Winding Hollow

Winding Hollow is a community of single family homes in Winter Springs, Florida, with a range of options priced between $234,900 and $759,000. There are currently a total of 3 homes for sale in Winding Hollow. The smallest Winding Hollow home presently available is a five bedroom three bathroom residence that is 2,284 square feet (2,100SF Under Air living space), and the largest of the Winding Hollow homes currently on the market has five beds and three baths and is a 4,372 square foot (3,657SF 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 $575. 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 although there are certain breed restrictions. 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 June 2026) reflects twelve homes changing hands, with an average asking price of $610,075 and an average selling price of $603,875. This represents a healthy list-to-sell price ratio of 99% and $189 per square foot. During this period, Winding Hollow homes for sale have taken an average of 50 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 BEX Realty agent, who would happily assist you further with all your Florida real estate needs.

Winding Hollow Homes For Sale