Aerial view of Windy Cove

Windy Cove
Homes for Sale in Windley Key, FL

All 7 homes for sale in Windley Key, FL · median $849,000 · Monroe County homes for sale

Community in Windley Key · Monroe County
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Built fromLive Florida Keys MLS dataUpdated twice daily

Nearby homes for sale

No active listings inside WINDY COVE 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.

84961 Old Highway #A1
$439K · 0.3 mi away
1 bd · 1 ba
84961 Old Highway #A1
Listed by Ocean Sotheby's International Realty
84961 Old Highway #41
$450K · 0.3 mi away
1 bd · 1 ba
84961 Old Highway #41
Listed by Berkshire Hathaway HomeServices Keys Real Estate - Islamorada
84961 Old Highway #LOT 27
$849K · 0.3 mi away
1 bd · 1 ba
84961 Old Highway #LOT 27
Listed by American Caribbean Real Estate, Christie's International Real Estate
84961 Old Highway #18
$850K · 0.3 mi away
2 bd · 2 ba
84961 Old Highway #18
Listed by Berkshire Hathaway HomeServices Keys Real Estate - Islamorada
84961 Old Highway #28
$375K · 0.3 mi away
1 bd · 1 ba
84961 Old Highway #28
Listed by Berkshire Hathaway HomeServices Keys Real Estate - Islamorada
133 Anglers Way
$1.70M · 0.4 mi away
2 bd · 2.5 ba
133 Anglers Way
Listed by eXp Realty LLC

Listing data from the MLS feeds named on each listing page; deemed reliable but not guaranteed. Refreshed nightly.

The market around Windy Cove

Windy Cove is too small for its own price trend, so here is the market around it.

Across Monroe County, 1,367 homes are active and 187 pending (12% under contract).

ZIP and county figures describe the wider market, not Windy Cove specifically. Momentum Research analysis of MLS records.

If we were buying in Windy Cove today, this is the order of operations we would run for our clients.

1

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.

2

Match the home to real comps. Recent sales of similar condition and lot, not the asking price, tell you what a home is worth.

3

Move deliberately, not desperately. Neither side has a decisive edge, so a well-prepared, fairly-priced offer wins without overpaying.

4

Line up financing and inspection early. A pre-approval and an inspection plan let you act fast and negotiate from evidence.

5

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 Windy Cove.

“

The location and the amenities are priced into every listing in Windy Cove. The deal is won or lost on condition, the comps, and the renovation math.

Jon Brooks · Founder, Momentum Realty
The takeaway

Selling here is won on condition and pricing to real comps, not an automated estimate. The right number comes from closed Windy Cove sales matched to your home.

What is your Windy Cove home worth?

Get a no-obligation home value based on real comparable sales in Windy Cove, 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 Windley Key →

Real comps, not an automated estimate.

Data sources & freshness

Under-contract sharesFlorida Keys MLS records, as of 2026-11-10

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 Keys 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 →

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A real valuation with real comps from a local listing agent, not an instant algorithm. Response within one business day.

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Email me new listings in Windy Cove

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.

Equal Housing Opportunity. Every community is open to everyone; alerts are about homes, never about who lives here.

Ask an agent about Windy Cove

Have a question about the homes, fees, rules or commute here? A Momentum agent who works Windy Cove will answer, and the answer is published on this page for the next buyer.

Property facts only: homes, fees, rules, commute. Every community is open to everyone; agents do not answer questions about who lives here.

Nearby Communities

Explore more neighborhoods near Windy Cove with Momentum Realty’s local guides.

Anglers Reef0.3 mi away · 52 homes, built 2007–09Bay Hammock1.4 mi awayRussell Estates1.8 mi away

Browse all neighborhood guides →

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