Homes for sale · Kissimmee, FloridaWindsor at Westside
Resort-style living minutes from the theme parks
89
Homes for sale
$490,000
Median list price
$182
Avg price / sqft
104
Median days on market
Windsor at Westside sits in the heart of Kissimmee's vacation-home corridor, a gated community where nearly every home comes with a private pool and the clubhouse amenities lean toward resort life rather than suburban routine. It's a community built for people who want to be close to Walt Disney World — about 18 minutes away — whether they're buying a short-term rental investment, a vacation retreat, or a full-time home with Florida sunshine built in.
For a buyer today, this is an active market with real inventory: 90 homes are listed, with a median list price of $489,000 and a wider range from $380,000 to $749,000. Homes here sell for a median of $515,000 and sellers are netting about 97% of asking, though the median 110-day time on market tells you buyers have room to be selective. If you're comparing options across the area, it's worth seeing how Windsor stacks up against other Kissimmee homes for sale and nearby communities like Storey Lake and Solara.
Windsor at Westside is a community in Kissimmee, Florida.
Quick facts
$380,000 – $749K price range
2,492 sqft median home
$584/mo median HOA
$3,525/mo median rent
99 sold in 12 months
Drive times
Living in Windsor at Westside
Windsor at Westside is a resort-style gated community in the Westside corridor of Kissimmee, Osceola County — a stretch of Central Florida built largely around proximity to the theme parks. The community's defining feature is clear in the data: all 90 active listings come with a private pool, and more than half sit behind gates. This is a place designed for Florida living at a slower, sunnier pace, where the amenities lean toward recreation and the floor plans toward space.
The community draws a mix of residents. Some are full-time owners who want room to spread out and a short drive to work in the Disney corridor. Others are seasonal snowbirds, and a significant share are vacation-home and short-term-rental investors drawn by the location and the pool-forward home designs. With a median home size around 2,492 square feet, homes here are built to accommodate larger families and rental groups alike.
It suits buyers who value amenities and location over quiet suburban anonymity. If you want a gated setting, a pool, and theme-park access measured in minutes rather than hours, Windsor delivers on all three. Buyers seeking a strictly residential, no-rentals neighborhood should weigh the community's investor-heavy character before committing.
Neighborhoods and communities in Windsor at Westside
Windsor at Westside is one community within a larger cluster of vacation-oriented neighborhoods along Kissimmee's Westside. Buyers comparing options often look at it alongside nearby communities that share the resort-home DNA. Each has its own amenity package, HOA structure, and price positioning, so it pays to tour a few before deciding.
Notable neighbors include Storey Lake and Solara, both known for resort clubhouses and short-term rental appeal similar to Windsor. Lake Marion Village offers another point of comparison in the Kissimmee market, while The Encore Club At Reunion sits among the higher-amenity options in the corridor.
For buyers whose priorities shift toward a quieter, age-restricted lifestyle rather than vacation-home energy, Solivita is a well-known 55+ community in the broader area. Weighing these communities side by side helps clarify whether Windsor's gated, pool-every-home formula matches what you want day to day.
Homes for sale in Windsor at Westside: prices and housing
The current market shows 90 active listings with a median list price of $489,000, spanning a range from $380,000 to $749,000. There are no listings above $1 million, which keeps Windsor firmly in the mid-to-upper tier of the Kissimmee vacation-home market rather than the luxury bracket. Over the past 12 months, 99 homes sold at a median price of $515,000, with sellers netting about 97% of asking on average.
The housing here is consistent in character: every active listing includes a private pool, and 52 of the 90 are gated. Pricing works out to roughly $182 per square foot against a median home size of 2,492 square feet, so buyers are generally paying for substantial, amenity-equipped homes. Waterfront inventory is scarce — just two active listings — and there is currently no golf, 55+, or new-construction product within the community.
Two carrying costs deserve close attention. The median HOA is about $584 per month, which is high and reflects the resort amenities and gated infrastructure, and median property taxes run around $7,920 per year. For investors, the median rent of $3,395 per month frames the income side of the equation. The median 110-day time on market suggests buyers can negotiate, so factor both the purchase price and these ongoing costs into your underwriting.
Schools in Windsor at Westside
Windsor at Westside falls within the Osceola County school district. The most commonly assigned schools for the community are Westside K-8 School, Celebration High School, and Osceola County School for the Arts. These cover the range from elementary through high school, with the School for the Arts serving as a specialized magnet option.
School zoning can and does change, and assignments sometimes vary by specific address even within a single community. Before making a decision based on a particular school, confirm the current zoning directly with the Osceola County school district using the exact property address.
Families buying here should also consider the community's investor and seasonal makeup when weighing schools as a factor — Windsor's appeal is split between year-round residents and vacation-home owners, which shapes the local family density differently than a purely residential subdivision would.
Getting around Windsor at Westside
Location is one of Windsor's strongest selling points. Walt Disney World is roughly 18 minutes away, which explains much of the community's vacation-rental demand and its appeal to anyone working in the theme-park corridor. Universal Orlando is about 32 minutes out, putting both major resort destinations within an easy drive.
For broader Central Florida access, Downtown Orlando is around 38 minutes and Orlando International Airport (MCO) about 43 minutes — manageable for travelers and commuters alike. Downtown Tampa sits roughly 68 minutes away, making a day trip to the Gulf Coast realistic. The Westside corridor connects to the region's major highways that feed these destinations.
As with most of Central Florida, a car is essential here. The community is oriented around driving, so plan on using personal vehicles for commuting, shopping, and errands rather than relying on transit.
Is Windsor at Westside a good place to live?
Windsor at Westside is a strong fit for a specific kind of buyer: someone who wants a gated, pool-equipped, resort-style home within an 18-minute drive of Disney, whether as a primary residence, a seasonal home, or a short-term rental investment. The data backs up that identity — every listing has a pool, most are gated, and the homes are spacious at a median of nearly 2,500 square feet. Pricing in the high-$400,000s to low-$500,000s keeps it accessible relative to Central Florida's luxury tiers.
The trade-offs are worth naming honestly. The median HOA of around $584 per month and property taxes near $7,920 per year add up to meaningful carrying costs, and the investor-and-vacation-rental character means the community feels more transient than a traditional residential neighborhood. The median 110-day time on market also signals that homes don't fly off the shelf, which is good news for buyers but something sellers should plan around.
For the right buyer, those trade-offs are a fair price for the location and lifestyle. If you value amenities, a pool, gated access, and proximity to the parks — and you've budgeted for the HOA and taxes — Windsor at Westside delivers a clear, consistent product. Buyers wanting a quieter, owner-occupied-only community should tour a few neighbors first to confirm the fit.
On the market now
Homes for sale in Windsor at Westside
View all 89 →
$649,000
8895 QIN LOOP, KISSIMMEE
8 bd · 6 ba · 4,041 sqft
$580,000
2108 ROME DRIVE, KISSIMMEE
6 bd · 4.5 ba · 3,142 sqft
$415,000
8882 GENEVE CT, KISSIMMEE
4 bd · 3.5 ba · 2,102 sqft
$488,000
8935 ZURICH LANE, KISSIMMEE
5 bd · 4 ba · 2,492 sqft
$437,500
1965 MAJORCA DRIVE, KISSIMMEE
5 bd · 4.5 ba · 2,263 sqft
$435,000
8812 CORCOVADO DRIVE, KISSIMMEE
5 bd · 4 ba · 2,492 sqft
$419,000
2433 DUBAI STREET, KISSIMMEE
5 bd · 4.5 ba · 2,263 sqft
$415,000
2415 DUBAI STREET, KISSIMMEE
5 bd · 4.5 ba · 2,263 sqft
$380,000
2015 MAJORCA DRIVE, KISSIMMEE
5 bd · 4.5 ba · 2,263 sqft
$449,990
2422 DUBAI STREET, KISSIMMEE
5 bd · 4.5 ba · 2,263 sqft
$424,900
8827 GENEVE COURT, KISSIMMEE
5 bd · 4.5 ba · 2,263 sqft
$560,000
8897 RHODES STREET, KISSIMMEE
6 bd · 4.5 ba · 3,142 sqft
Every active listing inside the Windsor at Westside boundary
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Browse Windsor at Westside
By feature — on the live map
Where the market lives
The numbers that matter
The Windsor at Westside market
99
Sold, last 12 months
$515,000
Median sold price
97%
Sale-to-list ratio
What sellers actually get vs asking
96 days
Median time to sell
Windsor at Westside vs Kissimmee
Median list price
Price per sqft
Days on market
Median sold price — 3-yr, 3-mo rolling
▼ 8.7% yr/yr
Homes sold per month
Live Stellar MLS data — every listing and closed sale inside the Windsor at Westside boundary. Rolling medians smooth single-month swings in small communities.
For the school run
Schools Windsor at Westside is zoned for
Attendance boundaries overlapping this community — always verify zoning with the district.
What it really costs
Owning here
Owning the median Windsor at Westside home
≈ $4,040/mo
$490,000 median · 20% down · 30-yr fixed at 6.9% · taxes/HOA from live listing data · insurance is a Florida estimate.
$584/mo
Median HOA
From current listings inside the boundary
$3,525/mo
Median rent
Homes for rent inside the boundary
Beyond the listings
Living in Windsor at Westside
Hobbies & Interests
Bookish
Always seeking the next book, article, or poem to read, this activity is prevalent in areas where reading is a way of life. Although a solo activity, the expression of the love of books is a bonding, communal experience.
Hobbies & Interests
Green Thumb
From tiny sprouts and window plants, to flower arrangements and designing a landscape, this population has an affinity for all things green.
Hobbies & Interests
Natural Beauty
This population marvels at the beauty of nature, and they want to capture every breath-taking scene.
Hobbies & Interests
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.
Hobbies & Interests
Handcrafted
The only thing more beautiful than handmade decor? The hands that made it. This population appreciates the time and care put into one-of-a-kind pieces.
Hobbies & Interests
Animal Advocates
Passionate about animal welfare, this population wants to know how best to care for their own pets (with toys and training) and help other animals find their fur-ever home.
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 at Westside FAQs
Is Windsor at Westside a good place to live?+
It suits buyers who want a resort-style, amenity-rich community close to the theme parks, and that same appeal makes it popular with vacation-home owners and investors. With every listing offering a private pool and more than half the homes gated, it's geared toward relaxed Florida living. Full-time residents, seasonal owners and short-term rental buyers all find a fit here.
Is Windsor at Westside expensive?+
It sits in the mid-range for the Kissimmee area, with a median list price of $489,000 and a median sold price of $515,000 over the past year. Homes range from $380,000 up to $749,000, and there are currently no listings above $1 million. Compared to other Kissimmee homes for sale, it offers larger, amenity-heavy pool homes at a premium that reflects the resort setting.
What do homes cost in Windsor at Westside?+
The median list price is $489,000 and homes are selling at a median of $515,000, with sellers getting about 97% of asking on average. At roughly $182 per square foot and a median size of 2,492 square feet, you're paying for spacious floor plans built with pools and rental use in mind.
How is the market in Windsor at Westside?+
There are 90 active listings and 99 homes have sold in the past 12 months, so there's steady turnover and real choice for buyers. The median time on market is about 110 days, which means buyers have negotiating room even as sellers hold near 97% of asking. It's a balanced market that rewards patience and comparison shopping.
What are the HOA fees and property taxes like?+
The median HOA runs about $584 per month, which is on the higher side and reflects the resort-style amenities and gated access across the community. Median property taxes come in around $7,920 per year. Budget for both when you compare the all-in cost against communities like Solara.
What schools are assigned to Windsor at Westside?+
The most common assigned schools are Westside K-8 School, Celebration High School, and Osceola County School for the Arts. Because zoning can change, confirm the exact assignment for any specific address with the Osceola County school district before you buy.
What's the commute like from Windsor at Westside?+
Walt Disney World is about 18 minutes away and Universal Orlando roughly 32 minutes, making this a strong base for anyone working in the theme-park corridor. Downtown Orlando is around 38 minutes and Orlando International Airport about 43 minutes, with Downtown Tampa reachable in roughly 68 minutes.
Is there new construction in Windsor at Westside?+
There are currently no new-construction listings active in the community, so buyers are shopping existing homes. That said, every active listing includes a private pool and the median home is a generous 2,492 square feet, so the resale inventory still delivers resort-ready features.
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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