Winter Oaks is a 2000s neighborhood in west Winter Garden, in the 34787 zip code. Homes are block and stucco. Most homes fall between about 1,700 and 3,100 square feet under air, the median lot is roughly a fifth of an acre, and a two car garage is standard.
Homes here carry an HOA, billed annually, typically around $400. Confirm the figure on a specific parcel before relying on it.
What the homes are
Built Essentially all built in the 2000s.
Construction Block and stucco. Shingle roofs are near universal.
Style Traditional, Contemporary, Bungalow. Predominantly two story.
Size Most homes fall between about 1,700 and 3,100 square feet under air.
Bedrooms Three bedrooms is the most common plan, then four.
Garage A two car garage is standard.
Lot The median lot is roughly a fifth of an acre.
HOA Billed annually, typically around $400. Confirm on a specific parcel before relying on it.
Where Winter Oaks is
Winter Oaks, centered at 28.559688, -81.598516. 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 Oaks, 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
28 min
17.0
Walt Disney World
30 min
21.0
Orlando International Airport
33 min
25.4
Universal Orlando
27 min
16.0
Public schools nearby
Tildenville Elementary School 4 min, 1.0 mi
SLV High School 5 min, 1.4 mi
Dillard Street Elementary School 6 min, 1.7 mi
Maxey Elementary School 6 min, 1.5 mi
Private schools nearby
Foundation Academy, Plant Street Campus 7 min, 1.3 mi
Parks and recreation
Veterans Memorial Park 3 min, 0.7 mi
Butterfly Garden, WO Trail 4 min, 1.1 mi
West Orange Trail 5 min, 1.6 mi
Maple Street Park 5 min, 1.4 mi
Groceries and errands
ALDI 4 min, 1.0 mi
The Ancient Olive Gourmet of Winter Garden 6 min, 1.5 mi
Nearest is not the same as zoned. The schools above are the closest ones to Winter Oaks 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 Oaks actually sold for over the last twelve months, how long they took, and what moved the price. It is built from 5 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 Winter Oaks
$640,000Median sale price
$271Median per square foot
21 daysMedian days to contract
5Homes sold in 12 months
Sale prices ran from $578,000 to $715,000, 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
$625,000
$283
3 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 2 sales, closed at 103.7% of asking2 days
Reduced at least once 3 sales, closed at 97.6% of the reduced price42 days
Sellers who priced correctly and held their number went under contract in a median 2 days. Sellers who had to reduce took 42 days and still closed at 97.6% of their already reduced price, after a typical cut of $26,000. Opening high costs time and money, in that order.
Seller concessions
40%Of sales included a seller credit
$5,750Typical credit when there was one
2 of 5Sales 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 3 sales60%
Cash 2 sales40%
Cash was 40% 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 Oaks, 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 Oaks in Winter Garden, 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.
