Cypress Club Homes with Tennis Court(s) Exterior Features

Welcome to Cypress Club, a picturesque subdivision nestled in the heart of Winter Springs, Florida, within the serene Seminole County. This charming community is the perfect blend of suburban tranquility and vibrant living, making it an ideal choice for families, retirees, and everyone in between.

Cypress Club is renowned for its beautifully designed homes, many of which feature stunning tennis courts right in their backyards. Imagine stepping outside your door to enjoy a friendly match or honing your skills on your private court, all while basking in the warm Florida sunshine. These exterior features not only promote an active lifestyle but also enhance the overall appeal of the homes, making them a perfect retreat for sports enthusiasts and leisure seekers alike.

The subdivision is surrounded by lush landscaping and mature trees, creating a serene atmosphere that residents adore. With easy access to local parks, shopping centers, and top-rated schools, Cypress Club offers convenience at every turn. Whether you’re taking a leisurely stroll through the neighborhood or enjoying a weekend barbecue with friends, the sense of community here is palpable.

Cypress Club is not just a place to live; it’s a lifestyle. With its inviting homes, luxurious amenities, and a strong sense of community, this subdivision is a hidden gem in Winter Springs. Come discover the charm of Cypress Club, where your dream home awaits, complete with your very own tennis court to enjoy!

Newest Cypress Club Homes with Tennis Court(s) Exterior Features

$199,900

2 Beds ⋅ 2 Baths ⋅ Cypress Club SubDv. ⋅ 32708 Zip Code

Move in Ready!...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

$269,000

3 Beds ⋅ 2 Baths ⋅ Cypress Club SubDv. ⋅ 32708 Zip Code

Discover effortless living in this immaculate 3-bedroom, 2-bath townhome nestled in the desirable Cypress Club at The Highlands. Thoughtfully maintained and beautifully updated, this residence offers the perfect blend of comfort, style, and convenience with a desirable split-bedroom floor plan—featuring one bedroom and a full bathroom on the main level, and the primary suite along with a third bedroom upstairs. Sliding glass doors open to a private screened porch, ideal for morning coffee, evening relaxation, or entertaining guests. This inviting space offers seamless indoor-outdoor living along with additional storage. The upgraded kitchen is a true highlight, showcasing solid wood cabinetry, modern countertops, and a breakfast bar perfect for casual dining or hosting friends and family. Two reserved parking spaces are conveniently located directly at your front door. Enjoy the resort-style lifestyle The Highlands is known for, offering a community pool, recreational building, tennis courts, and scenic hiking trails. Ideally located near I-4 and SR-417, commuting and weekend adventures are effortless. HOA fees provide exceptional value, covering exterior building and grounds maintenance, community amenities, —delivering peace of mind and truly low-maintenance living. IMPORTANT MESSAGE- While this townhouse HOA fees may seem higher, it covers roof replacement and maintenance (brand new 2026), exterior maintenance, landscaping, and more. A single-family home may have lower HOA fees, but usually comes with higher maintenance costs, more upkeep, and added stress - making the overall expense very similar in the end, with far less hassle in a townhouse community. Schedule your private showing today and make this exceptional townhome yours.

446 Club Drive, Winter Springs

Start Your Search