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 August 2026.
What homes sold for in Winding Bay
$787,000Median sale price
$251.19Median per square foot
36 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 | $255.58 | 51 days |
| 3,000 sq ft and up | 9 | $870,000 | $248.33 | 20 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.
Condition moves the price more than anything else
Median price per square foot by the condition each listing described.
Renovated or updated 11 sales, 20 days to contract$238.23
Sold as is or dated 5 sales, 6 days to contract$265.28
$-27.05More per square foot, renovated over dated
$-40,573On a 1,500 sq ft home
$-67,622On a 2,500 sq ft home
Condition is inferred from how each listing described itself, so treat it as a strong signal rather than an inspection. The two bars above look close because they are drawn from zero; the gap between them is the part worth acting on.
Notice that the dated homes sold faster, in a median 6 days against 20 days. Selling quickly and selling high are not the same thing. Homes needing work are priced to move and are picked up quickly by buyers who intend to renovate, while a finished home waits for the buyer willing to pay for the finish. If you are deciding whether to improve before listing, the price column matters more than the days column.
What a pool is worth here
Homes with a private pool sold at a median $287.67 per square foot against $238.23 without one, a difference of $49.43 per square foot. That comes from 9 sales with a pool and 11 without.
Homes priced right sold far faster
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 priced correctly and 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. Opening high costs time and money, in that order.
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.
What is around Winding Bay
Drive times below are measured on the road network from the centre 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 |
Schools nearby- Water Spring Elementary School 1.3 mi
- Water Spring Middle School 1.4 mi
- Atwater Bay Elementary 2.0 mi
- Horizon High School Performing Arts Center 2.0 mi
Parks and recreation- Winding Bay Preserve 0.8 mi
- Watermark Park 2.3 mi
- Lakeshore Private Park 2.7 mi
Groceries and errands- Target Grocery 1.2 mi
- Publix Super Market at Waterleigh Village 1.6 mi
- Alfresco Market 2.1 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 25 August 2026. Businesses open and close; if something here has changed, tell me and I will correct it.
Homes for sale in Winding Bay right now
Current listings appear below and update automatically as homes come on and off the market. If nothing is showing, there is nothing available in Winding Bay today, which happens in a neighborhood this size.
About this data. Source is the Stellar MLS feed for Winding Bay in Winter Garden, Orange County, covering closed sales from 30 August 2025 through 25 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. 0 records were excluded as off-market transfers rather than open market sales. Condition is inferred from listing descriptions. Data believed accurate but not guaranteed; listings and closings change daily.
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.
