Windsor Hill is a neighborhood in northeast Windermere, in the 34786 zip code, built mostly in the 1990s. Homes are block and stucco. Most homes fall between about 2,900 and 5,300 square feet under air, the median lot is roughly half an acre, and a three car garage is standard.
Homes here carry an HOA, billed annually, typically around $777. Confirm the figure on a specific parcel before relying on it.
What the homes are
Built Mostly built in the 1990s, with homes from 1989 to 2025.
Construction Block and stucco. Shingle roofs are near universal.
Style Contemporary, Traditional, Florida. Predominantly two story.
Size Most homes fall between about 2,900 and 5,300 square feet under air.
Bedrooms Four bedrooms is the most common plan, then five.
Garage A three car garage is standard.
Lot The median lot is roughly half an acre.
HOA Billed annually, typically around $777. Confirm on a specific parcel before relying on it.
Where Windsor Hill is
Windsor Hill, centered at 28.512585, -81.51562. 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 Windsor Hill, 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 Windsor Hill 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 Windsor Hill actually sold for over the last twelve months, how long they took, and what moved the price. It is built from 3 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 Windsor Hill
$1,037,500Median sale price
$320Median per square foot
2 daysMedian days to contract
3Homes sold in 12 months
Sale prices ran from $950,000 to $1,060,000, which is a wide spread and the reason a single neighborhood median is a starting point rather than an answer.
Homes priced right sold far faster
Median days to go under contract. Shorter is better.
Never reduced 2 sales, closed at 98.6% of asking2 days
Reduced at least once 1 sales, closed at 94.6% of the reduced price38 days
Sellers who priced correctly and held their number went under contract in a median 2 days. Sellers who had to reduce took 38 days and still closed at 94.6% of their already reduced price, after a typical cut of $51,000. Opening high costs time and money, in that order.
Seller concessions
67%Of sales included a seller credit
$6,250Typical credit when there was one
2 of 3Sales 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 sales100%
Cash was 0% 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 Windsor Hill, 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 Windsor Hill in Windermere, 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.
