Windward Cay Homes with Tennis Court(s) Community Type

Welcome to Windward Cay, a stunning community nestled in the heart of Naples, Florida, within the beautiful Collier County. This picturesque neighborhood offers a perfect blend of luxury living and recreational opportunities, making it an ideal destination for those seeking a vibrant lifestyle in one of Florida's most sought-after areas.

Windward Cay is renowned for its charming homes, many of which feature private tennis courts, allowing residents to indulge in their passion for the game right in their own backyard. Whether you're a seasoned player or just starting out, these courts offer the perfect setting for friendly matches and family fun. Imagine stepping out of your elegant home and onto your very own court, surrounded by lush landscaping and the warm Florida sun.

The community is designed with a friendly, welcoming atmosphere, where neighbors become friends and every day feels like a vacation. With a variety of homes available, from spacious single-family residences to luxurious villas, Windward Cay caters to diverse lifestyles and preferences. Each property is thoughtfully designed with modern amenities and stylish finishes, ensuring that you can enjoy both comfort and elegance.

In addition to the tennis courts, Windward Cay is conveniently located near Naples' pristine beaches, upscale shopping, and fine dining establishments. The vibrant cultural scene and outdoor recreational activities make this community a haven for those who appreciate the finer things in life.

Experience the charm of Windward Cay, where luxury meets leisure in the heart of Naples. Your dream home awaits!

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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