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Orange County › Winter Garden › Windward Cay
Windward Cay, Winter Garden
Windward Cay is a 2000s neighborhood in south Winter Garden, in the 34787 zip code. Homes are stucco and block. Most homes fall between about 2,700 and 3,500 square feet under air, the median lot is roughly a quarter acre, and a three car garage is standard.
Homes here carry an HOA, billed quarterly, typically around $235. Confirm the figure on a specific parcel before relying on it.
What the homes are
- Built Essentially all built in the 2000s.
- Construction Stucco and block. Shingle roofs are near universal.
- Size Most homes fall between about 2,700 and 3,500 square feet under air.
- Bedrooms Five bedrooms is the most common plan, then four.
- Garage A three car garage is standard.
- Lot The median lot is roughly a quarter acre.
- HOA Billed quarterly, typically around $235. Confirm on a specific parcel before relying on it.
Where Windward Cay is
Drive times below are measured on the road network from the center of Windward Cay, 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 | 24 min | 17.1 |
| Walt Disney World | 22 min | 11.1 |
| Orlando International Airport | 29 min | 25.5 |
| Universal Orlando | 26 min | 10.6 |
Public schools nearby
- Keene’s Crossing Elementary School 8 min, 2.3 mi
- Whispering Oak Elementary School 9 min, 3.6 mi
- Windermere High School 9 min, 2.6 mi
- SunRidge Elementary School 13 min, 5.5 mi
Private schools nearby
- Foundation Academy, Tilden Campus 5 min, 2.0 mi
Parks and recreation
- Summerport Park 8 min, 2.3 mi
- Vineyard Square Bark Park 8 min, 3.0 mi
- Horizon West Regional Park 8 min, 3.8 mi
- Shoshonei Park 9 min, 3.9 mi
Groceries and errands
- Armazém X Winter Garden 2 min, 0.4 mi
- Target Grocery 6 min, 1.7 mi
- ALDI 8 min, 2.7 mi
- Publix Super Market at Cornerstone at Summerport 8 min, 2.7 mi
Nearest is not the same as zoned. The schools above are the closest ones to Windward Cay 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 Windward Cay 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 Windward Cay
Sale prices ran from $755,500 to $774,000, 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.
Sellers who priced correctly and held their number went under contract in a median 4 days. Sellers who had to reduce took 31 days and still closed at 95.7% of their already reduced price, after a typical cut of $15,000. Opening high costs time and money, in that order.
Seller concessions
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
Cash was 33% 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 Cay, 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 Cay 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.