Homes for sale · Kissimmee, FloridaWindsor Hills
Resort-Style Living Minutes From Disney
55
Homes for sale
$395,000
Median list price
$264
Avg price / sqft
82
Median days on market
Windsor Hills sits just 19 minutes from Walt Disney World, and its DNA shows it — this is a gated, amenity-rich community built for the short-term rental and vacation-home crowd as much as for full-time residents. Pools are the default here, not the exception, and the clubhouse-and-townhome layout gives the place a relaxed, resort feel. If you want to be close to the parks without living on top of them, this is a practical middle ground.
The market reality: with 55 active listings and a median list price of $395,000, Windsor Hills is one of the more accessible gated pockets near the attractions, though the median HOA of $575/month reflects the resort-level amenities. Homes are moving at a measured pace — a median of 82 days on market, with sellers netting about 97% of asking. If you're weighing this against other Kissimmee homes for sale, the trade-off is higher monthly carrying costs in exchange for turnkey, rental-friendly ownership.
Windsor Hills is a community in Kissimmee, Florida.
Quick facts
$249,000 – $729K price range
1,440 sqft median home
$575/mo median HOA
$2,520/mo median rent
79 sold in 12 months
Drive times
Living in Windsor Hills
Windsor Hills is a resort-style community in the Osceola County portion of Kissimmee, built around the idea of being close to the theme parks without living in their shadow. Walt Disney World is roughly 19 minutes away, and that proximity shapes everything about the place — from the heavy presence of vacation homes to the amenity-first layout. The community is predominantly gated, with 43 of the 55 active listings sitting behind controlled entry, which gives it a secure, managed feel.
The housing here is designed for comfort and easy maintenance, with private pools common across the inventory — 31 of the current listings include one. That makes Windsor Hills a natural fit for short-term rental owners, snowbirds, and investors who want a turnkey property near the attractions. It also works for full-time residents who prioritize amenities and security over a large private lot.
Who it suits best is clear from the data: buyers comfortable with a monthly HOA in exchange for resort living and rental flexibility. If you want a traditional single-family neighborhood with low fees and a big yard, this isn't that. But if your priority is being minutes from Disney in a gated, amenity-rich setting, Windsor Hills delivers exactly that profile.
Neighborhoods and communities in Windsor Hills
Windsor Hills itself functions as a defined community within Kissimmee rather than a cluster of separately branded subdivisions. The dominant characteristic across its sections is gating and shared resort amenities, which is why the large majority of active listings fall within gated areas. Buyers browsing the broader Kissimmee homes for sale market will notice Windsor Hills stands out for how consistently it leans into the vacation-home model.
Within the community, the practical distinctions come down to home type and amenity access rather than named enclaves. Expect a mix of townhome-style and single-family vacation residences, most built around pool access and proximity to the central clubhouse facilities. Pricing ranges from $249,000 at the entry end to $729,000 at the top, so there's meaningful variety in size and finish.
Because the community data doesn't break out separately named subdivisions, the best approach is to shop by what matters to you — gated access, a private pool, or a specific price band. An agent who knows the community can point you toward the sections that best match your goals, whether that's rental income or a full-time residence.
Homes for sale in Windsor Hills: prices and housing
The current market shows 55 active listings with a median list price of $395,000, spanning a range from $249,000 to $729,000. Homes trade at roughly $264 per square foot, and the median home size is about 1,440 square feet — a profile that reflects the community's compact, amenity-driven designs rather than sprawling custom estates. Over the last 12 months, 79 homes sold, with a median sold price of $420,000.
The pace of the market is steady: the median days on market is 82, and sellers are receiving about 97% of asking price on average. That gives buyers a reasonable window to evaluate properties and negotiate, without the extreme urgency seen in tighter markets. The housing is almost entirely existing resale — there is no new construction among the current listings, and none of the active inventory tops $1 million.
Carrying costs are the number to watch. The median HOA is $575/month, which is substantial but funds the resort amenities and gated security, and median property taxes run about $4,613 per year. For investors, the median rent of $2,520/month helps offset those costs, which is a big part of why the community appeals to the short-term and long-term rental crowd.
Schools in Windsor Hills
Windsor Hills falls within the Osceola County School District, but the specific zoned schools aren't identified in the current data set. Because attendance boundaries can change and vary by exact address, the reliable way to confirm your zoned elementary, middle, and high school is to run the property address through the Osceola County School District's school-locator tool before making an offer.
This matters most for full-time buyers with school-age children, since much of Windsor Hills is oriented toward vacation and rental use. If schools are central to your decision, verify assignments early rather than relying on general neighborhood reputation.
When you tour homes, your agent can help you pull the current zoning for each specific listing, since two homes in the same community can occasionally fall into different attendance areas. Treat the district's official locator as the final word rather than any third-party listing site.
Getting around Windsor Hills
Windsor Hills is positioned for quick access to Central Florida's main draws. Walt Disney World is about a 19-minute drive, making the community one of the closer gated options to the parks. For anyone working in or visiting the theme-park and hospitality corridor, that short hop is the community's defining advantage.
Beyond Disney, Universal Orlando and Orlando International Airport (MCO) are each roughly 36 minutes away, and Downtown Orlando is about 40 minutes. That puts the region's airport, additional attractions, and urban core all within a manageable drive, which is useful for both residents and the rental guests who frequent the area.
Like most of the Kissimmee attractions corridor, this is a car-dependent location — you'll want a vehicle for daily errands and commuting. The payoff is a central position that keeps the parks, the airport, and Orlando proper all within reach of a single home base.
Is Windsor Hills a good place to live?
Windsor Hills is a strong choice for a specific kind of buyer: someone who wants resort-style amenities, gated security, and a location minutes from Walt Disney World. With a median list price of $395,000 and 31 of 55 active listings offering a private pool, it delivers turnkey living at an accessible entry point for the area. Investors and part-time owners benefit further from solid rental demand, with median rents around $2,520/month.
The honest trade-offs are the carrying costs and the community's vacation-home character. A median HOA of $575/month plus roughly $4,613 in annual property taxes adds up, and the rental-heavy makeup means it may feel less like a traditional owner-occupied neighborhood. There's also no new construction and no inventory above $1 million, so buyers seeking brand-new or luxury-estate homes will look elsewhere.
For buyers who value location and amenities over a large lot or low fees, Windsor Hills makes a lot of sense — and the measured market, with homes averaging 82 days to sell and sellers getting about 97% of asking, gives you room to buy thoughtfully. Weigh it against the wider Kissimmee homes for sale market, and the decision usually comes down to whether proximity to Disney and resort living justify the monthly costs for your plans.
On the market now
Homes for sale in Windsor Hills
View all 55 →
$439,000
2553 MANESHAW LANE, KISSIMMEE
3 bd · 3 ba · 1,440 sqft
$360,000
2593 MANESHAW LANE, KISSIMMEE
3 bd · 3 ba · 1,440 sqft
$678,000
2669 MANESTY LANE, KISSIMMEE
6 bd · 4 ba · 2,812 sqft
$599,999
7718 TEASCONE BOULEVARD, KISSIMMEE
6 bd · 4 ba · 2,812 sqft
$349,900
2785 ALMATON LOOP UNIT 303, KISSIMMEE
3 bd · 2 ba · 1,246 sqft
$335,000
2788 ALMATON LOOP UNIT 401, KISSIMMEE
3 bd · 2 ba · 1,246 sqft
$250,000
2781 ALMATON LOOP UNIT 302, KISSIMMEE
2 bd · 2 ba · 1,081 sqft
$470,000
2579 MANESHAW LANE, KISSIMMEE
3 bd · 3 ba · 1,440 sqft
$325,000
2817 ALMATON LOOP UNIT 304, KISSIMMEE
3 bd · 2 ba · 1,450 sqft
$695,000
2564 ARCHFELD BOULEVARD, KISSIMMEE
6 bd · 4 ba · 2,812 sqft
$379,000
7654 COMROW STREET UNIT 205, KISSIMMEE
3 bd · 2 ba · 1,410 sqft
$649,000
2648 DINVILLE STREET, KISSIMMEE
5 bd · 5 ba · 2,297 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
79
Sold, last 12 months
$420,000
Median sold price
97%
Sale-to-list ratio
What sellers actually get vs asking
55 days
Median time to sell
Windsor Hills vs Kissimmee
Median list price
Price per sqft
Days on market
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
≈ $3,250/mo
$395,000 median · 20% down · 30-yr fixed at 6.9% · taxes/HOA from live listing data · insurance is a Florida estimate.
$575/mo
Median HOA
From current listings inside the boundary
$2,520/mo
Median rent
Homes for rent inside the boundary
Population
485
Median age
38
Median income
$78,581
Median home value
$360,900
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
David Ramirez
Real Estate Agent
Colleen Brown
REALTOR®
Nicholas Giaccone
Director of Agent Success
Straight answers
Windsor Hills FAQs
Is Windsor Hills a good place to live?+
It suits buyers who want resort-style amenities and proximity to the parks — Walt Disney World is about 19 minutes away. The community leans toward vacation homes and rentals, so it's especially strong for investors or part-time residents. Full-time buyers who value gated security and a pool will find plenty to like among the 55 active listings.
Is Windsor Hills expensive?+
It's mid-range for the area, with a median list price of $395,000 and listings running from $249,000 up to $729,000. The bigger cost to plan for is the median HOA of $575/month, which covers the community's resort amenities. Compared with other Kissimmee homes for sale, the entry price is accessible but the monthly carrying cost is higher.
What do homes cost in Windsor Hills?+
The median list price is $395,000 and the median sold price over the last 12 months was $420,000. Pricing works out to about $264 per square foot against a median home size of 1,440 square feet. Expect most inventory to fall in the gated, pool-equipped tier that defines the community.
How is the market right now?+
There are 55 active listings and homes are taking a median of 82 days to sell, so buyers have room to negotiate. Over the past year, 79 homes closed, with sellers receiving about 97% of their asking price on average. That combination points to a steady, balanced market rather than a frenzied one.
What are the HOA fees and property taxes?+
The median HOA runs about $575/month, which is high but reflects the resort-level amenities and security that come with the community. Median property taxes are around $4,613 per year. Factor both into your monthly budget, especially if you're comparing against non-gated neighborhoods.
What are the schools like in Windsor Hills?+
Windsor Hills is served by Osceola County public schools, but specific zoned assignments aren't listed in the current data. Because attendance boundaries can shift, confirm the exact zoned elementary, middle, and high school with the Osceola County School District using the property address before you buy. This is especially worth doing if schools are a priority for a full-time move.
How is the commute from Windsor Hills?+
The community is built around easy access to the attractions corridor — Walt Disney World is about 19 minutes away, and both Universal Orlando and Orlando International Airport are roughly 36 minutes. Downtown Orlando is around 40 minutes. It's a convenient base for anyone working in or near the theme-park and hospitality economy.
Is there new construction in Windsor Hills?+
There is no new construction among the current active listings — Windsor Hills is an established, built-out community. Buyers are purchasing existing resale homes, 31 of which currently include a private pool. If a brand-new build is essential, you'll want to look at newer developments elsewhere in Kissimmee.
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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