Windward Square is a 1970s neighborhood in Winter Park, in the 32792 zip code. Homes are block and stucco, predominantly single story. Most homes fall between about 900 and 1,500 square feet under air, and the median lot is about 0.07 acres.
Homes here carry an HOA, billed monthly, typically around $72. Confirm the figure on a specific parcel before relying on it.
The neighborhood was platted in four secs, which is why listings appear under Windward Square, Windward Square Sec 1, Sec 2 and Sec 3. They are one community and they trade as one market.
What the homes are
Built Essentially all built in the 1970s.
Construction Block and stucco. Shingle roofs are near universal.
Size Most homes fall between about 900 and 1,500 square feet under air.
Bedrooms Two bedrooms is the most common plan, then three.
Lot The median lot is about 0.07 acres.
HOA Billed monthly, typically around $72. Confirm on a specific parcel before relying on it.
Where Windward Square is
Windward Square, centered at 28.62152, -81.31036. 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 Windward Square, 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
23 min
10.3
Orlando International Airport
29 min
23.0
Winter Park
13 min
4.2
Heathrow and Lake Mary offices
31 min
15.6
Public schools nearby
Eastbrook Elementary School 5 min, 1.5 mi
Aloma Charter High School 6 min, 1.5 mi
Lakemont Elementary School 9 min, 2.6 mi
Aloma Elementary 7 min, 1.9 mi
Private schools nearby
Chesterton Academy of Orlando 4 min, 0.9 mi
Lake Forrest Preparatory School 6 min, 1.8 mi
Parks and recreation
Branch Tree Park 6 min, 1.6 mi
Winter Park Estates Park 8 min, 2.0 mi
Phelps Park 9 min, 2.5 mi
Lake Knowles Park 9 min, 2.9 mi
Groceries and errands
In-N-Out Market 4 min, 0.8 mi
SuperFresh Market 2 min, 0.6 mi
Publix Super Market at Casselberry Commons 5 min, 1.0 mi
Nearest is not the same as zoned. The schools above are the closest ones to Windward Square 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 2 September 2026. Businesses open and close; if something here has changed, tell me and I will correct it.
This page tracks what homes in Windward Square actually sold for over the last twelve months, how long they took, and what moved the price. It is built from 11 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 August 2026.
What homes sold for in Windward Square
$270,000Median sale price
$242Median per square foot
13 daysMedian days to contract
11Homes sold in 12 months
Sale prices ran from $183,000 to $324,000, 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
11
$270,000
$242
13 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 7 sales, closed at 100% of asking7 days
Reduced at least once 4 sales, closed at 98% of the reduced price46 days
Sellers who priced correctly and held their number went under contract in a median 7 days. Sellers who had to reduce took 46 days and still closed at 98% of their already reduced price, after a typical cut of $11,500. Opening high costs time and money, in that order.
Seller concessions
45%Of sales included a seller credit
$5,000Typical credit when there was one
5 of 11Sales 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
FHA 4 sales36%
Conventional 3 sales27%
Cash 3 sales27%
VA 1 sales9%
Cash was 27% 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 Windward Square, 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 Windward Square in Winter Park, Seminole County, covering closed sales from 5 September 2025 through 31 August 2026, refreshed monthly and current as of August 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.
