Windward Cay Condos for Sale

Welcome to Windward Cay, a charming community nestled in the heart of Naples, Florida, in beautiful Collier County. This hidden gem offers the perfect blend of tranquility and convenience, making it an ideal destination for those seeking a serene lifestyle without sacrificing accessibility to the vibrant offerings of Naples.

Windward Cay boasts a collection of well-appointed condos for sale, each designed to provide comfort and style. With spacious layouts, modern finishes, and stunning views of lush landscapes, these residences are perfect for both year-round living and seasonal escapes. Imagine waking up to the gentle sounds of nature, enjoying your morning coffee on a private balcony, and basking in the warm Florida sun.

The community is not just about beautiful homes; it also offers a wealth of amenities that cater to an active lifestyle. Residents can take advantage of the inviting swimming pool, tennis courts, and walking trails that wind through the picturesque surroundings. For those who love the outdoors, Windward Cay is just a short drive away from Naples' renowned beaches, golf courses, and shopping districts.

Investing in a condo at Windward Cay means embracing the Naples lifestyle, characterized by stunning sunsets, fine dining, and a vibrant arts scene. Whether you are looking for a vacation retreat or a permanent residence, Windward Cay presents an exceptional opportunity to own a piece of paradise in one of Florida's most sought-after areas. Don’t miss your chance to explore the condos for sale and discover the charm of Windward Cay today!

Newest Windward Cay Condos for Sale

$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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