Neighborhood · Kissimmee, Florida
Windward Cay
Compact Kissimmee living within reach of the parks
1
Homes for sale
$356,000
Median list price
$227
Avg price / sqft
72
Median days on market
Windward Cay is a small residential pocket of Kissimmee in Osceola County, close enough to the theme-park corridor to make weekend trips easy but far enough to feel like a neighborhood rather than a tourist zone. Walt Disney World sits about 29 minutes away, with Universal Orlando and Orlando International Airport both roughly 36 minutes out, so commutes and airport runs stay manageable. Homes here are modestly sized — a median of around 1,570 square feet — which suits first-time buyers and downsizers looking for something practical. If you want to see how it stacks up against the broader market, browse Kissimmee homes for sale alongside larger vacation-focused communities like Storey Lake and Solara.
The market here is thin and moves fast: right now there's a single active listing at $356,000, and homes that sold over the past year did so in a median of just three days. Sellers have been getting about 97% of asking on average, with five homes trading in the last twelve months at a median of $340,000. With such limited inventory, buyers should be ready to act — and worth comparing against nearby options like Lake Marion Village and Windsor at Westside if timing doesn't line up.
Windward Cay is a community in Kissimmee, Florida.
Quick facts
$356,000 – $356K price range
1,570 sqft median home
$50/mo median HOA
$1,200/mo median rent
3 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 →Find your fit
Browse Windward Cay
By feature — on the live map
The numbers that matter
The Windward Cay market
3
Sold, last 12 months
$330,000
Median sold price
96%
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
▼ 15.3% 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
≈ $2,616/mo
$356,000 median · 20% down · 30-yr fixed at 6.9% · taxes/HOA from live listing data · insurance is a Florida estimate.
$50/mo
Median HOA
From current listings inside the boundary
$1,200/mo
Median rent
Homes for rent 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 compact Kissimmee neighborhood that balances a residential feel with genuinely short drives to the parks — about 29 minutes to Walt Disney World and roughly 41 minutes to Downtown Orlando. Assigned schools include Osceola County School for the Arts and Celebration High School. It suits buyers who want proximity to the corridor without living in the middle of it.
Is Windward Cay expensive?+
It sits in a mid-market range for the area, with the current active listing at $356,000 and an average of about $227 per square foot. The median sold price over the past year was $340,000, so it's more attainable than many of the larger resort-style communities like Solara.
What do homes cost in Windward Cay?+
The one active listing is priced at $356,000, and recent sales landed at a median of $340,000. With a typical home near 1,570 square feet and pricing around $227 per square foot, you're generally looking at three-bedroom-scale homes rather than large estates.
How is the market in Windward Cay?+
It's fast and tight — only one home is active right now, and homes over the past year sold in a median of just three days. Five homes closed in the last twelve months with sellers averaging about 97% of asking, so serious buyers should be prepared to move quickly and may want to watch Storey Lake for backup options.
What about HOA fees and property taxes?+
The median HOA is around $50 a month, which is on the lower side for the area. Property taxes run a median of about $5,756 per year, so factor both into your monthly budget when comparing homes.
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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