Windward Cay Homes with Tennis Court(s) Community Type

Welcome to Windward Cay, a hidden gem nestled in the heart of Naples, Florida, within the picturesque Collier County. This charming community captures the essence of Florida living, offering a perfect blend of luxury, leisure, and active lifestyle. Windward Cay is not just a place to call home; it’s a vibrant community where residents can thrive, socialize, and enjoy the beautiful Florida weather year-round.

One of the standout features of Windward Cay is its homes with tennis courts, catering to both avid players and those who appreciate the sport's social aspects. Imagine stepping out of your exquisite residence and onto a pristine court, ready to engage in a friendly match or simply practice your serve. The community fosters a spirit of camaraderie, where neighbors become friends and tennis becomes a shared passion.

The homes in Windward Cay are designed with elegance and comfort in mind, boasting spacious layouts and modern amenities. Each property is surrounded by lush landscaping, creating a serene environment that enhances the overall appeal of the community. Whether you’re seeking a cozy retreat or a family-friendly abode, Windward Cay has something for everyone.

Beyond the courts, residents can explore the nearby attractions that Naples is famous for, including stunning beaches, upscale shopping, and gourmet dining options. With its prime location and exceptional amenities, Windward Cay is more than just a community; it’s a lifestyle choice that promises a fulfilling and active way of life in sunny Florida. Come discover your dream home in Windward Cay, where every day feels like a vacation!

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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