Winter Oaks

Winter Oaks is a community of single family homes in Winter Garden, Florida, with a range of options priced between $420,000 and $725,000. There is currently a total of 1 home for sale in Winter Oaks. The Winter Oaks home presently available is a five bedroom three bathroom residence that is 1,898 square feet (1,297SF Under Air living space), and the largest of the Winter Oaks homes currently on the market has five beds and three baths and is a 3,844 square foot (3,092SF Under Air) residence.

Property management fees in Orange County vary depending on the community and sometimes vary between homes in the community. The current HOA fees for homes in Winter Oaks are $146. This fee includes grounds maintenance, the community pool, real estate taxes for common areas, and recreation facilities. Please check the individual listing pages for the exact homeowners association fees for a particular Winter Oaks home.

Winter Oaks amenities include a clubhouse, and swimming pool. There is also a community park, as well as a playground.

The Winter Oaks HOA rules do allow homeowners to have pets. Dogs and cats are allowed.

There are four commercial airports that serve Winter Oaks - Orlando Executive (ORL), which is sixteen miles away; Orlando International (MCO), which is twenty miles away; Kissimmee Gateway (ISM), which is twenty one miles away, and Orlando Sanford International (SFB), which is twenty seven miles away from Winter Oaks.

Winter Oaks real estate activity on the Winter Garden MLS during the past year (as of October 2025) reflects four homes changing hands, with an average asking price of $516,225 and an average selling price of $509,719. This represents a healthy list-to-sell price ratio of 99% and $204 per square foot. During this period, Winter Oaks homes for sale have taken an average of just 15 days to sell.

In addition, there are numerous other communities in Winter Garden to choose from, or you may browse all available Winter Garden Real Estate, including some new construction opportunities. Homes for sale in Winter Oaks are selling quickly. Set up a new listing alert, and we will notify you immediately when a new home in Winter Oaks 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.

Winter Oaks Homes For Sale

Under Contract

$725,000

$850,000

MLS#MFRO6337147

724 Chase Oaks Ct
Winter Garden, FL 34787

5

3

2

3,844 SqFt

0.15 Acres

49 Days

1 Active Listing in Winter Oaks