Cypress Club Homes with Tennis Court(s) Exterior Features

Welcome to Cypress Club, a hidden gem nestled in the heart of Winter Springs, Florida, within the beautiful Seminole County. This charming subdivision offers a perfect blend of tranquility and community spirit, making it an ideal place for families, retirees, and everyone in between.

Cypress Club is renowned for its lush landscapes and meticulously maintained homes that exude curb appeal. One of the standout features of this community is its dedication to an active lifestyle, highlighted by the presence of tennis courts that invite residents to engage in friendly matches and social gatherings. Imagine stepping out your front door to enjoy a game of tennis under the warm Florida sun, or hosting weekend barbecues with neighbors in the inviting common areas.

The homes in Cypress Club are designed with comfort and style in mind. Many properties boast spacious interiors, modern amenities, and beautifully landscaped yards that provide a serene backdrop for relaxation. The community's commitment to maintaining its natural beauty ensures that you can enjoy morning strolls or evening bike rides along the picturesque streets.

Cypress Club also benefits from its prime location in Winter Springs, where residents can easily access shopping, dining, and outdoor recreational activities. With its friendly atmosphere and vibrant community, Cypress Club is not just a place to live; it's a place to thrive. Come discover the lifestyle that awaits you in this enchanting neighborhood, where every day feels like a vacation. Your dream home in Cypress Club is just around the corner!

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

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