Winding Cypress Homes with Tennis Amenities

Winding Cypress Homes with Tennis Amenities

Welcome to Winding Cypress, a stunning community nestled in the heart of Naples, Florida. This picturesque subdivision is designed for those who appreciate the beauty of nature and the luxury of modern living. With its lush landscapes and serene surroundings, Winding Cypress offers a tranquil escape while still being close to all the vibrant attractions of Naples.

One of the standout features of Winding Cypress is its exceptional amenities, particularly for tennis enthusiasts. The community boasts state-of-the-art tennis facilities, providing residents with the perfect opportunity to hone their skills or enjoy friendly matches with neighbors. Whether you're a seasoned player or just starting out, you'll find the courts to be an inviting space to engage in this beloved sport.

The homes in Winding Cypress are thoughtfully designed to blend elegance with comfort. Many properties feature open floor plans, gourmet kitchens, and spacious living areas, making them perfect for entertaining or enjoying quiet evenings at home. The community's emphasis on outdoor living is evident, with many homes offering private lanai spaces that overlook the stunning natural landscapes.

Living in Winding Cypress means embracing a lifestyle filled with leisure and recreation. Beyond tennis, residents can enjoy a plethora of amenities, including a resort-style pool, fitness center, and walking trails that wind through the community's beautiful scenery. With its prime location in Collier County, you'll also have easy access to Naples' world-class dining, shopping, and pristine beaches.

Discover the charm of Winding Cypress, where luxury meets an active lifestyle, and make this vibrant community your new home!

Newest Winding Cypress Homes with Tennis Amenities

$1,295,000
3 Beds ⋅ 3 Baths ⋅ 226027501 MLS ⋅ Winding Cypress BLDG.
PRICED TO SELL! Discover exceptional value in one of Naples’ most desirable lifestyle communities, Winding Cypress. Ideally situated on an oversized preserve lot with peaceful pond views, this beautifully maintained Pinnacle floor plan offers over 2,500 square feet of living space with 3 spacious bedrooms, 3 full bathrooms, and a versatile den. Built in 2020, this move-in-ready residence combines elegant finishes, thoughtful upgrades, and outstanding indoor-outdoor living. The expansive outdoor area features a large picture-window screened lanai, gas-heated saltwater pool and spa, custom outdoor kitchen, and generous brick-paver lanai with a covered entertaining area—perfect for enjoying the Naples lifestyle year-round. A newly installed electric hurricane screen provides additional protection and convenience. The home is equipped with whole-house hurricane shutters, a whole-house generator capable of supporting the pool and spa, and an oversized 3-car garage with epoxy flooring and hurricane-rated, insulated garage doors. Additional attic insulation and a separate garage A/C system provide the option for climate-controlled storage or workspace. The beautifully appointed kitchen features white quartz countertops, premium stainless steel appliances, a gas cooktop, and a beverage refrigerator. The spacious primary suite offers exceptional organization with a custom California Closets design, while the custom pantry provides additional storage and functionality. Beyond the residence, Winding Cypress offers an exceptional resort-style lifestyle. The impressive clubhouse features a heated resort pool and spa, poolside dining at The Shady Palm, state-of-the-art fitness center, library, and elegant gathering rooms. Residents also enjoy tennis and pickleball courts, bocce, dog parks, a community garden, and scenic walking and nature trails. Beautifully maintained grounds and a welcoming atmosphere create a true sense of community, all while being conveniently located near the best of Naples. Located in an X flood zone, with no flood insurance required, this exceptional home offers the perfect combination of luxury, privacy, recreation, and peace of mind. Priced to sell and offering tremendous value, this is an opportunity to own a beautifully upgraded home in one of Naples’ premier communities.

6907 Cocoplum St, Naples
$599,900
3 Beds ⋅ 2 Baths ⋅ 226024508 MLS ⋅ Winding Cypress BLDG.
Welcome to your private paradise in the highly sought-after, resort-style community of Winding Cypress! This TURNKEY FURNISHED true 3-bedroom, 2-bathroom villa offers the ultimate blend of luxury, comfort, and effortless living is move-in ready for your immediate enjoyment. The 2-car attached garage—complete with convenient overhead storage racks and additional utility sink—offer great convenience. Discover a bright, open-concept living space featuring seamless tile flooring throughout. The spacious great room flows effortlessly into your own private outdoor oasis. The enlarged screened lanai offers you enjoyment of a private pool and outdoor grill kitchen, located on a exceptionally private lot that offers a serene, peaceful retreat for relaxation or entertaining. The owner’s suite serves as a tranquil escape, boasting elegant tray ceilings and an ensuite bath complete with a dual-sink vanity, a walk-in shower, a linen closet, and a generous walk-in closet. Two additional bedrooms provide ample space and privacy for visitors and guests. Key upgrades and features include: Brand-NEW HVAC Unit for year-round comfort and energy efficiency. Storm Smart ELECTRIC STORM SHUTTERS on the rear lanai. ACCORDION SHUTTERS on all exterior windows for ultimate peace of mind and storm protection. Winding Cypress is renowned for its world-class amenities, including a resort-style pool, a resident-only restaurant, pickleball, tennis, bocce, a state-of-the-art fitness center, two dog parks, and a vibrant social calendar. Perfectly positioned just minutes from the award-winning beaches of both Naples and Marco Island, as well as shopping, dining, and entertainment, this property is an ideal choice for a full-time residence, a seasonal retreat, or a savvy investment option. Don't miss this rare opportunity to live the Florida dream!

7156 Live Oak Dr, Naples
$575,000
2 Beds ⋅ 2 Baths ⋅ 226008768 MLS ⋅ Winding Cypress BLDG.
Experience elevated resort-style living in the highly desirable community of Winding Cypress. This impeccably maintained and tastefully updated 2-bedroom plus den, 2-bath villa offers soaring 9’4” ceilings and an attached two-car garage, delivering both comfort and functionality in a truly move-in-ready residence. Thoughtful upgrades include a newer refrigerator and hot water heater, upgraded pavers, plantation shutters, and additional enhancements that add both style and peace of mind. The flexible den provides the perfect space for a home office, guest retreat, or additional lounge area. Winding Cypress is designed for those who value lifestyle. Nearly two-thirds of the community is preserved as tranquil natural landscape and wooded conservation, creating a serene, private atmosphere rarely found this close to everything. Ideally located just 8 miles from Downtown Naples and 9 miles from Marco Island, you are moments from world-class dining, shopping, and Gulf beaches. Residents enjoy an impressive amenity package featuring pickleball, bocce, clubhouse, resort-style pool and spa, community park, social rooms, and more. Opportunities like this are rare. Schedule your private showing today.

7666 Jacaranda Ln, Naples
Start Your Search