Neighborhood · Kissimmee, Florida
Windsor Hills
Gated pool homes minutes from Disney's front gate
47
Homes for sale
$399,000
Median list price
$266
Avg price / sqft
25
Median days on market
Windsor Hills sits in the resort corridor of Kissimmee, a gated community built around vacation living just 19 minutes from Walt Disney World. Most of the neighborhood's homes come with private pools and sit behind guarded entrances, which is why so many owners split their time between full-time living and short-term rental income. With Universal Orlando and MCO both about 36 minutes out, it's a practical base whether you're here for theme parks, work, or both.
The market here reads squarely mid-range for the area: 45 homes are active with a median list price of $380,000, and sales over the past year closed at a median of $405,000. Homes move at a healthy clip — 25 days on market and sellers netting about 97% of asking — so if you find the right pool home, don't expect it to linger. Buyers comparing options often look at nearby resort communities like Storey Lake and Solara, or the age-restricted Solivita for a different pace.
Windsor Hills is a community in Kissimmee, Florida.
Quick facts
$240,000 – $700K price range
1,440 sqft median home
$625/mo median HOA
$2,773/mo median rent
84 sold in 12 months
Drive times
On the market now
Homes for sale in Windsor Hills
View all 47 →
$699,000
7765 TOSTETH STREET, KISSIMMEE
6 bd · 4 ba · 2,812 sqft
$639,000
2689 MANESTY LANE, KISSIMMEE
5 bd · 5 ba · 2,297 sqft
$419,000
2530 MANESHAW LANE, KISSIMMEE
3 bd · 3 ba · 1,440 sqft
$695,000
7805 BEECHFIELD STREET, KISSIMMEE
6 bd · 4 ba · 2,812 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
7664 COMROW STREET UNIT 204, KISSIMMEE
3 bd · 2 ba · 1,450 sqft
$329,000
2821 ALMATON LOOP UNIT 205, KISSIMMEE
3 bd · 2 ba · 1,410 sqft
$325,000
2788 ALMATON LOOP UNIT 404, KISSIMMEE
3 bd · 2 ba · 1,450 sqft
$289,000
2774 ALMATON LOOP UNIT 202, KISSIMMEE
2 bd · 2 ba · 1,081 sqft
Every active listing inside the Windsor Hills boundary
Open full map search →Find your fit
Browse Windsor Hills
By feature — on the live map
Where the market lives
The numbers that matter
The Windsor Hills market
84
Sold, last 12 months
$402,500
Median sold price
97%
Sale-to-list ratio
What sellers actually get vs asking
58 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
▲ 50.0% 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
≈ $3,321/mo
$399,000 median · 20% down · 30-yr fixed at 6.9% · taxes/HOA from live listing data · insurance is a Florida estimate.
$625/mo
Median HOA
From current listings inside the boundary
$2,773/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.
People who close here
Our Kissimmee experts
Iain Robinson
Broker Associate
Dan Schriver
REALTOR®
David Ramirez
Real Estate Agent
Colleen Brown
REALTOR®
Straight answers
Windsor Hills FAQs
Is Windsor Hills a good place to live?+
It's a gated, amenity-heavy community where 36 of 45 active listings sit behind controlled access and 23 include private pools, so it suits buyers who want resort-style living close to the parks. Walt Disney World is about 19 minutes away and MCO around 36, making it convenient for both residents and frequent travelers. It's also a popular pick for owners who want a home that doubles as a rental.
Is Windsor Hills expensive?+
It lands in the mid-range for the Kissimmee resort corridor, with a median list price of $380,000 and an average of $265 per square foot. Listings run from $240,000 up to $700,000, and there are currently no homes above $1M, so the ceiling stays accessible. Compared with nearby Storey Lake and other resort communities, the pricing is competitive for a gated pool home.
What do homes cost in Windsor Hills?+
The median list price is $380,000, while homes sold over the past 12 months closed at a median of $405,000. The median home size is about 1,440 square feet at roughly $265 per square foot. Expect most inventory in the $240,000 to $700,000 band.
How is the market right now?+
It's moving briskly — the median days on market is just 25, and sellers are getting about 97% of asking on average. Eighty-five homes sold in the past year against 45 active today, so demand stays steady. If you like a pool home here, be ready to act quickly.
What about HOA fees and property taxes?+
HOA dues are on the higher side at a median of $695 a month, which reflects the gated access and shared resort amenities typical of the Kissimmee vacation communities. The median property tax runs about $4,454 a year. Factor both into your monthly numbers, especially if you plan to rent the home short-term.
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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