Skysail homes for sale
As of October 16, 2026, 22 homes are for sale in Skysail, Naples, FL, priced from $346K to $1.18M with a median asking price of $603K (about $285 per square foot).

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Homes for sale in Skysail
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New · 2 days1 / 37
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New · 14 days1 / 46
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Waterfront1 / 38
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Waterfront1 / 18
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1 / 32Listings are shown courtesy of the listing brokerages. Information is deemed reliable but not guaranteed.
Questions about Skysail
How many homes over $3M are for sale in Skysail?
There are no homes listed at $3M or more in Skysail right now, and 22 active listings overall. Listings change daily.
What do luxury homes cost in Skysail?
Current asking prices run $346K to $1.18M, with a median of $603K or roughly $285 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 Skysail?
Skysail is a single-family neighborhood in Naples, FL. Current listings include homes with 2 to 5 bedrooms, 1,507 sq ft to 3,393 sq ft, built 2022 to 2026. 11 listings are new construction.
Are homes in Skysail on the water?
Of the 22 current listings, 8 are waterfront, 2 have a private pool, per MLS data. Water type and access vary by street and building, so confirm each home's details before relying on them.
What are the association fees in Skysail?
Current listings report association fees of $603 to $953 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 Skysail?
47 sales closed in the past 12 months at a median of $504K, with a median of about 89 days on market and a median sale-to-list ratio of 95.3%. A small number of sales means these medians are only a guide.
Who can show me homes in Skysail?
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 Skysail. Call or text (239) 851-2556.
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- Quail West16 homes at $3M+
- Royal Harbor15 homes at $3M+
- Mediterra12 homes at $3M+
- Palisades9 homes at $3M+
- Aqua8 homes at $3M+