Cypress Shadows

Cypress Shadows is a community of single family homes in Kissimmee, Florida, with a range of options priced between $320,000 and $383,000. There are currently a total of 2 homes for sale in Cypress Shadows. The smallest Cypress Shadows home presently available is a three bedroom two bathroom residence that is 1,680 square feet, and the largest of the Cypress Shadows homes currently on the market has four beds and two baths and is a 2,450 square foot (1,936SF 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 Cypress Shadows range from $225 to $260. This fee includes recreation facilities. Please check the individual listing pages for the exact homeowners association fees for a particular Cypress Shadows home.

Sports facilities include basketball court. There is also a community park, as well as a playground.

The Cypress Shadows HOA rules do allow homeowners to have pets although there are certain breed restrictions. There is a limitation on pet size. Dogs and cats are allowed.

There are four commercial airports that serve Cypress Shadows - Kissimmee Gateway (ISM), which is four miles away; Orlando International (MCO), which is sixteen miles away; Orlando Executive (ORL), which is twenty two miles away, and Lakeland Linder International (LAL), which is 38 miles away from Cypress Shadows.

Cypress Shadows real estate activity on the Kissimmee MLS during the past year (as of September 2025) reflects three homes changing hands, with an average asking price of $343,233 and an average selling price of $341,633. This represents a healthy list-to-sell price ratio of 100% and $148 per square foot. During this period, Cypress Shadows homes for sale have taken an average of 155 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 Cypress Shadows are selling quickly. Set up a new listing alert, and we will notify you immediately when a new home in Cypress Shadows 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.

Cypress Shadows Homes For Sale

Reduced

$383,000

$398,000

MLS#MFRS5114225

2109 Woodsedge Dr
Kissimmee, FL 34746

4

2

2

2,450 SqFt

0.16 Acres

329 Days

$320,000

MLS#MFRG5101601

4306 Hidden Meadow Dr
Kissimmee, FL 34746

3

2

2

2,246 SqFt

0.13 Acres

8 Days

2 Active Listings in Cypress Shadows