Location: Winter Springs
Do Not Show Listings
1838 SENECA BLVD, WINTER SPRINGS, FL 32708
$749,9003 Days on yellowkey MLS ID: O6411007
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 3195 Built: 1993Monthly Fee: $8 Tax: $5,731 (2025)Community: Tuscawilla Unit 14BSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$5,731
Elementary School: Lawton Elementary
High School: Oviedo High
Tax Year: 2025
Middle School: Indian Trails Middle
Remarks: Rare opportunity to own a spacious pool home on a private 2.1-acre conservation homesite in the highly desirable Chelsea Woods section of Tuscawilla. Offering 4 bedrooms, 3 bathrooms and over 3,100 square feet of living space, this home features a dedicated office with custom built-ins, formal living and dining areas, a wood-burning fireplace, and a large upstairs loft that provides flexible space for a media room, game room, home gym, or additional living area. The kitchen overlooks the main living spaces and pool area, while French doors open to an expansive covered lanai and screened pool enclosure designed for year-round Florida living. Step outside and enjoy your own backyard retreat featuring a large pool and spa with waterfall features, outdoor grilling area, generous deck space, mature landscaping, and peaceful conservation views with no rear neighbors. Major improvements include a roof replaced approximately 3 years ago and HVAC systems replaced approximately 3 years ago, providing peace of mind for years to come. Conveniently located near top-rated Seminole County schools, parks, golf, shopping, dining, and major commuter routes. Optional HOA membership available. Homes offering this combination of acreage, privacy, pool, location, and living space rarely become available.
Listing is courtesy of: HOPKEY REALTY (407-454-1217)
Listing Agent: Uno Sorlie (407-454-1217)
1618 WRENTHAM CT, WINTER SPRINGS, FL 32708
$799,9003 Days on yellowkey MLS ID: O6411489
Bed: 5 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 3286 Built: 2004Monthly Fee: $100 Tax: $7,344 (2025)Community: Barrington EstatesSpa: NoSingle Family
Taxes:$7,344
Middle School: Jackson Heights Middle
Remarks: Florida living at its finest! Nestled within the quaint gated community of Barrington Estates in Winter Springs, this stunning two-story home is ideally situated on a private cul-de-sac with no front or rear neighbors. Enjoy serene pond and conservation views from the front of the home, while the expansive fenced backyard overlooks mature trees, creating exceptional privacy and tranquility. Inside, the grand entry opens to elegant living and dining spaces highlighted by soaring ceilings and an impressive staircase. Luxury vinyl flooring flows throughout the first floor, adding both style and durability. The first-floor primary suite offers a private retreat featuring dual walk-in closets, separate vanities, a water closet, and a walk-in shower. The main level also includes a half bath, laundry room with access to the 3-car garage, and a spacious open-concept kitchen overlooking the family room perfect for entertaining. The chef’s kitchen is beautifully appointed with a large island and sink, granite countertops and backsplash, stainless steel appliances, double ovens, beverage fridge, oversized pantry, and an eat-in dining area. French doors seamlessly connect the indoor living spaces to the lanai and pool area. A dramatic double staircase leads to the second floor where you’ll find a spacious bonus room surrounded by four additional bedrooms. Two bedrooms feature walk-in closets, while the fourth bedroom serves as a private ensuite complete with two closets and a tub/shower combination bath. An additional full bath with a linen closet is also located upstairs. Wood flooring throughout the staircase, bonus room, and upstairs bedrooms adds warmth and elegance, while abundant windows fill the home with natural light. Designed for both entertaining and everyday living, the outdoor space offers the perfect backyard retreat featuring a sparkling saltwater pool with sun shelf, pavered pool deck, covered lanai, and cozy fire pit. Additional highlights include a paver driveway and an exceptional location with convenient access to Toll Road 417 and SR-434. Zoned for A-rated Oviedo schools and just minutes from shopping, restaurants, Oviedo on the Park, Winter Springs Town Center, UCF, Research Park, and Oviedo Medical Center. Community amenities include a playground, and the home is just a short distance from the Seminole Trail, ideal for biking, walking, and enjoying the outdoors. Welcome Home!
Listing is courtesy of: URBANISTA BROKERS (407-619-7272)
Listing Agent: Anna Lohr (321-277-4797)
424 FLATWOOD DR, WINTER SPRINGS, FL 32708
$525,00019 Days on yellowkey MLS ID: S5149589
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2164 Built: 1997Monthly Fee: $82 Tax: $3,052 (2024)Community: Tusca OaksSingle Family
Taxes:$3,052
Elementary School: None
High School: None
Tax Year: 2024
Middle School: None
Remarks: Excellent opportunity in desirable Tusca Oaks/Tuscawilla area. Spacious 4BR/2.5BA with functional floor plan, generous room sizes, and strong curb appeal. Home has been well maintained and is in mostly original condition, offering buyers the chance to update to their personal taste while gaining value in a highly desirable Seminole County location. Brand New Roof - 1 yr old. Community features including mature landscaping, sidewalks, and convenient access to parks, trails, golf, shopping, dining, and major roads. Strong owner-occupancy area with long-term neighborhood stability. Easy to show.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Alexandra Arena Gil (321-228-6377)
268 TAVESTOCK LOOP, WINTER SPRINGS, FL 32708
$569,90017 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
Elementary School: Layer Elementary
High School: Winter Springs High
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)
1444 BIRD RD, WINTER SPRINGS, FL 32708
$838,500257 Days on yellowkey MLS ID: O6344113
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2350 Built: 1977 Tax: $2,076 (2024)Community: Watts FarmsSingle Family
Taxes:$2,076
Elementary School: Sterling Park Elementary
Middle School: South Seminole Middle
Remarks: One or more photo(s) has been virtually staged. ONE OF A KIND! Stunning Renovated Lakefront Home on Private Peninsula – Welcome to your fully reimagined lakefront retreat at 1444 Bird Road in the heart of Winter Springs. Nestled along the serene shores of Lake Tony, this highly detailed, professionally rehabbed home blends modern luxury with timeless Florida charm. From the moment you arrive, you’ll notice the thoughtful craftsmanship and attention to detail throughout. The home has been completely renovated from top to bottom, featuring a bright, open-concept layout with abundant natural light and stunning lake views from multiple living spaces. The designer kitchen is a true centerpiece, showcasing amazing cabinetry, premium quartz countertops, stainless steel appliances, and a spacious island perfect for entertaining. The living and dining areas flow seamlessly, creating an inviting space for gatherings or quiet evenings overlooking the water. Retreat to the primary suite, where you’ll find a spa-inspired bathroom with high-end finishes, elegant tile work, and a relaxing atmosphere designed for comfort. Additional bedrooms offer flexibility for guests, family, or a home office. Step outside to your private backyard oasis, where you can enjoy peaceful mornings or breathtaking sunsets on Lake Tony. Whether you’re kayaking, fishing, or simply unwinding by the water, this property offers the ultimate lakefront lifestyle. Additional upgrades include updated systems, modern fixtures, and quality finishes throughout—providing peace of mind and move-in-ready convenience. Located in a desirable Winter Springs neighborhood with easy access to top-rated schools, parks, shopping, and dining, this home is a rare opportunity to own a turnkey lakefront property. Don’t miss your chance to experience luxury living on Lake Tony—schedule your private showing today.
Listing is courtesy of: KEEN REALTY GROUP, INC. (407-699-2127)
Listing Agent: Bobby Keen (407-951-2300)
1421 HAPPY BIRD LN, WINTER SPRINGS, FL 32708
$563,408200 Days on yellowkey MLS ID: O6359884
REDUCED by $10,040 (1.8%) on 05/28/2026
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2502 Built: 2019Monthly Fee: $130 Tax: $4,781 (2024)Community: Tuskawilla Crossings 34'SSingle Family
Taxes:$4,781
Remarks: Welcome home! Fall in love this welcoming two-story home that features 4 bedrooms and 3.5 bathrooms, perfectly positioned across from the Cross Seminole Trail. Start your day with a cup of coffee on the charming covered front porch, where you can take in the refreshing breeze and picturesque views of the 13-mile trail that winds through Seminole County and connects to other scenic trails. Step inside to discover an inviting open floor plan enhanced by beautiful wood-style tile flooring. Prepare your favorite meals in the gourmet kitchen with stainless steel appliances, pantry, modern fixtures, and breakfast bar ideal for casual dining. The open-concept living and dining areas create the perfect setting for effortless entertaining. The primary suite, conveniently located on the first floor, includes a walk-in closet and a private ensuite bathroom with dual sinks and a walk-in shower. Ascend to versatile loft area upstairs offering additional space for work, play, or relaxation. You will also appreciate the secondary primary suite on this level, complete with a walk-in closet, dual sinks, and shower. Additionally, two generously sized bedrooms await your use along with a full bathroom. Outside, unwind on the covered back patio, surrounded by vinyl fencing for added privacy. A rear-facing two-car garage with a paver driveway completes the property. This home is part of the Tuskawilla Crossing community, which includes a dog park, a sparkling community pool for leisurely fun, and a playground. The area is rich in dining and shopping options and provides easy access to the 417. Situated in Seminole County which is well known for its public school system. Don’t miss the chance to make this exceptional home yours—schedule a showing today!
Listing is courtesy of: RE/MAX ASSURED (800-393-8600)
Listing Agent: Brent Dehoop (407-448-8971)
109 CHERRY CREEK CIR, WINTER SPRINGS, FL 32708
$1,090,00026 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
Elementary School: Keeth Elementary
Remarks: Tucked behind the gates of The Reserve at Tuscawilla, this estate unfolds in a way that feels both grounded and quietly impressive, offering a sense of space, privacy, and ease that is increasingly rare to find. Set on over half an acre, 109 Cherry Creek Circle invites you to settle into a lifestyle where everyday living flows effortlessly into moments worth celebrating. From the moment you arrive, there is a feeling of arrival that stays with you. Mature landscaping, a side-entry three-car garage, and the understated presence of a custom Von Jacobs-built home set the tone. Inside, natural light filters through high ceilings and classic architectural details, guiding you through a layout designed for both connection and retreat. The main living areas feel open yet intimate, centered around a warm gas fireplace and views that draw your attention immediately to what makes this home so special. The backyard is not simply an amenity. It is the heart of the experience. Designed for gathering, the outdoor living space offers multiple destinations to relax, entertain, and unwind. A deep resort-style pool and spa invite long afternoons in the sun, while Tennessee River Rock accents, a dedicated fire pit lounge, and an expansive lanai create layers of texture and ambiance. Evenings here feel effortless, whether hosting friends around the summer kitchen with its Viking grill and Texas smoker or enjoying a quiet night under the stars. It is a setting that naturally becomes part of your daily rhythm. Inside, the kitchen remains connected to it all, with a layout that keeps conversations going from room to room. A gas cooktop, double ovens, and a thoughtfully designed breakfast nook provide a space that is both functional and welcoming. Formal living and dining rooms offer flexibility, whether gathering for holidays or creating a more intimate setting for guests. The primary suite is privately positioned on the first floor, offering a calm and comfortable retreat at the end of the day. Its recently remodeled bath brings a fresh, spa-like feel while honoring the home’s timeless character. Additional bedrooms on the main level are thoughtfully arranged, while an expansive upstairs suite provides flexibility for guests, multigenerational living, or a private office and lounge. There is a sense throughout the home that it has been well cared for and intentionally updated where it matters most. Major improvements including the roof (2017), HVAC (2017), whole-house replumbing (2024), and water heater (2025) allow the next owner to step in with confidence, while leaving room to personalize over time in a way that reflects their own style. Beyond the home itself, life in The Reserve at Tuscawilla offers a lifestyle many seek and few find. Quiet, tree-lined streets, a gated setting, and a strong sense of community create an environment that feels both secure and welcoming. Just moments away, Tuscawilla Country Club becomes an extension of home, with golf, tennis, dining, and social events that bring neighbors together. Nearby trails, top-rated schools, and convenient access to major roadways complete the picture of daily ease. This home represents a rare opportunity to own within one of Winter Springs’ most established and desirable communities. It is a place that feels lived in, loved, and ready for its next chapter, where the value is not only in the features, but in the life it quietly supports.
Listing is courtesy of: COLDWELL BANKER REALTY (407-696-8000)
Listing Agent: Kara Lushear (321-663-5550)
820 WAKULLA LN, WINTER SPRINGS, FL 32708
$419,90024 Days on yellowkey MLS ID: TB8504175
REDUCED by $5,000 (1.2%) on 05/28/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1658 Built: 2012Monthly Fee: $167 Tax: $5,649 (2025)Community: Winter Spgs Village Ph 1Single Family
Taxes:$5,649
Remarks: Move-in ready and thoughtfully updated, this 3-bedroom, 2-bath home offers bright, comfortable living with fresh interior paint, new carpet, and new light fixtures throughout. The open main living area flows easily into the kitchen, where new quartz countertops, a new range, microwave, and dishwasher add style and everyday functionality. A new roof provides valuable peace of mind, while the spacious bedrooms, inviting natural light, and practical layout create a home that feels both polished and livable. With tasteful updates already complete, this home is ready to welcome its next owner.
Listing is courtesy of: OFFERPAD BROKERAGE FL, LLC (813-534-6326)
Listing Agent: Rob Jones (844-448-0749)
907 GLEN ABBEY CIR, WINTER SPRINGS, FL 32708
$420,0004 Days on yellowkey MLS ID: O6411321
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1791 Built: 1997Monthly Fee: $126 Tax: $2,093 (2025)Community: Greenbriar Sub Ph 2Single Family
Taxes:$2,093
Remarks: Welcome home to this beautiful, move-in-ready residence nestled in the highly sought-after Greenbriar at Tuscawilla community! This charming 3-bedroom, 2-bath home offers a highly functional single-story layout with an open floor plan and split-bedroom design, creating both comfortable everyday living and added privacy. The spacious living and dining areas feature vaulted ceilings and abundant natural light, making the home feel bright and inviting. The oversized primary suite offers a relaxing retreat complete with a large walk-in closet and private bath. Enjoy low-maintenance living with a low HOA that includes lawn maintenance, plus access to the community pool. As an added option, Tuscawilla Country Club offers dining, fitness facilities, a junior Olympic pool, tennis courts and leagues, pickleball, golf, and social events. Conveniently located near SR 417, SR 434, and Red Bug Lake Road, you'll have easy access to shopping, dining, and entertainment. Don’t miss your opportunity to own this sweet home in one of Winter Springs’ most desirable communities. Schedule your private showing today!
Listing is courtesy of: REAL BROKER, LLC (855-450-0442)
Listing Agent: Jennifer Draper (321-439-7204)
448 MACGREGOR RD, WINTER SPRINGS, FL 32708
$350,00053 Days on yellowkey MLS ID: O6397231
REDUCED by $10,000 (2.8%) on 05/27/2026
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1477 Built: 1993Monthly Fee: $6 Tax: $1,141 (2024)Community: Highland Village 2Spa: NoSingle Family
Taxes:$1,141
Remarks: Explore 448 MacGregor Rd, a individual residence with a straightforward design and integrated features. The interior includes a fireplace, and the primary bedroom features a walk in closet; the primary bathroom provides double sinks and a Jacuzzi. The exterior includes a covered patio and a fenced in backyard, providing an enclosed outdoor area. This property contains practical elements for daily living. Included 100-Day Home Warranty with buyer activation
Listing is courtesy of: OPENDOOR BROKERAGE LLC (480-462-5392)
Listing Agent: Karen Albright (480-462-5392)
1534 WESCOTT LOOP, WINTER SPRINGS, FL 32708
$735,000113 Days on yellowkey MLS ID: O6380652
REDUCED by $10,000 (1.3%) on 05/25/2026
Bed: 6 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 3426 Built: 2004Monthly Fee: $100 Tax: $5,527 (2025)Community: Barrington EstatesSpa: YesSingle Family
Taxes:$5,527
Remarks: At ADJUSTED price of $735,000 for this stunning six-bedroom, four-bath home in a gated community, perfectly positioned with a view of a conservation lot without rear neighbors. Winter Springs address, with top-rated Oviedo Schools! Soak up the Florida lifestyle in this stunning backyard retreat with a sparkling pool and spa. Brand new pool heater plus a spacious outdoor kitchen, complete with a dedicated gas grill area, seating space, and brand new refrigerator. It is the ideal place to enjoy warm Florida days and breezy nights. Inside, the home offers a highly desirable layout, with both the primary suite and an additional bedroom on the first floor, perfect for a mother-in-law suite, guests, or a home office. The open living areas feature tile flooring throughout the main level, while the kitchen is finished with granite countertops and ample workspace for everyday living and hosting. Upstairs, you’ll find generously sized secondary bedrooms and baths, providing flexibility for large families, multigenerational living, or vacation use. The peaceful conservation views create a private, serene backdrop both indoors and out. Located in a gated community, this home combines space, privacy, and resort-style amenities in one exceptional property.
Listing is courtesy of: PALMANO GROUP RE BROKERAGE LLC (321-214-1211)
Listing Agent: Denise Pohlmann (407-701-3346)
805 LEOPARD TRL, WINTER SPRINGS, FL 32708
$565,00024 Days on yellowkey MLS ID: O6405925
0 Days Off yellowkey (back on 5/27/2026)
REDUCED by $10,000 (1.7%) on 05/25/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2608 Built: 1978 Tax: $2,946 (2024)Community: Winter Spgs Unit 4Single Family
Taxes:$2,946
Remarks: Under contract-accepting backup offers. Welcome to 805 Leopard Trail in Winter Springs, a 4-bedroom, 2-bath pool home located in a quiet, established no HOA community. Situated on approximately half an acre, this property offers a rare combination of space, privacy, and natural surroundings. The home features a functional layout with comfortable living areas, while large windows and sliding glass doors provide natural light and seamless access to the backyard. Step outside to a truly special outdoor setting, where mature trees, natural surroundings, and the sounds of nature create a peaceful and private atmosphere. The backyard is a standout feature, complete with a private pool and plenty of space to relax or entertain. The pool area is also plumbed for a future outdoor kitchen, offering additional potential. With a generous lot size, there is ample room for recreation, storage, or future improvements. Conveniently located near University of Central Florida, Central Winds Park, Oviedo Mall, as well as shopping, dining, and major roadways including SR 434 and SR 417, this property offers both tranquility and accessibility in a desirable Winter Springs location.
Listing is courtesy of: RE/MAX PRIME PROPERTIES (407-347-4512)
Listing Agent: Wilfred Sierra Sosa, Pa (863-588-8303)
1513 BLACK BEAR CT, WINTER SPRINGS, FL 32708
$1,479,50087 Days on yellowkey MLS ID: O6385058
1 Days Off yellowkey (back on 5/27/2026)
REDUCED by $69,500 (4.5%) on 04/16/2026
Bed: 4 Bath: 5.0 Gar: 3 Liv Area Sq Ft: 6175 Built: 1989Monthly Fee: $142 Tax: $23,523 (2025)Community: Bear Creek EstatesSingle Family
Taxes:$23,523
Remarks: Under contract-accepting backup offers. Welcome to this exceptional home in the exclusive gated community of Bear Creek Estates, set on over an acre of lush wooded greenbelt with beautiful landscaping and a circular driveway that creates outstanding curb appeal. The over 6,000 sq. ft. (includes 1 car garage/hobby room of approx. 280 sq.ft.) home features a new architectural tile roof (less than one year old) and 10-foot ceilings throughout the first floor, creating a bright and spacious feel. Inside, you’ll find elegant formal living and dining spaces, a private home office, and a comfortable family room overlooking the sparkling pool and lanai. The home offers oversized secondary bedrooms with seating areas, plus a large additional bedroom that can serve as an office, art studio or flex space. Entertainment is exceptional with two theater spaces, The main floor home theater is projector-ready, with acoustic panels, granite snack counter, an electronic masking screen and wiring for 7.1 sound. The upstairs primary bedroom is massive in size and the ideal retreat to unwind at end of the day! Complete with its sitting area and outdoor deck with stunning panoramic views of lush nature. The upstairs primary suite in this home also includes a projector drop-down screen and wiring for 5.1 sound. The private backyard retreat features a beautiful pool with LED lighting, waterfall feature, and updated pump and filter (2023), along with panoramic views of lush green space. Additional highlights include a smart audio system controlled by smartphone app, extensive network wiring, pre-wiring for security cameras, well-fed irrigation, and a backyard telescope pier with power and ethernet. In Winter Springs, this home offers peaceful luxury living while being close to shopping, dining and major commuting routes.
Listing is courtesy of: PREMIER SOTHEBYS INT'L REALTY (407-333-1900)
Listing Agent: Lynda Miller (407-620-2924)
143 HAYES RD, WINTER SPRINGS, FL 32708
$479,00016 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)
560 PLEASANT GROVE DR, WINTER SPRINGS, FL 32708
$425,00034 Days on yellowkey MLS ID: O6401016
REDUCED by $20,000 (4.5%) on 05/20/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1654 Built: 1996Monthly Fee: $78 Tax: $5,669 (2024)Community: Tusca OaksSingle Family
Taxes:$5,669
Remarks: Welcome to Tuska Oaks—a well-established community in the heart of Winter Springs known for its convenience and neighborhood feel. Tucked away on a quiet cul-de-sac, this 3-bedroom, 2-bath home offers over 1,600 square feet of comfortable living space with a smart, open layout and soaring vaulted ceilings. The kitchen features granite countertops, stainless steel appliances, and ample cabinet space, opening seamlessly into the dining room area—ideal for everyday living and entertaining. Tile flooring runs throughout the home with laminate or LVP in the bedrooms and bathrooms, making maintenance simple and clean. Major updates have already been handled for you, including a roof replaced in 2018, A/C replaced in 2020, newer water heater (2024), and interior and exterior paint completed just 3 years ago. The secondary bathroom has been fully remodeled, adding a fresh, updated touch. Step outside to a screened-in back porch overlooking a fully fenced backyard, offering privacy and space for pets, play, or outdoor gatherings. Residents of Tuska Oaks enjoy a low HOA and access to a community pool , all while being conveniently located near shopping, dining, and top-rated Seminole County schools.
Listing is courtesy of: KELLER WILLIAMS ADVANTAGE III (407-207-0825)
Listing Agent: David Fraser (407-920-9749)
108 SUNDANCE CT, WINTER SPRINGS, FL 32708
$349,9009 Days on yellowkey MLS ID: O6409784
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1161 Built: 1997Monthly Fee: $140 Tax: $3,505 (2025)Community: The SeasonsSingle Family
Taxes:$3,505
Remarks: Welcome home to this beautifully remodeled gem tucked away on a quiet cul-de-sac in desirable Winter Springs! From the moment you walk in, you’ll fall in love with the bright, open-concept layout designed for easy living and effortless entertaining. With 1,161 sq ft under air, every inch of this home has been thoughtfully updated and filled with charm. The stunning fully remodeled kitchen is the heart of the home, featuring modern finishes, updated cabinetry, and a welcoming flow into the spacious living and dining areas. Both bathrooms have also been completely renovated, creating a fresh, stylish feel throughout. Step through the back doors and discover your own private retreat — a peaceful backyard backing directly to a beautiful conservation area with no rear neighbors, offering the perfect blend of privacy and nature. Imagine morning coffee with serene views or relaxing evenings enjoying the Florida breeze. Even better, the major 4 systems have all been replaced within the last 5 years, giving buyers confidence and peace of mind for years to come. Whether you’re a first-time buyer, downsizing, or simply looking for a turnkey home in an amazing location, this one checks all the boxes. Conveniently located near shopping, dining, parks, and great schools, this is the opportunity you’ve been waiting for. Sold as-is and ready for its next owner to fall in love!
Listing is courtesy of: JEMINI REALTY CORP (407-765-7292)
Listing Agent: Matias Gomez (407-535-0991)
1018 WEATHERED WOOD CIR, WINTER SPRINGS, FL 32708
$369,00011 Days on yellowkey MLS ID: O6408847
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1718 Built: 1978Monthly Fee: $107 Tax: $1,316 (2025)Community: Wedgewood Unit 2Single Family
Taxes:$1,316
Remarks: Welcome to refined, low-maintenance living in the highly sought-after Wedgewood Golf Villas within Tuscawilla. Perfectly positioned in one of Seminole County’s most established golf communities, this beautifully maintained residence offers the ideal blend of comfort, privacy, and convenience with golf cart-friendly streets, mature surroundings, and HOA-maintained lawn care for truly effortless ownership. Thoughtfully updated with a ROOF (2019), HVAC system (2017), and freshly painted exterior (2026), this move-in-ready 3-bedroom, 2-bath home showcases timeless appeal and functional design. Inside, abundant natural light, soaring vaulted ceilings, and a warm, inviting layout create an atmosphere that feels both spacious and intimate. The expansive great room, anchored by a charming fireplace, serves as the heart of the home — ideal for entertaining or quiet evenings in. A generously sized 315-square-foot screened lanai extends the living space outdoors, overlooking a large private fenced backyard with endless potential for a custom outdoor retreat, garden, or entertaining space. The first-floor primary suite offers a peaceful sanctuary with a spacious en-suite bath featuring a walk-in shower. Plush carpeting adds warmth throughout the living areas and bedrooms, while durable tile flooring enhances the kitchen and baths. Residents enjoy private access to scenic walking trails along the golf course, as well as close proximity to the private Tuscawilla Country Club, Trotwood Park, shopping, dining, nature trails, and top-rated Seminole County schools, with easy connectivity to SR 417 for commuting throughout Central Florida. Offering 1,713 square feet under air and 2,131 total square feet, this exceptional residence presents an outstanding opportunity for discerning buyers seeking comfort, community, and a lock-and-leave lifestyle in the heart of Tuscawilla.
Listing is courtesy of: HOME WISE REALTY GROUP, INC. (407-712-2000)
Listing Agent: Darryl Donkel (407-325-1234)
758 N GRETNA CT, WINTER SPRINGS, FL 32708
$430,00026 Days on yellowkey MLS ID: O6404912
REDUCED by $20,000 (4.4%) on 05/25/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2150 Built: 1977Monthly Fee: $33 Tax: $4,783 (2024)Community: Highlands Sec 4Single Family
Taxes:$4,783
Remarks: Welcome to this versatile and beautifully updated 4-bedroom, 3-bathroom home offering both comfort and opportunity. From the moment you step inside, you’re greeted by a warm, inviting atmosphere that instantly feels like home. The rich vinyl flooring stretches seamlessly throughout, adding both elegance and durability, while the light-colored walls reflect natural light to create a bright, airy space that feels open yet cozy. The heart of the home is a stunning kitchen equipped with newer appliances, including a brand-new refrigerator, making it perfect for everyday living and entertaining. Both the guest and primary bathrooms have been tastefully updated, adding a fresh and contemporary feel. One of the standout features of this property is its flexible layout. The Florida room and back bedroom have been thoughtfully converted into a secondary living space, ideal for generating supplemental income, accommodating guests, or creating a private in-law suite. This area can also be easily reintegrated into the main home if desired. Additional highlights include a HVAC system installed in 2020, providing peace of mind and energy efficiency. Whether you're looking for a primary residence with income potential or a spacious home with adaptable living areas, this property offers incredible value and flexibility.
Listing is courtesy of: KELLER WILLIAMS ADVANTAGE REALTY (407-977-7600)
Listing Agent: Nicholas Kovats (321-356-4072)
629 RYAN CT, WINTER SPRINGS, FL 32708
$479,00023 Days on yellowkey MLS ID: O6396980
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)
140 SEVILLE CHASE DR, WINTER SPRINGS, FL 32708
$779,90059 Days on yellowkey MLS ID: O6395594
Bed: 5 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3129 Built: 1999Monthly Fee: $184 Tax: $5,857 (2024)Community: Seville ChaseSingle Family
Taxes:$5,857
Remarks: Welcome to a residence that truly embodies the phrase "NEIGHBOR'S ENVY, OWNER'S PRIDE" - an exceptional opportunity to own a showpiece home in the gated enclave of Seville Chase where smart living meets timeless elegance. This impeccably maintained, Solar-Powered SMART home offers an unparalleled blend of luxury, comfort, and sustainability. With Fully Paid Solar Panels keeping monthly electric cost under $45. The property greets you with commanding curb appeal, an extra-wide driveway, and an oversized side-entry garage, setting the tone for what lies within. Step inside to discover a designer-inspired interior adorned with gleaming cherry hardwood floors, elegant French doors, soaring tray ceiling, gracefully rounded architectural walls, and refined crown molding- each detail curated for those with a taste for elevated living. The heart of the home, a chef's kitchen, showcases Granite countertops, luxurious 42" cherry cabinetry with crown molding, a built-in desk, ample storage, and sleek stainless-steel appliances-perfectly blending form and function. A thoughtful 3-way split floor plan ensures privacy and space for all, with the primary suite offering a serene retreat complete with his and her walk-in closet and shared linen cabinetry. The fifth bedroom, with its custom-built-in shelving, is ideally suited for a nursery, personal library, or a quiet study. At the Rear, a True Showstopper awaits - an Expansive 1,000+ sq ft screened and paved lanai, fully outfitted with a complete outdoor kitchen, with ADDITIONALD NEW FULL SIZE REFRIGERATOR, Gas hook-up with Range, Microwave, etc. ready to host unforgettable evenings under the stars. Surrounded by Fresh landscaping, New Sod, and vibrant plantings with a gazebo this home has been lovingly updated with a new roof in 2016, solar in 2021, and two high-efficiency A/C systems (5-ton in 2016 and 3-ton in 2014). Ideally located in the highly acclaimed Seminole County School District, and just minutes from premium shopping and places to worship, this is more than a home, it's a lifestyle. Experience the beauty, serenity, and elegance this exceptional property has to provide. Your home awaits. DO NOT FORGET TO CLICK THE LINK TO SEE THE VIDEO WALK-THROUGH.
Listing is courtesy of: WEICHERT REALTORS HALLMARK PROPERTIES (407-644-5385)
Listing Agent: Joji Jacob (407-747-3681)
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