Winter Springs FL Single Family Homes for Sale

4 Beds ⋅ 3 Baths ⋅ Huntridge SubDv. ⋅ 32708 Zip Code

There’s something about a home that makes everyday life feel a little more like vacation and this Winter Springs pool home delivers just that. Set on a spacious lot in the established Huntridge community, this 4-bedroom, 3-bath home offers nearly 2,850 square feet with room to gather, work, entertain and unwind. Soaring ceilings and abundant natural light create an open, airy feel, while the family room with wood-burning fireplace gives the home a warm, inviting center. A separate office/bonus space adds flexibility for working from home, hobbies or a quiet retreat. Out back, bring vacation home with your own private pool, covered lanai and summer kitchen, an ideal setup for long Florida afternoons, weekend cookouts and evenings spent lingering outside. The primary suite opens directly to the pool area and features a generous walk-in closet and spacious bath. Beyond the house, Winter Springs offers an easygoing, outdoor-focused lifestyle with nearby Trotwood Park, miles of walking and biking along the Cross Seminole Trail, Tuscawilla Country Club, and shopping and dining around Winter Springs Town Center and Tuskawilla Road.

248 Huntridge Way, Winter Springs

$490,000

4 Beds ⋅ 3 Baths ⋅ Oak Forest Unit 8 SubDv. ⋅ 32708 Zip Code

Spacious 4 bedroom, 3 bathroom pool home off of Tuskawilla Rd! This home features two story ceiling in the formal living and dining room. The staircase and second story walkway over look the entrance and formal areas. The family room has a fireplace and is joined with the kitchen. On the first floor are also three large bedrooms, two of the bedrooms have attached baths. The primary bedroom is upstairs and has double walk in closets, and an oversized en suite bathroom. The pool has a screen enclosure and the yard is fenced. Roof replaced in 2022, complete Replumb ins 2023.

1142 Oday Drive, Winter Springs

$299,900

3 Beds ⋅ 2 Baths ⋅ Wildwood SubDv. ⋅ 32708 Zip Code

WINTER SPRINGS 3-BEDROOM HOME UNDER $300K — PAID-OFF SOLAR, 2022 ROOF AND MOVE-IN READY! If you're comparing homes under $300,000, take a closer look at what 736 Summerland Drive offers: a renovated 3-bedroom, 2-bath single-family home with approximately 1,298 square feet, paid-off solar panels, a newer roof and access to community amenities. Inside, the updating has already been completed. The refreshed kitchen features modern cabinetry, stone countertops, stainless steel appliances and updated finishes, complemented by renovated bathrooms, flooring, lighting and a clean, contemporary feel throughout the home. But the value here goes beyond cosmetic updates. The roof was replaced in 2022, and the solar system is paid off—meaning there is no solar loan for the buyer to assume. These are meaningful improvements already in place rather than projects or expenses waiting for the next owner. The 3-bedroom, 2-bath layout provides flexibility for everyday living, working from home, guests or hobbies, while the home's manageable footprint offers comfortable living without unnecessary upkeep. The community also offers amenities including a swimming pool, tennis courts and playground, providing additional recreational options without the maintenance of a private pool. Conveniently located in Winter Springs with access to shopping, dining, recreation and major Central Florida roadways. If your search is focused on getting the most for your money under $300,000, compare the entire package at Summerland: 3 bedrooms | 2 bathrooms | Approximately 1,298 sq. ft. | Renovated interior | 2022 roof | Paid-off solar | Community amenities | Winter Springs location The renovation gets your attention. The roof, paid-off solar, location and price are what make the value worth a closer look. Schedule your private showing today.

736 Summerland Drive, Winter Springs

$475,000

3 Beds ⋅ 2 Baths ⋅ Eagles Watch Ph 1 SubDv. ⋅ 32708 Zip Code

Property is well maintained, had been owned by a former major league baseball prayer. Adjacent to a nice secluded pond. The pool and lanai area is wonderful for quiet sitting, meditation, reading and then jump into the pool for a refreshing dip. The subdivision is one minute from a convenience store and access to Rt 417 highway to all parts of Central Florida. Spacious master bedroom with very big walk-in closet. This is in move-in condition subject only to your color decorations. Part of the Tuscawilla Master Community !!

133 Redtail Place, Winter Springs

$374,400

3 Beds ⋅ 3 Baths ⋅ Greenspointe SubDv. ⋅ 32708 Zip Code

Welcome to this beautifully updated 3 bedroom, 3 bath home nestled in an established Winter Springs community! Conveniently located near shopping, dining, parks, and major roadways, including SR 417 and I-4, this home combines comfort, style, and an incredibly versatile floor plan. Freshly painted inside and out, the home features new carpet, updated bathrooms, and spacious living areas filled with natural light. The beautifully updated kitchen showcases soft close cabinetry, quartz countertops, stainless steel appliances, and a modern tile backsplash. A unique kitchen opening overlooks the adjacent nook and provides views of the outdoors, creating an open and connected feel. The spacious living room is designed for both relaxing and entertaining, featuring a wood burning fireplace, ceiling fan, and large windows overlooking the lush backyard. The versatile bedroom layout is truly a standout feature. One bedroom and a full bathroom are located downstairs, while the two upstairs bedrooms each feature their own private en-suite bathroom, providing excellent privacy and flexibility for family, guests, or a dedicated home office or guest space. Sliding glass doors lead to an impressive elevated balcony, while the lower level provides additional patio space for enjoying the peaceful outdoor setting. Step outside and enjoy a private backyard surrounded by mature tropical landscaping and no rear neighbors, creating a peaceful Florida retreat. A two car garage and durable tile roof add even more appeal. With its stylish updates, unique floor plan, private outdoor spaces, and exceptional bedroom configuration, this Winter Springs home is a rare find that combines space, comfort, privacy, and functionality. Schedule your private showing today!

662 Nighthawk Circle, Winter Springs

$429,900

3 Beds ⋅ 2 Baths ⋅ Greenbriar SubDv. ⋅ 32708 Zip Code

Welcome home to this beautiful, move-in ready single-story residence situated in the highly desirable Greenbriar community in Winter Springs! Nestled along the manicured grounds near Tuscawilla Golf and Country Club, this updated 3-bedroom, 2-bathroom home features 1,587 sq. ft. of comfortable, functional living space with a 2-car attached garage. Major big-ticket improvements offer complete peace of mind, including a brand-new roof, new energy-efficient windows, a new water heater, and a 5-year-young HVAC system. Step inside to an inviting open layout filled with natural light and stylish upgrades throughout. The kitchen and bathrooms feature stunning quartz countertops, creating a fresh, modern aesthetic that makes daily living and entertaining a joy. The primary bedroom serves as a peaceful retreat complete with an updated private en-suite bathroom, while two additional spacious bedrooms offer perfect flexibility for guest quarters, a nursery, or a dedicated home office. Outside, enjoy a low-maintenance lot with mature landscaping and beautiful community surroundings. The Greenbriar neighborhood features tree-lined streets, a community park, and a sparkling pool—all zoned for top-rated Seminole County schools (Rainbow Elementary, Indian Trails Middle, and Winter Springs High). Conveniently located near shopping, dining, parks, and major roadways, this turn-key property is completely ready for its new owners—schedule your private showing today!

998 White Springs Lane, Winter Springs

$360,000

2 Beds ⋅ 2 Baths ⋅ Greenbriar Sub Ph 2 SubDv. ⋅ 32708 Zip Code

Rare opportunity to own in one of Winter Springs' most sought-after communities! Located in the heart of Tuscawilla, this home offers an exceptional combination of location, lifestyle, and potential. Enjoy a spacious layout, mature landscaping, and a private setting just minutes from top-rated Seminole County schools, Tuscawilla Country Club, parks, trails, shopping, and dining. Whether you're looking for your forever home or your next investment, opportunities like this don't come along often.

923 Torrey Pine Drive, Winter Springs

$399,999

3 Beds ⋅ 2 Baths ⋅ Sunrise Unit 2-B SubDv. ⋅ 32708 Zip Code

LOCATION, SPACE AND A NEW ROOF IN WINTER SPRINGS! This 3-bedroom, 2-bath home offers 2,116 sqft on a 0.28-acre corner lot directly across from Sunrise Community Park, in one of Seminole County's most sought-after cities. The seller will install a brand-new roof prior to closing once the home is under contract, so one of the biggest items is already taken care of. The home is generously sized throughout, with large rooms and a split-bedroom floor plan that works well for a home office, guests or entertaining. Many of the big projects are already done, including a complete repipe, a renovated kitchen, a remodeled primary bath, and fresh interior and exterior paint. Beyond that, it's ready for your vision and finishing touches, a rare chance to add your own style and build equity in a neighborhood where homes hold their value. Outside, the fully fenced backyard has plenty of room for gardening, pets, play or weekend barbecues, and the corner lot gives you extra space and breathing room. A 2-car garage, a low annual HOA, and a location outside the high-risk flood zone (Flood Zone X) add to the value. Then there's the location. Winter Springs offers a small-town feel with big-city access. You're served by Seminole County's highly regarded public schools and close to the Cross Seminole Trail, Central Winds Park, local shopping and dining, and quick connections to SR 417 and SR 434 for easy commutes around Orlando. Homes this size, on a lot like this, in a city like Winter Springs, don't come along often. All proposals welcome. Come see it and make it yours.

1298 Madelena Avenue, Winter Springs

$350,000

2 Beds ⋅ 2 Baths ⋅ Highland Village 1 SubDv. ⋅ 32708 Zip Code

Great Opportunity in Winter Springs! This single family home has 2 bedrooms, 2 bathrooms, and a large upstairs bonus room - great for an office (or used as another bedroom!). Upon entry you'll be impressed with the high vaulted ceilings and wide open view to the living and dining room. The Primary Bedroom is well sized, and the bathroom features a large walk-in closet, dual sinks, and a shower garden tub. The kitchen has newer appliances and solid wood cabinets. Check out the back yard - it's one of the largest lots in the community - with beautiful grass and a new fence! There's also a screened-in back porch and a large shed - great for storage. 2021 ROOF! Amazing Seminole County Schools!

321 Kirkcaldy Drive, Winter Springs

$374,900

3 Beds ⋅ 2 Baths ⋅ North Orlando Ranches Sec 02 SubDv. ⋅ 32708 Zip Code

Welcome to this charming 3-bedroom, 2-bathroom home in the desirable North Orlando Ranches neighborhood. This home features a classic, traditional floor plan that provides distinct and comfortable living spaces. The heart of the home is a cozy living room anchored by a beautiful fireplace, perfect for relaxing evenings. The kitchen has been thoughtfully updated, boasting durable countertops and modern stainless-steel appliances. The primary bedroom offers plenty of storage with a large walk-in closet. Step outside to discover your own private pool, creating a wonderful outdoor retreat for cooling off and unwinding. The location is exceptionally convenient, situated near top-rated schools, shopping, dining, and major highways for an easy commute to local essentials and employment hubs. Schedule your private showing today! One or more photos in this listing have been virtually staged.

629 Alton Road, Winter Springs

$665,000

4 Beds ⋅ 3 Baths ⋅ Chestnut Estates Ph 2 SubDv. ⋅ 32708 Zip Code

MOTIVATED SELLER! Elegant conservation retreat in prestigious Chestnut Estates-Tuscawilla. On a quiet cul-de-sac, this impeccably maintained four-bedroom, three-bath residence offers a rare combination of privacy, timeless comfort and everyday luxury. Backing to a serene conservation area with no rear neighbors, the home is surrounded by mature landscaping and picturesque natural views, creating a peaceful retreat, and rear patio has new pavers. Thoughtfully designed with a desirable split-bedroom floor plan, the spacious interior offers functionality and elegance. Generous closet space, large pantry and built-in workspace provide everyday convenience, while the open concept kitchen flows seamlessly into the family room and casual dining area, creating a warm and welcoming atmosphere that's ideal for gathering with family and friends. An oversized bonus room/enclosed Florida room with rich wood flooring expands the living space and offers endless possibilities, including a game room, music room and fitness studio. Enhanced with a mini-split system installed in 2025, this versatile space provides year-round comfort and is the ideal setting for entertaining or enjoying quiet evenings while overlooking the tranquil conservation backdrop. Roof (2023) with secondary barrier, HVAC (2025) with AC purification system included, plumbing updates and newer water heater. Schedule your private showing today!

223 Blue Creek Drive, Winter Springs

$600,000

5 Beds ⋅ 3 Baths ⋅ Winter Spgs Unit 4 SubDv. ⋅ 32708 Zip Code

Seller is willing to contribute towards Buyers closing costs with reasonable offer. Welcome home to this thoughtfully updated 5-bedroom, 3-bath residence nestled on an oversized lot beneath a canopy of mature trees in the highly sought-after Tuskawilla community of Winter Springs. Offering over 2,500 square feet of thoughtfully designed living space, this home features a desirable split floor plan with the primary suite tucked away in its own private wing, creating a peaceful retreat from the secondary bedrooms. At the heart of the home is the beautifully remodeled kitchen, featuring quartz countertops, updated cabinetry, modern fixtures, updated appliances, and plenty of space for gathering with family and friends. The spacious living and dining areas provide an inviting setting for everyday living and entertaining, while the fully enclosed Florida room serves as a true extension of the home, making it the perfect place to host movie nights, enjoy your morning coffee, or unwind while overlooking the spacious backyard shaded by mature trees. Recent improvements include luxury vinyl plank flooring and baseboards throughout, fresh interior and exterior paint, refreshed landscaping, an updated sprinkler system, a whole-house water softener and filtration system, and two beautifully renovated bathrooms featuring updated vanities, flooring, fixtures, toilets, and shower tile. Additional major updates include a roof replaced in 2018, HVAC replaced in 2020, updated plumbing, and an electrical panel replaced in 2023, providing added peace of mind for years to come. Located in one of Winter Springs' most established communities, residents enjoy a voluntary HOA, optional memberships to Tuskawilla Country Club with golf, swimming, fitness, tennis, and social amenities, nearby Trotwood Park, golf cart-friendly streets, and access to Seminole County's top-rated schools. Conveniently located near shopping, dining, and SR-417, this home offers the perfect combination of modern updates, timeless character, and an exceptional location.

1015 Antelope Trail, Winter Springs

$335,000

3 Beds ⋅ 2 Baths ⋅ Foxmoor Unit 3 SubDv. ⋅ 32708 Zip Code

MOVE-IN READY HOME on an amazing 0.3-acre corner lot! In the heart of Seminole County's Winter Springs lies your future home. This warm, cozy yet spacious home with an oversized primary bedroom and wood-burning fireplace will make you fall in love. The dining area flows into the kitchen and then into the family room, overlooking a sweeping backyard that's perfect for indoor-outdoor living. Fresh interior paint and new flooring enhance the home's appeal. Additional highlights include a spacious 2-car garage and access to highly regarded Seminole County schools. Conveniently located near major highways, shopping, dining, and parks, this home offers a blend of comfort and convenience. Schedule your showing today.

717 Lancewood Drive, Winter Springs

$464,000

3 Beds ⋅ 2 Baths ⋅ North Orlando Ranches Sec 02 SubDv. ⋅ 32708 Zip Code

Welcome home to this beautifully maintained 3-bedroom, 2-bath residence nestled on a picturesque lot in the desirable North Orlando Ranches community. Offering the freedom of no HOA, this move-in-ready home combines comfort, style, and an unbeatable location. Step inside to discover a bright, open floor plan highlighted by vaulted ceilings, a charming bay window in the dining room, and a modern kitchen designed for both everyday living and effortless entertaining. Throughout the home, you’ll find no carpet—only attractive ceramic tile and laminate flooring for easy maintenance. The spacious primary suite features a walk-in closet and a private ensuite bathroom complete with a large walk-in shower. An inside laundry room adds convenience with a utility sink and additional storage space. Relax year-round in the air-conditioned Florida room, where French doors open to a peaceful, shaded backyard—perfect for morning coffee, outdoor gatherings, or simply enjoying the natural surroundings. Located within the highly acclaimed Seminole County Public School district, this exceptional home is just minutes from SR 434, shopping, dining, parks, and entertainment, making commuting and daily errands a breeze. Don’t miss this wonderful opportunity to own a move-in-ready home in one of Winter Springs’ most desirable locations. Schedule your private showing today!

619 Coral Way, Winter Springs

$420,000

3 Beds ⋅ 2 Baths ⋅ Oak Forest Unit 2b SubDv. ⋅ 32708 Zip Code

Discover 963 Sequoia Dr, recently updated with fresh interior paint and partial flooring replacement throughout the residence. The kitchen includes all stainless steel appliances, complementing the updated interior. The exterior features a patio, fully fenced in backyard, a practical storage shed, and an in ground pool. This updated residence provides comfort and an exceptional outdoor retreat ready for everyday enjoyment. City of Winter Springs Oak Forest maintenance assessment: $60 annually, collected with the property tax bill. This is not an HOA fee. Included 100-Day Home Warranty with buyer activation

963 Sequoia Drive, Winter Springs

1329 Augusta National Boulevard, Winter Springs

$529,900

3 Beds ⋅ 2 Baths ⋅ Country Club Village Unit 3 SubDv. ⋅ 32708 Zip Code

Renovated, remodeled, and reimagined in the highly sought-after Country Club Village at Tuskawilla. This beautifully renovated residence has been thoughtfully transformed with an extraordinary level of quality and attention to detail, delivering a truly turnkey opportunity for today’s discerning buyer - NO EXPENSE SPARED! Extensive recent improvements include a NEW TILE ROOF (July 2025), new gutters, all-new plumbing throughout (2026), fresh interior and exterior paint, and newly textured ceilings throughout, creating a clean, modern aesthetic from top to bottom. Inside, elegance meets functionality with stunning European white oak wood flooring throughout the main living areas, complemented by new carpet in the secondary bedrooms for added comfort. The heart of the home is the beautifully reimagined kitchen, featuring new 42-inch cabinetry, quartz countertops, all-new appliances, and a designer backsplash that adds both sophistication and visual appeal. Entertain effortlessly with a stylish wet bar complete with a beverage refrigerator and matching designer backsplash. Every bathroom has been completely remodeled, showcasing luxurious finishes and quartz surfaces throughout. Additional upgrades include new lighting fixtures inside and out, new door handles and hinges, new plugs and switches, custom roller shades throughout, and a custom closet system in the primary suite. Outside, refreshed landscaping enhances curb appeal and completes this impressive renovation, making this home a rare blend of timeless design, modern luxury, and move-in-ready convenience. The HOA-maintained lawn allows for low-maintenance living, while the location places you just moments from the private Tuscawilla Country Club. Zoned for some of the highest-rated public schools in the state and offers exceptional convenience—just 25 minutes from downtown Orlando, 30 minutes to Orlando International Airport, and less than an hour from Florida’s beautiful beaches and world-renowned theme parks. This property may be under audio/visual surveillance.

1329 Augusta National Boulevard, Winter Springs

$349,900

3 Beds ⋅ 2 Baths ⋅ North Orlando 2nd Add SubDv. ⋅ 32708 Zip Code

PRICE REDUCTION / BACK on Market after REFRESH & REMODEL for NEW ROOF, NEW BATHROOMS, NEW A/C, NEW EXT PAINT, and MORE! -- Sweet & spacious 3 bed, 2 bath, 1368 sq ft, home on a corner lot in the heart of Winter Springs in a much sought after neighborhood. Fresh Interior Paint, New Kitchen with a floating Island workspace, SS appliances, Tile flooring throughout Dining area, Living and Family Room, inside laundry room. Big, open, wrap-around porch in back is pre-plumbed & trussed for possible expansion of Primary Bedroom. LARGE Fenced backyard, with FRUIT TREES, mature oaks and tidy landscaping. Single car garage can be used as office/storage. Additional Family Room has been added on. Really LOVELY home, TERRIFIC area, GREAT schools! This one is a gem, perfect for first-time buyers! **Note to Investors - offers will need to be at or near full-price**

101 S Flamingo Avenue, Winter Springs

$605,000

5 Beds ⋅ 2 Baths ⋅ Parkstone SubDv. ⋅ 32708 Zip Code

Enjoy waterfront views and your own private pool in this spacious 5-bedroom, 2-bath home located in the highly sought-after gated community of Parkstone in Winter Springs. Perfectly positioned with tranquil pond views, this home offers a desirable three-way split floor plan, open living spaces, and an ideal blend of comfort, functionality, and outdoor living. Inside, you’ll find luxury vinyl plank flooring throughout the main living areas, a beautifully updated kitchen featuring granite countertops, refinished cabinetry, and a stylish backsplash, along with tastefully remodeled bathrooms showcasing shaker-style vanities, updated fixtures, and wood-look tile flooring. Energy-efficient upgrades include Low-E double-hung windows, an updated roof (2021), Carrier HVAC system, LED lighting, a whole-house water filtration system, two mini-split air conditioning systems (2025), and an energy-efficient year-round. The backyard is also been fully fenced, creating a private space for pets, play, and outdoor enjoyment. Step outside to your own backyard retreat featuring a sparkling pool, relaxing spa, and picturesque water views. Whether you’re entertaining guests or enjoying a quiet evening watching the sunset over the pond, this outdoor space is sure to impress. Additional features include pool deck speaker pre-wiring and a 220-volt outlet ready for an electric vehicle charger. Parkstone residents enjoy an exceptional lifestyle with lawn maintenance included in the HOA, a community pool, fishing pier, tennis courts, playgrounds, walking trails, scenic ponds, and gated security. The community borders the Cross Seminole Trail and is just a short walk to Central Winds Park and the dog park. Located in Seminole County with highly rated A-rated schools and convenient access to shopping, dining, and major roadways, this home truly offers the best of Florida living. Don’t miss your opportunity to own this exceptional waterfront home in one of Winter Springs’ most desirable communities!

216 Tavestock Loop, Winter Springs

$344,000

3 Beds ⋅ 3 Baths ⋅ Highlands Sec 1 SubDv. ⋅ 32708 Zip Code

Welcome to 830 Dunbar Ter, a residence arranged for everyday comfort and practical living. The interior features a fireplace, serving as a central point, while the kitchen contains an accent backsplash that provides a subtle design element. Exterior amenities include a substantial deck that connects directly to a fully fenced in backyard, suitable for various outdoor activities. Move right into comfort and refined outdoor living.

830 Dunbar Terrace, Winter Springs

$515,000

5 Beds ⋅ 3 Baths ⋅ Seven Oaks SubDv. ⋅ 32708 Zip Code

Explore 811 Maple Leaf Loop, recently enhanced with fresh interior paint. The kitchen includes a functional island, and the primary bathroom provides double sinks for practical use, a walk in closet and convenience of a separate tub and shower. Beyond the interior, exterior grounds feature a covered patio and a fenced in backyard. Discover modern comfort and practical living in this updated residence. Included 100-Day Home Warranty with buyer activation

811 Maple Leaf Loop, Winter Springs

$284,999

3 Beds ⋅ 2 Baths ⋅ North Orlando Terrace SubDv. ⋅ 32708 Zip Code

3 BEDROOM 2 BATH HOME LOCATED ON CUL DE SAC STREET. WOOD CABINETS, SOLID SURFACE COUNTERS IN KITCHEN WITH NEW SINK.. SPLIT BEDROOM PLAN. FENCED REAR YARD. NEW ROOF IN 2025. NEW VINYL SIDING ON GARAGE. NEWLY REPAINTED INSIDE IN SEPTEMBER 2026.. . GREAT HOME FOR OWNER OCCUPANT OR INVESTOR.

207 Birch Terrace, Winter Springs

$349,900

3 Beds ⋅ 2 Baths ⋅ The Seasons SubDv. ⋅ 32708 Zip Code

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!

108 Sundance Court, Winter Springs

$557,900

4 Beds ⋅ 3 Baths ⋅ Parkstone SubDv. ⋅ 32708 Zip Code

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!

268 Tavestock Loop, Winter Springs

$324,900

3 Beds ⋅ 2 Baths ⋅ Highland Village 1 SubDv. ⋅ 32708 Zip Code

Seller is offering to contribute towards the buyer's closing cost up to $5,000. Welcome home to this cozy 3-bedroom, 2-bath bungalow-style home located in the resort-like Highlands community, offering 1,178 sq. ft. of living space. This home features vaulted ceilings, ceramic tile throughout, fresh interior paint, and a newly renovated kitchen with granite countertops, solid wood shaker-style cabinets, and black appliances. Major updates include a 2025 water heater and a new electrical panel inside and outside. The generously sized primary bedroom includes a built-in California Closets system, providing stylish and highly functional custom storage. The secondary and third bedrooms are also well-sized—perfect for guests, family, or easily converted into a home office. Washer and dryer are included in the sale. Enjoy the covered and screened lanai overlooking a charming New Orleans-style courtyard with pavers, a firepit, and a lamp post. The oversized, fully fenced, and cleared backyard offers plenty of space to relax, entertain, or garden, providing a strong sense of privacy. The Highlands is a highly sought-after, established community with low HOA fees and beautiful mature trees throughout. Amenities include an Olympic-size community pool, walking trails, playground, tennis court, volleyball court, and a clubhouse. Ideally situated just off State Road 434 Florida and Tuskawilla Road, this home offers quick access to Winter Springs Town Center for shopping and dining, and is just a short stroll from Torcaso Park—a lively neighborhood park featuring basketball courts, soccer and football fields, playgrounds for all ages, a splash pad, sand play areas, and picnic pavilions, perfect for both active days and relaxed family outings.

335 Kirkcaldy Drive, Winter Springs

$459,900

4 Beds ⋅ 3 Baths ⋅ Sunrise Estates Unit 1 SubDv. ⋅ 32708 Zip Code

NEW PRICE! MAJOR UPDATES & AN AMAZING BACKYARD RETREAT! Discover a home that offers more than just a place to live — Welcome to this 4-bedroom, 2.5-bath home offering 2,152 SqFt of living space on a spacious 10,019-square-foot lot in the desirable Sunrise Estates community of Winter Springs. BIG-TICKET UPDATES ALREADY COMPLETED! Enjoy added peace of mind with a NEW ROOF (2023), A/C (2020), WATER HEATER (2023), and WHOLE-HOME WATER SOFTENER (2024). Additional features include updated bathrooms, fresh interior paint, ceramic tile flooring, soaring vaulted and cathedral ceilings, and an alkaline water filtration system at the kitchen sink. Step inside and discover a unique multi-level layout designed to offer both comfortable gathering spaces and privacy. The main level welcomes you with spacious formal living and dining areas, while the eat-in kitchen features solid wood cabinetry, solid-surface countertops, a pantry, and generous storage. Just a few steps down, the impressive 21x18 family room creates the perfect setting for relaxing or entertaining, complete with a charming stone wood-burning fireplace and French doors leading to the outdoor living area. Upstairs, you’ll find all four bedrooms, including a spacious primary suite with a walk-in closet. YOUR OWN PRIVATE BACKYARD RETREAT AWAITS! Imagine enjoying your morning coffee on the oversized 21x14 covered and screened lanai, hosting weekend gatherings, or unwinding after a long day. The fully fenced backyard offers a gas fire pit, an additional outdoor fire pit, garden space, a dedicated dog run, play area, and storage shed. A private irrigation well helps maintain the landscaping without using metered household water. Additional highlights include an indoor laundry room, two-car garage, extended driveway parking, public water and sewer, and a LOW HOA: $30 PER MONTH! Located in a non-flood zone and NO rental restrictions, this property offers flexibility for homeowners and investors alike. LOCATION, LOCATION, LOCATION! Conveniently situated near Rainbow Elementary School, Winter Springs Town Center, Oviedo, Tuskawilla Road, shopping, dining, parks, and SR-417, providing easy access to Orlando, UCF, and Lake Mary. A FANTASTIC OPPORTUNITY TO ENJOY SPACE, MAJOR UPDATES, AND OUTDOOR LIVING IN WINTER SPRINGS! The property is vacant and ready for its next owner. Seller may consider assistance toward buyer’s closing costs with an acceptable offer. DON’T MISS YOUR OPPORTUNITY — SCHEDULE YOUR PRIVATE SHOWING TODAY!

1304 Ortega Street, Winter Springs

$1,200,000

5 Beds ⋅ 4 Baths ⋅ Tuscawilla SubDv. ⋅ 32708 Zip Code

Experience the beauty of city living on 2.3 acres in the highly desirable city of Winter Springs with no HOA—where open space, natural surroundings, and an equestrian friendly lifestyle come together. This unique property offers the freedom of rural living while remaining conveniently located near the Tuscawilla area. The fully usable acreage is ideal for horses, cattle, or other livestock. If livestock isn’t your preference, the expansive space is perfect for recreational vehicles, racing cars, or other outdoor hobbies. The 5 bedroom, 3 bath home is solid and ready for your personal updates. A standout feature is the 1,500 sq. ft. garage, offering ample room for a boat, race cars, or additional storage. This 2.3 acre parcel is one of the few remaining equestrian friendly properties in the city of Winter Springs, providing a rare combination of comfort, privacy, and natural surroundings. The home is zoned for highly rated Seminole County schools, offering the perfect blend of private country living and excellent educational opportunities. Seller motivated!

1281 Natures Way, Winter Springs

$389,900

3 Beds ⋅ 2 Baths ⋅ Oak Forest Unit 2a SubDv. ⋅ 32708 Zip Code

Virtually Staged. **NEW PRICE! Now offered at $389,900!** Discover this 3-bedroom, 2-bath home in desirable Winter Springs, conveniently located in a sought-after school zone. The split-bedroom floor plan offers privacy, while the open kitchen with an eat-in area flows into the formal dining and living rooms. Enjoy Florida living from the **large covered porch overlooking the spacious backyard**, with convenient garage access to the rear yard. Great location near schools, parks, shopping, dining, and major roadways. **Come see why this Winter Springs home deserves a spot on your must-see list!**

1012 Forest Circle, Winter Springs

$285,000

3 Beds ⋅ 2 Baths ⋅ Seasons The SubDv. ⋅ 32708 Zip Code

MOTIVATED SELLERS!!! 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.

421 Horizon Drive, Winter Springs

$242,000

3 Beds ⋅ 2 Baths ⋅ Deersong 2 SubDv. ⋅ 32708 Zip Code

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? Buyer needs concessions / closing costs? 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..

270 San Gabriel Street, Winter Springs

$3,700,000

5 Beds ⋅ 7 Baths ⋅ Lake Jessup SubDv. ⋅ 32708 Zip Code

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.

1112 Orange Avenue, Winter Springs

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Winter Springs FL Single Family Homes for Sale

There are 79 single family homes for sale in Winter Springs, Florida as of 2026-11-05, at a median list price of $449,900 and a median of 54 days on market. Detached homes, which make up most of what is for sale here.

Winter Springs single family homes for sale at a glance

Active single family homes	79
Share of the Winter Springs market	66.4% of 119 listings
Median list price	$449,900
Median price per square foot	$251
Median size	1,784 square feet
Median year built	1987
Median days on market	54
On market 60+ days	34 (43.04%)

Source: Stellar MLS via the Bridge RESO feed, pulled 2026-11-05. Updated weekly.

How Winter Springs single family homes compare to the rest of the city

The median single family home in Winter Springs asks $449,900 against $389,900 for the city as a whole, and $251 per square foot against $237. Single Family Homes make up 66.4% of everything on the market here.

50 of them, 63.29%, are asking less than they did originally, at a median reduction of 4.02%. That is the size of a first concession, not a final one.

Winter Springs single family homes by price range

Under $250,000	1	1.3%
$250,000 to $400,000	28	35.4%
$400,000 to $600,000	33	41.8%
$600,000 and up	17	21.5%

Winter Springs single family homes by bedroom count

2 bedrooms	3
3 bedrooms	44
4 bedrooms	22
5 bedrooms+	10

Zip codes

32708 (79)

Frequently asked questions

How many single family homes are for sale in Winter Springs, FL?

There were 79 active single family homes listed in Winter Springs as of 2026-11-05, 66.4% of the 119 residential listings in the city. That count comes from the Stellar MLS feed and is refreshed weekly.

What is the median price of a single family home in Winter Springs, FL?

The median asking price was $449,900 as of 2026-11-05, or about $251 per square foot. The median single family home on the market is 1,784 square feet and was built in 1987.

How long do single family homes take to sell in Winter Springs?

Median days on market was 54 as of 2026-11-05. 34 of the 79 active single family homes, 43.04%, have been listed 60 days or longer, and that is usually where the negotiating room is.

Are Winter Springs single family homes cheaper than houses in Winter Springs?

The median single family home asks $449,900 against $389,900 for all Winter Springs listings, and $251 per square foot against $237 citywide. Price per square foot is the fairer comparison.

The Homes In Orlando Team at NextHome Neighborhood Realty works with buyers and sellers across six Central Florida counties and publishes market data for Orange, Seminole, Lake, and Volusia. Call or text 407-616-9019 to see any Winter Springs listing on this page.