Windward Cay Condos for Sale

Welcome to Windward Cay, an enchanting subdivision nestled in the heart of Naples, Florida, in Collier County. This charming community is a hidden gem, offering a perfect blend of tranquility and accessibility, making it an ideal haven for those seeking a vibrant lifestyle in sunny Florida.

Windward Cay is renowned for its picturesque landscape, featuring lush greenery and serene waterways that create a peaceful atmosphere. The community is designed for both relaxation and recreation, boasting a range of amenities, including a sparkling swimming pool, tennis courts, and scenic walking paths. Residents can enjoy leisurely strolls or bike rides while soaking in the beautiful Florida sunshine.

For those in search of condos for sale, Windward Cay offers a variety of options to suit different tastes and budgets. These well-appointed condos feature spacious layouts, modern finishes, and private balconies that provide breathtaking views of the surrounding nature. Whether you’re looking for a cozy retreat or a stylish residence, Windward Cay has something for everyone.

Living in Windward Cay means you're just a short drive away from Naples' stunning beaches, upscale shopping, and gourmet dining. The vibrant downtown area is brimming with cultural attractions, art galleries, and lively events, ensuring there's always something to do.

Discover the charm of Windward Cay and embrace a lifestyle that combines comfort, convenience, and community spirit. Whether you're a first-time buyer or looking for a vacation home, these condos for sale present an incredible opportunity to experience the best of Naples living. Don’t miss out on your chance to call Windward Cay home!

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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