Skysail
Homes for Sale in Naples, FL
All 2,295 homes for sale in Naples, FL · median $439,000 · 553 homes for sale in 34120 · Collier County homes for sale
True comps, carrying-cost math, and listings before the portals.
Photo via Florida Gulf Coast MLS
As of November 2026, Skysail in Naples, FL has 22 homes for sale and 1 pending, asking from $345,525 to $1,180,661 (median $560,851). Over the 12 months ending 2026-11-11, 14 recorded sales closed at a median of $550,000, $247 per square foot, a median 101 days on market, sellers accepting 93% of original asking. Homes listed or recently sold were built 2022–2026 with 16 new construction; 5 of 23 report an HOA (median $217/mo); 16 of the 23 geocoded homes sit in a FEMA special flood hazard zone (median elevation 15 ft). At the median price and Collier County's FY2025-26 rate of 11.05 mills, annual property tax runs about $6,080 ($5,640 with the full homestead exemption).
Last 30 days in Skysail: 8 new listings (median asking $496,118), 1 under contract right now. As of November 11, 2026, Listing information provided by the Florida Gulf Coast Multiple Listing Service, Inc. Information is deemed reliable but not guaranteed by the MLS to be accurate.
Homes For Sale Right Now in Skysail
Live MLS inventory for Skysail. Every active listing, what is under contract right now, and the last 12 months of closed sales, refreshed twice a day. Closed comps beat an algorithm's guess every time.
Active · 8 daysTop listing
Active · 163 days
Active · 188 days
Active · 8 days
Active · 43 days
Active · 41 days
Active · 32 days
Active · 108 days
Active · 40 days
Active · 5 days
Active · 41 days
Active · 41 days
Active · 40 days
Active · 135 daysActive and pending Skysail listings as of 2026-11-11, priced high to low. Listing information provided by the Florida Gulf Coast Multiple Listing Service, Inc. Information is deemed reliable but not guaranteed by the MLS to be accurate. Tap any home to ask about it.
Skysail is a new-construction community — every home on record was built between 2022 and 2024, with a median year built of 2024, so there's no resale layer to compare against. That newness is the price driver: buyers are paying for current-code construction and largely unlived-in space, not for location premium or established landscaping.
The 8% year-over-year pull-back and a 75-day median days on market tell you this is a community still finding its price level as inventory from the initial build-out competes for buyers. With 204 homes total and only 25 closings in the recent window, pricing power sits with buyers willing to be patient and sellers who price to the current market rather than to last year's comps.
Figures in this note are as of July 29, 2026. The live market numbers elsewhere on this page update nightly and are newer.
Skysail right now
🟢 Buyer-leaning market. 18.9 months of supply and 4% of the inventory already under contract give buyers above-average negotiating leverage.Why it matters: months of supply is how long today's inventory would last at today's sales pace; under-contract share is the portion of homes for sale that already have a buyer.Momentum Research analysis of Florida Gulf Coast MLS records, as of November 11, 2026. Confidence: Very High (23 active and pending listings, 14 closed sales in 12 months).
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· Updated November 12, 2026 · Live data: Florida Gulf Coast MLS, refreshed twice daily · MLS facts carry their source; interpretation lines are Momentum Research · Data sources & freshness
The 60-Second Overview
Skysail market snapshot (as of November 11, 2026): the median sale price is about $550K ($247 per sq ft over the trailing 12 months of closed sales), a median 101 days on market for closed sales, and 18.9 months of supply, a buyer-leaning market.
In ZIP 34120 (Naples), 459 homes closed in the last 12 months at a median of $577K ($323/sq ft), with a median 59 days on market. Right now 596 active and 114 pending listings put supply at about 15.6 months — a soft market. See the live ZIP 34120 housing market and the Collier County market.
County records show 68 qualified sales in Skysail across 2024–2025 (41 in 2024, 27 in 2025), median $564,800 — the last recorded sale per parcel on the Florida DOR 2025 assessment roll, independent of the MLS.
Flood zones in Skysail: of 13 listing addresses checked against the FEMA National Flood Hazard Layer, 8% sit outside the FEMA Special Flood Hazard Area (Zone X); 92% are in an A-series high-risk zone where flood insurance is required with a federally backed mortgage. Individual parcels vary - verify any specific address at msc.fema.gov. See flood zones by neighborhood in Naples.
Skysail is a community of 167 homes in Naples, Collier County, built between 2022 and 2024 (median 2023), with a median living area of about 2,581 square feet. 24% of parcels are homesteaded, the owner-occupancy proxy in the Florida DOR assessment roll (2025 roll, public records).
Skysail is a ground-up Naples community in Collier County built almost entirely within the last few years, which puts it in a different conversation than older, established neighborhoods — the homes are new, but the market here is still thin and still settling.
The setting & the homes.
Aerial and on-site photos of Skysail. Swipe to explore the community.
Swipe or use the arrows → tap any photo to enlarge
SkysailSkysailSkysailSkysailSkysailSkysailSkysailSkysailPhotos from Florida Gulf Coast MLS listings in Skysail; content deemed reliable but not guaranteed.
Who Skysail is best for.
Best for
- Buyers prioritizing new construction over an established neighborhood feel
- Buyers comfortable negotiating in a market with limited recent closings and a recent price pull-back
- Buyers who want a larger floor plan, at or near the 2,603-square-foot median, in a Naples location
Probably not for
- Buyers who want confirmed, built-out community amenities in place before purchasing
- Buyers who need a deep resale comp history to validate a purchase price
- Buyers expecting rapid appreciation given the current year-over-year decline
Skysail on the map.
Every active, pending, and recently sold home, plotted. Toggle the layers and tap a home for the details.
Listing locations from Florida Gulf Coast MLS. Map data © OpenStreetMap contributors.
The Skysail buying strategy.
If we were buying in Skysail today, this is the order of operations we would run for our clients.
Underwrite the condition first. Price the roof, HVAC, and systems honestly before judging any list price; condition swings value here more than square footage alone.
Match the home to real comps. Recent sales of similar condition and lot, not the asking price, tell you what a home is worth.
Use your leverage. With inventory sitting, there is room to negotiate on anything dated or overpriced and to ask for repairs or a rate buydown.
Line up financing and inspection early. A pre-approval and an inspection plan let you act fast and negotiate from evidence.
Keep an agent in your corner. The listing agent works for the seller; we represent you and prepare a hand-built valuation before any offer in Skysail.
A community still being priced, not just built
At a median price of $506,500 and a median living area of 2,603 square feet, Skysail lands in the larger-home end of new construction without being positioned as an entry-level product. The median price-per-square-foot of $245.58 gives a separate read on value across the mix of homes currently listed, and with construction dates bunched between 2022 and 2024, condition variance between homes is driven far more by floor plan, lot, and builder finish level than by age or deferred maintenance.
The homestead share of 25.2% is worth sitting with. It suggests a meaningful portion of Skysail's owners are not claiming it as a primary residence, which is common in newer Naples-area communities that draw second-home and investment buyers. That has real implications for resale timing and for how much of the community you'll see occupied versus vacant or rented at any given point. No community amenities are currently identified from MLS listings, so buyers should treat this as a housing product first and confirm any HOA, recreational, or common-area features directly with a listing before assuming they exist.
The location and the amenities are priced into every listing in Skysail. The deal is won or lost on condition, the comps, and the renovation math.
Momentum Buy Score.
Our proprietary 0 to 10 read across the factors that decide how a home in Skysail buys, holds, and resells. Momentum Research; not an appraisal.
Momentum Intelligence Scores are our proprietary, qualitative assessment on a 0 to 10 scale, built from the record-level market data on this page. They are a framework for comparing communities, not a guarantee of future value and not advice on a specific home; unlike an automated value estimate they do not price your home, they grade the community on evidence you can inspect. Composite is the plain average of the 3 factors (2.5). Basis: Liquidity & Demand 18.9 months of supply; Owner Commitment 24% owner-occupied; Pricing Power 92.8% sale-to-list. Refreshed with each data update.
Why work with Momentum here
In a community this new, with this few closings to draw on, pricing a home well means reading a thin data set correctly rather than leaning on a large comp pool. We track Skysail's closings as they happen, not on a lag, so you're negotiating off current conditions — including the recent price pull-back — rather than last year's numbers.
Skysail in 15 seconds.
Tools for a Skysail buy.
Free calculators to pressure-test the real cost before you tour.
Selling here is won on condition and pricing to real comps, not an automated estimate. The right number comes from closed Skysail sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Skysail, the right list price comes from recent comparable sales matched to your home's condition and location, not an automated estimate.
What is your Skysail home worth?
Get a no-obligation home value based on real comparable sales in Skysail, not an automated guess. Tell us about your home and we will personally prepare your numbers and a pricing strategy. No obligation, no spam.
See all homes for sale in Naples →
Recently off market in Skysail
Homes in Skysail that recently left the market. Each address opens its public-record profile: county-recorded value, property taxes, the last recorded sale, community sales history, and what is for sale nearby now. 17 on record.
- 3967 Pegasus Way · off market
- 3993 Perseus St · off market
- 4058 Aquila Pl · off market
- 4073 Aquila Pl · off market
- 4174 Pegasus Way · off market
- 4235 Pegasus Way · off market
- 4491 Centaurus Cir · off market
- 4519 Centaurus Cir · off market
| Location | Naples, Collier County, FL · ZIP 34120 |
|---|---|
| Homes in the community | 167 (FL DOR 2025 assessment roll) |
| Years built | 2022–2024 (median 2023) |
| Typical living area | 2,581 sq ft (median) |
| Home types (current listings and sales) | singlefamilyresidence 78%, condos 17% |
| Sale prices, last 12 months | $550,000 median across 14 closed sales · $247 per sq ft |
| Days on market (closed sales) | 101 median |
| For sale right now | 22 active, 1 pending · median asking $560,851 · 18.9 months of supply |
| Owner-occupied (homestead) share | 24% |
Data as of November 11, 2026. Listing information provided by the Florida Gulf Coast Multiple Listing Service, Inc. Information is deemed reliable but not guaranteed by the MLS to be accurate; housing-stock figures from Florida Department of Revenue public records. Market figures describe homes, not residents. Cite as: Momentum Realty, “Skysail key facts,” movewithmomentum.com/neighborhoods/skysail, data as of November 11, 2026.
Housing distress & ownership in Skysail, Naples
Who owns here, how much is not owner-occupied, and how much for-sale inventory is under distress.
Source: Momentum Realty Research. Ownership & parcels from the FL DOR 2025 tax roll; distress from MLS active-listing status/remarks; price from MLS closed sales. Listing information provided by the Florida Gulf Coast Multiple Listing Service, Inc. Information is deemed reliable but not guaranteed by the MLS to be accurate. Deemed reliable but not guaranteed.
Just listed in Skysail
The newest homes for sale in Skysail right now, newest first. Each link opens the full listing with every photo, the price history and a tour request.
- 4475 Centaurus Cir $496,500 · 3 bd · 2 ba · 1,860 sq ft · new today Courtesy of Neal Communities Realty, Inc.
- 4467 Centaurus Cir $495,736 · 3 bd · 2 ba · 1,778 sq ft · new today Courtesy of Neal Communities Realty, Inc.
- 5093 Draco Cir $384,420 · 3 bd · 3 ba · 1,994 sq ft · new today Courtesy of Neal Communities Realty, Inc.
- 5042 Draco Cir 2906 $355,517 · 3 bd · 3 ba · 1,507 sq ft · new today Courtesy of Neal Communities Realty, Inc.
- 5129 Draco Cir 0105 $346,780 · 3 bd · 3 ba · 1,790 sq ft · new today Courtesy of Neal Communities Realty, Inc.
- 4154 Pegasus Way $585,000 · 4 bd · 3 ba · 2,351 sq ft · listed Nov 7, 2026 Courtesy of Realty One Group MVP
Checked against the MLS nightly. All new listings in this market.
Every Home for Sale in Skysail Right Now (23)
All 23 active and pending Skysail listings with a detail page, newest first, refreshed twice a day from the MLS.
- 5093 Draco Cir · $384,420 · 3 bd / 3 ba · listed Oct 27, 2026 · listed by Neal Communities Realty, Inc.
- 4154 Pegasus Way · $585,000 · 4 bd / 3 ba · listed Oct 23, 2026 · listed by Realty One Group MVP
- 4065 Aquila Pl · $700,000 · 3 bd / 3 ba · listed Oct 14, 2026 · listed by John R Wood Properties
- 4101 Pegasus Way · $599,900 · 3 bd / 3 ba · listed Oct 3, 2026 · listed by Compass Florida, LLC
- 4310 Cepheus Way · $1,180,661 · 3 bd / 3 ba · listed Sep 30, 2026 · listed by Neal Communities Realty, Inc.
- 4691 SkySail Dr · $657,185 · 3 bd / 2 ba · listed Sep 30, 2026 · listed by Neal Communities Realty, Inc.
- 4236 Pegasus Way · $554,621 · 3 bd / 3 ba · listed Sep 30, 2026 · listed by Neal Communities Realty, Inc.
- 4239 Pegasus Way · $669,404 · 4 bd / 3 ba · listed Sep 29, 2026 · listed by Neal Communities Realty, Inc.
- 4671 SkySail Dr · $566,802 · 2 bd / 2 ba · listed Sep 29, 2026 · listed by Neal Communities Realty, Inc.
- 4564 Centaurus Cir · $554,900 · 3 bd / 2 ba · listed Sep 29, 2026 · listed by Realty One Group MVP
- 4475 Centaurus Cir · $496,500 · 3 bd / 2 ba · listed Sep 29, 2026 · listed by Neal Communities Realty, Inc.
- 5042 Draco Cir 2906 · $355,517 · 3 bd / 3 ba · listed Sep 29, 2026 · listed by Neal Communities Realty, Inc.
- 5129 Draco Cir 0105 · $346,780 · 3 bd / 3 ba · listed Sep 29, 2026 · listed by Neal Communities Realty, Inc.
- 4056 Pegasus Way · $697,900 · 3 bd / 3 ba · listed Sep 28, 2026 · listed by Realty One Group MVP
- 4636 Skysail Dr · $454,900 · 3 bd / 2 ba · listed Sep 20, 2026 · listed by Realty One Group MVP
- 4467 Centaurus Cir · $495,736 · 3 bd / 2 ba · listed Sep 11, 2026 · listed by Neal Communities Realty, Inc.
- 4003 Pegasus Way · $649,000 · 3 bd / 3 ba · listed Sep 10, 2026 · listed by Coldwell Banker Realty
- 3998 Perseus St · $650,000 · 3 bd / 3 ba · pending · listed Sep 5, 2026 · listed by Real Broker, LLC
- 4647 SkySail Dr · $758,102 · 3 bd / 3 ba · listed Aug 23, 2026 · listed by Neal Communities Realty, Inc.
- 3995 Pegasus Way · $895,900 · 5 bd / 6 ba · listed Aug 13, 2026 · listed by ND Realty
- 3980 Pegasus Way · $509,000 · 3 bd / 2 ba · listed Aug 13, 2026 · listed by John R Wood Properties
- 4653 Centaurus Cir · $439,900 · 3 bd / 2 ba · listed Aug 13, 2026 · listed by Realty One Group MVP
- 5034 Draco Cir · $345,525 · 3 bd / 3 ba · listed Aug 13, 2026 · listed by Neal Communities Realty, Inc.
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Naples guides & data
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- Home insurance cost
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Florida buyer guides
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- Florida property tax calculator
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- The 4-point inspection, explained
- Florida flood insurance calculator
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Streets in this community
Street-level pages: every home on record, what sold and what is for sale on each street.
- Pegasus Way (16 homes on record)
- Centaurus Circle (13 homes on record)
- Skysail Drive (8 homes on record)
4% of homes for sale in Skysail are already under contract (under contract ÷ under contract + active listings) — a read on how much of the available inventory buyers have already claimed. Source: MLS data (2026-11-12).
What it really costs to own in Skysail
The parts of the monthly number a mortgage calculator leaves out, from the tax roll, the MLS, Citizens and FEMA. Property facts only.
| Property tax | Current owners' bills run a median of $7,621/yr across 22 listings here (MLS tax records, 2026-11-12). |
|---|---|
| HOA dues | Median $217/month across 7 MLS listings (most billed quarterly; 2026-11-12). Dues cover what the documents say they cover; ask for the budget and reserve study. |
| Home and flood insurance | The average Citizens Property Insurance premium in Collier County is $2,147/yr (2,002 policies, Citizens detail by county, April 2026); private-market quotes depend on roof age, wind mitigation and construction. Flood: of 13 listing addresses checked against the FEMA flood map, 8% sit outside the high-risk zone and 92% inside one, where flood insurance is required with a federally backed mortgage. Statewide, a Zone X flood policy runs about $500-$700/yr and a high-risk zone $1,200-$2,500/yr (FEMA Risk Rating 2.0 averages, not quotes). |
| Roof and age | Median build year 2026 across 46 listings. Newer roofs and current wind-mitigation features usually mean the lower end of insurance quotes. |
Estimated carrying cost at the median asking price, before the mortgage: about $1,031/month (tax $635, HOA $217, insurance $179). An estimate from the sources above, not a quote.
Email me new listings in Skysail
One e-mail a day, only when a home lists here, with price, beds, baths and a link to every listing. Straight from the MLS feed; no account needed.
Ask an agent about Skysail
Have a question about the homes, fees, rules or commute here? A Momentum agent who works Skysail will answer, and the answer is published on this page for the next buyer.
Frequently Asked Questions
What is the median home price in Skysail?
How long do homes in Skysail take to sell?
Is Skysail a buyer's or seller's market right now?
How many homes are in Skysail?
What share of Skysail is owner-occupied?
When were the homes in Skysail built?
Who is the best real estate agent for Skysail?
How do I find a top Naples real estate agent who knows Skysail?
Can Momentum Realty connect me with an agent for Skysail?
Where is Skysail, and what county is it in?
Is Skysail in a flood zone?
Is Skysail a good place to live?
Should you buy in Skysail?
An honest fit check. We will tell you when it is not your community.
Data sources & freshness
| Live listings | Florida Gulf Coast MLS, refreshed twice daily (last: November 11, 2026) |
| Community market stats | Florida Gulf Coast MLS closed sales, 12-month windows ending November 11, 2026 |
| Housing stock & ownership | Florida DOR assessment roll (street-list match (3 streets, ZIP 34120)) |
| Under-contract shares | Florida Gulf Coast MLS records, as of 2026-11-11 |
| Historical depth | Closed-sale records back to 2026 (14 transactions analyzed) |
Verify the primary sources yourself: Florida DOR · U.S. Census · FEMA flood maps · Citizens Property Insurance.
Momentum Research figures are our own analysis of Florida Gulf Coast MLS records; MLS data is deemed reliable but not guaranteed. Methodology: how Momentum market scores are computed. Market metrics describe homes for sale and recent sales, not residents.
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See how Skysail fits the bigger picture — live prices, inventory, and Momentum Scores: