Homes for Sale in Windley Key, FL

6 homes are for sale in Windley Key, FL as of 2026-09-06. The median list price is $899,000, most homes list between $439K to $1.30M, and the median listing has been on the market 147 days. 0 homes came on the market this week.

Newest homes for sale in Windley Key

The most recently listed homes in Windley Key, newest first, with photos. Each card opens the full listing with every photo, the community’s sales history and a tour request. Homes marked New listed in the last seven days.

$439,000

1 bd · 1 ba

84961 Old Highway #A1

Windley Key

Listing courtesy of Ocean Sotheby's International Realty

$450,000

1 bd · 1 ba

84961 Old Highway #41

Windley Key

Listing courtesy of Berkshire Hathaway HomeServices Keys Real Estate - Islamorada

$899,000

1 bd · 1 ba

84961 Old Highway #LOT 27

Windley Key

Listing courtesy of American Caribbean Real Estate, Christie's International Real Estate

$899,000

2 bd · 2 ba

84961 Old Highway #18

Windley Key

Listing courtesy of Berkshire Hathaway HomeServices Keys Real Estate - Islamorada

$1.15M

2 bd · 2.5 ba

102 Anglers Way

Windley Key

Listing courtesy of Berkshire Hathaway HomeServices Florida Realty - Coral Springs

$1.30M

2 bd · 2.5 ba

104 Anglers Way

Windley Key

Listing courtesy of Casa Miami Real Estate

Windley Key homes for sale by price

Every active listing in Windley Key grouped by price, with the newest listings in each band. The median is $899,000; the busiest band is $400K – $500K.

$400K – $500K: 2 homes

• $439,000 · 1 bd / 1 ba · 84961 Old Highway #A1
• $450,000 · 1 bd / 1 ba · 84961 Old Highway #41

$750K – $1M: 2 homes

• $899,000 · 1 bd / 1 ba · 84961 Old Highway #LOT 27
• $899,000 · 2 bd / 2 ba · 84961 Old Highway #18

$1M and up: 2 homes

• $1.15M · 2 bd / 2.5 ba · 102 Anglers Way
• $1.30M · 2 bd / 2.5 ba · 104 Anglers Way

What is for sale in Windley Key: property types

• Single-family homes: 5
• Manufactured homes: 1

What a home in Windley Key costs to own

Take the median $899,000 listing with 20% down at today’s 6.71% 30-year rate: principal and interest run about $4,646/month. All in, plan on roughly $4,646/month plus any HOA or CDD assessment.

Explore Windley Key

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Common questions

Listings, counts and prices are from Momentum Realty’s MLS record of active residential listings in Windley Key as of 2026-09-06 and refresh as homes list and sell. Listing data provided by Florida Keys MLS, Inc. Information is deemed reliable but is not guaranteed by the MLS to be accurate. The data relating to real estate for sale on this page comes in part from the Internet Data Exchange (IDX) program of the MLS(s) named above; listings held by brokerages other than Momentum Realty are marked with the listing brokerage’s name. Information is deemed reliable but not guaranteed. Estimates are not guarantees. Equal Housing Opportunity.