Cypress Club Homes with Playground Exterior Features

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

Cypress Club is known for its inviting atmosphere, where neighbors become friends and outdoor living is celebrated. One of the standout features of this community is its beautifully designed homes, each boasting unique architectural styles that harmonize with the lush surroundings. Many residences come equipped with playground exterior features, providing a safe and fun environment for children to play and grow. Imagine your little ones laughing and making memories right in your own backyard!

The community also benefits from an array of amenities that enhance the quality of life for its residents. Enjoy leisurely strolls along tree-lined streets, or take advantage of the nearby parks and recreational areas, perfect for picnics, sports, and family gatherings. With a strong sense of community spirit, Cypress Club hosts various events throughout the year, fostering connections among neighbors and creating a warm, welcoming vibe.

Located just a short drive from the bustling city of Orlando, residents of Cypress Club enjoy easy access to shopping, dining, and entertainment options, all while being able to retreat to their peaceful sanctuary at day’s end. If you’re seeking a place where community and comfort converge, look no further than Cypress Club in Winter Springs. Come discover your dream home in this enchanting subdivision today!

Newest Cypress Club Homes with Playground 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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