Winding Cypress Homes with Tennis Court(s) Community Type

Welcome to Winding Cypress, an exquisite community nestled in the heart of Naples, Florida, within the picturesque Collier County. This enchanting development is designed for those who appreciate the finer things in life, offering a perfect blend of luxury, comfort, and an active lifestyle.

Winding Cypress is renowned for its stunning homes, each thoughtfully crafted to embody the spirit of Florida living. From spacious floor plans to elegant finishes, these residences are designed to cater to your every need. Whether you’re seeking a cozy retreat or a grand family home, you’ll find the perfect match here.

One of the standout features of Winding Cypress is its commitment to promoting an active lifestyle. The community boasts a variety of amenities, including beautifully maintained tennis courts that invite residents to engage in friendly matches or hone their skills. Whether you're a seasoned player or just starting, the tennis courts provide an excellent opportunity for socializing and staying fit.

Beyond tennis, Winding Cypress offers a vibrant community spirit, with plenty of opportunities to connect with neighbors through various social events and activities. Enjoy leisurely strolls along the scenic pathways, relax at the resort-style pool, or explore the lush natural surroundings that make Naples a true paradise.

With its prime location, residents of Winding Cypress can easily access the stunning beaches, world-class dining, and upscale shopping that Naples is famous for. Embrace the Florida lifestyle and make Winding Cypress your new home, where luxury meets leisure in a community designed for you.

Newest Winding Cypress Homes with Tennis Court(s) Community Type

$599,900

3 Beds ⋅ 2 Baths ⋅ 226024508 MLS

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 Drive, Naples

$575,000

2 Beds ⋅ 2 Baths ⋅ 226008768 MLS

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 Lane, Naples

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