Neighborhood · Windermere, Florida
Windsor Hill
Estate-scale living in the heart of Windermere
2
Homes for sale
$7,249,950
Median list price
$457
Avg price / sqft
30
Median days on market
Windsor Hill sits among the large-lot enclaves that give Windermere its reputation for space and privacy, the kind of area where homes are measured in the thousands of square feet rather than tucked shoulder to shoulder. Neighbors here run in the same circles as the established addresses at Isleworth and Keenes Pointe, with pool homes and generous grounds the norm. It's a quiet, residential pocket that trades density for elbow room.
For a buyer today, this is a thin, high-end market: just two homes are active, with list prices spanning $1.5M to nearly $13M and a median asking price north of $7M. Over the past year only three homes changed hands, closing at a median of $1,040,000 with sellers collecting about 97% of their asking price. If you want the scale of Isleworth or the community feel of Summerport but want to keep options open, it pays to watch this one closely and move when the right listing appears.
Windsor Hill is a community in Windermere, Florida.
Quick facts
$1,499,900 – $13M price range
12,912 sqft median home
$101/mo median HOA
3 sold in 12 months
On the market now
Homes for sale in Windsor Hill
$1,499,900
9527 QUEENSBURY COURT, WINDERMERE
5 bd · 5 ba · 5,378 sqft
$12,999,999$13,430,000
9621 WINDY RIDGE ROAD, WINDERMERE
9 bd · 13 ba · 20,445 sqft
Every active listing inside the Windsor Hill boundary
Open full map search →Find your fit
Browse Windsor Hill
By feature — on the live map
Where the market lives
The numbers that matter
The Windsor Hill market
3
Sold, last 12 months
$1,040,000
Median sold price
97%
Sale-to-list ratio
What sellers actually get vs asking
2 days
Median time to sell
Windsor Hill vs Windermere
Median list price
Price per sqft
Days on market
Median sold price — 3-yr, 3-mo rolling
▼ 1.3% yr/yr
Homes sold per month
Live Stellar MLS data — every listing and closed sale inside the Windsor Hill boundary. Rolling medians smooth single-month swings in small communities.
For the school run
Schools Windsor Hill is zoned for
Attendance boundaries overlapping this community — always verify zoning with the district.
What it really costs
Owning here
Owning the median Windsor Hill home
≈ $39,928/mo
$7,249,950 median · 20% down · 30-yr fixed at 6.9% · taxes/HOA from live listing data · insurance is a Florida estimate.
$101/mo
Median HOA
From current listings inside the boundary
Population
934
Median age
47
Median income
$250,001
Median home value
$830,900
Beyond the listings
Living in Windsor Hill
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.
Relationships
Top 14% in the U.S.Networking
Driven to succeed in the business world, this population seeks to progress in their career through networking happy hours, summits, and connecting with other professionals online.
Emotional
Top 14% 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
Top 15% in the U.S.Happy Place
Expressing feelings of safety, comfort and happiness - especially with loved ones.
Appearance oriented
Top 16% in the U.S.Body Art
Who says the body isn't a canvas? This population loves talking about tattoos, body art and piercings.
Hobbies & Interests
Top 18% 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.
Straight answers
Windsor Hill FAQs
Is Windsor Hill a good place to live?+
It's a quiet, low-density corner of Windermere built around large lots and estate-scale homes, near established communities like Lakeside Village. Homes are assigned to Olympia High, Gotha Middle, and Thornebrooke Elementary, and pool homes are the norm here. If you value space and privacy over a dense, walkable feel, it fits.
Is Windsor Hill expensive?+
Yes — it sits at the top of the Windermere market. Active list prices range from $1.5M to nearly $13M with a median around $7.25M, though actual sales over the past year closed at a median of $1,040,000. The wide gap between list and sold reflects how few and how varied the homes are.
What do homes cost in Windsor Hill?+
Sold prices over the last 12 months centered on $1,040,000, while the two current listings carry a much higher median ask of about $7.25M. Pricing works out to roughly $457 per square foot, and homes here are large — a median of about 12,912 square feet. Expect real variation depending on the property.
How is the market in Windsor Hill?+
It's small and slow-moving by design: only three homes sold in the past year and just two are active now. Sellers averaged about 97% of asking, and the median time on market was around 30 days for what did sell. With so little inventory, serious buyers should be ready to act when a listing matches.
What are the HOA fees and property taxes?+
HOA dues run a median of about $101 a month, which is modest for homes of this size. Property taxes are the bigger line item, with a median around $17,017 a year reflecting the high assessed values here. Budget for the taxes more than the HOA.
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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