Naples, FL · single-family neighborhood

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).

4310 Cepheus Way, Skysail
Current listing in Skysail: 4310 Cepheus Way $1.18M · Listing courtesy of Neal Communities Realty, Inc.
22Active homes
$346K – $1.18MList price range
$285Median list $ / sq ft
47Closed sales, 12 months

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For sale

Homes for sale in Skysail

All Naples homes $3M+ →
4310 Cepheus Way, Naples1 / 23
$1,180,661
4310 Cepheus WaySkysail · Naples
3 bd3 ba2,698 sf
Listing courtesy of Neal Communities Realty, Inc.
4647 Skysail Dr, Naples
$958,732
4647 Skysail DrSkysail · Naples
3 bd2.5 ba2,427 sf
Listing courtesy of Neal Communities Realty, Inc.
3995 Pegasus Way, NaplesWaterfront1 / 48
$895,900
3995 Pegasus WaySkysail · Naples
5 bd5 ba3,393 sf
Listing courtesy of ND Realty
3993 Perseus St, NaplesWaterfront1 / 25
$739,900
3993 Perseus StSkysail · Naples
3 bd2.5 ba2,309 sf
Listing courtesy of John R Wood Properties
4691 Skysail Dr, Naples1 / 21
$729,000
4691 Skysail DrSkysail · Naples
3 bd2 ba2,309 sf
Listing courtesy of Neal Communities Realty, Inc.
4056 Pegasus Way, Naples1 / 36
$719,900
4056 Pegasus WaySkysail · Naples
3 bd2.5 ba2,233 sf
Listing courtesy of Realty One Group MVP
4065 Aquila Pl, NaplesNew · 2 days1 / 37
$700,000
4065 Aquila PlSkysail · Naples
3 bd3 ba2,456 sf
Listing courtesy of John R Wood Properties
4239 Pegasus Way, Naples1 / 18
$669,404
4239 Pegasus WaySkysail · Naples
4 bd3 ba2,332 sf
Listing courtesy of Neal Communities Realty, Inc.
3998 Perseus St, NaplesWaterfront1 / 50
$650,000
3998 Perseus StSkysail · Naples
3 bd3 ba2,454 sf
Listing courtesy of Real Broker, LLC
4003 Pegasus Way, NaplesWaterfront1 / 49
$649,000
4003 Pegasus WaySkysail · Naples
3 bd2.5 ba1,966 sf
Listing courtesy of Coldwell Banker Realty
4101 Pegasus Way, NaplesNew · 14 days1 / 46
$639,900
4101 Pegasus WaySkysail · Naples
3 bd2.5 ba2,064 sf
Listing courtesy of Compass Florida, LLC
4671 Skysail Dr, Naples1 / 30
$566,802
4671 Skysail DrSkysail · Naples
2 bd2 ba1,904 sf
Listing courtesy of Neal Communities Realty, Inc.
4564 Centaurus Cir, NaplesWaterfront1 / 38
$554,900
4564 Centaurus CirSkysail · Naples
3 bd2 ba1,859 sf
Listing courtesy of Realty One Group MVP
4236 Pegasus Way, Naples1 / 17
$554,621
4236 Pegasus WaySkysail · Naples
3 bd2.5 ba2,064 sf
Listing courtesy of Neal Communities Realty, Inc.
3980 Pegasus Way, Naples1 / 42
$509,000
3980 Pegasus WaySkysail · Naples
3 bd2 ba1,812 sf
Listing courtesy of John R Wood Properties
4475 Centaurus Cir, Naples1 / 21
$496,500
4475 Centaurus CirSkysail · Naples
3 bd2 ba1,860 sf
Listing courtesy of Neal Communities Realty, Inc.
4467 Centaurus Cir, NaplesWaterfront1 / 18
$495,736
4467 Centaurus CirSkysail · Naples
3 bd2 ba1,778 sf
Listing courtesy of Neal Communities Realty, Inc.
4636 Skysail Dr, Naples1 / 31
$454,900
4636 Skysail DrSkysail · Naples
3 bd2 ba1,848 sf
Listing courtesy of Realty One Group MVP
4653 Centaurus Cir, Naples1 / 36
$439,900
4653 Centaurus CirSkysail · Naples
3 bd2 ba1,548 sf
Listing courtesy of Realty One Group MVP
5042 Draco Cir #2906, Naples1 / 32
$355,517
5042 Draco Cir #2906Skysail · Naples
3 bd2.5 ba1,507 sf
Listing courtesy of Neal Communities Realty, Inc.
5129 Draco Cir #0105, Naples1 / 32
$346,780
5129 Draco Cir #0105Skysail · Naples
3 bd2.5 ba1,790 sf
Listing courtesy of Neal Communities Realty, Inc.
5034 Draco Cir, Naples1 / 32
$345,525
5034 Draco CirSkysail · Naples
3 bd2.5 ba1,507 sf
Listing courtesy of Neal Communities Realty, Inc.

Listings 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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