Windward Cay Homes with Tennis Court(s) Amenities

Welcome to Windward Cay, a charming subdivision nestled in the heart of Naples, Florida, within the picturesque Collier County. Known for its lush landscapes and serene environment, Windward Cay offers the perfect blend of tranquility and luxury, making it an ideal destination for families, retirees, and anyone seeking a vibrant community.

One of the standout features of Windward Cay is its exceptional homes equipped with tennis court amenities. Imagine stepping out of your beautifully appointed residence and onto a private tennis court, where you can enjoy a friendly match with neighbors or refine your skills in the Florida sunshine. This unique feature not only promotes an active lifestyle but also fosters a sense of community among residents who share a passion for the sport.

The homes in Windward Cay are designed with elegance and comfort in mind, featuring spacious layouts, modern finishes, and stunning outdoor spaces. Many properties boast picturesque views of the surrounding greenery, providing a peaceful retreat after a long day. With easy access to Naples' pristine beaches, upscale shopping, and delectable dining options, residents are never far from the best that this coastal paradise has to offer.

Whether you’re an avid tennis player or simply looking for a vibrant community to call home, Windward Cay is a hidden gem in Naples. Experience the luxury of living in a neighborhood that prioritizes both recreation and relaxation. Come explore the beautiful homes and welcoming atmosphere that make Windward Cay the perfect place to live, play, and thrive!

Newest Windward Cay Homes with Tennis Court(s) Amenities

$1,375,000

3 Beds ⋅ 3 Baths ⋅ 2026023271 MLS ⋅ Windstar BLDG.

Skip Windstar's 7-year golf waitlist — full golf membership transfers at closing. Windstar on Naples Bay caps golf membership at 350. The waitlist currently runs approximately seven years. This sale is the shortcut: seller relinquishes their full golf membership at closing, giving the buyer immediate access to the Tom Fazio championship course, clubhouse, and practice facility — no waitlist (initiation fee and dues apply). The home: fully furnished 3BR/3BA two-story townhouse with den and 1-car garage, directly on the golf course inside Windstar's private gates — Naples' only gated golf community with direct bay access, a private marina, and its own beach on Keewaydin Island. The water: deeded Boat Slip #13 at Southpointe Yacht Club — deep-water marina fully rebuilt in 2023 with new pilings and composite docks. Direct Naples Bay and Gulf access, no bridges. Slip ownership includes private marina pool/spa and common area. Golf in the morning. Gulf by afternoon. Home on the course. One closing delivers all three. Furnished. Move-in ready.

4700 Yacht Harbor Dr Unit 622, Naples

$425,000

3 Beds ⋅ 2 Baths ⋅ 2026028731 MLS ⋅ Windstar BLDG.

Discover exceptional value and an unbeatable lifestyle in this beautifully maintained first-floor residence located in the prestigious gated community of Windstar on Naples Bay. Offering nearly 1,800 square feet of thoughtfully designed living space, this 2-bedroom, 2-bathroom condo with a den features soaring vaulted ceilings, crown molding, plantation shutters, and an attached one-car garage. Perfectly positioned just steps from the community pool, the screened lanai overlooks lush tropical landscaping and the picturesque 7th tee, creating a peaceful backdrop that perfectly complements the community's renowned golf lifestyle. A fully paid reverse osmosis water treatment system provides an added level of comfort and value. Windstar is one of Naples' most exclusive communities, offering a rare combination of championship golf and direct Gulf access. Residents enjoy a private boat shuttle to Keewaydin Island, a 72-slip deep-water marina, and a beautifully redesigned clubhouse with waterfront dining overlooking Naples Bay. The community also features tennis, bocce, a state-of-the-art fitness center, and a vibrant social calendar, with residents receiving priority on the waitlist for Social and Social Summer Golf Memberships. Ideally located just minutes from the vibrant Bayshore Arts District, Naples Botanical Garden, and less than four miles from the world-class dining, shopping, and white sand beaches of 5th Avenue South, this home offers the perfect opportunity for full-time living, a seasonal retreat, or an exceptional investment in one of Naples' most desirable waterfront communities.

4700 Yacht Harbor Dr Unit 612, Naples

Start Your Search