provide flexible space for family, guests, or a home office. The real showstopper waits out back. Step onto the screened-in porch and enjoy your own private pool, perfect for cooling off under the Florida sun or relaxing as you take in the serene water views. The corner-lot setting adds extra elbow room and a sense of openness rarely found. With its prime location, modern finishes, and resort-style outdoor living, this Winter Springs gem checks every box. Schedule your private showing today and make it yours before it's gone!
Listing is courtesy of: REAL BROKER, LLC (855-450-0442)
Listing Agent: Kathy Williams (407-230-7305)
1016 WALNUT CREEK CV, WINTER SPRINGS, FL 32708
$539,9001 Day on yellowkey MLS ID: O6414948
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2375 Built: 2003Monthly Fee: $150 Tax: $3,482 (2025)Community: Parkstone Unit 4Spa: NoSingle Family
Taxes:$3,482
Remarks: Welcome to this beautifully maintained 4-bedroom, 2.5-bath home nestled on a quiet cul-de-sac in the highly desirable gated community of Parkstone. From the moment you arrive, you'll appreciate the inviting curb appeal, fresh exterior paint, and the pride of ownership throughout. Step inside to discover a light and bright interior filled with airy, spacious living areas designed for both everyday comfort and effortless entertaining. Gorgeous luxury vinyl plank flooring flows throughout the main living spaces, while brand-new carpet adds warmth and comfort to the upstairs bedrooms. Entertaining is a breeze in the large dining room with easy access to the kitchen and family room. The heart of the home opens seamlessly to your private backyard retreat, featuring a sparkling saltwater pool, new sod, and a fully fenced yard that offers both privacy and space to relax, play, or entertain. Whether enjoying a morning coffee poolside or hosting weekend gatherings, this outdoor space is sure to impress. Soaring ceilings on the first floor add to the spacious feeling throughout. Step into the pristine primary suite located on the first floor as an added bonus! Primary bath with separate soaking tub, glass enclosed shower and dual sink vanity make this an owner's dream. Major updates provide peace of mind, including ROOF 2019, AC 2024, FRESHLY PAINTED INTERIOR 2021, HOT WATER HEATER 2021,transferable TERMITE BOND, NEW CARPETS in all bedrooms, NEWLY PAINTED POOL DECK and Taexx, an inovative built-in "tubes in the wall" pest control system .....what more could you ask for? One of the many perks of living in Parkstone is that the HOA takes care of lawn maintenance, giving you more time to enjoy the community and everything the area has to offer. Located just minutes from the popular Central Winds Park, you'll have easy access to festivals, sporting events, walking trails, and community activities year-round. You'll also love being close to Winter Springs Town Center, where shopping, dining, and everyday conveniences are just around the corner. This welcoming home offers the perfect blend of comfort, convenience, and lifestyle in one of Winter Springs' most sought-after gated communities.
Listing is courtesy of: RE/MAX TOWN & COUNTRY REALTY (407-695-2066)
Listing Agent: Colleen Kahl (407-630-0027)
1441 FOREST HILLS DR, WINTER SPRINGS, FL 32708
$420,0001 Day on yellowkey MLS ID: O6413957
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1731 Built: 1985Monthly Fee: $90 Tax: $2,546 (2025)Community: Wedgewood Tennis VillasSingle Family
Taxes:$2,546
Remarks: Welcome to this beautifully maintained and updated 3 bedroom, 2 bath home with a 2-car garage, ideally situated in the highly desirable Tuscawilla community of Winter Springs. Offering a combination of modern updates, timeless character and serene waterfront views, this move in ready home is a rear find. Step inside to discover an inviting floor plan, featuring ceramic tile and laminate flooring throughout, providing both style and easy maintenance. The updated kitchen is designed for everyday living and entertaining, complete with modern cabinetry, stainless steel appliances, granite countertops, with a black side by side refrigerator, skylight that fills the space with natural light and a built-in wine rack for added charm. The spacious family room serves as the heart of the home, highlighted by a striking brick wood burning fireplace and elegant exposed wood beams that adds warmth and architectural character. Sliding glass doors create a seamless connection between the indoor living spaces and the outdoors while framing beautiful views of the pond. Relax and unwind in the screened in porch overlooking the tranquil water, where you can enjoy peaceful mornings, evening sunsets and the beauty of Florida's natural surroundings. The primary suite and additional bedrooms offer comfortable living spaces, with sliding glass door access providing abundant natural light and picturesque views. The home also offers valuable peace of mind with major updates already completed, including a new roof installed in 2022 and a new HVAC system installed in 2021. Located in the sought after Tuscawilla community, residents enjoy convenient access to parks, walking trails, golf, tennis facilities, shopping, dining, and top rated Seminole County schools. Whether you are looking for your forever home or a peaceful retreat, this waterfront gem delivers comfort, convenience and lasting value. Don't miss your opportunity to own this beautifully updated pond-view home in one of Winter Springs' most desirable neighborhood.
Listing is courtesy of: KELLER WILLIAMS ADVANTAGE III (407-207-0825)
Listing Agent: Karen Khairullah-Wallace (407-256-3465)
1406 BLUMBERG BLVD, WINTER SPRINGS, FL 32708
$425,00030 Days on yellowkey MLS ID: O6408695
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)
161 BEAR SPRINGS DR, WINTER SPRINGS, FL 32708
$444,990105 Days on yellowkey MLS ID: O6386458
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
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)
173 BEAR SPRINGS DR, WINTER SPRINGS, FL 32708
$439,990105 Days on yellowkey MLS ID: O6386437
REDUCED by $45,000 (9.3%) on 06/01/2026
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.
600 NORTHERN WAY #906, WINTER SPRINGS, FL 32708
$290,000139 Days on yellowkey MLS ID: O6375918
REDUCED by $20,000 (6.5%) on 06/01/2026
Bed: 3 Bath: 3.0 Liv Area Sq Ft: 1609 Built: 2016 Tax: $4,259 (2024)Community: Tuscany Place Ph 1Condo
Taxes:$4,259
Remarks: Turnkey townhouse in Tuscany Place is totally move-in ready. The townhouse style is limited to only a few homes in the new phase of this wonderful, gated community. Built in 2016 and much newer than many competing condos/townhomes. All 3 bedrooms have their own private full bathrooms. The first-floor bedroom with en-suite bath is great for guests, home office, or multigenerational living. Brand new roof (2026). Newer HVAC (2020). Low maintenance townhouse-style living. Spacious open-concept kitchen and overall excellent layout. This home's natural focal point is the kitchen with granite countertops, and there's an extra-large kitchen island, which provides essential counter space and storage, cabinets and drawers, and room for a breakfast bar. The kitchen leads to the rest of the living and family room combination, which features glass sliding doors to the patio and a staircase to a great split plan layout for the bedrooms upstairs. This home has all the features you’re looking for including a laundry room with large-size appliances, walk-in closets, a huge refrigerator, dedicated trash drawer in the kitchen, blinds and window treatments, and modern fixtures throughout the home. See yourself living in the heart of beautiful Winter Springs. Low monthly fee covers access to the community pool, exterior maintenance and landscaping, sewer, and trash services. Very close to all the shopping and restaurants at Winter Springs Town Center, and Trotwood Park is right at your doorstep. Contact us today to schedule a private tour!
Listing is courtesy of: JR REALTY GROUP LLC (407-920-4624)
Listing Agent: John Vincent (407-534-9764)
1112 ORANGE AVE, WINTER SPRINGS, FL 32708
$3,998,000433 Days on yellowkey MLS ID: O6298615
Bed: 5 Bath: 6.5 Gar: 6 Liv Area Sq Ft: 8685 Built: 2008 Tax: $14,976 (2024)Community: Lake JessupSpa: YesSingle Family
Taxes:$14,976
Remarks: Opportunities like this are almost impossible to find in Central Florida. Situated on 5.33 pristine lakefront acres with no HOA, this extraordinary estate is commercially zoned, creating a unique opportunity for a variety of potential business uses, including a luxury wedding venue, private event space, corporate retreat, boutique hospitality concept, or an exceptional live-work estate. With its breathtaking setting, grand architecture, and resort-style amenities, the property offers a level of versatility rarely available in today's market. Inspired by the elegance of the Italian countryside, the residence makes a lasting first impression with a dramatic front waterscape, lush gardens, and timeless architectural details. Inside, guests are welcomed by a grand foyer featuring exquisite marble finishes and a spectacular custom-painted 24-karat gold dome. Designed for both entertaining and everyday luxury, the expansive living spaces showcase panoramic views of beautiful Lake Jessup, soaring ceilings, stunning chandeliers, and a grand marble fireplace. The thoughtfully designed "H" floor plan encompasses more than 8,000 square feet of air-conditioned living space, offering five spacious bedrooms and six-and-a-half bathrooms, all conveniently situated on a single level. The primary suite is a true private retreat, featuring eight sets of French doors opening directly to the pool and lakefront, a custom-designed closet that doubles as a safe room, and a spa-inspired bathroom complete with a tranquil garden retreat. The gourmet chef's kitchen is equipped with top-of-the-line appliances, custom cabinetry, and an oversized walk-in butler's pantry designed to accommodate large-scale entertaining. Additional luxury amenities include a temperature-controlled wine cellar, private movie theater, dedicated nanny or guest quarters, and a six-car garage with extensive attic storage. Outside, the estate transforms into a private resort. A spectacular sports pool with multiple water features serves as the centerpiece, complemented by a summer kitchen, wet bar, outdoor fireplace, and expansive covered veranda overlooking the serene waters of Lake Jessup. Whether hosting elegant weddings, unforgettable events, corporate gatherings, or private family celebrations, the setting is simply unmatched. Combining custom craftsmanship, Tuscan and Greek-inspired design elements, commercial zoning flexibility, and an irreplaceable waterfront location, this remarkable estate offers a truly rare opportunity to own one of Central Florida's most unique properties. Schedule your private tour today to experience the endless possibilities and extraordinary lifestyle this one-of-a-kind property provides.
Listing is courtesy of: THE AGENCY FL (407-335-4119)
Listing Agent: Brian Hyser (407-951-2472)
270 SAN GABRIEL ST, WINTER SPRINGS, FL 32708
$249,900217 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: Price Improvement to $259,000 * Quick Closing Available. Welcome to 270 San Gabriel Street in Winter Springs—now offered at an updated price and ready for its next owner. This well-maintained, single-story home features vaulted ceilings and a bright, open layout that creates a comfortable and inviting living space. With neutral finishes and ceramic tile flooring throughout, the home is truly move-in ready. All appliances are included for added convenience. Enjoy morning coffee or unwind in the evening on the oversized screened patio, offering a private outdoor retreat. Additional exterior storage provides practical space for bikes, tools, and seasonal items. Located just minutes from the scenic Cross Seminole Trail, the Deersong community also offers access to a pool and cabana for residents to enjoy. Nearby parks, shopping, dining, and top-rated Seminole County schools add to the home’s appeal. Considering making a move to downsize? First-time homebuyer? investor? or seeking a low-maintenance second home in Central Florida? Schedule your private showing today. With a newly reduced price and quick closing available, this is an excellent opportunity to own a well-cared-for home in a desirable location..
Listing is courtesy of: MAINFRAME REAL ESTATE (407-513-4257)
Listing Agent: Alie Gattis (407-760-1488)
1110 SHADOWBROOK TRL, WINTER SPRINGS, FL 32708
$575,00013 Days on yellowkey MLS ID: O6413323
0 Days Off yellowkey (back on 6/15/2026)
Bed: 4 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 2214 Built: 1998Monthly Fee: $50 Tax: $3,542 (2025)Community: Winding Hollow Unit 4Single Family
Taxes:$3,542
Remarks: Under contract-accepting backup offers. Nestled within the DESIRABLE Winding Hollow community, this residence presents a CHARMING front exterior, highlighted by a meticulously maintained lawn and lush landscaping. An inviting entryway, featuring distinctive double doors, sets a welcoming tone upon arrival. The interior unfolds into an OPEN CONCEPT living, dining, and kitchen area, designed for both comfort and connectivity. The spacious living room offers ample space for various arrangements, and overlooks the lanai & pool. Perfectly positioned adjacent to the living room, the DINING area is bathed in NATURAL LIGHT from the large window enhancing the home's OPEN and airy feel. Culinary endeavors are elevated in the well appointed GORGEOUS kitchen, boasting GRANITE countertops, SS appliances, and abundant wooden cabinet space for storage. The KITCHEN is the heart of the home with a LARGE ISLAND offering a vantage point into the family and dining areas, fostering a sense of togetherness. An additional eat-in kitchen area provides flexibility for casual dining. This home encompasses 4 well-proportioned bedrooms and 3 FULL bathrooms, spanning 2,214 square feet. The PRIMARY suite offers a private retreat, featuring a double vanity, a LUXURIOUS soaking tub, and a separate walk-in shower, creating a spa-like experience. The additional bathrooms are thoughtfully designed with contemporary fixtures and tiled showers, ensuring comfort and style. Practical amenities include a dedicated laundry room, equipped with a stacked washer and dryer and ample storage cabinets, enhancing daily convenience. A 3-car garage provides extensive parking and storage solutions, catering to diverse needs. OUTDOOR LIVING is seamlessly integrated with a screened-in patio, offering a comfortable space to relax and enjoy the surroundings. Beyond the patio, a sparkling POOL invites recreation and leisure, and is the perfect oasis for unwinding. The property's location offers exceptional convenience to a wealth of local amenities. Proximate to the vibrant Winter Springs Town Center, an array of shopping and dining options are readily available. Award-winning CENTRAL WINDS PARK provides expansive green spaces with a DOG PARK and 14 PICKLEBALL COURTS, and the CROSS SEMINOLE TRAIL is right outside the neighborhood. Top Rated Seminole County Schools and easy access to the 417. This home has it ALL. Make YOUR showing appointment today.
Listing is courtesy of: KELLER WILLIAMS WINTER PARK (407-545-6430)
Listing Agent: Dawn Tinder (407-733-6846)
1411 BORG LN, WINTER SPRINGS, FL 32708
$385,000137 Days on yellowkey MLS ID: O6378665
REDUCED by $14,000 (3.5%) on 06/10/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1368 Built: 1981Monthly Fee: $90 Tax: $1,871 (2024)Community: Wedgewood Tennis VillasSingle Family
Taxes:$1,871
Remarks: Price Reduced!! Your wait is over! Welcome to your new home! This beautiful 3 bedroom, 2 bath home delivers 1,368 sq. ft. of peaceful living area in a quiet corner lot. Located in the gorgeous Tuskawilla Country Club community, this home features luxury vinyl flooring throughout the house. Entertain effortlessly with a spacious kitchen featuring stainless steel appliances, recessed lighting, and 42” upgraded cabinets. The main floor master bedroom has walk in closet and access to the covered patio. House has been updated with a new roof in 2023, A/C unit in 2018, Water Heater in 2020, luxury vinyl floors and vinyl fencing. Enjoy the Florida outdoors with a covered and screened in porch to entertain and gaze out over the huge fenced in backyard. Winter Springs is an established community know for its A-Rated schools, "Tree lined streets", golf courses, tennis, and with easy access to shopping at Oviedo Marketplace, Trotwood park and the 417. Schedule a showing today and come experience Winter Springs living.
Listing is courtesy of: SOLID OAK REAL ESTATE LLC (321-888-9232)
Listing Agent: Trevor Laug (321-888-9232)
268 TAVESTOCK LOOP, WINTER SPRINGS, FL 32708
$569,90034 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)
30 SABLE CT, WINTER SPRINGS, FL 32708
$569,000124 Days on yellowkey MLS ID: O6382648
REDUCED by $10,000 (1.7%) on 04/12/2026
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2674 Built: 1976 Tax: $3,043 (2024)Community: TuscawillaSpa: NoSingle Family
Taxes:$3,043
Remarks: REDUCED! Beautiful Executive 4 bedroom POOL home in Tuscawilla Country Club Golf Community! NO HOA! Mediterranean feel with wrought iron accents and courtyard. Huge Kitchen with island in the middle. All appliances. Hot water heater 2017. Lots of cabinet space. Spacious eat-in area beside kitchen. Formal Dining and Living rooms. Large bedrooms. Big Owners bedroom with walk-in closet and updated bath. Inside laundry room. Large Pool (updated to salt system) 8 feet deep. Big fenced yard. Screened in porch. Oversized 2 car side entrance garage (currently part of garage is an office but could easily be converted back). Community allows golf carts. Plenty of room to park jet skis, boats, and RV. Great location near shopping, restaurants, hospital, and major roads. Good schools. Country Club has golf, tennis, swimming, and dining membership. Trotwood park has basketball and tennis courts, soccer field, and covered picnic area. Many parks in neighborhood. Close to Seminole Trail for walking and bike riding. Move right in! Must Seee!
Listing is courtesy of: HOME SOLD NETWORK LLC (407-257-6223)
Listing Agent: Julie Bailey (407-257-6223)
421 HORIZON DR, WINTER SPRINGS, FL 32708
$294,900110 Days on yellowkey MLS ID: O6384932
REDUCED by $5,000 (1.7%) on 06/14/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1069 Built: 1998Monthly Fee: $142 Tax: $3,681 (2025)Community: Seasons TheSingle Family
Taxes:$3,681
Elementary School: Winter Springs Elementary
Remarks: Welcome to 421 Horizon Drive in Winter Springs, located in The Seasons community. This move-in ready home checks all the big boxes upfront: a 50-year Rhino shingle roof (2019), a 3.5-ton 14 SEER AC unit with heat pump and updated ductwork, a new electric panel, and a 2019 water heater. Beautifully maintained and thoughtfully updated throughout, this one-story home offers 3 bedrooms, 2 bathrooms, and 1,069 square feet of living space. Inside, you'll find newer Mohawk laminate flooring in the main living areas and bedrooms, tile in the kitchen and baths, updated light fixtures, newer ceiling fans, upgraded baseboards, and modernized doors and hardware throughout. The primary suite features a fully renovated bathroom with a walk-in shower, glass enclosure, rain shower head, and updated vanity. The guest bathroom has also been extensively renovated. High and vaulted ceilings enhance the open great room and dining space, while the sliding glass doors lead to an extended and stamped concrete patio within a private vinyl fenced yard, ideal for relaxing or entertaining. Located on a quiet cul-de-sac with assigned parking and curb parking available, this home is just a short walk to the community pool and directly across from the park, playground, and tennis courts. The HOA covers lawn maintenance, making for easy, low-maintenance living in a prime Seminole County location zoned for Winter Springs schools.
Listing Agent: Peter Luu (321-917-7864)
1115 ARBOR GLEN CIR, WINTER SPRINGS, FL 32708
$750,0005 Days on yellowkey MLS ID: O6416243
Bed: 4 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 2608 Built: 1993Monthly Fee: $58 Tax: $5,397 (2025)Community: Tuscawilla Parcel 90Spa: NoSingle Family
Taxes:$5,397
Remarks: A perfect blend of comfort, style, and location. This beautifully maintained, custom 4-bedroom, 3-bath POOL home in the Tuscawilla community of Arbor Glen checks all the boxes. Spanning 2,620 square feet, this one-story, 3-car side-entry garage home offers the privacy of a fully fenced backyard with screened-in pool and no rear neighbors. After a refreshing swim in the NEWLY RESURFACED POOL (5/26), you can rinse off in the outdoor shower or step into the cabana bath with direct access from the patio. This split floor plan includes vaulted ceilings that create an airy atmosphere throughout, and the primary suite offers private lanai and pool access, perfect for morning coffee. The 4th bedroom is both functional and versatile, with a built-in desk/workstation and a queen-size Murphy bed. The large kitchen boasts stainless steel appliances, granite countertops, and a bright breakfast nook with a frameless bay window overlooking the pool. All the main living areas and bedrooms feature rich wood flooring. Other noted features: BRAND NEW POOL PUMP (5/26), freshly painted pool deck, washer/dryer included, gas fireplace, and newer roof (2020) & A/C (2019). Nestled in the desirable Seminole County school zone, with easy access to shopping, dining, parks, golfing at Tuscawilla Country Club, and pickleball at Central Winds Sports complex. This home has it all!
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Ericka Stephens (407-468-0510)
984 TURKEY HOLLOW CIR, WINTER SPRINGS, FL 32708
$410,00021 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: Virtually Staged. A spacious 3-bedroom, 2-bathroom home located in the highly sought-after community of Oak Forest in Winter Springs. Known for its beautiful tree-lined streets, mature oak trees, and quiet suburban charm, this family-friendly neighborhood also offers access to top-rated schools and is conveniently located near popular restaurants, shopping, and everyday conveniences. Inside, this home features a versatile and functional floor plan with a spacious family room, separate living room, dining room, large kitchen, dedicated office space, and an indoor laundry room. The detached shed provides the perfect opportunity for extra storage, a workshop, or hobby space. Step outside to enjoy the private backyard complete with a fire pit — ideal for relaxing or entertaining guests. The garage has been split into an office and storage space but can be converted back into a two car garage. Major upgrades and improvements include an updated roof (2018), gutters(2018), HVAC system(2022), windows(2020), garage door(2020), hot water heater(2021), electrical panels(2023), and added insulation(2019). Additional features include an indoor electric fireplace (2022), and numerous updates throughout, offering peace of mind and move-in-ready convenience. Call today to schedule your private tour!
Listing is courtesy of: ALL REAL ESTATE & INVESTMENTS (407-917-8206)
Listing Agent: Kelsey Payton (407-718-2967)
214 CHESTNUT RIDGE ST, WINTER SPRINGS, FL 32708
$600,000116 Days on yellowkey MLS ID: O6372400
REDUCED by $25,000 (4.0%) on 06/03/2026
Bed: 4 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 2474 Built: 2001Monthly Fee: $42 Tax: $5,539 (2024)Community: Chestnut Ridge In TuscawillaSpa: NoSingle Family
Taxes:$5,539
Remarks: WOW, BEST PRICE IN Winter Springs inside Executive TUSCAWILLA! Incredible opportunity. Here is your future DREAM HOME! Best price DIRECT GOLF FRONT HOME IN ORLANDO! Why wait to build on a 50 ft lot when you can live in a custom home Did you ever dream of drinking your Coffee daily while looking at a pristine GOLF course and Conservation view? Maintenance free yard that is DIRECTLY on the 16th hole of the Tuscawilla Golf Course. Builder of this neighborhood built this One of a kind home for himself and it has a one of a kind view. VIEW VIDEO WALK THROUGH TOUR. Energy Efficient SOLAR that is PAID FOR! Chestnut Ridge is a serene Winter Springs community in Seminole County This exquisite property, situated on .24 acres of loads of landscaping, with amazing azaleas with many colors, is the epitome of luxury living, perfect for executive families seeking a harmonious blend of comfort and elegance. Boasting an impressive 4 bedrooms and 3 bathrooms, this custom-built home offers a spacious upstairs private en suite featuring 1 bedroom and 1 bath, ideal for guests, playroom or a secluded home office. A true Gardeners Paradise. The interior is nothing short of breathtaking with soaring 10’ ceilings and solid red oak flooring that greets you in the foyer and extends through the kitchen and breakfast nook. The heart of the home, a chef's kitchen, is adorned with quality chestnut wood cabinets, sleek granite countertops, and a wet bar island, perfect for entertaining. Hallway complete with bright skylights that lead to bedroom 2 and 3 that actually both have access to the hall Jack n Jill bath. Three way split floor-plan offers loads of lifestyle options. Attention to detail is evident with 5 1/4” baseboards, recessed lighting, and a luxurious custom built-in entertainment center. Cozy up by the gas-burning fireplace or enjoy the oversized 860 SF 3-car garage/workshop, equipped with an insulated ceiling and reinforced garage doors, offering ample space for vehicles and projects alike. Custom Built pergola off the garage offers additional charm. So Many options. Complete with a direct wire for a generator access. The master suite is a sanctuary with a generous 8' x 12' walk-in closet featuring custom solid walnut cabinets. Bask in the Florida sunshine on your awning-covered rear deck with a view of the golf course and conservation area. Built in 2001 with a new roof in 2020, this move-in ready home benefits from top-of-the-line “Low E” windows, R-30 attic insulation. Yard is LOW MAINTENANCE! Location is paramount, with proximity to quality schools, shopping, dining, and major employment hubs.You are upgrading your LIFESTYLE in this neighborhood. HIGHLIGHTED EXTRAS Throughout. Along with the purchase this home comes with 20 solar panels, that are PAID FOR, which can provide 7.8 kWh are connected with the Duke power grid. The electric bill reflects how much power you use and how much you push back to the grid. You are credited equally for power pushed back in the final monthly amount due. Additionally, there is a backup battery which in the event of power outage will provide 6 dedicated circuits for the house with standby power during brief power outages."A" Rated schools, all three! A MUST SEE!
Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)
Listing Agent: Laurie Cain (407-484-9944)
4901 PETRA CT, WINTER SPRINGS, FL 32708
$674,90019 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
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)
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