Neighborhood · Kissimmee, Florida
Windsor Hills
Resort-style living minutes from the theme parks
50
Homes for sale
$402,000
Median list price
$269
Avg price / sqft
35
Median days on market
Windsor Hills sits on the west side of Kissimmee, close enough to Walt Disney World that a park day is a 19-minute drive rather than a road trip. This is a vacation-home community at heart — gated streets, private pools, and the kind of turnkey homes that work as well for a family as they do for short-term rental owners. If you want that same resort energy nearby, communities like Storey Lake and Solara round out the corridor.
Right now there are 50 active listings with a median list price of $402,000, and the range runs from $275,000 up to $699,000. Homes are moving in a healthy 34.5 days, sellers are collecting about 97% of asking, and 86 homes have closed here over the past year. Compared to the broader pool of Kissimmee homes for sale, this is a focused, amenity-heavy market — worth knowing the HOA and rental rules before you write an offer.
Windsor Hills is a community in Kissimmee, Florida.
Quick facts
$275,000 – $699K price range
1,440 sqft median home
$604/mo median HOA
$2,748/mo median rent
86 sold in 12 months
Drive times
On the market now
Homes for sale in Windsor Hills
View all 50 →
$699,000
7765 TOSTETH STREET, KISSIMMEE
6 bd · 4 ba · 2,812 sqft
$695,000
2630 DINVILLE STREET, KISSIMMEE
6 bd · 3.5 ba · 2,855 sqft
$679,000
7777 TEASCONE BOULEVARD, KISSIMMEE
5 bd · 5 ba · 2,297 sqft
$425,000
7674 OTTERSPOOL STREET, KISSIMMEE
3 bd · 3 ba · 1,440 sqft
$420,000
7677 FITZCLARENCE STREET, KISSIMMEE
3 bd · 3 ba · 1,440 sqft
$419,000
2545 RENSHAW STREET, KISSIMMEE
3 bd · 3 ba · 1,440 sqft
$345,000
2821 E ALMATON LOOP UNIT 401, KISSIMMEE
3 bd · 2 ba · 1,246 sqft
$329,000
2821 ALMATON LOOP UNIT 205, KISSIMMEE
3 bd · 2 ba · 1,410 sqft
$329,000
7664 COMROW STREET UNIT 204, KISSIMMEE
3 bd · 2 ba · 1,450 sqft
$325,000
2788 ALMATON LOOP UNIT 404, KISSIMMEE
3 bd · 2 ba · 1,450 sqft
$288,000
7671 COMROW STREET UNIT 302, KISSIMMEE
2 bd · 2 ba · 1,081 sqft
$319,000$325,000
7664 COMROW STREET UNIT 101, KISSIMMEE
3 bd · 2 ba · 1,246 sqft
Every active listing inside the Windsor Hills boundary
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Browse Windsor Hills
By feature — on the live map
Where the market lives
The numbers that matter
The Windsor Hills market
86
Sold, last 12 months
$402,500
Median sold price
97%
Sale-to-list ratio
What sellers actually get vs asking
63 days
Median time to sell
Windsor Hills vs Kissimmee
Median list price
Price per sqft
Days on market
Median sold price — 3-yr, 3-mo rolling
▲ 20.6% yr/yr
Homes sold per month
Live Stellar MLS data — every listing and closed sale inside the Windsor Hills boundary. Rolling medians smooth single-month swings in small communities.
For the school run
Schools Windsor Hills is zoned for
Attendance boundaries overlapping this community — always verify zoning with the district.
What it really costs
Owning here
Owning the median Windsor Hills home
≈ $3,316/mo
$402,000 median · 20% down · 30-yr fixed at 6.9% · taxes/HOA from live listing data · insurance is a Florida estimate.
$604/mo
Median HOA
From current listings inside the boundary
$2,748/mo
Median rent
Homes for rent inside the boundary
Population
686
Median age
31
Median income
$92,154
Median home value
$297,100
Beyond the listings
Living in Windsor Hills
Hobbies & Interests
Top 2% 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.
Entertainment
Top 5% in the U.S.Film Lovers
Movie buffs and binge watchers expressing their love for movies, storytelling, and the film making process.
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.
Entertainment
Top 13% in the U.S.Live Experiences
When it comes to entertainment, this population is looking for the ultimate experience. Whether it's a charity fundraiser or a concert, elements such as lights, sounds, and merchandise are critical for a good time.
Entertainment
Top 15% in the U.S.Lighthearted Fun
This population is all about keeping the mood light and good, clean fun. Common activities include spending time outdoors, catching up with friends, and dancing.
Food & Drink
Top 18% 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.
Straight answers
Windsor Hills FAQs
Is Windsor Hills a good place to live?+
It's a gated, resort-style community where 40 of the 50 active listings sit behind gates and 29 include a pool, so day-to-day life leans toward relaxed and amenity-rich. Disney is about 19 minutes away and Orlando International Airport roughly 36, which suits both families and owners renting to travelers. Assigned schools include Westside K-8 School and Celebration High School.
Is Windsor Hills expensive?+
The median list price is $402,000, which lands in the mid-range for the Kissimmee resort corridor, and closed prices have tracked right alongside at a $402,500 median over the past year. Listings run from $275,000 to $699,000, so there's real room depending on size and finish. It's worth comparing against nearby Storey Lake before you decide.
What do homes cost in Windsor Hills?+
Expect a median around $402,000, with an average of $269 per square foot and a median home size of about 1,440 square feet. The full active range is $275,000 to $699,000, so pools, upgrades, and rental income potential drive most of the spread.
How is the market in Windsor Hills right now?+
With 50 active listings and 86 sales over the past 12 months, inventory and demand are fairly balanced. Homes are averaging 34.5 days on market and sellers are getting about 97% of asking, which points to a steady market where well-priced homes still move. You'll find a similar rhythm across Kissimmee homes for sale.
What about HOA fees and property taxes?+
The median HOA here runs about $604 per month, which is on the higher side but reflects the gated amenities and often bundled services common in resort communities. Median property tax is around $4,614 per year, and for context median rent sits near $2,748 per month. Always confirm exactly what the HOA covers and any short-term rental rules before closing.
Keep exploring
More Kissimmee 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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