Leeward Cay
Homes for Sale in Naples, FL
All 2,301 homes for sale in Naples, FL · median $439,000 · Collier County homes for sale
True comps, carrying-cost math, and listings before the portals.
Leeward Cay is a community in Naples, Collier County, FL. Across Naples as a whole, 1,831 homes closed in the last 12 months at a median of $577,000, 76 median days on market. At that median and Collier County's FY2025-26 rate of 11.05 mills, annual property tax runs about $6,380 ($5,940 with the full homestead exemption).
With only three closings in the current window, Leeward Cay is a thin-data market — the $1,137,000 median and $484.86 per-square-foot figure are real, but they reflect a small handful of sales, not a broad trend line. Treat both as a directional read rather than a precise ceiling or floor.
A median 25-day time on market is brisk for a price point north of a million, which tells us that whatever does list here is being priced and presented correctly from day one. For sellers, that argues for pricing tight to recent comps rather than testing the market. For buyers, it means hesitation on a well-positioned listing can cost you the deal.
Figures in this note are as of July 29, 2026. The live market numbers elsewhere on this page update nightly and are newer.
Nearby homes for sale
No active listings inside Leeward Cay right now. These are the 6 closest homes on the market, by straight-line distance from the community's center; some may sit just outside its boundary.
Listing data from the MLS feeds named on each listing page; deemed reliable but not guaranteed. Refreshed nightly.
The 60-Second Overview
Leeward Cay is a small, higher-priced pocket of the Naples market in Collier County, where limited recent sales activity means each closing carries outsized weight on the numbers.
Pre-construction details are compiled from public records, builder announcements and builder listings, and are subject to change without notice; figures are deemed reliable but not guaranteed. Momentum Research figures are our own analysis. This page describes homes, pricing and community attributes, not residents.
Who Leeward Cay is best for.
Best for
- Buyers with a budget in the seven-figure range looking in the Naples market
- Sellers who can price tight to recent comps and want a market that has been moving in roughly a month
- Buyers comfortable doing property-level diligence rather than relying on published amenities
Probably not for
- Buyers who need a confirmed clubhouse, pool, or gated amenity package before making an offer
- Anyone trying to draw firm conclusions from community-wide pricing trends given the limited closing volume
- Buyers working with a budget well under the current median price point here
The market around Leeward Cay
Leeward Cay is too small for its own price trend, so here is the market around it.
Across Collier County, 5,183 homes are active and 932 pending (15% under contract).
ZIP and county figures describe the wider market, not Leeward Cay specifically. Momentum Research analysis of MLS records.
The Leeward Cay buying strategy.
If we were buying in Leeward Cay 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.
Move deliberately, not desperately. Neither side has a decisive edge, so a well-prepared, fairly-priced offer wins without overpaying.
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 Leeward Cay.
A thin market at a high price point
The math here is straightforward but requires context: a median price of $1,137,000 against a median $484.86 per square foot points to homes that are both larger and finished to a higher standard than the broader Naples market, without any single data point strong enough to draw a firm line under it. With just three closings feeding the window, one unusually large or unusually modest sale can move the median meaningfully — so use these figures as a starting point for a conversation, not a final answer.
No community amenities are currently identified from MLS listings, which is common in smaller or non-amenitized enclaves — it does not necessarily mean amenities do not exist, only that they are not showing up in the data we can verify. Anyone evaluating Leeward Cay should confirm directly what, if anything, is attached to ownership here before assuming a pool, gate, or clubhouse is or is not part of the deal.
The location and the amenities are priced into every listing in Leeward Cay. The deal is won or lost on condition, the comps, and the renovation math.
Why work with Momentum here
In a market this thin, the comps that exist need to be read correctly rather than taken at face value. We pull the underlying sales behind these numbers, verify what each home actually offered before landing on price, and help you decide whether the median is a realistic target or a number three transactions happened to produce.
Leeward Cay in 15 seconds.
Tools for a Leeward Cay 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 Leeward Cay sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Leeward Cay, the right list price comes from recent comparable sales matched to your home's condition and location, not an automated estimate.
What is your Leeward Cay home worth?
Get a no-obligation home value based on real comparable sales in Leeward Cay, 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 →
Should you buy in Leeward Cay?
An honest fit check. We will tell you when it is not your community.
Data sources & freshness
| Under-contract shares | Florida Gulf Coast MLS records, as of 2026-11-11 |
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.
Own a home here?
You just read the data. Now see what your home is worth.
The numbers on this page move markets in the aggregate. The number that matters to you is what a buyer pays for your address. A Momentum agent can price yours against live local comps.
Looking to buy here? Search homes for sale →
What’s your home worth in your area?
A real valuation with real comps from a local listing agent, not an instant algorithm. Response within one business day.
See how Leeward Cay fits the bigger picture — live prices, inventory, and Momentum Scores: