Windward Cay Real Estate

Introducing Windward Cay: A Premier Development in Naples, FL

Nestled in the heart of Collier County, Naples, Florida, stands as a city renowned for its stunning beaches, upscale amenities, and vibrant lifestyle. Among the exceptional real estate offerings in this coveted location is the prestigious development of Windward Cay. Boasting an unrivaled combination of luxury, convenience, and natural beauty, Windward Cay is the epitome of contemporary living in Naples.

Situated within the thriving state of Florida, Windward Cay offers residents an idyllic retreat from the hustle and bustle of everyday life. With its prime location in Collier County, this development provides easy access to all the amenities and attractions that Naples has to offer. From world-class dining and shopping to championship golf courses and pristine beaches, residents of Windward Cay are never far from the best that Naples has to offer.

The homes within Windward Cay are meticulously designed to exude elegance and sophistication. With a variety of architectural styles and floor plans to choose from, residents can find their perfect sanctuary tailored to their unique preferences. Each residence is thoughtfully crafted with high-end finishes, spacious layouts, and state-of-the-art amenities, ensuring a luxurious and comfortable lifestyle.

Beyond the individual homes, Windward Cay offers an array of community amenities for residents to enjoy. From beautifully landscaped common areas to recreational facilities such as swimming pools, fitness centers, and walking trails, there is something for everyone within this exclusive development.

If you are seeking a truly exceptional living experience in Naples, look no further than Windward Cay. With its prime location, luxurious homes, and unparalleled amenities, this development sets a new standard for contemporary living in Collier County. Discover the beauty and sophistication of Windward Cay and make your dream of living in Naples a reality.

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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