Grayson Square

Grayson Square is a community of townhouses in Winter Park, Florida, with a range of options priced between $452,000 and $465,000. There are currently a total of 3 townhouses for sale in Grayson Square. The smallest Grayson Square townhouse presently available is a three bedroom two bathroom residence that is 2,300 square feet (1,801SF Under Air living space), and the largest of the Grayson Square townhouses currently on the market has three beds and two baths and is a 2,301 square foot (1,907SF Under Air) residence.

Property management fees in Orange County vary depending on the community and sometimes vary between townhouses in the community. The current HOA fees for townhomes in Grayson Square range from $375 to $387. This fee includes grounds maintenance, building maintenance, maintaining the community roads, the community pool, property insurance, pest control, and Cable TV & internet. Please check the individual listing pages for the exact homeowners association fees for a particular Grayson Square townhouse.

The Grayson 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 Grayson Square - Orlando Executive (ORL), which is six miles away; Orlando Sanford International (SFB), which is twelve miles away; Orlando International (MCO), which is thirteen miles away, and Kissimmee Gateway (ISM), which is twenty four miles away from Grayson Square.

Grayson Square real estate activity on the Winter Park MLS during the past year (as of September 2025) reflects four townhouses changing hands, with an average asking price of $444,970 and an average selling price of $428,250. This represents a healthy list-to-sell price ratio of 96% and $200 per square foot. During this period, Grayson Square townhouses for sale have taken an average of 95 days to sell.

In addition, there are numerous other communities in Winter Park to choose from, or you may browse all available Townhouses for sale in Winter Park. Townhouses for sale in Grayson Square are selling quickly. Set up a new listing alert, and we will notify you immediately when a new townhouse in Grayson 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.

Grayson Square Townhouses For Sale

Reduced

$465,000

$580,000

MLS#MFRO6266098

2774 Bright Bird Ln
Winter Park, FL 32792

3

3

1

2,301 SqFt

0.04 Acres

284 Days

Reduced

$459,900

$474,900

MLS#MFRO6289327

2037 Canny Cv
Winter Park, FL 32792

3

3

2

2,300 SqFt

0.05 Acres

201 Days

$452,000

MLS#MFRO6276659

2033 Canny Cv
Winter Park, FL 32792

3

3

1

2,300 SqFt

0.04 Acres

238 Days

3 Active Listings in Grayson Square