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.
What the homes are
Built Mostly built in the 1970s, with homes from 1975 to 1980.
Construction Block and stucco. Built-Up roofs on 40% of homes.
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 28.621226, -81.310346. 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.
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 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 Windward Square actually sold for over the last twelve months, how long they took, and what moved the price. It is built from 13 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.
What homes sold for in Windward Square
$267,400Median sale price
$238Median per square foot
13 daysMedian days to contract
13Homes 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
13
$267,400
$238
13 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 9 sales, closed at 100% of asking7 days
Reduced at least once 4 sales, closed at 98% of the reduced price46 days
Sellers who 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.
Seller concessions
54%Of sales included a seller credit
$6,510Typical credit when there was one
7 of 13Sales 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 5 sales38%
Conventional 4 sales31%
Cash 3 sales23%
VA 1 sale8%
Cash was 23% 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 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.
