Mindy DolleDomain Realty · Naples
(239) 851-2556
Naples, FL · condominium community

Windward Cay homes for sale

As of October 24, 2026, 5 homes are for sale in Windward Cay, Naples, FL, priced from $425K to $2.1M with a median asking price of $1.1M (about $503 per square foot).

640 2nd St #2, Windward Cay
Current listing in Windward Cay: 640 2nd St #2 $2.1M · Listing courtesy of John R Wood Properties
5Active homes
$425K – $2.1MList price range
$503Median list $ / sq ft
4Closed sales, 12 months

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Questions about Windward Cay

How many homes over $3M are for sale in Windward Cay?

There are no homes listed at $3M or more in Windward Cay right now, and 5 active listings overall. Listings change daily.

What do luxury homes cost in Windward Cay?

Current asking prices run $425K to $2.1M, with a median of $1.1M or roughly $503 per square foot. Floor, view, finish and, for single-family homes, lot and water frontage account for most of the spread.

What kinds of homes are in Windward Cay?

Windward Cay is a condominium community in Naples, FL. Current listings include homes with 2 to 3 bedrooms, 1,589 sq ft to 2,218 sq ft, built 1985 to 2003.

What are the association fees in Windward Cay?

Current listings report association fees of $1,033 to $3,989 per quarter. What a fee covers differs by building or community, so ask for the budget and the reserve and milestone-inspection documents before you buy.

How fast do homes sell in Windward Cay?

4 sales closed in the past 12 months at a median of $695K, with a median of about 91 days on market and a median sale-to-list ratio of 92.5%. A small number of sales means these medians are only a guide.

Is Windward Cay a golf community?

The MLS lists golf among the community features on 4 of the 5 current listings here, and 4 have a golf course view. Whether a club membership is required, optional or sold separately differs by community and sometimes by building, so ask for the membership terms and current fees before you compare prices.

Is Windward Cay gated?

Yes, according to the MLS: all 4 listings that report gate status here are marked Gated.

What amenities does Windward Cay offer?

Community features most often listed in the MLS for homes here: Pool (4 of 5), Golf Equity (4 of 5), Bike And Jog Path (4 of 5), Clubhouse (4 of 5), Restaurant (4 of 5), Tennis Court(s) (4 of 5). These come from listing records, so confirm what is included, and what costs extra, with the association.

What should I check before buying a home in Windward Cay?

Start with the association: the budget, reserves and any special assessments, and what the current fees cover. Then check the flood zone and elevation, an insurance quote, any club or amenity membership and its transfer rules, and what comparable homes have actually sold for. Mindy can pull the closed sales for Windward Cay and walk you through the documents.

Who can show me homes in Windward Cay?

Mindy Dolle, a licensed Florida real estate sales associate with Domain Realty, can arrange showings, pull comparable sales and review association documents for homes in Windward Cay. Call or text (239) 851-2556.

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