Neighborhood · Windermere, Florida
Windsor Hill
Spacious estate living in the heart of Windermere
3
Homes for sale
$1,499,900
Median list price
$426
Avg price / sqft
31
Median days on market
Windsor Hill is a pocket of large, well-built homes in Windermere, a part of Orange County known for its lakes, mature oaks, and low-key luxury just west of Orlando. Homes here run big — the median floor plan is over 5,300 square feet — and every active listing right now comes with a pool, which tells you exactly what daily life looks like. Zoned for Olympia High, Gotha Middle, and Thornebrooke Elementary, it sits within reach of established Windermere communities like Keenes Pointe, Isleworth, and Summerport.
This is a small, tightly-held market: just three homes are active today and only three sold over the past year. Pricing starts around $1.45M with a median list of $1,499,900, and sellers are getting about 97% of asking with a median 31 days on market. If you want a large home in a low-inventory Windermere neighborhood, you'll be moving quickly when the right listing appears.
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
On the market now
Homes for sale in Windsor Hill
$1,499,900
9527 QUEENSBURY COURT, WINDERMERE
5 bd · 5 ba · 5,378 sqft
$1,450,000
9548 CROWN PRINCE LANE, WINDERMERE
4 bd · 4 ba · 3,997 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
≈ $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.
On the calendar
Near Windsor Hill
Jul
12
Sun
Rumba Brunch
11:30am
Every Sunday, attendees have the opportunity to immerse themselves in the authentic rumba music played live by wandering guitarists and vocalists. To accompany the riveti…
Jul
12
Sun
Walt Disney World Park Meetup
The Orlando Social Network (OSN) is a vibrant community that facilitates adults in meeting, connecting, and building friendships through a variety of fun events, includin…
Jul
12
Sun
Vibe, Sip, and Make Jewelry
Wanda Taylor, a seasoned craftswoman, invites the community to a workshop where she'll share her expertise in creating a wide range of handcrafted items. Attendees will h…
Jul
12
Sun
Bite30
Bite30 in Orlando, FL, USA, is a culinary celebration that spotlights the creativity and talent of Central Florida’s top chefs and restaurants. For a set price, diners ca…
Jul
12
Sun
Bands, Brew, and BBQ
Bands, Brew, and BBQ brings together live country and rock music with delicious food and refreshing drinks for a lively summer experience at SeaWorld Orlando. You can enj…
Jul
12
Sun
Cirque du Soleil: Drawn to Life
1:30pm
Drawn to Life is a Cirque du Soleil and Disney collaboration featuring acrobatics, animation, and theatrical magic. The show brings classic Disney drawings to life in a d…
Straight answers
Windsor Hill FAQs
Is Windsor Hill a good place to live?+
It's a strong fit if you want a large, pool-equipped home in a quiet corner of Windermere. Floor plans run around 5,378 square feet on median, and the area is zoned for Olympia High, Gotha Middle, and Thornebrooke Elementary. It's a small, established neighborhood rather than a busy master-planned community.
Is Windsor Hill expensive?+
Yes — this is a luxury segment, with all active listings priced above $1M and a median list of $1,499,900. Prices range from $1,450,000 up to $12,999,999, so there's real spread depending on the property. Compared to nearby Isleworth, it's a smaller and more contained slice of the Windermere luxury market.
What do homes cost in Windsor Hill?+
Active listings currently center on a $1,499,900 median list price, and homes over the past year sold at a median of $1,040,000. That works out to about $426 per square foot on average across a median home size of roughly 5,378 square feet.
How is the market right now?+
It's low-inventory and tight — just three homes are active and three sold in the last 12 months. Sellers are averaging about 97% of their asking price, with a median 31 days on market, so well-priced homes don't linger long. There's also one new-construction option among the current listings.
What about HOA fees and property taxes?+
The median HOA here is about $105 per month, which is reasonable for a neighborhood of this size and quality. Property taxes run higher given the home values, with a median around $13,931 per year. Budget for both when you're comparing against other Windermere communities.
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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