Sleepy Hollow Port Orange

Sleepy Hollow is a community of single family homes in Port Orange, Florida, with a range of options priced between $299,900 and $409,000. There are currently a total of 2 homes for sale in Sleepy Hollow. The smallest Sleepy Hollow home presently available is a three bedroom two bathroom residence that is 2,120 square feet (1,247SF 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 3,324 square foot (2,862SF Under Air) residence.

Property management fees in Volusia 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 $340 to $390. This fee includes the community pool, and recreation facilities. Please check the individual listing pages for the exact homeowners association fees for a particular Sleepy Hollow home.

Sleepy Hollow amenities include a swimming pool, and a state-of-the-art fitness center. Sports facilities include tennis courts.

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 - Daytona Beach International (DAB), which is five miles away; New Smyrna Beach Municipal (EVB), which is six miles away; Orlando Sanford International (SFB), which is twenty eight miles away, and Orlando Executive (ORL), which is 45 miles away from Sleepy Hollow.

Sleepy Hollow real estate activity on the Port Orange MLS during the past year (as of October 2025) reflects five homes changing hands, with an average asking price of $302,500 and an average selling price of $285,920. This represents a healthy list-to-sell price ratio of 95% and $113 per square foot. During this period, Sleepy Hollow homes for sale have taken an average of 44 days to sell.

In addition, there are numerous other communities in Port Orange to choose from, or you may browse all available Port Orange 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

Reduced

$409,000

$449,000

MLS#MFROM692252

772 Horseman Dr
Port Orange, FL 32127

3

2

2

3,169 SqFt

0.21 Acres

272 Days

Under Contract

$389,599

$410,000

MLS#MFRV4943939

744 Horseman Dr
Port Orange, FL 32127

4

2

2

3,324 SqFt

0.26 Acres

74 Days

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2 Active Listings in Sleepy Hollow