Winding Hollow

Winding Hollow is a community of single family homes in Winter Springs, Florida, with a range of options priced between $275,000 and $759,000. There are currently a total of 5 homes for sale in Winding Hollow. The smallest Winding Hollow home presently available is a four bedroom three bathroom residence that is 2,361 square feet (2,159SF Under Air living space), and the largest of the Winding Hollow homes currently on the market has six beds and three baths and is a 4,612 square foot (3,660SF Under Air) residence.

Property management fees in Seminole County vary depending on the community and sometimes vary between homes in the community. The current HOA fees for homes in Winding Hollow are $500. This fee includes grounds maintenance, real estate taxes for common areas, and recreation facilities. Please check the individual listing pages for the exact homeowners association fees for a particular Winding Hollow home.

There is also a community park, as well as a playground.

The Winding Hollow HOA rules do allow homeowners to have pets. Dogs and cats are allowed.

There are four commercial airports that serve Winding Hollow - Orlando Sanford International (SFB), which is six miles away; Orlando Executive (ORL), which is eleven miles away; Orlando International (MCO), which is nineteen miles away, and Kissimmee Gateway (ISM), which is 30 miles away from Winding Hollow.

Winding Hollow real estate activity on the Winter Springs MLS during the past year (as of September 2025) reflects twelve homes changing hands, with an average asking price of $613,142 and an average selling price of $602,375. This represents a healthy list-to-sell price ratio of 98% and $197 per square foot. During this period, Winding Hollow homes for sale have taken an average of 91 days to sell.

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

Winding Hollow Homes For Sale