Community location

SkySail, East Naples · Naples, Florida

Updated
Sold $400,000 – $1,183,100 past 18 months
Asking now $345,525 – $1,180,661
Annual fees $2,400 – $3,700 middle range · varies by property type
Property tax rate 1.21% about $5,100 a year on a $512,000 single-family home, no exemptions applied, plus CDD assessment
Homes built 2022–2025 across 264 homes
Primary residence 56% of homes claimed as one
My community rating 3.5

Sold, property tax rate, homes built and primary residence are from county records.

Type, amenities & maintenance

Community type

Amenities

What your fees pay for in SkySail — the amenities available here, and the maintenance and services behind them.

Maintenance

Fees in SkySail typically cover street lighting, lawn and grounds maintenance, street maintenance, irrigation water, exterior pest control, recreational facilities, trash removal, and sewer.

Building types, pets & leasing

Pets

Pets are allowed in SkySail. The terms, such as how many pets and what size, can differ from home to home.

Homes here allow pets without approval. Where limits are stated they run to 45 lb.

Leasing

The minimum lease is 180 or 182 days, depending on the home, and up to 2 leases are allowed each year.

Restrictions

Homes here are deed restricted. Deed restrictions are recorded against the property and pass with it, so they apply to every owner. They typically cover exterior changes and how a home is used, and the community's recorded documents set out the detail.

Homes for sale in SkySail

Looking for something specific in SkySail? Refine these homes by type, beds, price, fees, and more.

Refine your search · 22 homes

Destinations & driving times from SkySail

Downtown at Fifth Avenue South is 27.1 miles from SkySail, about 43 minutes by car. The nearest beach access is Vanderbilt Beach at Bluebill Ave., 19.6 miles, about 34 minutes by car. It is 31 minutes to Galleria Shoppes at Vanderbilt for dining and shopping, 37 minutes to Artis—Naples for the performing arts, and 12 minutes to Big Corkscrew Island Regional Park for parks and recreation. The drive to Southwest Florida International Airport (RSW) is about 53 minutes.

Every destination named here is described in the Destinations chapter of the 2027 Naples Buyer’s Guide.

Driving times are estimated from the community’s mapped center or primary access point, using OpenStreetMap road data.

Dining & Shopping near SkySail, by driving distance
NameMilesETA
Galleria Shoppes at Vanderbilt 18.2 mi 31 min
Mercato 19.9 mi 34 min
Waterside Shops 22.2 mi 37 min
Venetian Village 24.4 mi 41 min
Coastland Center 25.2 mi 40 min
Miromar Outlets 26.5 mi 40 min
Fifth Avenue South 27.1 mi 43 min
Coconut Point 27.2 mi 43 min
Third Street South 28.3 mi 46 min
Gulf Coast Town Center 30.9 mi 43 min

Sales history · 18 months

Over the past 18 months the county recorded 90 single-family sales at a median of $512,000 in SkySail.

Single-family
$512,000 1,922 sq ft
median of 90 sales · 264 homes
25th $440,000 75th $623,600
May 2025 $417,500 – $747,000 monthly median Oct 2026

Types follow county records, which classify by how a home is owned rather than how it is built. Attached villas and townhouses appear within them according to how each home is deeded.

Source: Collier County Property Appraiser · 18 months to September 2026 · October 2026 from closed sales reported to M.L.S. of Naples, Inc.; county records for those months are still being finalized.

Flood zones & evacuation

100% of homes in SkySail sit on a lot mostly inside a FEMA Special Flood Hazard Area, chiefly zone AH, where a federally backed mortgage requires flood insurance — measured across 264 mapped homes, and it varies from home to home. For hurricane evacuation SkySail is in Collier Zone F (98% of homes).

Two different things, measured by two different agencies. Evacuation zones are about storm surge and who leaves first. Flood zones are FEMA’s insurance rating, and they vary from home to home.

Hurricane evacuation zone

Zone F Collier

The last zone called, and only in the strongest storms.

Called firstCalled last
FEMA flood zone
100% sit on a lot mostly inside a Special Flood Hazard Area, where a federally backed mortgage requires flood insurance.
In the Special Flood Hazard AreaOutside it
AE 127 homes 1% annual chance, with a set base flood elevation
AH 137 homes Shallow ponding, 1–3 ft

FEMA flood maps and Collier County Emergency Management. A revised Collier County flood map is in preparation and may change these zones.

Flood zone varies by home — each home’s page shows its own.
A starting point, not a determination. Your lender will require its own flood zone determination before closing, and your insurer will normally require an elevation certificate — a surveyor’s measurement of how high the building actually sits — before quoting. Those documents govern; this does not replace either. Zones can also be amended individually through FEMA.

Flood zones, evacuation, and insurance are explained in the Risk, Resilience & Insurance chapter of the 2027 Naples Buyer’s Guide.

Jeffrey Waldman

Jeffrey Waldman

REALTOR® and Owner, Naples Abodes

Call (239) 450-3763 Text (239) 450-3763

Florida License SL3295589

“…very professional, friendly and knowledgeable.”
Kim & Khanh Bui

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