Windward Cay Real Estate

Welcome to Windward Cay, a hidden gem nestled in the heart of Naples, Florida. This charming community embodies the quintessential Florida lifestyle, offering a perfect blend of tranquility and modern convenience. Windward Cay is renowned for its beautifully designed homes, lush landscapes, and a welcoming atmosphere that makes it an ideal choice for families, retirees, and everyone in between.

Situated in Collier County, Windward Cay is conveniently located just minutes away from Naples' pristine beaches, upscale shopping, and delectable dining options. Residents can enjoy the vibrant local culture, with art galleries, theaters, and farmer's markets just a short drive away. The nearby Gulf of Mexico invites you to spend your days lounging on the beach, sailing, or engaging in various water sports.

The community features a variety of amenities designed to enhance your lifestyle. Take a refreshing dip in the community pool, unwind in the spa, or enjoy a leisurely stroll along the scenic walking paths surrounded by swaying palms and vibrant flora. For those who love outdoor activities, Windward Cay is in proximity to several golf courses, parks, and nature preserves, ensuring that adventure is never far from home.

Whether you’re looking for a year-round residence or a seasonal retreat, Windward Cay offers a unique opportunity to embrace the best of Naples living. With its charming homes and prime location, you’ll find the perfect place to create lasting memories. Discover the enchanting allure of Windward Cay, where your dream Florida lifestyle awaits!

Newest Listings in Windward Cay

$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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