Windward Cay Homes with Tennis Court(s) Community Type

Windward Cay Homes with Tennis Court(s) Community Type

Welcome to Windward Cay, an exquisite community nestled in the heart of Naples, Florida, where luxury meets leisure in a stunning tropical setting. Located in Collier County, Windward Cay offers an idyllic lifestyle, perfect for those who appreciate the finer things in life. This charming community is not just a place to live; it's a lifestyle that harmonizes comfort, recreation, and a sense of belonging.

Windward Cay is renowned for its beautiful homes, many of which feature private tennis courts, making it a haven for tennis enthusiasts and active families alike. Imagine stepping out of your beautifully designed home and onto your very own court, where you can enjoy morning matches or evening practice under the stars. The community's emphasis on outdoor living and wellness is evident in its well-maintained amenities and lush landscapes.

Beyond the tennis courts, Windward Cay boasts a vibrant community spirit, with friendly neighbors and social events that foster connections and camaraderie. The nearby beaches, world-class dining, and shopping experiences of Naples add to the allure, ensuring that residents have access to both relaxation and excitement.

Whether you're looking for a seasonal retreat or a permanent residence, Windward Cay offers a unique blend of luxury and leisure. Experience the joys of living in a community designed for those who appreciate an active lifestyle while enjoying the beautiful Florida sunshine. Discover your dream home in Windward Cay today, where every day feels like a vacation!

Newest Windward Cay Homes with Tennis Court(s) Community Type

4600 Yacht Harbor Drive Unit 412, Naples
$1,099,000
2 Beds ⋅ 2 Baths ⋅ 226037973 MLS
Welcome to 4600 Yacht Harbor Drive in Windward Cay at Windstar on Naples Bay, one of Naples’ most desirable gated waterfront communities. This beautifully renovated, furnished end-unit residence offers 2 bedrooms plus a den, 2 full bathrooms, and approximately 2,185 square feet of inviting living space with tranquil golf course views. Rich hardwood flooring, solid-core doors, crown molding, plantation shutters, custom lighting, and thoughtfully selected finishes create a warm, refined interior. The expansive chef’s kitchen features custom cabinetry, granite countertops, a beautiful backsplash, an induction cooktop, a pot filler, and generous storage, making it equally suited to everyday living and entertaining. The spacious primary suite provides a peaceful retreat with custom closet built-ins and a beautifully appointed bathroom. Additional highlights include a formal dining room, a versatile den ideal for a home office or additional guest space, custom window treatments, a stackable washer and dryer, and an approximately 8-by-6-foot storage room. Overlooking Windstar’s picturesque 8th fairway, the residence enjoys a serene backdrop of lush tropical landscaping and beautifully maintained greens. Windward Cay residents enjoy a heated community pool, grilling area, elevator access, and an intimate residential setting. Windstar on Naples Bay offers an exceptional collection of amenities, including a Tom Fazio-designed 18-hole golf course, driving range, and a newly renovated clubhouse with spectacular Naples Bay views. The brand-new, recently completed fitness center adds another highlight to the community’s active lifestyle, complementing its tennis courts and bocce facilities. A full-service deep-water marina with direct Gulf access enhances the waterfront experience, while a seasonal boat shuttle to Windstar’s private beach on Keewaydin Island offers a secluded Gulf-front escape. Golf and clubhouse memberships are available separately, subject to availability and club requirements. Ideally located just minutes from downtown Naples, Fifth Avenue South, Third Street South, acclaimed dining, shopping, and Gulf beaches, Windstar also offers convenient access to the Bayshore Arts District, Naples Botanical Garden, and Naples Pickleball Center. For buyers considering The Moorings, Park Shore, or Gulf Shore Boulevard, Windstar presents a compelling opportunity to enjoy a gated waterfront community with exceptional amenities, natural beauty, and proximity to everything Naples has to offer. Discover beautifully renovated interiors, peaceful golf course views, and the best of the Southwest Florida lifestyle. One or more photos have been virtually staged, AI-generated, or rendered.

4600 Yacht Harbor Drive Unit 412, Naples
4650 Yacht Harbor Drive Unit 124, Naples
$649,000
2 Beds ⋅ 2 Baths ⋅ 226038417 MLS
Golf Course Views and Private Beach Access on Naples Bay! Welcome to this completely updated, second-floor gem in the prestigious Windstar on Naples Bay community. Offering 1,589 square feet of thoughtfully curated living space, this move-in ready 2-bedroom-plus-den features a new custom-built Murphy bed that seamlessly transforms the space  into an immediate third guest suite. This residence has been beautifully modernized throughout and delivers the ultimate Southwest Florida lifestyle with absolutely zero post-closing work required. Start your day with coffee on your private lanai overlooking the pristine greens on the 7th hole, relax by the expansive community pool, or embark on a waterfront adventure aboard Windstar's private shuttle boat, the Keewaydin Queen, which takes residents directly to a private island beach. Ideally located just 10 minutes from downtown Naples and historic Olde Naples, you will enjoy effortless daily access to world-renowned dining, luxury shopping, entertainment, and the distinct charm of Fifth Avenue South. Whether you are seeking a full-time residence, an effortless seasonal retreat, or a prime investment opportunity, this condo offers an exceptional blend of modern updates, flexible living space, scenic golf views, and stunning daily sunsets. Experience championship golf along the bay, boating adventures, and exclusive beach access all in one remarkable, highly sought-after Naples community.

4650 Yacht Harbor Drive Unit 124, Naples
4700 Yacht Harbor Drive Unit 622, Naples
$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
4700 Yacht Harbor Drive Unit 612, 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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