Windward Cay Homes with Tennis Court(s) Community Type

Welcome to Windward Cay, a hidden gem nestled in the heart of Naples, Florida, where the allure of coastal living meets the excitement of an active lifestyle. This charming community, located in Collier County, offers a unique blend of luxurious homes and top-tier amenities, making it the perfect destination for those seeking both relaxation and recreation.

Windward Cay is renowned for its stunning residences, many of which boast private tennis courts, allowing residents to indulge in their passion for the sport right at home. Imagine stepping out your back door to a perfectly maintained court, ready for a friendly match with neighbors or a challenging game with friends. The community’s commitment to promoting an active lifestyle is evident in its well-kept facilities and beautifully landscaped surroundings.

Beyond the tennis courts, Windward Cay offers a serene atmosphere with lush greenery and tranquil waterways, perfect for unwinding after a day of activity. The nearby beaches of Naples are just a short drive away, providing residents with easy access to sun-soaked sands and breathtaking sunsets over the Gulf of Mexico.

With a vibrant community spirit, Windward Cay is not just a place to live; it’s a lifestyle choice. Embrace the charm of Naples and discover the perfect home where tennis and tranquility await. Whether you’re a seasoned player or just starting, Windward Cay invites you to experience the joy of living in a community that truly values both leisure and luxury. Come and explore your future home today!

Newest Windward Cay Homes with Tennis Court(s) Community Type

$1,375,000

3 Beds ⋅ 3 Baths ⋅ 2026023271 MLS

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 Drive Unit 622, Naples

$425,000

3 Beds ⋅ 2 Baths ⋅ 2026028731 MLS

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 Drive Unit 612, Naples

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