Winding Bay is a 2020s neighborhood in south Winter Garden, in the 34787 zip code. Homes are block and stucco. Most homes fall between about 2,100 and 3,700 square feet under air, the median lot is about an eighth of an acre, and a two car garage is standard.
Homes here carry an HOA, billed monthly, typically around $67. Confirm the figure on a specific parcel before relying on it.
What the homes are
Built Essentially all built in the 2020s.
Construction Block and stucco. Shingle roofs are near universal.
Size Most homes fall between about 2,100 and 3,700 square feet under air.
Bedrooms Four bedrooms is the most common plan, then five, then three.
Garage A two car garage is standard.
Lot The median lot is about an eighth of an acre.
HOA Billed monthly, typically around $67. Confirm on a specific parcel before relying on it.
Where Winding Bay is
Winding Bay, centered at 28.388967, -81.634065. 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 Winding Bay, 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
35 min
26.7
Walt Disney World
16 min
8.2
Orlando International Airport
40 min
35.0
Universal Orlando
35 min
25.6
Public schools nearby
Water Spring Elementary School 8 min, 2.1 mi
Atwater Bay Elementary 8 min, 2.9 mi
Horizon High School Performing Arts Center 9 min, 3.4 mi
Horizon High School 9 min, 3.2 mi
Private schools nearby
Lake Pointe Academy K-8 14 min, 5.9 mi
Pinecrest Academy Four Corners 14 min, 6.0 mi
Parks and recreation
Winding Bay Preserve 4 min, 1.1 mi
Watermark Park 9 min, 3.9 mi
Lakeshore Private Park 9 min, 3.2 mi
Groceries and errands
Target Grocery 9 min, 3.0 mi
Publix Super Market at Waterleigh Village 5 min, 1.8 mi
Nearest is not the same as zoned. The schools above are the closest ones to Winding Bay 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 1 September 2026. Businesses open and close; if something here has changed, tell me and I will correct it.
This page tracks what homes in Winding Bay actually sold for over the last twelve months, how long they took, and what moved the price. It is built from 20 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 Winding Bay
$787,000Median sale price
$251Median per square foot
46 daysMedian days to contract
20Homes sold in 12 months
Sale prices ran from $520,000 to $1,100,000, 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
2,000 to 3,000 sq ft
11
$570,000
$256
51 days
3,000 sq ft and up
9
$870,000
$248
41 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.
Price cuts and time to contract
Median days to go under contract. Shorter is better.
Never reduced 11 sales, closed at 99.4% of asking6 days
Reduced at least once 9 sales, closed at 99.1% of the reduced price95 days
Sellers who held their number went under contract in a median 6 days. Sellers who had to reduce took 95 days and still closed at 99.1% of their already reduced price, after a typical cut of $50,000.
Seller concessions
20%Of sales included a seller credit
$5,750Typical credit when there was one
4 of 20Sales 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 15 sales75%
VA 3 sales15%
Cash 2 sales10%
Cash was 10% 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 Winding Bay, 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 Winding Bay in Horizon West, Orange County, covering closed sales from 8 October 2025 through 3 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.
