Casselberrry/Winter Springs / Tuscawilla Homes with Tennis Court(s) Amenities

Casselberrry/Winter Springs / Tuscawilla Homes with Tennis Court(s) Amenities

Welcome to the charming communities of Casselberry, Winter Springs, and Tuscawilla, nestled in the heart of Seminole County, Florida. Known for their lush landscapes and family-friendly atmosphere, these areas offer a perfect blend of suburban tranquility and vibrant community life. With an abundance of parks, top-rated schools, and a variety of shopping and dining options, residents enjoy a lifestyle that is both convenient and fulfilling.

One of the standout features of homes in this region is the availability of properties with private tennis courts. Imagine stepping out of your back door to your very own slice of paradise, where you can practice your serve or enjoy a friendly match with friends and family. These homes not only cater to tennis enthusiasts but also provide an ideal setting for outdoor gatherings and relaxation.

The neighborhoods here are characterized by their welcoming spirit and strong sense of community. Whether you’re taking a leisurely stroll through the scenic parks or participating in local events, you’ll find a warm and inviting atmosphere that makes you feel right at home.

With a range of architectural styles and price points, there’s something for everyone in Casselberry, Winter Springs, and Tuscawilla. If you’re seeking a home that combines luxury with active living, look no further than these stunning properties with tennis court amenities. Experience the joy of living in a community that not only meets your lifestyle needs but also enriches your everyday life. Welcome to your new home in Florida’s beautiful Seminole County!

Newest Casselberrry/Winter Springs / Tuscawilla Homes with Tennis Court(s) Amenities

$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
$175,000
2 Beds ⋅ 2 Baths ⋅ Mount Greenwood Unit 4 Of SubDv. ⋅ 32708 Zip Code
INVESTOR SPECIAL! RENOVATION OPPORTUNITY IN WINTER SPRINGS! Bring your vision and transform this 2-bedroom, 1.5-bath townhouse into something special. This property is being sold AS-IS and is in need of a full renovation, offering an excellent opportunity for investors, renovators, or buyers looking to create a home tailored to their own style. The two-story layout features a spacious living room, first-floor kitchen, and two bedrooms upstairs, including a generously sized primary bedroom. A rear porch with storage provides additional outdoor space, while the community offers a pool, playground, and tennis courts for residents to enjoy. The property also includes assigned parking with a spot right out front. Located in Winter Springs with convenient access to major roads, shopping, dining, parks, and area schools, this property has the potential to become a fantastic primary residence, rental, or investment project. Bring your contractor, bring your vision, and unlock the potential! Cash financing only. Buyer to independently verify all information, measurements, restrictions, and renovation requirements.

284 Woodgreen Lane, Winter Springs
$284,000
3 Beds ⋅ 2 Baths ⋅ Seasons The SubDv. ⋅ 32708 Zip Code
Welcome to 412 Horizon Drive, a well maintained home in the heart of Winter Springs with the updates already taken care of. Inside, you’ll find a welcoming kitchen with granite countertops, stylish cabinetry, stainless steel appliances, and ceramic tile and wood laminate flooring throughout. The primary bathroom is a standout, featuring a barn door entry, large tiled shower, rainfall shower system, and handheld wand. Recent improvements include a 2018 roof, 2019 HVAC and refrigerator, stove and microwave replaced in 2024, updated windows, and fresh exterior paint completed in August 2026. The backyard offers plenty of room to entertain, relax, or create your own outdoor retreat. Conveniently located near shopping, dining, parks, and everyday conveniences, this Winter Springs home is ready for its next owner.

412 Horizon Drive, 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
$140,000
1 Beds ⋅ 1 Baths ⋅ Baytree Village SubDv. ⋅ 32708 Zip Code
Virtually Staged. Price improvement for the perfect starter home, investment opportunity or downsizing. Excellent condition! Not every condo feels like HOME the moment you walk in—but this one does. EXCELLENT CONDITION! Tucked beneath the canopy of mature oaks in The Highlands of Winter Springs, this beautifully UPDATED FIRST FLOOR ONE BEDROOM/ONE BATH condominium offers the perfect blend of comfort, convenience, and carefree Florida living. Forget carrying groceries upstairs or tackling weekend projects. This move-in ready home has ceramic tile flooring throughout the main living areas, new luxury vinyl in the bedroom, new appliances, updated lighting, modern ceiling fans, a new water heater - A/C system replaced in 2019. The bedroom features custom-built closet organizers that maximize storage, while two additional exterior storage closets provide room for bicycles, holiday décor, tools, and outdoor gear. In 2010 all interior elements of the building were replaced with new electric, plumbing, doors, windows and all drywall and studs. One of the home's best features is the oversized screened porch—a private outdoor living space where you can sip your morning coffee, read a book, or unwind at the end of the day while enjoying the peaceful, tree-lined setting that has made The Highlands one of Winter Springs' most beloved communities. Life here extends well beyond your front door. Residents enjoy miles of scenic walking and nature trails, a community pool, tennis courts, pickleball courts, clubhouse, playground, and beautifully landscaped common areas that encourage an active outdoor lifestyle. Whether you're taking an evening stroll beneath the oak trees, meeting neighbors for a game of pickleball, or spending the afternoon poolside, you'll quickly see why so many people love calling The Highlands home. Located in the heart of Winter Springs, you'll be just minutes from top-rated Seminole County schools, shopping, dining, medical facilities, parks, and major roadways including SR 434, SR 417, and US 17-92, making commuting to Orlando, Winter Park, Lake Mary, and the surrounding area simple and convenient. Whether you're searching for your first home, a winter retreat, an investment property, or an easy, low-maintenance lifestyle, this updated Winter Springs condo delivers exceptional value in a location that continues to be one of Central Florida's most desirable places to live.

220 Moree Loop Unit 2, 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
$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
$199,900
2 Beds ⋅ 2 Baths ⋅ Cypress Club SubDv. ⋅ 32708 Zip Code
Great investment property!...Beautiful 2/2 townhome in highly desirable Cypress Club community in The Highlands of Winter Springs, located in close proximity to SR 434! **Freshly Painted with light and neutral colors throughout! Vaulted ceiling in the very spacious/huge... family/great room with a wood burning fireplace! Split bedroom floorplan, with one bedroom downstairs. Brand new ceiling fan in upstairs bedroom. Tub and shower combination and linen closets in both bathrooms. Tile flooring in the living areas and laminate in the bedrooms. **Brand New Lennox A/C system and a washer and dryer included! Screened and Covered porch and an outside storage closet for additional storage. Two pools: the Cypress Club Community pool, and The Highlands master community pool! Brand new roofs in the community, HOA covers building insurance and grounds maintenance. Two assigned parking spaces. The community offers a fabulous club house, nature walking trails, parks, playground and tennis courts. Located close to shops and restaurants and very close to SR 434, SR 17/92 and SR 417 for easy commuting.

497 Club Drive, 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
$474,900
4 Beds ⋅ 3 Baths ⋅ Sunrise Estates Unit 1 SubDv. ⋅ 32708 Zip Code
New roof 2023, AC 2020, water heater 2023, whole-home water softener 2024. Non-flood zone. No rental restrictions. HOA only $30/month. The expensive questions are already answered on this Winter Springs home. Major systems have been replaced, the 4-point inspection is straightforward, and insurance-friendly construction (block and stucco, slab foundation, shingle roof 2023) keeps ownership costs predictable. 4 bedrooms, 2.5 baths, 2,152 SqFt of living area on a 10,019 SqFt lot in Sunrise Estates, a short walk to Rainbow Elementary and minutes from Tuskawilla Road, Winter Springs Town Center, Oviedo, and the 417 for an easy commute to Orlando, UCF, and Lake Mary. The three-level split layout gives you the separation most homes in this price range can't have. The main level holds the formal living and dining rooms and a 11x18 eat-in kitchen with pantry, storage closet, solid wood cabinets, and solid surface counters. One level down is a 21x18 family room with a stone wood-burning fireplace and French doors to the lanai. Upstairs, all four bedrooms: a 15x17 primary suite with walk-in closet and ceiling fan, plus three additional bedrooms with built-in closets. Cathedral and vaulted ceilings, ceramic tile throughout, updated bathrooms, freshly painted interior, and an indoor laundry room. Alkaline water filtration at the kitchen sink. Outside is where this home stands apart. A 21x14 covered and screened lanai with ceiling fan and gas fire pit opens to a fully fenced backyard with a second natural fire pit, play area, dog run, garden space, storage shed, and an irrigation system on a private sprinkler well, so the lawn stays green without a water bill. Two-car garage with opener plus open driveway parking. Community amenities include playground and tennis courts. Zoning PUD. Public water and sewer. Schedule your showing today! Seller may consider buyer closing-cost assistance with an acceptable offer.

1304 Ortega Street, Winter Springs
$170,000
3 Beds ⋅ 2 Baths ⋅ Baytree Village SubDv. ⋅ 32708 Zip Code
One or more photo(s) has been virtually staged. Welcome to Baytree Village in the heart of Winter Springs—where beautifully landscaped grounds and a welcoming atmosphere create the perfect place to call home. This MOVE-IN READY second-floor condo offers 3 bedrooms, 2 full baths, and added privacy, all in a prime location close to top-rated schools, parks, shopping, dining, and major roadways for an easy commute. Step inside to a bright, open-concept living and dining area featuring a wall of windows and two sets of triple sliding glass doors, filling the space with natural light and providing seamless access to a large screened balcony with peaceful garden views—perfect for relaxing or entertaining. The kitchen is well-equipped with stainless steel appliances, ample cabinet and countertop space, and easy-care tile flooring. The spacious primary suite offers a comfortable retreat, while two additional bedrooms provide flexibility for guests, a home office, or additional living space. Additional highlights include in-unit laundry and extra storage off the balcony. Residents of Baytree Village enjoy well-maintained amenities and close proximity to local parks, including Audubon Park just minutes away. Seller is willing to cover up to six (6) months of the buyer’s Homeowners Association (HOA) dues with an acceptable offer. Whether you're a first-time buyer, downsizing, or investing, this is an opportunity you won’t want to miss. Schedule your private showing today!

240 Moree Loop Unit 3, Winter Springs
$267,500
3 Beds ⋅ 2 Baths ⋅ Cypress Club SubDv. ⋅ 32708 Zip Code
Virtually Staged. Welcome to 476 Club Drive, a beautifully maintained 3-bedroom, 2-bath townhome in the highly sought-after Cypress Club section of The Highlands in Winter Springs. NEW ROOF 2026, NEW WATER HEATER 2026, 2020 A/C, FULL-HOME REPIPE 2016, and WHOLE-HOME WATER SOFTENER 2016! This spacious home offers a flexible floor plan, peaceful wooded views, and an impressive list of updates. The main level features knockdown ceilings, updated recessed lighting, and an inviting living and dining area overlooking the serene, tree-lined surroundings. A step-down enclosed patio provides additional living space and a wonderful private retreat for relaxing or entertaining. A downstairs bedroom with an adjacent full bath offers flexibility for guests, a home office, or multi-generational living. Upstairs, two spacious bedrooms feature soaring ceilings and abundant natural light. The generous primary suite offers ample closet space, tranquil wooded views, and a private bath with a Jacuzzi tub and separate shower. A dedicated tankless water heater serves the Jacuzzi tub and primary suite bathroom, adding an extra level of comfort and convenience. Enjoy the added benefit of a covered carport with TWO dedicated parking spaces, keeping your vehicles protected from the Florida sun and weather. Cypress Club is the only section of The Highlands with its own private pool, while residents also enjoy access to the community’s outstanding amenities, including multiple pools, tennis courts, walking trails, parks, pavilions, BBQ areas, clubhouse, volleyball, and basketball courts. Located in desirable Winter Springs, this move-in-ready townhome combines thoughtful updates, flexible living spaces, natural surroundings, covered parking, and an exceptional amenity-rich community. Don’t miss the opportunity to make 476 Club Drive your new home!

476 Club Drive, Winter Springs
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