Highland Square

Highland Square is a community of single family homes in Davenport, Florida, with a range of options priced between $269,900 and $365,000. There are currently a total of 2 homes for sale in Highland Square. The smallest Highland Square home presently available is a three bedroom two bathroom residence that is 1,581 square feet (1,108SF Under Air living space), and the largest of the Highland Square homes currently on the market has four beds and two baths and is a 2,923 square foot (2,008SF Under Air) residence.

Property management fees in Polk County vary depending on the community and sometimes vary between homes in the community. The current HOA fees for homes in Highland Square range from $63 to $256. This fee includes real estate taxes for common areas. Please check the individual listing pages for the exact homeowners association fees for a particular Highland Square home.

The Highland 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 Highland Square - Kissimmee Gateway (ISM), which is fifteen miles away; Lakeland Linder International (LAL), which is twenty six miles away; Orlando International (MCO), which is twenty eight miles away, and Orlando Executive (ORL), which is 33 miles away from Highland Square.

Highland Square real estate activity on the Davenport MLS during the past year (as of November 2025) reflects four homes changing hands, with an average asking price of $302,475 and an average selling price of $297,450. This represents a healthy list-to-sell price ratio of 98% and $139 per square foot. During this period, Highland Square homes for sale have taken an average of 33 days to sell.

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

Highland Square Homes For Sale

Reduced

$348,500

$354,500

MLS#MFRO6322645

141 Winsor Ave
Davenport, FL 33837

4

2

2

2,309 SqFt

0.16 Acres

138 Days

Reduced

$305,000

$400,000

MLS#AX-11691246

669 Sierra Cir
Davenport, FL 33837

3

2

2

2,057 SqFt

369 Days

2 Active Listings in Highland Square