Windward Cay Kissimmee

Windward Cay is a community of single family homes in Kissimmee, Florida, with a range of options priced between $350,000 and $390,000. There are currently a total of 2 homes for sale in Windward Cay. The smallest Windward Cay home presently available is a three bedroom two bathroom residence that is 1,857 square feet (1,382SF Under Air living space), and the largest of the Windward Cay homes currently on the market has three beds and two baths and is a 2,175 square foot (1,590SF Under Air) residence.

Property management fees in Osceola County vary depending on the community and sometimes vary between homes in the community. The current HOA fees for homes in Windward Cay range from $225 to $300. This fee includes. Please check the individual listing pages for the exact homeowners association fees for a particular Windward Cay home.

The Windward Cay HOA rules do allow homeowners to have pets. Dogs and cats are allowed.

There are four commercial airports that serve Windward Cay - Kissimmee Gateway (ISM), which is three miles away; Orlando International (MCO), which is thirteen miles away; Orlando Executive (ORL), which is eighteen miles away, and Orlando Sanford International (SFB), which is 35 miles away from Windward Cay.

Windward Cay real estate activity on the Kissimmee MLS during the past year (as of May 2026) reflects three homes changing hands, with an average asking price of $334,666 and an average selling price of $326,667. This represents a healthy list-to-sell price ratio of 98% and $100 per square foot. During this period, Windward Cay homes for sale have taken an average of 70 days to sell.

In addition, there are numerous other communities in Kissimmee to choose from, or you may browse all available Kissimmee Real Estate, including some new construction opportunities. Homes for sale in Windward Cay are selling quickly. Set up a new listing alert, and we will notify you immediately when a new home in Windward Cay hits the market. You can also always contact your ZFC Real Estate agent, who would happily assist you further with all your Central Florida real estate needs.

Windward Cay Homes For Sale

Reduced

$364,900

$369,000

MLS#MFRS5143726

2201 Chappell Ct
Kissimmee, FL 34746

3

2

2

1,945 SqFt

0.16 Acres

86 Days

Under Contract

$350,000

$380,000

MLS#MFRS5134904

4729 Windwood Dr
Kissimmee, FL 34746

3

2

2

1,857 SqFt

Pool

0.12 Acres

234 Days

You may also be interested in Windward Cay in Winter Garden.

2 Active Listings in Windward Cay