Preston Square

Preston Square is a community of single family homes, and townhomes in Windermere, Florida, with a range of options priced between $199,900 and $650,000. There is currently a total of 1 home for sale in Preston Square. The Preston Square home presently available is a three bedroom two bathroom residence that is 1,560 square feet (1,098SF Under Air living space), and the largest of the Preston Square homes currently on the market has three beds and two baths and is a 3,293 square foot (2,575SF 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 Preston Square are $128 and $152 to $287 for a townhome. This fee includes grounds maintenance, building 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 Preston Square home.

Preston Square amenities include a swimming pool. Sports facilities include basketball court. There is also a community park, as well as a playground.

The Preston Square 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 Preston Square - Kissimmee Gateway (ISM), which is fourteen miles away; Orlando Executive (ORL), which is fifteen miles away; Orlando International (MCO), which is sixteen miles away, and Orlando Sanford International (SFB), which is 30 miles away from Preston Square.

Preston Square real estate activity on the Windermere MLS during the past year (as of October 2025) reflects two homes changing hands, with an average asking price of $635,000 and an average selling price of $635,000. This represents a healthy list-to-sell price ratio of 100% and $195 per square foot. During this period, Preston Square homes for sale have taken an average of 34 days to sell.

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

Preston Square Homes For Sale

$485,000

MLS#MFRO6342723

6864 Helmsley Cir
Windermere, FL 34786

3

2

2

2,386 SqFt

0.15 Acres

6 Days

1 Active Listing in Preston Square