Sleepy Hollow

A charming brick entrance, towering, shady trees, and lush flora welcomes Sleepy Hollow residents, a community located in Longwood with single-family homes for sale. True to its name, the Sleepy Hollow is nicely tucked away in a woodland retreat all of its own, yet it’s close to shops, restaurants, and activities.

Sleepy Hollow Homes for Sale

Sleepy Hollow Real Estate Market Statistics

Average Price $555K
Lowest Price $534K
Highest Price $575K
Total Listings 2
Avg. Days On Market 79
Avg. Price/SQFT $257
List to Sell Price Percentage 98 %

Property Types (active listings)


Located just east of 1-4 and FL-434 and Tarry Town Trail, Sleepy Hollow features 160 single-family homes of varying architectural styles, including ranch and modern. Built between the 1970s and early 1980s, this community features oversized lots – some that are 1 acre or more – that afford residents a great deal of privacy, room for RV parking, and the opportunity to enjoy and be one with nature. Home sizes vary but generally range from approximately 2,000 square feet to 3,500 square feet with 3 to 5 bedrooms, 2 to 3.5 baths, and 2-car garages.

In addition to the woodland environment, residents can also enjoy the multiple community amenities available in Sleepy Hollow. Not only does the community feature a playground, tennis courts, and basketball courts, but several amenities that would be typically be found in a resort-style community, such as pickleball courts, a climbing wall, and a horseshoe pit. A fire pit and picnic tables are also featured within a gated community park area, providing residents many ways to spend time with family and friends and get to know neighbors.

Nearby, Reiter Park is a perfect place to take the kids for the day. With its playground, splash pad, fishing pier, boardwalk, and walking path, this park is sure to be a hit with everyone in the family. Explore Cross Seminole Trail – Big Tree Park with a boardwalk that winds through a forest and over a hammock swamp. The park also features picnic tables and a playground for the little ones.

Shopping and dining are also convenient to Sleepy Hollow, despite its secluded setting. There’s a grocery store just under 2 miles away at Springs Plaza Shopping Center. Several additional shopping centers are very convenient, as well, including Longwood Village, which is less than one mile away, Renaissance Center, featuring a Whole Foods Market, which is just 3 miles away, and the Altamonte Mall.

Call us today to find out more about Sleepy Hollow.

Sleepy Hollow Community Information

Location: Tarry Town Trail and FL-434, just east of I-4
Year(s) Built: 2016 - New Homesites Available
Homesites: 530+ 
HOA: Yes
Square Footage: 1,841 - 3,568
Community Amenities: Playground, tennis courts, basketball courts, pickleball courts, climbing wall, horseshoe pit, fire pit, and picnic tables 

Seminole County Public Schools

  • Altamonte Elementary: Grades Pre-K - 5th  Distance: 2 miles
  • Rock Lake Middle School: Grades 6th - 8th  Distance: 1 mile
  • Lyman High School: Grades 9th - 12th  Distance: 3 miles

Dining and Shopping

  • Longwood Village Shopping Center – Distance: .5 mile
  • Longwood Hills Market with Publix Grocery Store – Distance: 1 mile
  • Plaza del Sol Shopping Center – Distance: 1 mile
  • Winn Dixie Grocery Store – Distance: 1 mile
  • Springs Plaza with Publix Grocery Store – Distance: 2 miles
  • Longwood Lakes Shopping Center – Distance: 3 miles
  • Renaissance Centre – Distance: 3 miles
  • Altamonte Mall – Distance: 3 miles
  • Brantley Square – Distance: 4 miles
  • West Town Corners – Distance: 4.5 miles
  • Downtown Orlando – Distance: 11 miles

Parks and Recreation

  • Highland Hills Park – Distance: 2 miles
  • Reiter Park – Distance: 2 miles
  • Shadow Hill Park – Distance: 2.5 miles
  • Aiguille Rock Climbing Center – Distance: 3 miles
  • Candyland Park – Distance: 3.5 miles
  • Cross Seminole Trail – Big Tree Park - Distance: 4 miles
  • Wekiva River Buffer Conservation Area – Distance: 4 miles
  • Plumosa Oaks Park – Distance: 4.5 miles
  • Greenwood Lakes Park – Distance: 5 miles
  • Lake Hodge Park – Distance: 5 miles
  • Secret Lake Park – Distance: 5 miles
  • Sunnytown Park – Distance: 5 miles
  • Walt Disney World Resort – Distance: 28 miles
  • Universal Studios – Distance: 20 miles
  • SeaWorld – Distance - 25 miles

Hospitals

  • Orlando Health South Seminole Hospital – Distance: 2 miles
  • AdventHealth Altamonte Springs – Distance: 3 miles

*Distances are approximately measured from the Sleepy Hollow community entrance.

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