Winter Run is a 1980s neighborhood in southwest Orlando, in the 32809 zip code. Homes are block and stucco, predominantly single story. Most homes fall between about 1,000 and 1,500 square feet under air, and the median lot is about an eighth of an acre.
Most of Winter Run carries no mandatory HOA.
What the homes are
Built Essentially all built in the 1980s.
Construction Block and stucco. Shingle roofs are near universal.
Size Most homes fall between about 1,000 and 1,500 square feet under air.
Bedrooms Three bedrooms is the most common plan.
Lot The median lot is about an eighth of an acre.
HOA Most of the neighborhood carries no mandatory HOA. Confirm on a specific parcel before relying on it.
Where Winter Run is
Winter Run, centered at 28.48463, -81.421897. 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 Run, 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
12 min
6.5
Walt Disney World
21 min
16.2
Orlando International Airport
22 min
14.4
Universal Orlando
14 min
3.6
Public schools nearby
Millennia Gardens Elementary 6 min, 1.6 mi
Shingle Creek Elementary School 9 min, 3.1 mi
Sadler Elementary School 7 min, 2.2 mi
Palmetto Elementary School 5 min, 1.7 mi
Private schools nearby
Way of Wisdom Academy Inc. 4 min, 1.2 mi
IEC Christian Academy 6 min, 2.0 mi
Legacy Christian Academy And Child Care 5 min, 1.7 mi
Parks and recreation
Shingle Creek Trail 9 min, 3.4 mi
Lake Ellenor Park 9 min, 3.3 mi
Clear Lake Park 10 min, 3.4 mi
Vogt-Meloon Park 10 min, 3.3 mi
Groceries and errands
Publix Super Market at Plaza at Millenia 3 min, 0.7 mi
Target Grocery 6 min, 1.0 mi
Super Fresh Market | Meat, Produce and Seafood 4 min, 1.1 mi
Nearest is not the same as zoned. The schools above are the closest ones to Winter Run 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 8 November 2026. Businesses open and close; if something here has changed, tell me and I will correct it.
This page tracks what homes in Winter Run actually sold for over the last twelve months, how long they took, and what moved the price. It is built from 8 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.
What homes sold for in Winter Run
$294,750Median sale price
$260Median per square foot
19 daysMedian days to contract
8Homes sold in 12 months
Sale prices ran from $275,000 to $350,000.
By size
Home size
Sales
Median price
Median $/sq ft
Median days
Under 2,000 sq ft
8
$294,750
$260
19 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 6 sales, closed at 100% of asking17 days
Reduced at least once 2 sales, closed at 97.5% of the reduced price50 days
Sellers who held their number went under contract in a median 17 days. Sellers who had to reduce took 50 days and still closed at 97.5% of their already reduced price, after a typical cut of $11,500.
Seller concessions
62%Of sales included a seller credit
$10,000Typical credit when there was one
5 of 8Sales 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 sales62%
FHA 2 sales25%
Cash 1 sale12%
Cash was 12% 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 Run, 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 Run in Oak Ridge, Orange County, covering closed sales from 13 November 2025 through 8 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. Data believed accurate but not guaranteed; listings and closings change daily.
