Sleepy Hollow Leesburg

Sleepy Hollow is a community of single family homes in Leesburg, Florida, with a range of options priced between $285,000 and $450,000. There are currently a total of 3 homes for sale in Sleepy Hollow. The smallest Sleepy Hollow home presently available is a three bedroom two bathroom residence that is 1,949 square feet (1,545SF Under Air living space), and the largest of the Sleepy Hollow homes currently on the market has four beds and three baths and is a 2,855 square foot (2,151SF 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 Sleepy Hollow range from $38 to $460. Please check the individual listing pages for the exact homeowners association fees for a particular Sleepy Hollow home.

The Sleepy Hollow HOA rules do allow homeowners to have pets. Dogs and cats are allowed.

There are four commercial airports that serve Sleepy Hollow - Orlando Sanford International (SFB), which is 36 miles away; Orlando Executive (ORL), which is 36 miles away; Orlando International (MCO), which is 41 miles away, and Kissimmee Gateway (ISM), which is 44 miles away from Sleepy Hollow.

Sleepy Hollow real estate activity on the Leesburg MLS during the past year (as of October 2025) reflects four homes changing hands, with an average asking price of $398,675 and an average selling price of $393,700. This represents a healthy list-to-sell price ratio of 99% and $138 per square foot. During this period, Sleepy Hollow homes for sale have taken an average of 73 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 Sleepy Hollow are selling quickly. Set up a new listing alert, and we will notify you immediately when a new home in Sleepy Hollow 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.

Sleepy Hollow Homes For Sale

$450,000

MLS#MFRG5102012

2721 Athens Dr
Leesburg, FL 34748

4

3

2

2,658 SqFt

Pool

0.18 Acres

17 Days

Reduced

$313,700

$328,700

MLS#MFRG5101188

200 Patrice Hope St
Leesburg, FL 34748

3

2

2

2,252 SqFt

0.23 Acres

40 Days

Reduced

$285,000

$315,000

MLS#RX-11089548

209 Round Man Street
Leesburg, FL 34748

4

2

2

2,658 SqFt

146 Days

You may also be interested in Sleepy Hollow in Port Orange.

3 Active Listings in Sleepy Hollow