Eastbrook Subdivision is a neighborhood in east Winter Park, in the 32792 zip code, built mostly in the 1950s. Homes are block and stucco, predominantly single story. Most homes fall between about 1,100 and 1,700 square feet under air, and the median lot is roughly a quarter acre.
Eastbrook Subdivision has an optional homeowners association rather than a mandatory one, so there is no deed restricted membership to inherit. Dues run about $30 annually for those who join. Confirm the position on a specific parcel before relying on it.
What the homes are
Built Mostly built in the 1950s, with homes from 1954 to 1965.
Construction Block and stucco. Shingle roofs are near universal.
Size Most homes fall between about 1,100 and 1,700 square feet under air.
Bedrooms Three bedrooms is the most common plan, then four.
Lot The median lot is roughly a quarter acre.
HOA Optional rather than mandatory, so there is no deed restricted membership. Dues run about $30 annually for those who join. Confirm on a specific parcel before relying on it.
Where Eastbrook Subdivision is
Eastbrook Subdivision, centered at 28.610391, -81.299502. 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 Eastbrook Subdivision, 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
21 min
9.7
Walt Disney World
37 min
29.6
Orlando International Airport
27 min
21.9
Universal Orlando
30 min
17.6
Public schools nearby
Aloma Charter High School 4 min, 0.9 mi
Eastbrook Elementary School 6 min, 1.9 mi
Aloma Elementary 5 min, 1.3 mi
Brookshire Elementary School 8 min, 2.3 mi
Private schools nearby
Chesterton Academy of Orlando 5 min, 1.4 mi
Parks and recreation
Goldenrod Park 4 min, 1.3 mi
Winter Park Estates Park 5 min, 1.3 mi
Cady Way Trail 6 min, 2.0 mi
Ward Park Loch Lomond Trail 6 min, 2.0 mi
Groceries and errands
ALDI 3 min, 0.5 mi
Fresh Produce, Fruit, Meat & Grocery 3 min, 0.7 mi
Nearest is not the same as zoned. The schools above are the closest ones to Eastbrook Subdivision 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 Orange County Public Schools before it matters to a decision.
Places and drive times from Google, checked 20 September 2026. Businesses open and close; if something here has changed, tell me and I will correct it.
This page tracks what homes in Eastbrook Subdivision actually sold for over the last twelve months, how long they took, and what moved the price. It is built from 3 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 Eastbrook Subdivision
$365,000Median sale price
$239Median per square foot
35 daysMedian days to contract
3Homes sold in 12 months
Sale prices ran from $338,500 to $425,113, 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
Under 2,000 sq ft
3
$365,000
$239
35 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 1 sales, closed at 96.1% of asking17 days
Reduced at least once 2 sales, closed at 100.1% of the reduced price109 days
Sellers who priced correctly and held their number went under contract in a median 17 days. Sellers who had to reduce took 109 days and still closed at 100.1% of their already reduced price, after a typical cut of $12,500. Opening high costs time and money, in that order.
Seller concessions
67%Of sales included a seller credit
$13,194Typical credit when there was one
2 of 3Sales carrying a credit
A seller credit covers part of the buyer's closing costs and comes off the seller's proceeds, so the headline sale price overstates what the seller kept. Budget for it if you are selling, and ask for it if you are buying.
How buyers paid
Conventional 2 sales67%
FHA 1 sales33%
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 Eastbrook Subdivision, 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 Eastbrook Subdivision in Winter Park, Orange County, covering closed sales from 25 September 2025 through 20 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.
