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Browse All Windward Cay Properties for Sale

$1,375,000
3 Beds ⋅ 3 Baths ⋅ 2026023271 MLS ⋅ Windward Cay 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

Courtesy of Homeinc Realty LLC.

$425,000
3 Beds ⋅ 2 Baths ⋅ 2026028731 MLS ⋅ Windward Cay 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

Courtesy of KW Elevate Luxury.

$725,000
2 Beds ⋅ 2 Baths ⋅ 226012602 MLS ⋅ Windward Cay BLDG.
Immediate Full Golf Membership to Windstar on Naples Bay available with purchase! (Separate fee) Beautifully updated 2-bedroom + den, 2-bath top-floor condo in Windward Cay at Windstar on Naples Bay, offering exceptional views of Windstar’s 7th fairway and desirable southwest exposure. This spacious residence features soaring ceilings, rich wood flooring throughout, and a stunning renovated kitchen with high-end appliances, crisp white shaker cabinetry, and granite countertops. Both bathrooms have been tastefully updated with modern finishes, creating a refined coastal aesthetic throughout. Offered furnished for a seamless, move-in-ready experience. The private single car garage provides added convenience and valuable storage. Windward Cay offers community elevators, a sparkling pool with a large sun deck, well-maintained buildings, and lush tropical landscaping. Windstar offers exceptional amenities including a Tom Fazio–designed golf course, newly redesigned clubhouse with sweeping views of Naples Bay, 72-slip deep-water marina with direct Gulf access in under ten minutes, clay tennis courts, bocce ball, state-of-the-art fitness center, and private Windstar boat shuttle to Keewaydin Island’s white sandy beach featuring a shaded pavilion, restrooms, kayaks, and exceptional shelling & fishing!

4650 Yacht Harbor DR Unit 133, Naples

Courtesy of Downing Frye Realty Inc..

Selling Office: John R Wood Properties.

$350,000
2 Beds ⋅ 2 Baths ⋅ 225083771 MLS ⋅ Windward Cay BLDG.
Welcome to Windward Cay, a charming enclave within the prestigious gated community of Windstar on Naples Bay. This desirable first floor end residence offers two bedrooms plus a den, two bathrooms, and an attached garage, providing comfort, privacy, and convenience. The spacious screened lanai invites you to unwind while enjoying peaceful views of the mangrove preserve and Windstar’s seventh fairway. Inside, the home is filled with natural light and features plantation shutters throughout, tile flooring in the main living areas, and soft carpeting in the bedrooms, creating a warm and inviting atmosphere. The generously sized kitchen is bright and functional, offering abundant cabinetry, ample counter space, and a cozy breakfast nook bathed in sunshine. Windward Cay is beautifully landscaped and designed for an active lifestyle, highlighted by its distinctive heart shaped community pool, spa, and cabana. Residents of Windstar on Naples Bay enjoy access to optional memberships and exceptional amenities, including a private Tom Fazio designed eighteen hole golf course, a newly completed and impressive clubhouse renovation, tennis, bocce, a private beach club on Keewaydin Island with daily shuttle service, sunset cruises, and convenient water taxi access to downtown waterfront dining. Ideally located in the vibrant Bayshore Arts District, this home is just minutes from Celebration Park, local markets, popular breweries, cocktail and wine bars, Naples Botanical Garden, Sugden Park, Naples Bay, and the East Naples Community Center. Downtown Naples shopping, dining, and renowned white sand beaches are only ten minutes away. This is an exceptional opportunity to enjoy the very best of the Southwest Florida lifestyle.

4700 Yacht Harbor DR Unit 613, Naples

Courtesy of John R Wood Properties.

Selling Office: ERA Naples Realty Services.

$665,000
3 Beds ⋅ 2.5 Baths ⋅ 225075980 MLS ⋅ Windward Cay BLDG.
Luxuriously Remodeled Coach Home in Windstar on Naples Bay Welcome to an exceptional opportunity to own a fully remodeled, end-unit coach home in the prestigious Windstar community—one of Naples’ most sought-after waterfront and golf neighborhoods. This elegant residence has been completely renovated in 2025, offering a seamless blend of modern sophistication and coastal charm. Spanning over 2,000 square feet of refined living space, this spacious home features brand new Luxury Vinyl Plank flooring throughout, setting the tone for a sleek and contemporary aesthetic. The gourmet kitchen and spa-inspired bathrooms have been meticulously redesigned with high-end finishes, custom cabinetry, and premium fixtures, ensuring both style and functionality. Positioned as a desirable end unit, the home is bathed in natural light from multiple exposures and showcases breathtaking views of Windstar’s lush fairways and a tranquil long lake vista. With three generously sized bedrooms plus a versatile den, this residence offers ample space for both relaxation and entertaining. Interior Highlights: Fully remodeled in 2025 with top-tier craftsmanship Open-concept layout with expansive living and dining areas Designer kitchen with quartz countertops, stainless steel appliances, and custom backsplash Luxurious bathrooms featuring walk-in showers, double vanities, and elegant tilework Private screened lanai overlooking golf and water views Attached garage and ample storage throughout Windstar on Naples Bay – Premier Amenities: Tom Fazio-designed championship golf course Newly redesigned clubhouse with panoramic views of Naples Bay 72-slip deep-water marina offering direct Gulf access in under 10 minutes Keewaydin Island Beach Club with private boat shuttle and exclusive membership Clay tennis courts, bocce ball, state-of-the-art fitness center, and vibrant social calendar Prime Location: Situated just minutes from Naples’ iconic 5th Avenue, residents enjoy easy access to world-class dining, boutique shopping, art galleries, and cultural attractions. The area’s pristine white-sand beaches are also just a short drive away, making this home the perfect launchpad for the ultimate Southwest Florida lifestyle.

4650 Yacht Harbor DR Unit 121, Naples

Courtesy of Realty One Group MVP.

Selling Office: William Raveis Real Estate.

$1,075,000
2 Beds ⋅ 2 Baths ⋅ 225070107 MLS ⋅ Windward Cay BLDG.
Welcome to 4460 Yacht Harbor Drive in desirable Windward Cay enclave in Windstar on Naples Bay. If you are considering Gulf Shore Blvd, Moorings or Park Shore condo living Windstar offers the waterfront lifestyle while being set back and protected from the bay for true peace of mind. This redesigned and fully renovated corner end-unit penthouse unit is located in a boutique 6-unit elevator building with only 2 units per floor and features 2 Bedrooms+den and 2 Baths in almost 2200 square feet of truly luxurious living space. Enter into a welcoming foyer to a truly fabulous open-concept living space with a contemporary light and airy vibe with soaring vaulted ceilings and stunning natural views all around. Spacious living room with walls of glass boasting unparalleled Audubon Society-certified views overlooking the serene 8th fairway, lake and tropical mangroves. A true chef's eat-in kitchen replete with custom shaker cabinetry, GE Monogram stainless steel appliances, pot filler, contemporary quartz countertops, open shelving with lighting, breakfast bar and custom built-in Brazilian walnut dining table ideal for daily dining and entertaining. Custom built-in office nook ideal for today's work from home lifestyle. Convenient laundry room with side by side washer/dryer, custom built-in cabinetry and counter affording great storage. Master suite oasis features spacious bedroom, dual walk-in closets with California custom built-ins and a spa-like master bath with a gorgeous oversized walk-in shower with dual rain heads, contemporary floating double vanity and freestanding soaking tub. Large guest bedroom with a gorgeous view plus a lovely full hall bathroom. Air conditioned glassed-in lanai currently used as a TV room could also be set up as a home office or additional guest quarters. Oversized covered parking for 2 vehicles and electrical outlet for your golf cart. No expense spared in this truly custom renovation with the finest of materials and craftsmanship a rarity to find this level of high-design and finish in a condo in Windstar. Windstar on Naples Bay is the only gated golf community with Tom Fazio designed 18-hole golf course that offers direct bay access, a private beach plus dock on Keewaydin Island with seasonal October-July boat shuttle included in your Windstar HOA plus a full service 73-slip deep water marina. Newly renovated clubhouse (separate membership) with multiple dining areas with stunning views of Naples Bay and Port Royal, 6 Har-Tru tennis courts, 3 bocce courts and a new state of the art fitness center slated for late 2026 completion. Preferred location just a short 2 mile drive via car, bike or golf cart to downtown's 5th Avenue South and 3rd Street South known worldwide for its fine dining, shopping and beaches. Situated in the vibrant Bayshore Arts District, Windstar is walkable to Naples Botanical Garden and Naples Pickleball Center home of the pickleball US Open. Easy access to I-75, Naples and Fort Myers airports.

4460 YACHT HARBOR DR, Naples

Courtesy of John R Wood Properties.

Selling Office: John R Wood Properties.

$2,195,000
4 Beds ⋅ 3.5 Baths ⋅ 225039473 MLS ⋅ Windward Cay BLDG.
A dreamy location only 6 houses from Naples famous sandy white beaches, one block to world famous 5th Avenue South & a short stroll to Third Street South’s world class shopping, art galleries and fine dining. This charming coastal inspired 4-Bedroom, 3-1/2 Bath Villa is exactly where you want to be. Warmth and character abound in this delightful home which lives comfortably for 2 people while also easily accommodating a large gathering of family and friends. Tastefully furnished, the relaxed main living and dining area have an abundance of natural light, and access to the inviting screened lanai overlooking beautiful tropical foliage. Just off the great room is the efficient eat-in kitchen which looks out to the pool area. Also on the main level is a bedroom with ensuite bath that is currently being used as a cozy den and work-from-home space (with a handy sofa bed to accommodate extra guests). Upstairs on the second level, the airy and romantic primary bedroom has a beautifully renovated en-suite bath. There are also 2 additional bedrooms and 2 more fully updated baths on this floor. Meander up one more floor and you’ll find the delightful third floor sleeping loft and comfy hang-out space. Surrounded by windows and situated above the swaying palms outside - this unique space could also be an inspiring artist’s loft, or fantastic workout/yoga/meditation retreat. There’s also a small, tree-top terrace that is a perfect place to enjoy one of Naples dazzling sunsets. Back on the main living level is a covered patio that overlooks and accesses the swimming pool and outdoor grill. Windward Cay is an intimate community of 4 meticulously maintained homes. There’s a one-car garage off the alley entrance, with room for a second vehicle on the garage apron. There’s also unrestricted free street parking just in front of the home on 6th Avenue South – which your visitors will greatly appreciate! Unique and special, this gorgeous home is a rare find, indeed.

180 6th AVE S Unit 3, Naples

Courtesy of Perrett Kennedy LLC.

Selling Office: Coldwell Banker Realty.

$483,000
3 Beds ⋅ 2 Baths ⋅ 225037921 MLS ⋅ Windward Cay BLDG.
The seller is paying ALL HOA fees for the rest of 2025, a generous $17,000 Buyer Credit that makes this home an unmatched value. This stunning second-floor residence in the coveted Windstar community is where modern elegance meets coastal living. A rare opportunity, this three-bedroom, two-bath home is packed with thoughtful upgrades and stylish touches throughout. From the moment you enter, you’ll notice the sleek, uniform tile flooring that flows seamlessly through the open-concept design, offering both beauty and easy maintenance. The chef-inspired kitchen is equipped with premium finishes and fixtures, making it a joy to cook and entertain. A flex space just off the kitchen serves perfectly as a home office, den, or creative retreat—tailored to your lifestyle. Enjoy the convenience of a private one-car garage, ideal for extra storage or your beach-ready gear. The screened lanai becomes your front-row seat to golden sunsets, adding a serene backdrop to evenings at home. Whether you’re hosting friends or winding down solo, this space is your own slice of paradise. Windstar on Naples Bay is a hidden gem, featuring an exclusive private beach with shuttle boat access to Keewaydin Island, a deep-water marina with Gulf access, and optional social and golf memberships to elevate your lifestyle. Residents enjoy a gated, amenity-rich environment just minutes from Downtown Naples and 5th Avenue South, known for its upscale boutiques, renowned restaurants, and lively arts scene.

4650 Yacht Harbor DR Unit 125, Naples

Courtesy of Alfred Robbins Realty Group.

Selling Office: Keller Williams Realty Naples.

$730,000
3 Beds ⋅ 3 Baths ⋅ 225021371 MLS ⋅ Windward Cay BLDG.
This spacious coach home boasts over 2,300 sq. ft. of living space with views of Windstar’s 7th fairway. As a beautiful end unit, it is filled with natural light and features 3 bedrooms + den and 3 full baths. Thoughtfully designed with quality furnishings and tasteful décor, this residence offers a warm and inviting atmosphere. Additional highlights include generously sized closets for extra storage, a large laundry room, and an attached garage. Windward Cay enhances the lifestyle with its tropical landscaping, excellent curb appeal, and a large heated community pool—making this an exceptional home in Windstar on Naples Bay! Windstar offers incredible amenities including: Tom Fazio designed golf course, newly redesigned clubhouse with spectacular views of Naples Bay, 72 slip deep-water marina with direct Gulf access in less than ten minutes, clay tennis courts, bocce ball, fitness, Keewaydin Island Beach Club with boat shuttle and private membership.

4700 Yacht Harbor DR Unit 621, Naples

Courtesy of Downing Frye Realty Inc..

Selling Office: Coldwell Banker Realty.

$675,000
2 Beds ⋅ 2 Baths ⋅ 224006702 MLS ⋅ Windward Cay BLDG.
GOLF MEMBERSHIP OPPORTUNITY AVAILABLE! End-unit 2 bed+ den condo with the option to purchase a transferable FULL GOLF MEMBERSHIP -YES-you can Beat The Wait-List!-Take a tour of the Newly Renovated Clubhouse! This unit has tile flooring thru-out, eat-in-kitchen, roomy seating alcove to expand any of your table choices & sitting possibilities, quartz countertops, all GE Profile appliances-double oven & French-door refrigerator, refaced cabinets with upper & lower under cabinet lighting, portable island to maximize space, den triples as guest room/office/zoom studio, 2-yr old AC, 1-yr old water heater, washer & dryer, attached 1 car garage. Partial furnishings included. Windstar is Naples' only gated golf community with its own marina and direct gulf access. Boat slips can be purchased or rented when available. Residents can ride the shuttle boat to their own private beach on Keewaydin Island! Windstar’ s Bayshore Arts District location is home to the Botanical Garden, hip eateries & a quick drive to downtown Naples-fine dining, shopping, galleries & beaches.

4800 Yacht Harbor DR Unit 811, Naples

Courtesy of MVP Realty Associates LLC.

Selling Office: Compass Florida LLC.

$500,000
2 Beds ⋅ 2 Baths ⋅ 224001558 MLS ⋅ Windward Cay BLDG.
This is the ultimate Naples lifestyle that you have been waiting for!!! First floor, end-unit, coach home with an attached garage!! CHECK OUT THE PRICE PER SQUARE FOOT!! This is the best value in ALL of Windstar! Welcome home to Naples only gated golf community on the bay with both a marina & a private beach! Located in the Bayshore Arts district; you are close to the Botanical Gardens, great restaurants, wonderful new art scene, and so much more! Memberships are available offering a world class fitness center & fine dining. Private boat shuttle to the resident beach on Keewaydin Island! The residence offers a very private, over-sized screened porch, an eat-in kitchen with stainless appliances, plus a breakfast bar and living room/dining room combo, perfect for entertaining. You will LOVE this floorplan!

4700 Yacht Harbor DR Unit 611, Naples

Courtesy of Coldwell Banker Realty.

Selling Office: Compass Florida LLC.

$650,000
3 Beds ⋅ 3 Baths ⋅ 223080150 MLS ⋅ Windward Cay BLDG.
Social Memberships now available! Enjoy the ultimate Florida lifestyle in this stunning 3-bed, 3-bath second-floor unit in the gated community of Windstar on Naples Bay. With one of the largest floor plans in the complex, attached one-car garage, and private views of the preserve and Tom Fazio-designed golf course, this unit is a dream. Recently updated, it offers modern design, vaulted ceilings, and a turnkey furnished setup. The updated kitchen features stainless steel appliances and custom cabinetry. The master suite is a luxurious retreat with a spacious bathroom and two walk-in closets. The 3rd bedroom also has an en-suite bathroom. Conveniently located near the Windward Kay community pool and within walking distance of the main clubhouse. Short drive to downtown Naples and access to unbeatable amenities, including a golf course, clubhouse, marina, tennis, gym, Beach Club with boat shuttle to Keewaydin Island, and private memberships available. Don't miss the video!

4800 Yacht Harbor DR Unit 822, Naples

Courtesy of REMAX Blue Skies.

Selling Office: John R Wood Properties.

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The data relating to real estate for sale on this web site comes in part from the Broker Reciprocity Program (BR Program) of M.L.S. of Naples, Inc. Properties listed with brokerage firms other than this company are marked with the BR Program Icon or the BR House Icon and detailed information about them includes the name of the listing brokers. The properties displayed may not be all the properties available through the BR Program. The information provided is for consumers’ personal, non-commercial use and may not be used for any other purpose.

Windward Cay Real Estate & Homes