Cypress Club Townhomes for Sale in Winter Springs - 7 townhouses

Remarks: Beautiful 2 bedroom 2 bathroom townhome within The Highlands Community. 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.

Listing is courtesy of: FLORIDA HOME TEAM REALTY LLC (407-774-8100)

Listing Agent: Paul Buscemi (407-716-2874)

Remarks: Beautiful 2/2 townhome in highly desirable Cypress Club community in The Highlands of Winter Springs, located in close proximity to SR 434! Light and neutral colors throughout, freshly painted approximately two years ago! *Vaulted ceiling in the spacious family/great room with a wood burning fireplace! Tile flooring in the living areas and laminate in the bedrooms. Split bedroom floorplan, with one bedroom downstairs. Tub and shower combination in both bathrooms. Newer a/c and a washer and dryer included! Screened and Covered porch and an additional outside storage closet for additional storage. Community pool in addition the master community pool! Two assigned parking spaces and additional visitor parking. 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.

Listing is courtesy of: WATSON REALTY CORP (407-323-3200)

Listing Agent: Edyta Olejnik (407-474-0213)

Remarks: 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. 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.

Listing is courtesy of: CALL IT CLOSED INTL REALTY (407-338-3339)

Listing Agent: Kathleen Harrison (407-435-9565)

Remarks: 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.

Listing is courtesy of: COLDWELL BANKER RESIDENTIAL RE (407-647-1211)

Listing Agent: Hanoi Burgos (407-342-1539)

Remarks: Under contract-accepting backup offers. 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 2020 A/C system, a full repipe completed in 2016, a 2016 water softener, and an electric water heater approximately 9 years old. Even better, a brand-new roof is currently being installed and is fully covered by the HOA—adding long-term value and convenience. 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!

Listing is courtesy of: KELLER WILLIAMS HERITAGE REALTY (407-862-9700)

Listing Agent: Jeff Singletary (407-383-1933)

Remarks: Beautiful 2 bedroom, 2 bathroom townhome in Winter Springs, located in the sought-after Cypress Club at The Highlands community, known for its lush landscaping, fantastic amenities, and serene walking trails. Step inside to a spacious open floor plan with soaring vaulted ceilings and tile flooring throughout the main living areas. The living room features a cozy wood-burning fireplace, creating a warm and inviting focal point. The galley kitchen is fully equipped with all appliances, a glass tile backsplash, and a closet pantry for added storage. This home offers double suites, thoughtfully split between the two levels, each with its own private bathroom. The upstairs loft provides the perfect flex space for a home office, reading nook, or creative studio. Step out back to a lovely screened patio overlooking a private, park-like setting with no rear neighbors, creating a peaceful outdoor retreat. An exterior storage closet offers convenient space for bikes, tools, or gardening supplies. Recent updates include a full professional re-pipe (2026), new water heater (2025), new refrigerator (2024), new interior paint in modern greige tones (2023), and new carpet in bedrooms and stairs (2023). This townhome includes two reserved parking spaces, side-by-side, including one covered carport space. Cypress Club residents enjoy their own private community pool along with full access to The Highlands’ amenities, including a lap pool, tennis courts, playground, BBQ/picnic areas, and more. Ideally located with easy access to SR-434, 17-92, SR-417, and I-4, and zoned for top-rated Seminole County schools. Outdoor recreation and weekend adventure are just minutes away with convenient access to the Cross Seminole Trail and Central Winds Park, offering miles of scenic biking and walking paths, sports fields, and community events. Everyday conveniences are equally close by, with Winter Springs Town Center and other major shopping plazas just a short drive away, providing easy access to grocery stores, fitness centers, banks, restaurants, and all your daily essentials.

Listing is courtesy of: INFINITY REAL ESTATE GROUP (407-760-0835)

Listing Agent: Tamara Martin (407-760-0835)

Remarks: Welcome to Cypress Club, a townhome community located in The Highlands within Winter Springs. Two bedrooms/two bath home is two stories offering split bedrooms. The living room/dining room combo provides high lofty ceilings with celestial windows providing natural sunlight to the home. Sliding glass doors open to a screen enclosed patio to the rear of the property that overlooks Winter Springs peaceful conservation area. Open stairwell that leads to the loft where you will find a spacious laundry arrangement set up. The master bedroom and bath are on the second floor. The home has been freshly painted. The Highlands offers many amenities to include tennis/pickle ball courts, basketball and volleyball, park with BBQ areas and a covered pavilion and boasts it's Junior Olympic size swimming pool. Playgrounds throughout the community. Cypress Club also provides a community pool. The roof is new 2026.

Listing is courtesy of: PAINE-ANDERSON PROPERTIES, INC (407-695-7898)

Listing Agent: Joyce Gary (407-782-3276)