Sleepy Hollow is a 1970s neighborhood in west Longwood, in the 32750 zip code. Homes are block and stucco, predominantly single story. Most homes fall between about 2,000 and 3,000 square feet under air, the median lot is roughly half an acre, and a two car garage is standard.
Homes here carry an HOA, billed annually, typically around $250. Confirm the figure on a specific parcel before relying on it.
What the homes are
Built Essentially all built in the 1970s.
Construction Block and stucco. Shingle roofs are near universal.
Style Ranch, Traditional. Predominantly single story.
Size Most homes fall between about 2,000 and 3,000 square feet under air.
Bedrooms Four bedrooms is the most common plan, then three.
Garage A two car garage is standard.
Lot The median lot is roughly half an acre.
HOA Billed annually, typically around $250. Confirm on a specific parcel before relying on it.
Where Sleepy Hollow is
Sleepy Hollow, centered at 28.705102, -81.378683. Drag to explore.Street level, inside the neighborhood. Drag to look around.
Drive times below are measured on the road network from the center of Sleepy Hollow, not straight-line distance, in free-flowing traffic. Treat them as the floor rather than the school-run average.
Driving to
Time
Miles
Downtown Orlando
20 min
13.5
Orlando International Airport
35 min
32.0
Winter Park
20 min
10.6
Heathrow and Lake Mary offices
17 min
8.3
Public schools nearby
Woodlands Elementary School 9 min, 2.6 mi
Altamonte Elementary School 8 min, 2.8 mi
Seminole County Virtual School 13 min, 5.0 mi
Sabal Point Elementary School 10 min, 4.0 mi
Private schools nearby
Sanlando Christian School 4 min, 1.3 mi
Parks and recreation
Shadow Hill Park 9 min, 2.9 mi
Sandalwood Park 7 min, 2.6 mi
Rolling Hills Community Park 5 min, 2.0 mi
Reiter Park 7 min, 2.8 mi
Groceries and errands
CORA 6 min, 2.3 mi
Publix Super Market at Longwood Hills Market 10 min, 3.3 mi
Cedano 7 min, 2.1 mi
Publix Super Market at Springs Plaza 8 min, 2.5 mi
Nearest is not the same as zoned. The schools above are the closest ones to Sleepy Hollow by distance. School attendance zones are set by the district, change from year to year, and can differ street to street inside one neighborhood. Confirm the assignment for a specific address with Seminole County Public Schools before it matters to a decision.
Places and drive times from Google, checked 6 September 2026. Businesses open and close; if something here has changed, tell me and I will correct it.
This page tracks what homes in Sleepy Hollow actually sold for over the last twelve months, how long they took, and what moved the price. It is built from 4 verified closed sales in the Stellar MLS feed, not from public estimates. Every figure is a net-of-concessions number, which is explained at the bottom. Updated September 2026.
Read this one loosely. Fewer than eight homes closed here in the last year, so every median on this page rests on a small sample and can swing on a single sale.
What homes sold for in Sleepy Hollow
$595,000Median sale price
$244Median per square foot
14 daysMedian days to contract
4Homes sold in 12 months
Sale prices ran from $550,000 to $610,000, which is a wide spread and the reason a single neighborhood median is a starting point rather than an answer.
By size
Home size
Sales
Median price
Median $/sq ft
Median days
2,000 to 3,000 sq ft
3
$585,000
$259
5 days
Larger homes usually show a lower price per square foot. That is normal and it is why a price per foot taken from the whole neighborhood should never be applied straight to one house.
Homes priced right sold far faster
Median days to go under contract. Shorter is better.
Never reduced 3 sales, closed at 98.4% of asking5 days
Reduced at least once 1 sales, closed at 102.3% of the reduced price65 days
Sellers who priced correctly and held their number went under contract in a median 5 days. Sellers who had to reduce took 65 days and still closed at 102.3% of their already reduced price, after a typical cut of $23,000. Opening high costs time and money, in that order.
How buyers paid
FHA 2 sales50%
Conventional 2 sales50%
Cash was 0% of purchases. A high cash share means a seller has buyers who do not depend on an appraisal, and a buyer using a loan is competing against offers that can close faster.
Questions about a specific home in Sleepy Hollow, or want to know what yours would sell for? Call or text Brenden Rendo at 407-616-9019 or send a message.
About this data. Source is the Stellar MLS feed for Sleepy Hollow in Longwood, Seminole County, covering closed sales from 11 September 2025 through 6 September 2026, refreshed monthly and current as of September 2026. Prices are net of seller concessions, so they reflect what the seller actually received rather than the headline number. Data believed accurate but not guaranteed; listings and closings change daily.
