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 inventory. Search current listings at /search.

What FEMA flood zone is Skysail in?

Skysail straddles more than one FEMA zone (Zones AH / AE); the exact zone depends on the lot, so insurance differs by parcel. Rick verifies the exact zone for any address.

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/school-choice that can vary by address; confirm before you offer.

What does it cost to own a home in Skysail?

For a $650,000 home in Skysail: ~$8,450/yr property tax, $3,250-$7,150/yr insurance, and $0-150/mo HOA. See the cost cheatsheet at /swfl-relocation-cost-cheatsheet.

What amenities does Skysail offer?

Skysail features Waterfront. Compare similar communities at /communities.

Naples, FL · Waterfront & Boating Communities

Skysail

Skysail is a residential community in Naples, Collier County, Southwest Florida.

Waterfront & Boating Communitiessingle-familyMid · $450K – $900KFEMA Zones AH / AE · varies by lot

Market Snapshot

Skysail market data

Live from the MLS · updated continuously. See all 15 listings →

Active Listings

for sale now

Median List Price

$535,000

active inventory

Median $/Sq Ft

$270

list price ÷ sqft

Avg Days on Market

days listed

Price Range

$345,525-$958,732

low to high

Sold (90 days)

$507,750

10 closed · median

Homes Built

2002-2026

Typical Home

3 bed · 1,966 sq ft

Waterfront

47% of homes

Median sold price · Skysail

$507,750last 3 months1.5% vs $515,474 prior 3 months

Median closed price by month · Skysail

22.6% MoM

$449,000Aug ’26 · 4 sales

Median of closed MLS sales each month over the available window. Months with too few sales are omitted; the range extends automatically as more sales close.

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

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Available Now

Homes for sale in Skysail(15)

Newest listings first, showing 12 of 15.

See all 15 homes →View on map →

Swipe to see more →

Recently Sold

Recent sales in Skysail

Home	Bd / Ba	Sq Ft	Sold	Sold Price
4235 Pegasus Way, Naples	4 / 3	2,601	Sep 2026	$679,000
4536 Centaurus Circle, Naples	3 / 2	1,778	Aug 2026	$445,000
4491 Centaurus Circle, Naples	3 / 2	1,860	Aug 2026	$453,000
4580 Skysail Drive, Naples	3 / 2	1,848	Aug 2026	$420,000

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

Price Range

Mid

Typically $450K – $900K

Flood Zone

Zones AH / AE

Varies by lot, verify your address

Shallow flooding (1–3 ft)

medium-confidence estimate, verify by address

Community Type

single-family

Region

Naples

Amenities & Lifestyle

What you get living in Skysail

Waterfront

Drive Times

Location & access

🏖️ Nearest Beach38 min
✈️ RSW Airport46 min
🏙️ Downtown Fort Myers34 min
🏥 Nearest Hospital33 min
🛣️ I-75 Access28 min

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.

Property Tax

$8,450

~$704/mo · Collier County millage ~1.3%

Insurance

$3,250, $7,150

Standard homeowners + wind

HOA Estimate

$0, $150/mo

Typically low/none

Estimates only. Florida Homestead Exemption (when you qualify) can knock $750-1,500 off the annual tax bill.

⚠️ Flood Zone Accuracy Note

Skysail is mapped primarily in Zone AH

Our analysis found 2 different flood zones within Skysail's footprint (Zone AH, Zone AE). The exact flood zone for any specific home depends on its parcel, homes on different streets, lots, or elevations within the same community can have different zone classifications.

Before making an offer, always verify the exact flood zone for the specific property address:

🔍 Verify on FEMA Map Service Center →Ask Rick for the Exact Zone →

Source: FEMA National Flood Hazard Layer · sampled at 5 points per community · confidence: medium

Schools

Schools serving Skysail

Elementary

Corkscrew Elementary School

FL DOE score 70/100 · 2024-25 grade

Middle

Corkscrew Middle School

FL DOE score 68/100 · 2024-25 grade

High

Palmetto Ridge High School

FL DOE score 65/100 · 2024-25 grade

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

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.

Ask About Skysail →Find Communities Like This (90-sec quiz)

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?: Skysail straddles more than one FEMA zone (Zones AH / AE), the exact zone depends on the specific lot, so insurance can differ street to street. 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.