Neighborhood · Kissimmee, Florida
Windward Cay
An easygoing Kissimmee address close to the parks
1
Homes for sale
$359,000
Median list price
$252
Avg price / sqft
150
Median days on market
Windward Cay is a small, residential pocket of Kissimmee in Osceola County, the kind of place where a low HOA and a straightforward single-family layout do the talking. You're roughly 29 minutes from Walt Disney World and 36 from both Universal Orlando and Orlando International Airport, which keeps commutes and theme-park runs manageable without putting you in the middle of the tourist crush. It sits within easy reach of larger Kissimmee communities like Storey Lake and Solara, so you get quiet without feeling cut off.
For a buyer today, this is a thin, patient market. There's just one active listing at $359,000, and homes have been taking their time — a median of 150 days on market over the past year. But five homes sold in the last 12 months at a median of $340,000, with sellers collecting about 97% of asking, so priced-right properties do trade. If Windward Cay itself is quiet, nearby Lake Marion Village and Windsor at Westside give you more inventory to compare against.
Windward Cay is a community in Kissimmee, Florida.
Quick facts
$359,000 – $359K price range
1,424 sqft median home
$25/mo median HOA
5 sold in 12 months
Drive times
On the market now
Homes for sale in Windward Cay
Every active listing inside the Windward Cay boundary
Open full map search →The numbers that matter
The Windward Cay market
5
Sold, last 12 months
$340,000
Median sold price
97%
Sale-to-list ratio
What sellers actually get vs asking
93 days
Median time to sell
Windward Cay vs Kissimmee
Median list price
Price per sqft
Days on market
Median sold price — 3-yr, 3-mo rolling
▼ 3.3% yr/yr
Homes sold per month
Live Stellar MLS data — every listing and closed sale inside the Windward Cay boundary. Rolling medians smooth single-month swings in small communities.
For the school run
Schools Windward Cay is zoned for
Attendance boundaries overlapping this community — always verify zoning with the district.
What it really costs
Owning here
Owning the median Windward Cay home
≈ $2,366/mo
$359,000 median · 20% down · 30-yr fixed at 6.9% · taxes/HOA from live listing data · insurance is a Florida estimate.
$25/mo
Median HOA
From current listings inside the boundary
Population
1,207
Median age
36
Median income
$51,474
Median home value
$101,300
Beyond the listings
Living in Windward Cay
Active
Top 3% in the U.S.Functional Fitness
Looking good and reaching fitness goals is all about discipline: Eat right. Work hard. No excuses. This population is more likely to view working out as a means to an end.
Active
Top 4% in the U.S.Fitness Obsession
Passionate about strength training, this population relies heavily on the encouragement of the exercise community. While these people seek the latest fitness techniques, they're also interested in supplements and equipment.
Appearance oriented
Top 12% in the U.S.Body Art
Who says the body isn't a canvas? This population loves talking about tattoos, body art and piercings.
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.
Food & Drink
Top 17% in the U.S.Fueling for Fitness
A population characterized by healthy eating. Often pre-planning for meals for the purpose of fitness and convenience. Likely to participate in meal prep trends.
Lifestyles
Top 18% in the U.S.Nerd Culture
These people aren't afraid to nerd out. Common activities include comic books, video games, and often intellectual pursuits.
People who close here
Our Kissimmee experts
Iain Robinson
Broker Associate
Dan Schriver
REALTOR®
David Ramirez
Real Estate Agent
Colleen Brown
REALTOR®
Straight answers
Windward Cay FAQs
Is Windward Cay a good place to live?+
It's a quiet residential neighborhood with a low HOA and an easy position relative to the parks — Disney is about 29 minutes and downtown Orlando roughly 41. Assigned schools include the Osceola County School for the Arts and Central Avenue Elementary. If you want more community amenities nearby, Solara is a short drive.
Is Windward Cay expensive?+
It sits in the mid-range for the area, with the single active listing at $359,000 and last year's median sold price at $340,000. That's approachable compared to some of Kissimmee's higher-priced resort communities, and there are no $1M+ or new-construction listings competing for attention right now.
What do homes cost in Windward Cay?+
The current active listing is priced at $359,000, and homes over the past year sold at a median of $340,000. At about $252 per square foot for a typical 1,424-square-foot home, you're looking at practical single-family sizes rather than sprawling floor plans.
How is the market in Windward Cay?+
It's a low-volume, patient market — just one home is active and only five sold in the last 12 months, with a median of 150 days on market. The upside is discipline on price: sellers averaged about 97% of asking, so well-prepared listings still find buyers. For broader options, compare against Storey Lake.
What are the HOA fees and property taxes like?+
The HOA is modest at a median of about $25 per month, which is unusually low for the Kissimmee area. Property taxes run around $2,883 per year at the median, keeping the overall carrying cost reasonable for a home in this price range.
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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