Naples, FL · Waterfront & Boating Communities
Skysail
Skysail is a residential community in Naples, Collier County, Southwest Florida.
Market Snapshot
Skysail market data
Live from the MLS · updated continuously. See all 11 listings →
Figures reflect current active listings (and recent closed sales where available) tagged to Skysail. Medians are indicative, not an appraisal, ask Rick for a comparative market analysis on a specific home.
On the Map
Where Skysail sits
Available Now
Homes for sale in Skysail
No active listings in Skysail right now
New homes list here weekly, search nearby or ask Rick to watch this community for you.
Recently Sold
Recent sales in Skysail
| Home | Bd / Ba | Sq Ft | Sold | Sold Price |
|---|---|---|---|---|
| 4247 Pegasus Way, Naples | 3 / 2.5 | 2,079 | Jul 2026 | $580,000 |
| 4087 Pegasus Way, Naples | 3 / 2 | 1,812 | Jul 2026 | $442,940 |
| 4652 Centaurus Circle, Naples | 4 / 2.5 | 2,428 | Jul 2026 | $699,500 |
| 4135 Pegasus Way, Naples | 3 / 2.5 | 2,014 | Jun 2026 | $506,500 |
Closed sales from the last 12 months. Ask Rick for a full comparable-sales report on any home you're considering.
At a Glance
Skysail at a glance
Amenities & Lifestyle
What you get living in Skysail
Cost of Ownership
Estimated yearly costs for a mid-tier home
Florida estimates based on a $650,000 home in Skysail. Actual numbers vary, book a Strategy Session for a live, parcel-specific quote.
Estimates only. Florida Homestead Exemption (when you qualify) can knock $750-1,500 off the annual tax bill.
Schools
Schools serving Skysail
Assigned schools based on current MLS listings in Skysail, with Florida Department of Education 2024-25 grades. Collier County uses zoning and school-choice options that can change by address and year, so confirm the exact assignment with the district before you offer.
Compare
Similar communities to consider
Ready to Look Closer?
Get live numbers for Skysail
HOA dues, current listings, recent sales, builder incentives, all change weekly. Book a free Strategy Session and I'll pull a live snapshot for Skysail tailored to your timeline and budget.
Good Questions
Skysail, frequently asked questions
- What are home prices like in Skysail?
- Skysail is in the mid price tier, typically Typically $450K – $900K. List prices vary by size, age, condition, and current inventory; search current listings or ask Rick for live comps.
- What FEMA flood zone is Skysail in?
- Flood zone varies by parcel, Rick verifies the exact zone for any address before you offer.
- What schools are near Skysail?
- Per current MLS listings, Skysail is served by Corkscrew Elementary School (grade A), Corkscrew Middle School (grade A), Palmetto Ridge High School (grade A). Collier County uses zoning and school-choice options that can vary by address, so confirm the exact assignment before you offer.
- What does it cost to own a home in Skysail?
- For a $650,000 home, estimate roughly $8,450/yr property tax, $3,250-$7,150/yr insurance, and $0-$150/mo HOA. Full breakdown in the SWFL cost cheatsheet.
- What amenities does Skysail offer?
- Skysail features Waterfront. Compare similar communities on the interactive map.