Winter Park Estates is a neighborhood in east Winter Park, in the 32792 zip code, built most often in the 1960s. Homes are block and stucco, predominantly single story. Most homes fall between about 1,200 and 2,100 square feet under air, and the median lot is roughly a quarter acre.
Winter Park Estates has an optional homeowners association rather than a mandatory one, so there is no deed restricted membership to inherit. Dues run about $20 annually for those who join. Confirm the position on a specific parcel before relying on it.
Winter Park Estates Park sits inside the subdivision.
What the homes are
Built Most often built in the 1960s (48% of homes), with homes from 1957 to 2020.
Construction Block and stucco. Shingle roofs on 87% of homes.
Size Most homes fall between about 1,200 and 2,100 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 $20 annually for those who join. Confirm on a specific parcel before relying on it.
Where Winter Park Estates is
Winter Park Estates, centered at 28.60464, -81.312722. 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 Winter Park Estates, 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
9.4
Walt Disney World
36 min
29.2
Orlando International Airport
29 min
12.6
Universal Orlando
29 min
17.3
Public schools nearby
Aloma Charter High School 3 min, 0.6 mi
Aloma Elementary 3 min, 0.9 mi
Brookshire Elementary School 5 min, 1.4 mi
Lakemont Elementary School 4 min, 1.5 mi
Private schools nearby
Chesterton Academy of Orlando 4 min, 1.1 mi
Christian Education at Woodruff Academy 4 min, 1.4 mi
Nearest is not the same as zoned. The schools above are the closest ones to Winter Park Estates 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 Winter Park Estates actually sold for over the last twelve months, how long they took, and what moved the price. It is built from 7 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 November 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 Winter Park Estates
$426,703Median sale price
$251Median per square foot
33 daysMedian days to contract
7Homes sold in 12 months
Sale prices ran from $330,000 to $540,000, 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
Under 2,000 sq ft
7
$426,703
$251
33 days
A price per foot taken from the whole neighborhood should never be applied straight to one house.
Price cuts and time to contract
Median days to go under contract. Shorter is better.
Never reduced 4 sales, closed at 98.2% of asking4 days
Reduced at least once 3 sales, closed at 87.9% of the reduced price170 days
Sellers who held their number went under contract in a median 4 days. Sellers who had to reduce took 170 days and still closed at 87.9% of their already reduced price, after a typical cut of $30,900.
Seller concessions
29%Of sales included a seller credit
$12,848Typical credit when there was one
2 of 7Sales 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 5 sales71%
Cash 1 sale14%
FHA 1 sale14%
Cash was 14% 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 Winter Park Estates, 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 Winter Park Estates in Winter Park, Orange County, covering closed sales from 8 November 2025 through 3 November 2026, refreshed monthly and current as of November 2026. Prices are net of seller concessions, so they reflect what the seller actually received rather than the headline number. One record was excluded as an off-market transfer rather than an open market sale. Data believed accurate but not guaranteed; listings and closings change daily.
