Neighborhood · Tavernier, Florida
Windley Key
A small island stretch in the Upper Keys
3
Homes for sale
$1,150,000
Median list price
$854
Avg price / sqft
136
Median days on market
Windley Key sits along the Overseas Highway in the Upper Keys, a compact island community where the water is never more than a few minutes away and everyday life runs at Keys pace. You're close to the resort scene at Cheeca Lodge Resort and the neighboring streets of Plantation Key, with dive shops, boat ramps, and reef access shaping the weekend rhythm.
For buyers, this is a thin, high-value market. There are just 3 active listings right now with a median list price of $1,150,000, and homes tend to sit — the median is 136 days on market. If you want to see everything currently available in one place, start with the live map and browse the wider pool of Tavernier homes for sale alongside it.
Windley Key is a community in Tavernier, Florida.
Quick facts
$298,000 – $1.2M price range
1,376 sqft median home
5 sold in 12 months
On the market now
Homes for sale in Windley Key
$298,000
84961 Old Hwy 17 Hwy, Islamorada FL 33036, ISLAMORADA
1 bd · 1 ba
$1,150,000
102 Anglers Way, Islamorada FL 33036, ISLAMORADA
2 bd · 2.5 ba · 1,376 sqft
$1,199,990
111 Anglers Way, Islamorada FL 33036, ISLAMORADA
2 bd · 2.5 ba · 1,376 sqft
Every active listing inside the Windley Key boundary
Open full map search →Find your fit
Browse Windley Key
By feature — on the live map
Where the market lives
The numbers that matter
The Windley Key market
5
Sold, last 12 months
$1,435,000
Median sold price
92%
Sale-to-list ratio
What sellers actually get vs asking
287 days
Median time to sell
Windley Key vs Tavernier
Median list price
Price per sqft
Days on market
Median sold price — 3-yr, 3-mo rolling
▲ 16.3% yr/yr
Homes sold per month
Live Stellar MLS data — every listing and closed sale inside the Windley Key boundary. Rolling medians smooth single-month swings in small communities.
For the school run
Schools Windley Key is zoned for
Attendance boundaries overlapping this community — always verify zoning with the district.
What it really costs
Owning here
Owning the median Windley Key home
≈ $6,964/mo
$1,150,000 median · 20% down · 30-yr fixed at 6.9% · taxes/HOA from live listing data · insurance is a Florida estimate.
Population
91
Median age
46
Median income
$63,278
Median home value
$1,369,300
Beyond the listings
Living in Windley Key
Hobbies & Interests
Top 1% in the U.S.Wanderlust
Always thinking about their next destination, this population loves exploring new places abroad or right in their own backyard. They hold onto past trips by sharing their favorite memories and pictures year round.
Lifestyles
Top 7% in the U.S.Wealth Signaling
Interested in the finer things life has to offer, this population wants to display their lifestyle by discussing luxury products. Often references jewelry, cars, and home features.
Pieces of History
You can find these people researching an upcoming exhibit at the natural history museum or learning about a famous monument. This population enjoys learning about the past.
Culture
Top 18% in the U.S.Sites to See
This population finds the most beautiful sites just by looking up. Sunrise, sunset or sometime in between, these people love to marvel at man-made and natural wonders.
Food & Drink
Top 18% in the U.S.Hops & Brews
Thirst isn't the only reason this population looks for a good brew. From beer drinkers on a budget to the millennial craft beer enthusiast, these men and women are passionate about different kinds of beer and how it's made.
Entertainment
Top 19% in the U.S.Live & Local Music
This population follows the music. From local bands to current acts at the local venue, you can find these people researching band tours and how to get backstage passes.
Straight answers
Windley Key FAQs
Is Windley Key a good place to live?+
It suits buyers who want a quiet, water-oriented slice of the Upper Keys with resort amenities close by. You're near Cheeca Lodge Resort and the established streets of Plantation Key, and daily life leans heavily toward boating, diving, and the reef. It's a small community, so expect neighbors rather than crowds.
Is Windley Key expensive?+
Yes — it's a premium Upper Keys market. The median list price is $1,150,000 and homes average $854 per square foot, though the current active range runs from $298,000 up to about $1,199,990. Over the past year, the median sold price was $1,435,000.
What do homes cost in Windley Key?+
Active listings currently span $298,000 to roughly $1,199,990, with a median list price of $1,150,000 and a median home size around 1,376 square feet. At an average of $854 per square foot, pricing reflects the island's compact, water-close location. You can compare current options against the broader Tavernier homes for sale.
How is the market in Windley Key?+
It's thin and slow-moving in the best sense — just 3 active listings and 5 sales over the past 12 months. Homes take time to sell, with a median of 136 days on market, but sellers still command strong prices, closing at 92% of asking. Track new activity on the live map.
What about HOA fees and property taxes?+
HOA data isn't available for the current active listings here, so budget on a per-property basis. Property taxes run a median of about $8,341 per year, in line with the area's higher home values. Your assigned schools would be Plantation Key School and Coral Shores High School.
Keep exploring
More Tavernier neighborhoods
Neighborhood boundary by edgeAI; listings matched to the polygon. IDX information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data is deemed reliable but is not guaranteed accurate by Stellar MLS.
Never miss a listing
New Windley Key homes, in your inbox
A daily digest of new Tavernier listings — straight from the MLS. Unsubscribe anytime.