Cypress Club Homes with Playground Community Features

Cypress Club Homes with Playground Community Features

Welcome to Cypress Club, a delightful subdivision nestled in the heart of Winter Springs, Florida, within the picturesque Seminole County. This charming community offers a 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 inviting atmosphere and beautifully designed homes that cater to a variety of lifestyles. Each residence is thoughtfully crafted, featuring modern amenities and spacious layouts that foster comfort and convenience. With a range of housing options available, prospective buyers will find something that suits their unique needs and preferences.

One of the standout features of Cypress Club is its family-friendly environment, complete with a well-maintained playground that promises endless fun for children. The community’s commitment to creating a safe and engaging space for families is evident in its thoughtfully designed recreational areas. Parents can relax knowing their little ones are just a stone's throw away from outdoor adventures and social interactions with neighborhood friends.

In addition to the playground, Cypress Club boasts a warm sense of community, where neighbors become friends and create lasting memories together. Enjoy leisurely strolls through tree-lined streets, participate in community events, or simply unwind in the serene surroundings of this idyllic neighborhood.

With its prime location in Winter Springs, residents of Cypress Club have easy access to shopping, dining, and top-rated schools, ensuring that everything you need is just moments away. Come discover the charm of Cypress Club, where your dream home awaits in a community that feels like family!

Newest Cypress Club Homes with Playground Community Features

$210,000
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
$219,500
2 Beds ⋅ 2 Baths ⋅ Cypress Club SubDv. ⋅ 32708 Zip Code
Beautiful 2 bedroom 2 bathroom townhome (Not a condo which means more financing choices for you as a buyer) within The Highlands Community. Brand New Roof on this townhome. The 20ft high ceiling in the Great Room gives this home a very open design with lots of natural light. Sliding doors lead out to a screened porch with separate locked storage space. Guest/2nd bedroom on the first floor with direct access to the 2nd bathroom. All appliances purchased New in 2022 and are included with sale. New A/C 2023. Upstairs flexible loft space makes for a nice home office. Large primary bedroom has beautiful laminate floors and plenty of closet space and updated bathroom. Two assigned parking spaces directly in front of your townhome makes coming home convenient. Cypress Club residents enjoy their Own Private Community Pool in addition to All Highlands amenities. They include Audibon Park with BBQ/Picnic Area, Playgrounds, Olympic Size Pool, Kiddie Pool, Nature Walking Trails & Tennis & Pickleball Courts and a Clubhouse. Zoned for highly rated Seminole County Schools with The Highlands elementary school located within the community. Nearby Cross Seminole Trail and Central Winds Park. Located close to 17-92, SR417, grocery stores, fitness clubs.

499 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
$215,000
2 Beds ⋅ 2 Baths ⋅ Cypress Club SubDv. ⋅ 32708 Zip Code
Move-in ready 2-bedroom, 2-bathroom single-level townhome in the heart of Winter Springs! Enjoy an updated kitchen with granite countertops, freshly painted interior, and new flooring. Relax on the screened and tiled lanai overlooking serene greenspace. This quiet, secluded community offers two assigned parking spaces and a community pool just steps from your front door. The HOA just installed brand new roofs throughout the community. Residents enjoy amenities including community pool, tennis courts, lush parks, and scenic walking trails throughout the neighborhood. Conveniently located near shopping, dining, entertainment, major highways, and all the area’s conveniences.

506 Club Drive, Winter Springs
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