Neighborhood · Windermere, Florida
Windsor Hill
Spacious estate living minutes from Orlando's best
3
Homes for sale
$1,499,900
Median list price
$426
Avg price / sqft
56
Median days on market
Windsor Hill sits in the heart of Windermere, where large lots and generously sized homes give the neighborhood an unhurried, estate feel. The median home here runs about 5,378 square feet, so buyers tend to be families or move-up owners who want room to spread out while staying close to the recognizable Windermere names like Keenes Pointe and Isleworth. Assigned schools include Olympia High, Gotha Middle, and Thornebrooke Elementary, and the location puts Universal Orlando about 11 minutes away and downtown Orlando roughly 17.
For a buyer today, this is a thin, high-end market: just three homes are active, with a median list price of $1,499,900 and asking prices reaching well beyond that. Homes sit an average of 56 days before selling, and over the past year only three closed — at a median of $1,040,000, with sellers collecting about 97% of asking. If Windsor Hill's inventory is tight, it's worth broadening your search across Windermere homes for sale or comparing nearby options in Summerport and Lakeside Village.
Windsor Hill is a community in Windermere, Florida.
Quick facts
$1,450,000 – $13M price range
5,378 sqft median home
$105/mo median HOA
3 sold in 12 months
Drive times
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
$1,450,000
9548 CROWN PRINCE LANE, WINDERMERE
4 bd · 4 ba · 3,997 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
≈ $9,379/mo
$1,499,900 median · 20% down · 30-yr fixed at 6.9% · taxes/HOA from live listing data · insurance is a Florida estimate.
$105/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 suits buyers who want space and a central Windermere location without being tucked deep into a guard-gated resort community. You get sizable homes averaging around 5,378 square feet, strong school assignments at Olympia High and Thornebrooke Elementary, and quick access to Universal Orlando in about 11 minutes. It sits comfortably alongside better-known names like Keenes Pointe.
Is Windsor Hill expensive?+
Yes — this is a luxury pocket of Windermere. The median list price is $1,499,900, and active asking prices range from $1,450,000 all the way up past $12,999,999. Every current listing is priced above $1M, so it's firmly a high-end market.
What do homes cost in Windsor Hill?+
Right now the median list price is $1,499,900, and homes trade at an average of about $426 per square foot on a median size near 5,378 square feet. Over the past year, three homes sold at a median of $1,040,000, which gives a realistic sense of where deals actually close versus where they list.
How is the Windsor Hill market right now?+
It's a low-inventory, patient market with only three active listings and three sales in the past twelve months. Homes take a median of 56 days to sell, and sellers are getting about 97% of their asking price on average. Because supply is so thin, it can help to widen your search across Windermere homes for sale.
What about HOA fees and property taxes?+
The median HOA here is about $105 per month, which is modest for a community at this price level. Property taxes run higher given home values — the median is roughly $13,931 per year. Budget for both when comparing against nearby neighborhoods like Summerport.
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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