Cypress Club Homes with Trees/Woods View

Welcome to Cypress Club, a picturesque subdivision nestled in the heart of Winter Springs, Florida, in beautiful Seminole County. This charming community is the perfect blend of tranquility and modern living, offering residents a serene escape surrounded by nature's beauty.

Cypress Club is renowned for its stunning homes that boast breathtaking views of lush trees and serene woodlands. Imagine waking up each morning to the gentle rustle of leaves and the soft chirping of birds, all while enjoying the comfort of your own home. These properties are designed to harmonize with the natural landscape, providing a peaceful ambiance that enhances your living experience.

The subdivision features a variety of thoughtfully designed homes, each offering spacious layouts and modern amenities. Whether you’re looking for a cozy retreat or a family-friendly residence, Cypress Club has something for everyone. With tree-lined streets and well-maintained common areas, the community exudes a warm and inviting atmosphere that fosters a strong sense of belonging.

Residents of Cypress Club enjoy easy access to local parks, recreational facilities, and top-rated schools, making it an ideal location for families and outdoor enthusiasts alike. The nearby nature trails invite you to explore the great outdoors, while the vibrant downtown Winter Springs area offers shopping, dining, and entertainment options just a stone's throw away.

Discover the charm of Cypress Club, where your dream home awaits amidst the beauty of Florida's natural landscape. Experience a lifestyle of comfort, community, and connection to nature in this enchanting subdivision. Welcome home!

Newest Cypress Club Homes with Trees/Woods View

$275,000

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

Welcome to 476 Club Drive, a beautifully cared-for townhome nestled in the highly sought-after Cypress Club section of The Highlands in Winter Springs—a community known for its incredible amenities and natural surroundings. This spacious 3-bedroom, 2-bath residence blends comfort, functionality, and peace of mind with key updates already completed. Enjoy the benefits of a new roof 2026, new water heater 2026, 2020 A/C system, a full repipe completed in 2016, and a 2016 whole home water softener. Inside, you’ll find an inviting layout with knockdown ceilings throughout the main level and an open living and dining area tucked toward the rear of the home for added privacy. Updated recessed lighting enhances the space, creating a warm and welcoming atmosphere. Just beyond, a step-down enclosed patio offers a serene retreat overlooking wooded views—perfect for relaxing or entertaining. The flexible floor plan includes a downstairs bedroom with an adjacent full bath, ideal for guests, a home office, or multi-generational living. Upstairs, two generously sized bedrooms feature soaring ceilings and abundant natural light. The primary suite offers ample closet space and tranquil views of the surrounding greenery, along with a spacious en-suite bath complete with a Jacuzzi tub and separate shower—perfect for unwinding after a long day. Cypress Club stands out as the only neighborhood within The Highlands with its own private pool, in addition to access to the community’s extensive amenities. Residents enjoy multiple pools, tennis courts, scenic walking trails, parks, pavilions, BBQ areas, a clubhouse, as well as volleyball and basketball courts—delivering a true Florida lifestyle right outside your door. Don’t miss this opportunity to own a move-in-ready home in one of Winter Springs’ most desirable communities!

476 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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