Neighborhood · Key Largo, Florida
Winston Waterways
Canal-front living at the top of the Keys
2
Homes for sale
$2,249,500
Median list price
$2,273
Avg price / sqft
175
Median days on market
Winston Waterways is a small waterfront neighborhood in Key Largo, the northernmost of the Florida Keys and the first stretch of tropical water you reach driving down from the mainland. Homes here sit on canals with quick access out to the water, and the pace is exactly what people picture when they imagine Keys life. Families are zoned for Key Largo School and Coral Shores High School, and neighboring pockets like Pamela Villa round out the area.
This is a thin, high-end market, so plan accordingly. Right now there are just 2 active listings, both waterfront and both above $1M, with a median list price of $2,249,500. Homes here take time to trade — the median is 175 days on market — so a serious buyer has room to negotiate rather than rush.
Winston Waterways is a community in Key Largo, Florida.
Quick facts
$1,999,000 – $2.5M price range
1,100 sqft median home
4 sold in 12 months
On the market now
Homes for sale in Winston Waterways
$2,500,000
128 La Paloma Rd, Key Largo FL 33037, KEY LARGO
3 bd · 2 ba · 1,100 sqft
$1,999,000
862 Cardinal Ln, Key Largo FL 33037, KEY LARGO
4 bd · 4 ba
Every active listing inside the Winston Waterways boundary
Open full map search →Find your fit
Browse Winston Waterways
By feature — on the live map
Where the market lives
The numbers that matter
The Winston Waterways market
4
Sold, last 12 months
$1,330,000
Median sold price
93%
Sale-to-list ratio
What sellers actually get vs asking
87 days
Median time to sell
Winston Waterways vs Key Largo
Median list price
Price per sqft
Days on market
Median sold price — 3-yr, 3-mo rolling
▲ 14.3% yr/yr
Homes sold per month
Live Stellar MLS data — every listing and closed sale inside the Winston Waterways boundary. Rolling medians smooth single-month swings in small communities.
For the school run
Schools Winston Waterways is zoned for
Attendance boundaries overlapping this community — always verify zoning with the district.
What it really costs
Owning here
Owning the median Winston Waterways home
≈ $12,622/mo
$2,249,500 median · 20% down · 30-yr fixed at 6.9% · taxes/HOA from live listing data · insurance is a Florida estimate.
Population
762
Median age
43
Median income
$75,692
Median home value
$466,100
Beyond the listings
Living in Winston Waterways
Hobbies & Interests
Top 8% 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.
Appearance oriented
Top 19% in the U.S.Body Art
Who says the body isn't a canvas? This population loves talking about tattoos, body art and piercings.
Emotional
Top 23% in the U.S.Awestruck
Great things are meant to be shared, and this population is eager to show others what they find to be amazing, beautiful and exciting.
Emotional
Heartfelt Sharing
This population is characterized by vulnerability. Looking to unload emotional burdens, activities include confessions, apologies, and long-form posts.
Entertainment
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.
Food & Drink
Trendy Eats
Meals are a social experience, and these foodies take it to the next level. This population can't wait to snap a pic of their plate and share it before chowing down.
Straight answers
Winston Waterways FAQs
Is Winston Waterways a good place to live?+
If you want canal-front Keys living at the northern, most accessible end of the island chain, it's a strong fit. Every active home here is on the water, and families are zoned for Key Largo School and Coral Shores High School. It's a quiet, small-scale neighborhood rather than a busy resort strip.
Is Winston Waterways expensive?+
Yes — this is a high-end waterfront market. The median list price is $2,249,500, and both current listings are above $1M. Even recent sales landed at a median of $1,330,000, so budget for premium Keys pricing.
What do homes cost in Winston Waterways?+
Active listings currently range from $1,999,000 to $2,500,000, with a median around $2,249,500. The average price per square foot runs about $2,273 on a median home size near 1,100 square feet, reflecting how much of the value is in the waterfront location. You can see what's available now on the live map.
How is the market in Winston Waterways?+
It's small and slow-moving, which favors prepared buyers. Only 4 homes sold in the past 12 months at a median of $1,330,000, and the current 2 listings have a median of 175 days on market. Sellers are accepting about 93% of asking on average, so there's room to make a reasoned offer.
What about HOA fees and property taxes?+
There's no HOA figure on record for the active listings here, so budget primarily for taxes and insurance. The median property tax comes in around $6,719 per year. As always in the Keys, factor in flood and windstorm insurance when you run your numbers on Key Largo homes for sale.
Keep exploring
More Key Largo 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.
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