Neighborhood · Kissimmee, Florida
Windsor At Waterside
Resort-style living minutes from the theme parks
33
Homes for sale
$570,000
Median list price
$173
Avg price / sqft
65
Median days on market
Windsor at Waterside sits in the Kissimmee corridor that draws buyers who want to be close to Central Florida's biggest attractions without living on top of them. Walt Disney World is about 28 minutes away, Universal Orlando and Downtown Orlando roughly 43 minutes each, and Orlando International Airport around 45 — a location that works equally well for a primary home, a second home, or a vacation-rental play. It shares that vacation-destination character with nearby communities like Storey Lake and Solara, while quieter, longer-term neighborhoods like Solivita and Lake Marion Village round out the wider Kissimmee market.
Right now there are 36 active listings in Windsor at Waterside with a median list price of $564,500, putting it in the mid-500s tier of the Kissimmee market. With no recorded sales in the past 12 months in this data set, buyers should lean on active pricing and current inventory rather than closed comps when shaping an offer. That's a lot of choice for a single community, so there's room to be selective on layout, condition, and price.
Windsor At Waterside is a community in Kissimmee, Florida.
Quick facts
$37,500 – $749K price range
3,142 sqft median home
$582/mo median HOA
$3,100/mo median rent
39 sold in 12 months
Drive times
On the market now
Homes for sale in Windsor At Waterside
View all 33 →
$559,000
1885 NICE COURT, KISSIMMEE
6 bd · 4.5 ba · 3,142 sqft
$739,999
8887 MENTON LOOP, KISSIMMEE
8 bd · 6 ba · 4,041 sqft
$699,900
2112 MOROCCO WAY, KISSIMMEE
7 bd · 5.5 ba · 3,314 sqft
$675,000
8825 RHODES STREET, KISSIMMEE
8 bd · 6 ba · 4,041 sqft
$629,000
1829 GOBI DRIVE, KISSIMMEE
8 bd · 6 ba · 4,041 sqft
$444,900
1974 MAJORCA DRIVE, KISSIMMEE
5 bd · 4.5 ba · 2,265 sqft
$690,000
1908 NICE COURT, KISSIMMEE
9 bd · 6 ba · 4,391 sqft
$416,999
1987 MAJORCA DRIVE, KISSIMMEE
4 bd · 3.5 ba · 2,263 sqft
$535,000
8913 RHODES STREET, KISSIMMEE
6 bd · 4.5 ba · 3,142 sqft
$749,000
1940 NICE COURT, KISSIMMEE
9 bd · 6 ba · 4,396 sqft
$412,900
2015 MAJORCA DRIVE, KISSIMMEE
5 bd · 4.5 ba · 2,263 sqft
$577,500$585,000
1881 NICE COURT, KISSIMMEE
7 bd · 5.5 ba · 3,314 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
39
Sold, last 12 months
$450,000
Median sold price
96%
Sale-to-list ratio
What sellers actually get vs asking
78 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
▼ 3.7% 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
≈ $4,633/mo
$570,000 median · 20% down · 30-yr fixed at 6.9% · taxes/HOA from live listing data · insurance is a Florida estimate.
$582/mo
Median HOA
From current listings inside the boundary
$3,100/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
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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