Hillside

Hillside is a community of single family homes in Leesburg, Florida, with a range of options priced between $314,999 and $364,500. There are currently a total of 4 homes for sale in Hillside. The smallest Hillside home presently available is a three bedroom two bathroom residence that is 2,302 square feet (1,725SF Under Air living space), and the largest of the Hillside homes currently on the market has four beds and two baths and is a 2,800 square foot (1,879SF Under Air) residence.

Property management fees in Lake County vary depending on the community and sometimes vary between homes in the community. The current HOA fees for homes in Hillside range from $67 to $200. Please check the individual listing pages for the exact homeowners association fees for a particular Hillside home.

The Hillside HOA rules do allow homeowners to have pets. There is a limit of how many pets you may have, and there is a restriction on pet size. Dogs and cats are allowed.

There are four commercial airports that serve Hillside - Orlando Sanford International (SFB), which is 36 miles away; Orlando Executive (ORL), which is 36 miles away; Orlando International (MCO), which is 42 miles away, and Kissimmee Gateway (ISM), which is 44 miles away from Hillside.

Hillside real estate activity on the Leesburg MLS during the past year (as of October 2025) reflects two homes changing hands, with an average asking price of $345,400 and an average selling price of $326,000. This represents a healthy list-to-sell price ratio of 94% and $127 per square foot. During this period, Hillside homes for sale have taken an average of just 16 days to sell.

In addition, there are numerous other communities in Leesburg to choose from, or you may browse all available Leesburg Real Estate, including some new construction opportunities. Homes for sale in Hillside are selling quickly. Set up a new listing alert, and we will notify you immediately when a new home in Hillside hits the market. You can also always contact your ZFC Real Estate agent, who would happily assist you further with all your Florida real estate needs.

Hillside Homes For Sale

$364,500

MLS#MFRW7878910

2536 Autumn Stream Dr
Leesburg, FL 34748

4

2

2

2,590 SqFt

0.19 Acres

20 Days

Reduced

$363,000

$387,000

MLS#MFRO6292663

2451 Spring Breeze Dr
Leesburg, FL 34748

4

2

2

2,590 SqFt

0.22 Acres

192 Days

Reduced

$350,990

$364,990

MLS#MFRG5097684

2532 Autumn Stream Dr
Leesburg, FL 34748

3

3

2

2,302 SqFt

0.22 Acres

103 Days

New Construction

Reduced

$314,999

$326,000

MLS#MFRS5118419

2587 Summer Star Way
Leesburg, FL 34748

3

2

2

2,354 SqFt

0.2 Acres

261 Days

4 Active Listings in Hillside