Windward Cay Homes with Pool Amenities

Welcome to Windward Cay, a hidden gem nestled in the heart of Naples, Florida. This charming neighborhood is renowned for its serene ambiance, friendly community, and proximity to the stunning Gulf Coast beaches. Windward Cay offers residents a perfect blend of tranquility and convenience, making it an ideal place to call home.

As you stroll through the tree-lined streets of Windward Cay, you’ll discover beautifully landscaped properties that reflect the pride of ownership in this close-knit community. The homes here boast a variety of architectural styles, each with its own unique charm. Many residences feature inviting outdoor spaces, but what truly sets Windward Cay apart is its abundance of homes with pool amenities. Imagine soaking up the Florida sun in your private oasis, hosting gatherings with friends and family, or enjoying a peaceful evening swim under the stars.

Living in Windward Cay means you’re just minutes away from Naples’ vibrant downtown area, where you can explore upscale shopping, exquisite dining, and cultural attractions. The nearby pristine beaches offer endless opportunities for relaxation and recreation, from sunbathing to water sports. For outdoor enthusiasts, the area is dotted with lush parks and nature preserves, providing ample opportunities to connect with nature.

Whether you're seeking a seasonal retreat or a year-round residence, Windward Cay is a community that truly embodies the essence of Florida living. With its inviting homes, pool amenities, and prime location, it’s no wonder that Windward Cay is a sought-after destination for those looking to enjoy the best of Naples. Come discover your dream home in this enchanting neighborhood today!

Newest Windward Cay Homes with Pool Amenities

$1,375,000

3 Beds ⋅ 3 Baths ⋅ 2026023271 MLS ⋅ Windstar 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 ⋅ Windstar 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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