Windward Isles Homes For Sale

Windward Isles homes for sale are cozy, comfortable luxury estates located in a private alcove in sophisticated central Naples. These top-of-the-line executive homes are stunning examples of luminous modern design and classical elegance. Blending contemporary sophistication and timeless coastal architecture, these stately houses are truly incomparable. Encased in beautiful stucco and stone, Windward Isles homes merge indoor and outdoor living with rich open-air living spaces and delightful museum-quality interiors. These houses feature only the most aesthetically appealing of materials to create an absolutely incandescent masterpiece product. If you're looking for a residence that feels bright, polished, and unendingly indulgent — or you have a bit of an artistic side — choose a Windward Isle home in Naples.

Connect with LuxHomesOfNaples to receive the latest information on Windward Isles. But first, read all about the radiant homes in this highly anticipated community.

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Windward Isle

18,566 Properties Found. Page 1 of 1,548.
Photo of Listing #222051703

Holly Hill Rd, ZOLFO SPRINGS

$39,999,990 - 1,676 Acres

MLS® # 222051703

SVN Lotus Comm. R.E. AdvisorsNaples Area Board of Realtors Logo
Photo of Listing #222025412

4100 Gulf Shore Blvd N, NAPLES

$35,000,000 - 4 Beds, 6 Baths, 10,000 Sf

MLS® # 222025412

Douglas Elliman Florida,LLCNaples Area Board of Realtors Logo
Photo of Listing #222006788

3001 Veterans Pky, CAPE CORAL

$35,000,000 - 76 Acres

MLS® # 222006788

Coldwell Banker RealtyNaples Area Board of Realtors Logo
Photo of Listing #222050197

3675 Gordon Dr, NAPLES

$31,000,000 - 6 Beds, 9 Baths, 7,873 Sf

MLS® # 222050197

Premier Sotheby's International RealtyNaples Area Board of Realtors Logo
Photo of Listing #222047889

5601 Palm Beach Blvd, FORT MYERS

$28,900,000

MLS® # 222047889

Tropics RealtyNaples Area Board of Realtors Logo
Photo of Listing #222029531

3595 Gin Ln, NAPLES

$27,900,000 - 4 Beds, 6 Baths, 7,173 Sf

MLS® # 222029531

William Raveis Real EstateNaples Area Board of Realtors Logo
Photo of Listing #222043262

3131 Gin Ln, NAPLES

$25,950,000 - 5 Beds, 7 Baths, 7,695 Sf

MLS® # 222043262

William Raveis Real EstateNaples Area Board of Realtors Logo
Photo of Listing #222056369

1030 Galleon Dr, NAPLES

$25,900,000 - 5 Beds, 7 Baths, 6,414 Sf

MLS® # 222056369

Coldwell Banker RealtyNaples Area Board of Realtors Logo
Photo of Listing #222036086

4120 Cutlass Ln, NAPLES

$25,900,000 - 6 Beds, 7 Baths, 7,964 Sf

MLS® # 222036086

Gulf Coast International PropNaples Area Board of Realtors Logo
Photo of Listing #222058982

600 Galleon Dr, NAPLES

$25,000,000 - 5 Beds, 9 Baths, 7,195 Sf

MLS® # 222058982

Douglas Elliman Florida,LLCNaples Area Board of Realtors Logo
Photo of Listing #222049819

2100 Davis Blvd, NAPLES

$25,000,000 - 96,884 Sf

MLS® # 222049819

William Raveis Real EstateNaples Area Board of Realtors Logo
Photo of Listing #222012423

970 Aqua Cir, NAPLES

$25,000,000 - 6 Beds, 9 Baths, 7,750 Sf

MLS® # 222012423

Premier Sotheby's Int'l RealtyNaples Area Board of Realtors Logo

Explore Windward Isles Real Estate

Within the doors of any home on the Windward Isles real estate market is a haven of the highest quality. Windward Isles homes come in 3 select models: Abacos, Grenada I, Grenada II. Each has its own distinct characteristics as well as a few standard, across-the-board features; the Abaco model is the only single-story plan among them. Features within these homes include zero-edge pools and luxe outdoor kitchens, elevated vaulted ceilings, and shimmering lighting. Clean cream hues define most homes; creamy carpeting, slick stone flooring, and add-ons such as spacious studies and 3 car garages are abundant. Floor plans range from 4,550 square feet to 5,800 square feet.

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Data last updated: October 3rd, 2022 at 4:45pm EDT and updating occurs daily

Naples Area Board of Realtors Logo 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 William Raveis Luxury Properties 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.