Windward Cay Homes with Sidewalk Amenities

Welcome to Windward Cay, a picturesque subdivision nestled in the heart of Naples, Florida, within the vibrant Collier County. This charming community is perfect for those seeking a blend of tranquility and convenience, making it an ideal place to call home.

Windward Cay boasts beautifully designed homes that reflect the quintessential Florida lifestyle. Each residence is thoughtfully crafted, featuring spacious layouts and modern amenities that cater to a variety of lifestyles. The community is adorned with lush landscaping and offers a serene atmosphere, perfect for unwinding after a long day.

One of the standout features of Windward Cay is its commitment to fostering a friendly neighborhood environment. With well-maintained sidewalks winding through the community, residents can enjoy leisurely strolls, morning jogs, or evening bike rides while soaking in the beautiful Florida sunshine. The sidewalks not only enhance the aesthetic appeal of the area but also promote an active lifestyle, encouraging residents to engage with their surroundings and neighbors.

Living in Windward Cay means having easy access to Naples' stunning beaches, world-class dining, and vibrant shopping districts. Whether you're exploring the local art scene or indulging in fresh seafood at a waterfront restaurant, you'll find that everything you need is just a stone's throw away.

Experience the charm and comfort of Windward Cay, where community spirit thrives and every day feels like a vacation. Discover your dream home in this beautiful Naples subdivision and embrace the Florida lifestyle you've always desired!

Newest Windward Cay Homes with Sidewalk Amenities

$1,375,000

3 Beds ⋅ 3 Baths ⋅ 2026023271 MLS ⋅ Windward Cay 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 ⋅ Windward Cay 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

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