Winter Springs Homes with Playground Amenities

Winter Springs Homes with Playground Amenities

Welcome to Winter Springs, a charming city located in Seminole County, Florida. Known for its picturesque landscapes and friendly community, Winter Springs offers a perfect blend of suburban tranquility and modern amenities.

One of the highlights of living in Winter Springs is the abundance of homes with playground amenities. Families with children or those who simply enjoy outdoor activities will find these homes to be a perfect fit. Imagine having a playground right in your backyard where your little ones can run, play, and make lasting memories.

Apart from the playground amenities, Winter Springs boasts a range of recreational opportunities for residents to enjoy. From parks and nature reserves to community events and sports facilities, there is always something to do for those who love the outdoors.

With its top-rated schools, safe neighborhoods, and convenient access to shopping and dining options, Winter Springs is a sought-after destination for homebuyers looking for a peaceful yet vibrant place to call home.

Whether you are looking to settle down with your family or seeking a serene retreat away from the hustle and bustle of the city, Winter Springs has something for everyone. Come and explore the real estate options in Winter Springs and find your perfect home in this welcoming community.

Newest Winter Springs Homes with Playground Amenities

154 Wooded Vine Drive, Winter Springs
$489,000
3 Beds ⋅ 3 Baths ⋅ Tuskawilla Crossings 34'S SubDv. ⋅ 32708 Zip Code
Welcome to Tuskawilla Crossings! Discover the perfect blend of comfort, style, and convenience in the heart of Winter Springs. Built by Lennar Homes in 2019, this beautifully maintained home offers modern finishes, thoughtful upgrades, and an exceptional location within the desirable Tuskawilla Crossings community. Step inside to a bright, welcoming interior featuring luxury vinyl plank flooring throughout and an open-concept main living area designed for both everyday living and entertaining. The spacious living and dining areas flow seamlessly into the modern kitchen, complete with a large quartz island, upgraded cabinetry, and plenty of workspace for cooking and gathering. A convenient guest half-bath completes the first floor. Upstairs, a spacious hallway leads to a generously sized primary suite featuring a walk-in closet, along with two additional well-appointed bedrooms and a convenient laundry room. Natural light fills the home, enhanced by custom retractable window shades that provide both style and privacy. Step outside and enjoy one of the home's standout features—a private backyard with no rear neighbors! The fully fenced yard offers plenty of room for outdoor entertaining and relaxation, while the covered patio creates the perfect space for enjoying your morning coffee or hosting friends and family. A covered walkway leads directly to the oversized rear-entry garage, adding both convenience and functionality. Life at Tuskawilla Crossings offers an impressive array of community amenities, including a community pool, dog park, playground, clubhouse, and covered pavilions with cookout areas. Nature lovers will appreciate being within walking distance of the nearby nature trail, making it easy to enjoy the outdoors right from home. And the location is hard to beat! With quick and convenient access to the 417, you'll have an easy commute and be just minutes from an abundance of shopping, dining, entertainment, and everyday conveniences—many within a 10-minute drive. Beautifully maintained, move-in ready, private, and ideally located—this Tuskawilla Crossings home offers the lifestyle you've been looking for. Come see it for yourself!

154 Wooded Vine Drive, Winter Springs
499 Club Drive, Winter Springs
$205,000
2 Beds ⋅ 2 Baths ⋅ Cypress Club SubDv. ⋅ 32708 Zip Code
Virtually Staged. As you arrive at this beautiful 2 bedroom + loft, 2 bath residence in a serene townhome community within The Highlands in Winter Springs, you’ll note a feeling of privacy, relaxation, and tranquility among the lush landscaping, fantastic amenities, and peaceful walking trails. TOUR THE HOUSE WITH THE VIRTUAL TOUR AND WALK THRU VIDEO LINKS. Step inside to a spacious open floorplan where light bathes the soaring vaulted ceilings and tile flooring runs throughout the main living areas. The family cook will enjoy preparing meals among the new appliances (2022) in the functional kitchen layout, while overlooking the great room and exterior nature views. Step out to the screened patio to enjoy your morning coffee, where you’ll also find an outside storage closet offering a convenient place for your bikes, tools, or gardening supplies. The layout of this home offers double suites, thoughtfully split between the two levels, each with a full bath with shower/tub combo. Upstairs, a bonus loft provides an ideal flex space for a home office, reading nook, or more! Life here is stress-free with a new roof (2026) and A/C (2023), and 2 reserved parking spaces, side-by-side, right outside your front door. Beyond the home itself, this community provides you a carefree lifestyle with the HOA taking care of exterior maintenance and landscaping, leaving you plenty of time to meet up with friendly neighbors to enjoy the private community pool within the neighborhood, as well as the Highlands’ exceptional amenities -- including a junior Olympic-size lap pool, tennis/pickleball courts, clubhouse, playground, and picnic areas, perfect for relaxing moments or social gatherings. Conveniently located with easy access to main thoroughfares, everyday conveniences are close by -- groceries, restaurants, shopping, banks, fitness centers, etc. – as well as top-rated Seminole County schools. Come see why your new neighbors already love to call the area home and are enjoying the care-free lifestyle you deserve!!

499 Club Drive, Winter Springs
1013 Walnut Creek Cove, Winter Springs
$499,900
3 Beds ⋅ 2 Baths ⋅ Parkstone Unit 4 SubDv. ⋅ 32708 Zip Code
Beautiful 4-bedroom POOL home with awesome pond front in the exclusive gated community of Parkstone! Formal Living, Dining, and Family rooms. Spacious eat-in kitchen with stainless steel appliances. Large owner's suite with huge closet and elegant garden tub and separate shower. High ceilings and tile flooring throughout house. One story home. New AC. Laundry room. Covered screened-in back porch with POOL and stunning view of the pond. 2 car garage. Roof about 5 years old. HOA mows yard. House is on a CUL-DE-ac so very quiet. Enjoy the community pool, splash pad, tennis courts, playground, and fishing pier. Near the Seminole Trail for biking and walking as well as Central Winds Park/dog park. Good schools. Great location. Must See!

1013 Walnut Creek Cove, Winter Springs
337 Twelve Oaks Drive, 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
654 Cypress Lane, Winter Springs
$322,500
3 Beds ⋅ 2 Baths ⋅ Wildwood SubDv. ⋅ 32708 Zip Code
***Selelr will replace roof prior to closing*** | 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
1378 Tarflower Drive, Winter Springs
$505,000
3 Beds ⋅ 3 Baths ⋅ Hickory Grove Twnhms SubDv. ⋅ 32708 Zip Code
Beautifully Upgraded Sofia Model Townhome on a Premium Conservation Lot! Welcome home to this exceptional Sofia Model townhome, featuring one of the community’s most desirable floorplans—with the primary suite conveniently located on the first floor and two additional bedrooms upstairs. This thoughtfully designed layout is ideal for families, first-time buyers, those looking to downsize, or anyone seeking comfortable living with flexibility for guests, a home office, or additional living space. Situated on a premium lot backing to a peaceful conservation/green area, this home offers a wonderful sense of privacy and a tranquil natural backdrop. Inside, numerous builder upgrades and thoughtful custom enhancements create a beautiful blend of modern style, classic elegance, and everyday functionality. Upgrades include enhanced tile, bathrooms, and kitchen finishes, complemented by a custom-designed stair railing that adds a distinctive touch of sophistication. The spacious primary suite features a custom-built walk-in closet, maximizing storage and organization. An Ecobee Smart Thermostat system with Smart Sensors provides efficient, convenient control of the home's comfort while helping manage energy usage. Premium professionally installed ceiling fans in every room provide excellent air circulation and year-round comfort. The home is also professionally wired for rear surround-sound speakers, making it ready for an enhanced entertainment experience. All the rooms have plenty of natural lights! The garage is equally practical, featuring large custom-built ceiling-hung storage, providing valuable additional space while keeping vehicles and everyday belongings organized. Enjoy an outstanding location within Hickory Grove. The community pool and dog park are just down the street, while the Cross Seminole Trail can be easily accessed just outside the community—perfect for walking, jogging, or biking. The Magnolia Square Fountain and Park and The Winter Springs Town Center are both approximately a five-minute walk away, with roughly a dozen food-and-beverage places within walking distance or a short drive away. Central Winds Park is only about a 10-minute drive away. Access to 417 is about 7-minute drive away. With its highly sought-after first-floor primary suite, premium conservation lot, extensive upgrades, custom touches, and exceptional walkable location, this townhome offers a rare combination of comfort, style, privacy, and convenience.

1378 Tarflower Drive, Winter Springs
998 White Springs Lane, 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
1114 Seafarer Lane, Winter Springs
$539,000
4 Beds ⋅ 2 Baths ⋅ Oak Forest SubDv. ⋅ 32708 Zip Code
Beautiful pool home in Oak Forest. NEW ROOF, NEW SOD Coming soon.. NEW INTERIOR PAINT and VINYL FLOORS. Gorgeous 42" kitchen cabinets with granite counters and large Island with seating and tiled backsplash. Both bathrooms have beautiful vanities and glass tiles and granite counters. Fourth bedroom has been turned into an office but could be converted back into a bedroom by adding a closet. Tall ceilings, tile and Vinyl floors throughout, open floorplan and neutral colors complete the interior package but there's more! Brick paver front entry and large screened pool area make this a home you won't want to miss. New SOD and landscaping will be done soon.

1114 Seafarer Lane, Winter Springs
220 Moree Loop Unit 2, Winter Springs
$140,000
1 Beds ⋅ 1 Baths ⋅ Baytree Village SubDv. ⋅ 32708 Zip Code
Virtually Staged. UPDATED FIRST-FLOOR CONDO IN THE HIGHLANDS OF WINTER SPRINGS! This move-in ready 1-bedroom, 1-bath condominium offers 710 square feet of comfortable living, an oversized screened porch, and convenient ground-floor access, no stairs to navigate. Set beneath mature oak trees, it combines an inviting interior with access to the outdoor amenities that make The Highlands a distinctive Seminole County community. The interior features ceramic tile flooring in the main living areas, new luxury vinyl flooring in the bedroom, new appliances, updated lighting & ceiling fans. A new water heater and an A/C system replaced in 2019 add value. In 2010, the building’s interior components were replaced, including electrical wiring, plumbing, doors, windows, drywall, and studs. Custom bedroom closet organizers help maximize storage, while two additional exterior storage closets provide space for bicycles, seasonal decorations, tools, and outdoor gear. The oversized screened porch extends your living space outdoors, offering a peaceful spot for morning coffee, reading, or relaxing with views of the tree-lined surroundings. The Highlands amenities include scenic walking and nature trails, a community pool, tennis and pickleball courts, a clubhouse, and a playground. Enjoy opportunities to walk, swim, play, and spend time outdoors close to home. Conveniently located near shopping, dining, medical facilities, and parks, with access to SR 434, SR 417, and US 17-92 for travel throughout Winter Springs, Lake Mary, Winter Park, and Orlando. Looking for a first home, a seasonal retreat, or a smaller home with less upkeep? This updated Winter Springs condo offers first-floor convenience, useful storage, and inviting outdoor space.

220 Moree Loop Unit 2, Winter Springs
216 Tavestock Loop, 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
1389 Ponce De Leon Boulevard, Winter Springs
$499,000
4 Beds ⋅ 2 Baths ⋅ Sunrise Unit 2-A SubDv. ⋅ 32708 Zip Code
BACK ON THE MARKET!!PRICE TO SELL. LOCATION, LOCATION, LOCATION! Beautifully remodeled home in the heart of Winter Springs, conveniently located near shopping, dining, banking, fresh market , Publix, Oviedo Mall, YMCA, and major roadways (417 & 408). This spacious residence features 4 bedrooms, 2 full bathrooms, 2 car garage and an open functional floor plan ideal for family living and entertaining, two large separate rooms :a dining room and a living room Recent updates include a water heater (2026)new porch (2026), A/C (2017), and roof (2017).the garage door was completely replaced ,including the tracks and motor(one month ago. The oversized backyard is shaded by magnificent historic oak trees and includes a utility/workshop, building gym, offering endless possibilities. The community features a playground, basketball court, and park, with an additional neighborhood park conveniently located right next door and the HOA fee is paid anually and is exceptionally affordable.

1389 Ponce De Leon Boulevard, Winter Springs
108 Sundance Court, 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
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