Windermere Crossing

Windermere Crossing is a gated community of single family homes in Winter Garden, Florida, with a range of options priced between $424,900 and $884,900. There are currently a total of 2 homes for sale in Windermere Crossing. The smallest Windermere Crossing home presently available is a five bedroom three bathroom residence that is 3,737 square feet (2,957SF Under Air living space), and the largest of the Windermere Crossing homes currently on the market has five beds and three baths and is a 4,844 square foot (3,909SF 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 Windermere Crossing range from $625 to $1,200. This fee includes grounds maintenance, maintaining the community roads, security, and recreation facilities. Please check the individual listing pages for the exact homeowners association fees for a particular Windermere Crossing home.

The Windermere Crossing 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 Windermere Crossing - Orlando Executive (ORL), which is fourteen miles away; Orlando International (MCO), which is seventeen miles away; Kissimmee Gateway (ISM), which is eighteen miles away, and Orlando Sanford International (SFB), which is twenty six miles away from Windermere Crossing.

Windermere Crossing real estate activity on the Winter Garden MLS during the past year (as of September 2025) reflects two homes changing hands, with an average asking price of $789,950 and an average selling price of $772,500. This represents a healthy list-to-sell price ratio of 98% and $166 per square foot. During this period, Windermere Crossing homes for sale have taken an average of 44 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 Windermere Crossing are selling quickly. Set up a new listing alert, and we will notify you immediately when a new home in Windermere Crossing 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.

Windermere Crossing Homes For Sale

$884,900

MLS#MFRO6345657

1061 Spring Mill Dr
Winter Garden, FL 34787

5

3

2

4,404 SqFt

Pool

0.34 Acres

8 Days

Under Contract

$799,000

$880,000

MLS#MFRA4649856

1125 English Garden Ln
Winter Garden, FL 34787

5

4

2

4,417 SqFt

Pool

0.35 Acres

157 Days

2 Active Listings in Windermere Crossing