Winter Springs Real Estate

Winter Springs Real Estate

Welcome to Winter Springs, Florida – a charming city nestled in the heart of Seminole County. Known for its picturesque landscapes and family-friendly atmosphere, Winter Springs offers a perfect blend of suburban tranquility and vibrant community life. With its lush parks, scenic lakes, and beautiful nature trails, this city is an outdoor enthusiast’s paradise, providing ample opportunities for hiking, biking, and enjoying the great Florida sunshine.

Winter Springs boasts a rich history and a commitment to preserving its natural beauty. The city is home to several well-maintained parks, including the popular Central Winds Park, which features sports fields, playgrounds, and picnic areas. For those who enjoy a leisurely stroll, the Cross Seminole Trail runs through the city, offering miles of paved paths for walking, jogging, and cycling.

Families will find an array of excellent schools and educational facilities, making Winter Springs an ideal place to raise children. The community is known for its friendly neighborhoods, where residents often come together for local events, farmers markets, and seasonal celebrations.

Conveniently located just a short drive from downtown Orlando, Winter Springs offers easy access to the attractions and amenities of the larger city while maintaining its own unique charm. From cozy cafes to quaint shops, you’ll find everything you need right at your doorstep.

Whether you’re looking to buy your first home, relocate, or invest in property, Winter Springs is a hidden gem that promises a high quality of life and a welcoming community. Discover the beauty and warmth of Winter Springs – your new home awaits!

Newest Listings in Winter Springs

$499,999
3 Beds ⋅ 3 Baths ⋅ Country Club Village Unit 1 SubDv. ⋅ 32708 Zip Code
Here it is all together with clear paragraph breaks. No extra chatter. Welcome to 1010 W. Pebble Beach Circle, tucked away in the desirable Country Club Village of Tuscawilla. From the moment you step inside, the home feels bright, open, and full of character, with soaring vaulted ceilings, exposed wood beams, skylights, and a striking stone fireplace anchoring the main living space. Updated laminate flooring flows through the spacious living and dining areas, while the kitchen features granite countertops and stainless appliances. A major highlight of the home is the first-floor primary suite, complete with a private bath and walk-in closet, offering added convenience and privacy. Upstairs, secondary bedrooms each enjoy their own balcony, creating little retreats for family or guests. The oversized screened and covered rear lanai feels like a true extension of the home, perfect for relaxing or entertaining year-round. Multiple private courtyards and mature landscaping add to the overall sense of privacy and charm. And With a 2022 AC, updated plumbing, water softener, and low-maintenance HOA care, this home offers comfort today and peace of mind for the future. All just minutes from Tuscawilla Country Club, Trotwood Park, trails, and great local dining.

1010 W Pebble Beach Circle, Winter Springs
$285,000
3 Beds ⋅ 2 Baths ⋅ Seasons The SubDv. ⋅ 32708 Zip Code
Welcome to 526 Seasons Court, where low-maintenance living meets comfort, convenience and a great community setting! This beautifully updated home is tucked away on a fantastic lot with a peaceful pond view in the backyard, offering a relaxing backdrop and a little extra privacy. Inside, the remodeled kitchen shines with modern white shaker cabinetry, quartz countertops and luxury vinyl plank flooring, creating a bright and inviting space that feels fresh and move-in ready. Major updates include a 2022 roof and 2021 HVAC, giving you peace of mind for years to come. The home also features a 1-car garage, one assigned parking space and plenty of guest parking. The low monthly HOA includes lawn maintenance, so you can spend less time on yard work and more time enjoying the community's impressive amenities, including a sparkling pool, playground, tennis courts and basketball courts. Located in desirable Winter Springs, this is an easy-to-love home offering the perfect combination of updates, amenities and low-maintenance living. Come see why this one is worth calling home!

526 Seasons Court, Winter Springs
$785,000
5 Beds ⋅ 4 Baths ⋅ Winding Hollow Unit 5 SubDv. ⋅ 32708 Zip Code
WELCOME HOME to 337 Twelve Oaks Drive! This stunning Wisteria II Model offers 5 bedrooms, 3.5 bathrooms, and 3,660 square feet of beautifully maintained living space, perfectly positioned on an oversized .25-acre premium waterfront lot in the sought-after Winding Hollow community of Winter Springs. From the moment you arrive, you'll appreciate the lush landscaping, exceptional curb appeal, and pride of ownership throughout this immaculate home. Inside, an abundance of thoughtful upgrades and elegant finishes create the perfect blend of comfort, style, and functionality. The renovated gourmet kitchen is truly the heart of the home, featuring floor-to-ceiling custom cabinetry, quartz countertops, a large center island, stainless steel appliance package, stylish tile backsplash, and a water filtration system. The spacious kitchen opens beautifully to the expansive family room, creating an ideal space for everyday living and entertaining. Additional upgrades include all-new windows and doors, beautiful wood-plank ceramic tile flooring, plantation shutters, and newer attic insulation, providing both style and improved energy efficiency. The first floor features a spacious primary suite, a versatile den/office, formal living room, formal dining room, and a huge family room with serene views of the private pool, expansive patio, and tranquil pond. The primary suite provides a peaceful retreat with plenty of space and privacy. Upstairs, you'll find three additional generously sized bedrooms, each offering large closets, along with two full bathrooms and an impressive 17' x 24' game room—perfect for a media room, playroom, home gym, or additional entertaining space. The three-car garage provides abundant storage and parking, and features a custom garage floor coating for a polished, durable finish. Step outside and experience your own private oasis. The sparkling pool, spacious patio, lush landscaping, and peaceful waterfront setting create the perfect backdrop for relaxing mornings, afternoon swims, and memorable gatherings with family and friends. Located in desirable Winding Hollow, this home offers an exceptional Winter Springs lifestyle with walking trails, community park areas, close proximity to top-rated Seminole County schools, shopping, Winter Springs Town Center, restaurants, Central Winds Park, the Seminole Trail, and more. With its premium waterfront setting, private pool, spacious floor plan, three-car garage, extensive upgrades, and beautifully appointed living spaces, 337 Twelve Oaks Drive is more than just a home—it’s a lifestyle!

337 Twelve Oaks Drive, Winter Springs
$325,000
3 Beds ⋅ 2 Baths ⋅ Wildwood SubDv. ⋅ 32708 Zip Code
Welcome to 654 Cypress Lane, a move-in-ready 3-bedroom, 2-bathroom home featuring fresh interior paint throughout. The main entry opens into a bright living room that connects seamlessly to the kitchen, complete with quartz countertops and stainless steel appliances. Designed with a practical split floor plan, the primary bedroom sits on one side of the home with its own en-suite bathroom, while two secondary bedrooms share a second full bath on the opposite side. A dedicated laundry room adds extra convenience. Out back, a screened-in back porch offers a quiet spot to relax, leading to a private, fenced yard framed by mature shade trees. Homeowners will also appreciate the benefit of a low HOA fee, with amenities such as a pool, basketball and tennis court, playground, dog park, and much more! Located in Winter Springs, this home puts you near top-rated Seminole County schools, local parks, and the Cross Seminole Trail. Enjoy easy access to shopping and dining at the Winter Springs Town Center, with quick routes to SR 417 for a smooth commute to UCF, Oviedo, and Orlando.

654 Cypress Lane, Winter Springs
$375,000
4 Beds ⋅ 4 Baths ⋅ Tuscawilla Unit 12 SubDv. ⋅ 32708 Zip Code
Looking for a home, you can make your own while living in it? This 4-bedroom, 3.5-bath single-family home provides an excellent opportunity for an owner-occupant to move in, make updates over time, and build equity while turning the property into their own. Also, a great opportunity for investors, landlords, and buyers looking for a fix-and-hold or value-add project. Located in the established Tuscawilla/Winter Springs area of Seminole County, this home sits on a spacious 0.34-acre lot enclosed by PVC fencing on all four sides in a nice neighborhood. The home features a huge living room, fireplace, ceiling fans throughout, covered porch, attached 2-car garage, skylights, and a screened lanai with pool and jacuzzi. The primary suite includes a double/split vanity with both a tub and separate shower. The spacious yard provides plenty of room to enjoy the outdoor space and make the property your own. Conveniently located near parks, shopping, schools, museums, UCF, Rollins College in Winter Park, Orlando Sanford International Airport, and Orlando International Airport. Whether you're searching for a fixer-upper, handyman special, owner-occupant opportunity, investment property, rental property, landlord opportunity, or value-add project, this property provides plenty of potential to update, improve, and build value over time. Being sold AS-IS.

1625 White Dove Drive, Winter Springs
$475,000
3 Beds ⋅ 2 Baths ⋅ Deer Run Unit 23a SubDv. ⋅ 32708 Zip Code
Tucked beneath a canopy of majestic oaks in the established Tuscawilla Forest community, this charming 3-bedroom, 2-bath, 2-car garage home offers approximately 1,700 square feet of living space on a spacious .26-acre lot—along with something you simply can't recreate overnight: character, mature landscaping and the welcoming feel of an established neighborhood. Cherished by the same homeowner since 2004, this has been a much-loved home for more than two decades. The owners have especially treasured their wonderful neighbors and convenient location, and now it's time for a new owner to begin their own chapter here. Step inside and you'll immediately appreciate the desirable split-bedroom floor plan, vaulted ceilings and skylights that bring natural light into the main living areas. At the heart of the home, the inviting living space features a double-sided fireplace, warm wood accents and built-in shelving. The kitchen offers real wood cabinetry, generous counter space, breakfast bar, stainless-steel appliances and stylish tile backsplash, opening naturally to the main living area. The primary suite offers a private retreat with a beautifully remodeled bath featuring dual vanities, soaking tub and separate glass-enclosed walk-in shower with striking tile and pebble-stone accents. The secondary bath has also been beautifully remodeled. MAJOR IMPROVEMENTS HAVE ALREADY BEEN MADE, including a NEW ROOF IN 2021 with new gutters and gutter guards, A/C SYSTEM IN 2020 with parts-and-labor warranty noted through 2030, REMODELED BATHROOMS IN 2024, PEX PLUMBING, TWO-TONE VINYL PRIVACY FENCE IN 2023 and NEW ST. AUGUSTINE GRASS IN 2023. Additional improvements include the updated kitchen, lighting and ceiling fans, flooring and sprinkler system. And then there's the OUTDOOR LIVING! Sliding glass doors lead to an expansive screened and covered lanai, perfect for morning coffee, weekend gatherings or simply enjoying Florida living. Beyond the lanai, the large, private fenced backyard is shaded by beautiful mature trees with plenty of room for gardening, pets, play, entertaining—or perhaps that future pool you've been dreaming about. Whether hosting friends, enjoying a quiet evening under the trees or simply unwinding after a long day, this backyard offers the space and privacy to enjoy being home. LOCATION, LOCATION, LOCATION! Enjoy the charm of an established Winter Springs neighborhood with access to Seminole County Public Schools while staying close to everything. Nearby Trotwood Park, Central Winds Park, Bear Creek Nature Trail and the Cross Seminole Trail provide walking, biking, sports, playgrounds and outdoor recreation. Shopping, dining and everyday conveniences are nearby, with easy access to Oviedo, UCF, Winter Park, SR 417 and the greater Orlando area. With its mature surroundings, nearby parks and trails, convenient location and the kind of neighbors the current owners will truly miss, it's easy to understand why they called this home for more than 20 years. Some homes simply have a story—and this one has been loved for more than two decades. Filled with memories and thoughtfully cared for through the years, 288 Ringwood Drive is ready for its next chapter...and its next owner to call it HOME.

288 Ringwood Drive, Winter Springs
$930,000
4 Beds ⋅ 3 Baths ⋅ Bentley Club At Bentley Green SubDv. ⋅ 32708 Zip Code
Welcome to 864 Bentley Green Circle, a move-in ready luxury sanctuary situated on a quiet cul-de-sac lot in Winter Springs. Offering 4 bedrooms, 3 full bathrooms, and over 2,200 square feet of meticulously updated living space, this home seamlessly blends sophisticated interior accents with private, resort-style outdoor living. Arrive via a grand circular drive centered around a professionally landscaped island, featuring a newly updated limestone walkway that creates an elegant entryway. Inside, the light-filled open floor plan boasts high ceilings, newly painted walls, transoms, interior glass doors, and smart recessed lighting with nightlight mode. The main living area features a custom black marble gas fireplace and expansive sliding glass doors leading out to the lanai. A formal dining room offers luxury vinyl flooring, custom crown molding, and a statement chandelier, while a dedicated lounge/den provides cozy custom built-ins and window seats. The gourmet kitchen comes complete with granite countertops, tile flooring, newly installed stainless-steel appliances (including a new refrigerator), and convenient access to a laundry area with a recently purchased, large-capacity washer and dryer set. The main-level owner's retreat serves as a true sanctuary, featuring hardwood floors, a sitting area, a built-in electric wall fireplace, space for a coffee station, a spacious walk-in closet, and a completely updated spa bath with a deep soaking tub and oversized glass shower. Upstairs, three additional hardwood-floored bedrooms include one configured as an executive home office with scenic views of the nearby pond and golf course. Step outside into your private backyard oasis featuring a saltwater pool and spa with a newly renovated screen enclosure, updated pool equipment, gas heater, and multi-color lighting. Relax under the custom covered lanai showcasing a real wood ceiling, ceiling fan, and custom recessed lights—complete with included patio furniture and exterior TV. The grounds feature manicured landscaping with lush palm trees, privacy hedges, and a tranquil side-yard "Zen garden" designed to attract butterflies and hummingbirds. Rounding out this exceptional property are dual driveways and a 2-car workshop garage equipped with built-in storage shelving and a 240-amp EV charging station.

864 Bentley Green Circle, Winter Springs
$559,900
4 Beds ⋅ 4 Baths ⋅ Parkstone Unit 3 SubDv. ⋅ 32708 Zip Code
Stunning - 2 story waterfront home in Parkstone ! Welcome to this beautifully designed two-story waterfront home in Winter Springs, Florida, offering 4 bedrooms, 3.5 bathrooms, contemporary style, and comfortable indoor-outdoor living. Ideally suited for those seeking a modern home in a desirable Central Florida community, this residence combines thoughtful design with serene waterfront views. Inside, the home features vinyl plank flooring throughout, creating a cohesive, contemporary look while offering durability and easy maintenance. The open-concept design provides an inviting flow between the living spaces, making the home ideal for both everyday living and entertaining. At the heart of the home is a gourmet kitchen featuring quartz countertops and stainless-steel appliances, complemented by a modern aesthetic and ample workspace. The kitchen seamlessly connects to the surrounding living areas, creating a natural gathering space for family and guests. The spacious two-story layout provides excellent separation between living and private spaces, with four bedrooms and three-and-a-half bathrooms offering flexibility for families, guests, a home office, or additional living needs. Step outside to the screened-in patio, where you can relax while taking in peaceful waterfront views. This covered outdoor area extends the home's living space and provides an ideal setting for morning coffee, evening gatherings, or simply enjoying the tranquil Florida surroundings. Located in Winter Springs, the property offers access to highly regarded schools, shopping, dining, parks, recreational amenities, and the many attractions of the greater Orlando area. With its contemporary finishes, spacious two-story design, gourmet kitchen, and waterfront setting, this home offers a desirable combination of modern Florida living and peaceful surroundings.

731 Seneca Meadows Road, Winter Springs
$665,000
4 Beds ⋅ 3 Baths ⋅ Tuscawilla Unit 14a SubDv. ⋅ 32708 Zip Code
Welcome to this exceptional 4-bedroom, 3-bath pool home with a dedicated office, situated on an oversized corner lot in the heart of Tuscawilla in Winter Springs. Featuring a unique three-way split floor plan, generous indoor and outdoor living spaces, and thoughtful updates throughout, this home offers the perfect combination of functionality, privacy, and Florida living. Step inside through the grand foyer, where a spacious dedicated office sits just off the entry and features French doors, crown molding, beautiful flooring, and plantation shutters. Continue into the inviting living room, highlighted by a brick accent wall, vaulted ceilings, and sweeping views of the pool and lanai. Natural light fills the space through an impressive three-panel sliding glass door that disappears into the wall, creating a seamless transition between indoor and outdoor living—perfect for entertaining. The open floor plan flows into a charming breakfast nook and spacious kitchen featuring an abundance of cabinetry and counter space, stainless steel appliances, and a breakfast bar for casual dining. For larger gatherings and special occasions, the separate formal dining room offers plenty of space and is finished with a beautiful statement chandelier. Privately positioned on one side of the home, the primary suite is a true retreat with vaulted ceilings and its own enclosed Florida room—an incredible space for morning coffee, a reading nook, or peaceful space. The expansive primary bathroom features dual vanities, a brand-new Kohler walk-in shower (2026), and a massive walk-in closet with direct access to the bedroom. The home's thoughtful three-way split design provides exceptional privacy. A second wing features two additional bedrooms and a spacious shared bathroom, while the third wing offers a separate bedroom with its own full bathroom and newly renovated shower (2025)—an ideal setup for guests, extended family, or in-law accommodations. Step outside and experience the Florida lifestyle with a sparkling saltwater pool, new pool heater (2025), and a generous covered lanai designed for year-round entertaining. Beyond the pool, the expansive, fully fenced backyard features new pavers (2024) and plenty of room to relax, play, garden, or entertain. Private and serene, this oversized corner lot provides outdoor space that is increasingly hard to find. Additional highlights include no HOA, a new roof and skylights (2019), new salt cell and pool heater (2024) and brand new A/C (2024). Located in sought-after Seminole County, this home is zoned for Oviedo High School and offers convenient access to everything the Tuscawilla community is known for, including walking trails, public parks, and Tuscawilla Country Club with golf, clay tennis courts, a lap pool, fitness center, and dining. With its oversized lot, three-way split floor plan, private pool, dedicated office, flexible living spaces, and incredible Tuscawilla location, this Winter Springs home delivers the space and lifestyle you've been searching for. Call for your private showing today!

674 Vistawilla Drive, Winter Springs
$549,000
3 Beds ⋅ 4 Baths ⋅ Seminole Crossing Townhomes SubDv. ⋅ 32708 Zip Code
Welcome to 1166 Spotted Sandpiper Loop in Winter Springs, a spacious three-story, 3-bedroom, 3.5-bath townhome in Seminole Crossing. With a floor plan that offers plenty of room to spread out, this home is one of only two townhomes in the community featuring this unique layout. Its multi-level design gives the home more character and separation than the typical boxy townhome, with gathering spaces and private retreats thoughtfully placed across three floors. The first floor features a private bedroom and full bathroom, making it ideal for guests, extended family, or a home office, along with an oversized rear-facing garage and covered front porch. Upstairs, the main living level brings the gourmet kitchen, dining area, and family room together in an open, light-filled space. Designed with both everyday living and entertaining in mind, the gourmet kitchen features a walk-in pantry, generous prep and storage space, and double ovens. French doors open to an expansive balcony, creating an inviting spot to enjoy some fresh air or unwind at the end of the day. The third floor is home to the primary suite, a second bedroom, and a flexible loft. The primary suite offers a large walk-in closet and spacious bathroom with dual sinks, soaking tub, and separate shower. The second bedroom also has a walk-in closet, with a full bathroom conveniently located just outside the bedroom, while the loft can easily become a lounge, media area, study, or home office. The laundry room is conveniently located nearby. One of the biggest perks of townhome living here is the maintenance-free exterior. The HOA takes care of the outdoor upkeep, including mowing, weeding, flower beds, tree trimming, and more. When the time comes, the HOA is also responsible for exterior painting and roof replacement, giving you even less to worry about. And the location makes everyday errands surprisingly easy. The Cross Seminole County Trail is just a short distance from the home located right outside the neighborhood, while nearby grocery stores and restaurants are also just a walk away. Starbucks is even closer, with Chick-fil-A, Wawa, and Ace Hardware coming soon. Residents also enjoy access to a community pool, sidewalks, and additional recreational spaces, with convenient access to SR 434, Winter Springs Town Center, Oviedo, and surrounding Seminole County. **This house comes with a REDUCED RATE through the seller's preferred lender. This is a lender-paid rate buydown that reduces the buyer's interest rate and monthly payment.**

1166 Spotted Sandpiper Loop, Winter Springs
$170,000
2 Beds ⋅ 2 Baths ⋅ Sheoah Sec 3 SubDv. ⋅ 32708 Zip Code
Welcome to this beautifully updated 2-bedroom, 2-bath first-floor condo located at 417 Sheoah Blvd, Apt 17, Winter Springs, FL 32708. This inviting home offers a spacious and comfortable floor plan with plenty of natural light throughout. The renovated kitchen provides a fresh and functional space and comes complete with all appliances. A washer and dryer are also included for added convenience. The home also features renovated bathrooms, adding to its fresh and move-in-ready appeal. The spacious living and dining areas feature tile flooring, creating an open and welcoming space for everyday living and entertaining. The generously sized primary bedroom features wood-look flooring and sliding glass doors that open directly to the outdoor patio, bringing in natural light and providing convenient access to the outdoor space. Enjoy the screened-in back porch and extended paver patio overlooking the community’s mature trees and green space. This inviting outdoor area offers a peaceful setting and added privacy, perfect for enjoying your morning coffee, relaxing outdoors, or entertaining guests. The community offers desirable amenities including a swimming pool and tennis courts. The HOA maintains the building exterior, roof, and community landscaping, providing valuable services for residents. The HOA fee is $485 per month. In addition, there is a separate Master Association fee of $436, paid annually at the beginning of the year. Conveniently located in Winter Springs, this updated first-floor condo offers a wonderful combination of renovated interiors, spacious living areas, inviting outdoor spaces, and community amenities. Enjoy a great location within the desirable Seminole County school district, with convenient access to shopping, dining, parks, and major roadways. Schedule your private showing today and discover everything this beautiful condo has to offer!

417 Sheoah Boulevard Unit 17, Winter Springs
$415,000
3 Beds ⋅ 2 Baths ⋅ Oak Forest Unit 2b SubDv. ⋅ 32708 Zip Code
Nestled in the desirable Oak Forest at Tuscawilla community, this 3 bedroom, 2 bathroom home is located near local parks, trails, shops, restaurants, and highly rated Seminole County schools. Inside, a spacious, open floor plan flows effortlessly between the living and dining areas, elevated throughout by custom crown molding and rich wood detailing that add a timeless, tailored feel rarely found at this price point. The lovely kitchen anchors the home with a center island and breakfast bar, perfect for casual meals or entertaining guests. The primary suite offers a peaceful retreat with a generous walk-in closet, while the additional bedrooms are equally impressive, each offering generous space and an abundance of natural light. Outside, a screened patio invites year-round outdoor living, and an attached 2 car garage completes this beautiful Winter Springs residence.

1067 Chokecherry Drive, Winter Springs
Start Your Search