Winter Woods is a neighborhood in Winter Park, in the 32792 zip code, built mostly in the 1970s. Homes are block and stucco, predominantly single story. Most homes fall between about 1,500 and 2,200 square feet under air, the median lot is roughly a fifth of an acre, and a two car garage is standard.
Winter Woods has an optional homeowners association rather than a mandatory one, so there is no deed restricted membership to inherit. Dues run about $15 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 1970s, with homes from 1968 to 1991.
Construction Block and stucco. Shingle roofs are near universal.
Size Most homes fall between about 1,500 and 2,200 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 Optional rather than mandatory, so there is no deed restricted membership. Dues run about $15 annually for those who join. Confirm on a specific parcel before relying on it.
Where Winter Woods is
Winter Woods, centered at 28.616595, -81.317138. 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 Woods, 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
22 min
10.4
Orlando International Airport
31 min
13.6
Winter Park
11 min
3.9
Heathrow and Lake Mary offices
31 min
15.8
Public schools nearby
Lakemont Elementary School 5 min, 1.8 mi
Aloma Charter High School 5 min, 1.6 mi
Aloma Elementary 6 min, 2.0 mi
Eastbrook Elementary School 7 min, 2.4 mi
Private schools nearby
Chesterton Academy of Orlando 3 min, 1.0 mi
Christian Education at Woodruff Academy 6 min, 1.9 mi
Nearest is not the same as zoned. The schools above are the closest ones to Winter Woods 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 9 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 Woods actually sold for over the last twelve months, how long they took, and what moved the price. It is built from 6 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 October 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 Woods
$513,000Median sale price
$280Median per square foot
5 daysMedian days to contract
6Homes sold in 12 months
Sale prices ran from $388,050 to $566,200.
By size
Home size
Sales
Median price
Median $/sq ft
Median days
Under 2,000 sq ft
6
$513,000
$280
5 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 5 sales, closed at 100% of asking4 days
Reduced at least once 1 sale, closed at 94.4% of the reduced price32 days
Sellers who held their number went under contract in a median 4 days. Sellers who had to reduce took 32 days and still closed at 94.4% of their already reduced price, after a typical cut of $10,000.
Seller concessions
83%Of sales included a seller credit
$1,950Typical credit when there was one
5 of 6Sales 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 4 sales67%
VA 1 sale17%
Cash 1 sale17%
Cash was 17% 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 Woods, 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 Woods in Winter Park, Seminole County, covering closed sales from 13 October 2025 through 8 October 2026, refreshed monthly and current as of October 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.
