Sleepy Hollow Leesburg

Sleepy Hollow is a community of single family homes in Leesburg, Florida, with a range of options priced between $260,000 and $419,900. 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 1,734 square feet (1,250SF Under Air living space), and the largest of the Sleepy Hollow homes currently on the market has four beds and two 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 are $38. 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 although there are some restrictions. 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 February 2026) reflects three homes changing hands, with an average asking price of $399,900 and an average selling price of $393,267. This represents a healthy list-to-sell price ratio of 98% and $138 per square foot. During this period, Sleepy Hollow homes for sale have taken an average of 41 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

$294,200

MLS#MFRO6370034

200 Patrice Hope St
Leesburg, FL 34748

3

2

2

2,252 SqFt

0.23 Acres

46 Days

Under Contract

$285,000

$315,000

MLS#RX-11089548

209 Round Man Street
Leesburg, FL 34748

4

2

2

2,658 SqFt

268 Days

Under Contract

$260,000

$280,000

MLS#MFRO6359183

212 Patrice Hope St
Leesburg, FL 34748

3

2

2

1,734 SqFt

0.17 Acres

97 Days

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

3 Active Listings in Sleepy Hollow