Neighborhood · Windermere, Florida
Wintermere Harbor
A quiet Windermere pocket built for space
1
Homes for sale
$759,900
Median list price
$234
Avg price / sqft
2
Median days on market
Wintermere Harbor sits in the heart of Windermere's lake country in Orange County, a small community where homes run large and streets stay quiet. With a median home size north of 3,200 square feet and a gated setting, it draws buyers who want room to spread out without leaving the Windermere school and lifestyle zone. You're within easy reach of the wider Windermere market and established names like Keenes Pointe, Isleworth, and Summerport.
The market reality here is simple: inventory is thin. There's currently a single active listing at $759,900, and homes that do come up move fast — the median days on market is just 1. Over the past year only two homes changed hands at a median of $782,500, with sellers collecting about 96% of asking, so serious buyers should be ready to act when something lists.
Wintermere Harbor is a community in Windermere, Florida.
Quick facts
$759,900 – $760K price range
3,249 sqft median home
$110/mo median HOA
2 sold in 12 months
On the market now
Homes for sale in Wintermere Harbor
Every active listing inside the Wintermere Harbor boundary
Open full map search →Find your fit
Browse Wintermere Harbor
By feature — on the live map
The numbers that matter
The Wintermere Harbor market
2
Sold, last 12 months
$782,500
Median sold price
96%
Sale-to-list ratio
What sellers actually get vs asking
78 days
Median time to sell
Wintermere Harbor vs Windermere
Median list price
Price per sqft
Days on market
Live Stellar MLS data — every listing and closed sale inside the Wintermere Harbor boundary. Rolling medians smooth single-month swings in small communities.
For the school run
Schools Wintermere Harbor is zoned for
Attendance boundaries overlapping this community — always verify zoning with the district.
What it really costs
Owning here
Owning the median Wintermere Harbor home
≈ $4,723/mo
$759,900 median · 20% down · 30-yr fixed at 6.9% · taxes/HOA from live listing data · insurance is a Florida estimate.
$110/mo
Median HOA
From current listings inside the boundary
Population
369
Median age
43
Median income
$224,336
Median home value
$771,900
Beyond the listings
Living in Wintermere Harbor
Hobbies & Interests
Top 1% in the U.S.Green Thumb
From tiny sprouts and window plants, to flower arrangements and designing a landscape, this population has an affinity for all things green.
Food & Drink
Top 2% in the U.S.Ingredient Attentive
These folks are conscious about what they eat. They're looking for ingredients that not only taste great, but also have great nutritional benefits.
Lifestyles
Top 6% 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.
Appearance oriented
Top 7% in the U.S.Trend Trackers
This population lives as fast as the culture. They like to keep up with the latest trends, especially when it comes to apparel and accessories.
Attitudes
Top 9% in the U.S.Deal Seekers
These people are hunting discounts, contests, and promotions. The population loves a good sale, and they can't wait to share their bargain finds and winnings with friends and family.
Appearance oriented
Top 11% in the U.S.Smart Chic
Passionate about style, smart chic searches high and low for the perfect look - but not one that will break the bank.
Straight answers
Wintermere Harbor FAQs
Is Wintermere Harbor a good place to live?+
It's a small, gated pocket of Windermere with generously sized homes and quiet streets, which appeals to families wanting space and privacy. Homes are assigned to West Orange High, Sunridge Middle, and Lake Whitney Elementary, and you're close to established communities like Keenes Pointe and Isleworth.
Is Wintermere Harbor expensive?+
It sits in the upper-middle of the Windermere range rather than at the luxury top end. The current active listing is priced at $759,900, and homes sold over the past year at a median of $782,500 — solid money, but below the $1M+ tier common elsewhere in Windermere.
What do homes cost in Wintermere Harbor?+
Pricing runs around $234 per square foot on a median home size of about 3,249 square feet. The lone active listing is $759,900, and the past year's two sales landed at a median of $782,500.
How is the market right now?+
It's fast and tight. There's only one active listing, and the median days on market is just 1, with sellers netting about 96% of asking — so when a home in Summerport or here comes up, buyers need to move quickly.
What about HOA fees and property taxes?+
The median HOA runs about $110 per month, which is modest for a gated community. Property taxes come in around $4,789 per year based on recent data.
Keep exploring
More Windermere 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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