Neighborhood · Kissimmee, Florida
Windsor At Waterside
Resort-style pool homes minutes from Disney
35
Homes for sale
$559,000
Median list price
$173
Avg price / sqft
131
Median days on market
Windsor At Waterside sits in the resort corridor west of Kissimmee, where the calendar runs on family visits and short-term stays as much as year-round living. Nearly every home here comes with a private pool, and gated entries are common — 18 of the 36 active listings sit behind a gate. It's a natural fit for buyers eyeing the vacation-rental crowd, with Walt Disney World about 28 minutes away and neighbors like Storey Lake and Windsor at Westside drawing the same short-term audience.
Today's market gives buyers room to negotiate: 36 homes are active with a median list price of $573,250, and properties are averaging 59.5 days on market before going under contract. Over the past year 41 homes sold at a median of $495,000, with sellers collecting about 96% of asking on average. If you're weighing income potential, compare the numbers here against Solara and other rental-focused communities nearby before you commit.
Windsor At Waterside is a community in Kissimmee, Florida.
Quick facts
$390,000 – $749K price range
3,314 sqft median home
$606/mo median HOA
$3,600/mo median rent
46 sold in 12 months
Drive times
On the market now
Homes for sale in Windsor At Waterside
View all 35 →
$570,000
2187 TRIPOLI COURT, KISSIMMEE
8 bd · 6 ba · 4,041 sqft
$570,000
2191 TRIPOLI COURT, KISSIMMEE
8 bd · 6 ba · 4,041 sqft
$699,000
2105 MALTA TERRACE, KISSIMMEE
8 bd · 6 ba · 4,034 sqft
$645,000$659,000
8853 RHODES STREET, KISSIMMEE
9 bd · 6 ba · 4,391 sqft
$695,000
2137 MALTA TERRACE, KISSIMMEE
8 bd · 6 ba · 4,041 sqft
$390,000$415,000
9025 RHODES STREET, KISSIMMEE
5 bd · 4.5 ba · 2,263 sqft
$549,990
1917 NICE COURT, KISSIMMEE
5 bd · 4 ba · 2,492 sqft
$424,900$450,000
2070 ROME DRIVE, KISSIMMEE
5 bd · 4.5 ba · 2,265 sqft
$499,900$519,900
1888 GOBI DRIVE, KISSIMMEE
6 bd · 4.5 ba · 3,142 sqft
$669,990$690,000
1908 NICE COURT, KISSIMMEE
9 bd · 6 ba · 4,391 sqft
$500,000
8912 RHODES STREET, KISSIMMEE
7 bd · 5.5 ba · 3,314 sqft
$440,000$444,900
1974 MAJORCA DRIVE, KISSIMMEE
5 bd · 4.5 ba · 2,265 sqft
Every active listing inside the Windsor At Waterside boundary
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Browse Windsor At Waterside
By feature — on the live map
Where the market lives
The numbers that matter
The Windsor At Waterside market
46
Sold, last 12 months
$510,000
Median sold price
96%
Sale-to-list ratio
What sellers actually get vs asking
83 days
Median time to sell
Windsor At Waterside vs Kissimmee
Median list price
Price per sqft
Days on market
Median sold price — 3-yr, 3-mo rolling
▼ 6.8% yr/yr
Homes sold per month
Live Stellar MLS data — every listing and closed sale inside the Windsor At Waterside boundary. Rolling medians smooth single-month swings in small communities.
For the school run
Schools Windsor At Waterside 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 Waterside home
≈ $4,619/mo
$559,000 median · 20% down · 30-yr fixed at 6.9% · taxes/HOA from live listing data · insurance is a Florida estimate.
$606/mo
Median HOA
From current listings inside the boundary
$3,600/mo
Median rent
Homes for rent inside the boundary
Population
145
Median age
38
Median income
$101,226
Median home value
$429,800
Beyond the listings
Living in Windsor At Waterside
Lifestyles
Top 3% 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.
Hobbies & Interests
Top 3% 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 13% in the U.S.Film Lovers
Movie buffs and binge watchers expressing their love for movies, storytelling, and the film making process.
Food & Drink
Top 16% 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.
Entertainment
Top 16% 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.
Emotional
Top 19% 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.
People who close here
Our Kissimmee experts
Iain Robinson
Broker Associate
Dan Schriver
REALTOR®
David Ramirez
Real Estate Agent
Colleen Brown
REALTOR®
Keep exploring
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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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