Momentum Housing Data · Home Values · Orange County
Buying here? See Winding Bay Preserve homes for sale and the Winding Bay Preserve community guide (Winter Garden).
Winding Bay Preserve (WINTER GARDEN, FL): 3 recorded closings in the 12 months ending 2026-09-20, a 4-year price record, and the year-by-year record — every number from recorded MLS closings, none from an estimate model.
In the current window, sellers accepted a median 83.9% of original asking; the median sale took 166 days (window ending 2026-09-20).
| Year | Median sold | Median $/sqft | Median DOM | Sold ÷ original ask | Sales |
|---|---|---|---|---|---|
| 2026 | $385,000 | $191 | 166 | 83.9% | 3 |
| 2024 | $460,000 | $222 | 26 | 97.3% | 4 |
| 2023 | $452,250 | $222 | 32 | 97.4% | 4 |
| 2022 | $414,000 | $201 | 4 | 100.0% | 7 |
Over the recorded series, Winding Bay Preserve’s median sold price moved from $414,000 (2022) to $385,000 (12 months ending 2026-09-20) — -7% over that span, with every year’s figure from recorded closings, not a model.
From the live MLS feed as of 2026-10-01: The homes listed or recently sold were built between 2019 and 2021 (median 2020); 5 of 5 listed or recently sold homes report an HOA, median $338/mo; none of the 5 geocoded listed or recently sold homes sits in a FEMA special flood hazard zone (median elevation 115 ft); the features listings here most often name are Playground, Pool, Dog Park, Clubhouse and Park. See the current Winding Bay Preserve listings →
At Winding Bay Preserve’s $385,000 median and Orange County’s adopted 16.67 mills (FY2025-26), a home assessed at that price carries roughly $6,420 a year in property tax before exemptions, or about $5,750 with the full Florida homestead exemption — a buyer’s first-year figure; a long-time owner’s Save Our Homes cap can be far lower, which is one reason resale taxes jump at closing. Municipal and special-district millage varies inside the county; see the Orange County tax page.
Current asking prices run a median $425,000 against the $385,000 recorded sold median (+10%) — the gap between what sellers hope and what the record shows. The market is carrying about 7.2 months of supply at the current sales pace. Demand check: 0% of Winding Bay Preserve’s listings are under contract, against 29% for ZIP 34787 and 23% for Orange County as a whole — the community is currently absorbing slower than its surroundings, which is negotiating information.
With asking prices running +10% over the recorded sold median, a Winding Bay Preserve listing priced against the closed record above stands out against its competition; one priced against the asking crowd joins the statewide list of homes that never sold.
We don’t publish algorithm guesses for specific homes — they can’t see condition, upgrades, or your lot. A local agent will prepare a records-based valuation from the same closed-sale data on this page, adjusted for your home. Free, no obligation.
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Communities buyers shopping Winding Bay Preserve are also weighing (nearest by map distance), each on its own recorded 12-month closings. A median well above the neighbors is a ceiling to price against; well below is where the value argument lives.
| Community | Median sold | Median $/sqft | Median DOM | Sales |
|---|---|---|---|---|
| storey grove | $517,500 | $223 | 22 | 21 |
| waterleigh | $575,000 | $255 | 40 | 183 |
| Palms Serenoa | $389,500 | $225 | 52 | 12 |
| Palms At Serenoa | $395,000 | $224 | 49 | 18 |
More Winding Bay Preserve: full community guide & homes for sale · choosing an agent here · should you sell now (statewide data) · what selling costs · cash offer vs. listing
Based on Stellar MLS data distributed by MLS GRID for the period 2021 through 2026. Compiled from recorded MLS closings; deemed reliable but not guaranteed. Figures are medians for the stated windows and change as new sales record; individual homes vary widely. No automated valuation for any specific property appears on this page. Equal Housing Opportunity. © 2026 Move With Momentum LLC — brokerage licensed in FL and GA. Disclosures
Content on this page is compiled from public records, MLS data, and automated data sources, and may contain errors or be out of date. It is provided for general information only and is not a representation about any specific property, community, builder, or association. Verify all information independently before relying on it.