The price range for this community is $415k to $1.4M
$1,375,000
3 Beds • 3 Baths • 2,178 Sqft
WINDSTAR
Skip Windstar's 7-year Golf Waitlist — Full Golf Membership Transfers At Closing. Windstar On Naples Bay Caps Golf Membership At 350. The Waitlist...
$1,250,000
2 Beds • 2 Baths • 2,348 Sqft
WINDSTAR
Welcome To A Boater's Dream In Regatta Landing At Windstar! Your 25ft Boat Dock With Lift Is Just Steps Away Is Included With The Purchase Of This ...
$1,249,000
2 Beds • 2 Baths • 2,348 Sqft
WINDSTAR
Experience The Best Of Naples Living In This Beautifully Appointed 2-bedroom, 2-bath Condominium In Regatta Landing At Windstar. Designed With An E...
$950,000
3 Beds • 2 Baths • 1,832 Sqft
WINDSTAR
Welcome To Spinnaker Point At Windstar On Naples Bay, Where Golf, Waterfront, And Refined Coastal Living Converge. This Beautifully Updated Coach H...
$725,000
2 Beds • 2 Baths • 1,822 Sqft
WINDSTAR
Turnkey Furnished With Peaceful Water Views In The Highly Sought After Community Of Windstar On Naples Bay, This Beautifully Updated Marina Cove Co...
$675,000
3 Beds • 2 Baths • 1,700 Sqft
WINDSTAR
Welcome To Marina Cove At Windstar On Naples Bay. This 3 Bedroom/2 Bath Coveted First Floor End Unit Unit Feels More Like A House. Open-concept Liv...
$449,000
2 Beds • 2 Baths • 1,561 Sqft
WINDSTAR
Discover This Beautifully Maintained First-floor Coach Home Perfectly Situated Just Steps From The Windstar Marina And Yacht Basin. The Inviting La...
$425,000
3 Beds • 2 Baths • 1,830 Sqft
WINDSTAR
Discover Exceptional Value And An Unbeatable Lifestyle In This Beautifully Maintained First-floor Residence Located In The Prestigious Gated Commun...
$425,000
2 Beds • 2 Baths • 1,414 Sqft
WINDSTAR
Welcome To 3522 Haldeman Creek Drive In The Community Of Compass Point Of Windstar On Naples Bay. This 2 Bedroom/2 Bathroom Corner End Unit On The ...
$415,000
2 Beds • 2 Baths • 1,414 Sqft
WINDSTAR
There Are Very Few Addresses In Naples Where You Can Wake Up To Water Views, Walk To A Deep Water Marina, And Live Inside A Private Gated Golf Comm...
| Listings | Average DOM | Average Price | Average $/SF | Median $/SF | |
|---|---|---|---|---|---|
| Active | 10 | 99 | $793,800 | $412 | $678 |
| Sold (past 6 months) | 33 | 192 | $1,472,595 | $542 | $495 |
As of July 14, 2026, there are currently 10 properties for sale in Leeward Cay at Windstar listed as active, with an average asking price of $794k. The highest-priced property is $1.4M; the lowest-priced property can be purchased for $415k. Leeward Cay at Windstar neighborhood listings have an average price of $412 per square foot, based on listings with 2 bedrooms, 2 baths, and 1,845 square feet of living space.
Leeward Cay at Windstar is a luxurious gated community located in Naples, Florida. The community is part of the larger Windstar on Naples Bay community and is situated along the bayfront, offering stunning views of the water and the surrounding natural beauty.
Leeward Cay at Windstar consists of 56 villas, each offering a spacious and open floor plan. The villas range in size from 1,894 to 2,685 square feet and feature two to three bedrooms. The community was built in the 1990s and many of the homes have since been updated or renovated to reflect modern design and functionality.
Residents of Leeward Cay at Windstar have access to a range of amenities, including a private marina, a golf course, tennis courts, and a fitness center. The community also offers a private beach club on Keewaydin Island, accessible by a community-owned boat shuttle.
Overall, Leeward Cay at Windstar is an ideal community for those seeking a luxurious and tranquil lifestyle in a picturesque bayfront setting. The community's amenities, coupled with its stunning natural surroundings, make it a highly sought-after destination in Naples, Florida.
Data last updated: July 14th, 2026 at 2:31am EDT and updating occurs daily
The data relating to real estate for sale on this Website come in part from the Broker Reciprocity Program (BR Program) of M.L.S. of Naples, Inc. Properties listed with brokerage firms other than Naples Homes - Florida Realty & Co 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.