Momentum Housing Data · Home Values · Orange County
Buying here? See Winter Oaks homes for sale and the Winter Oaks community guide (Winter Garden).
Winter Oaks (WINTER GARDEN, FL): 5 recorded closings in the 12 months ending 2026-09-20, a 7-year price record, and sales split by price band and home size — every number from recorded MLS closings, none from an estimate model.
In the current window, sellers accepted a median 96.1% of original asking; the median sale took 21 days (window ending 2026-09-20).
| Year | Median sold | Median $/sqft | Median DOM | Sold ÷ original ask | Sales |
|---|---|---|---|---|---|
| 2026 | $640,000 | $271 | 21 | 96.1% | 5 |
| 2025 | $518,438 | $271 | 12 | 96.9% | 4 |
| 2024 | $532,500 | $257 | 18 | 94.2% | 8 |
| 2023 | $512,500 | $238 | 17 | 98.6% | 4 |
| 2022 | $489,500 | $227 | 4 | 105.1% | 6 |
| 2017 | $302,000 | $139 | 4 | 98.6% | 6 |
| 2016 | $238,000 | $141 | 29 | 97.2% | 4 |
Over the recorded series, Winter Oaks’s median sold price moved from $238,000 (2016) to $640,000 (12 months ending 2026-09-20) — +169% over that span, with every year’s figure from recorded closings, not a model.
The recorded series starts in 2016 at $238,000. Annual sales volume here has ranged from 0 to 8 closings a year (10-yr average 3.5). With roughly 3.5 closings a year, Winter Oaks’s medians move in steps, not curves — a handful of unusual sales can swing a year, which is why the sales count sits next to every figure above.
Of the 12 recorded Winter Oaks closings since 2024, half landed between $505,156 and $628,750 (the middle two quartiles); the lowest recorded sale was $420,000 and the highest $720,000. If your home sits outside the middle band, the reason usually shows up in the size table below before it shows up in condition.
| Sold price band | Share of closings | Sales |
|---|---|---|
| Under $475,000 | 1 (8%) | |
| $475,000 – $550,000 | 4 (33%) | |
| $550,000 – $625,000 | 3 (25%) | |
| $625,000 – $700,000 | 2 (17%) | |
| None and up | 2 (17%) |
From the live MLS feed as of 2026-10-01: The homes listed or recently sold were built between 2003 and 2005 (median 2004); 7 of 7 listed or recently sold homes report an HOA, median $146/mo; none of the 5 geocoded listed or recently sold homes sits in a FEMA special flood hazard zone (median elevation 116 ft); the features listings here most often name are Pool, Community Mailbox, Deed Restrictions, Playground and Golf Carts OK. See the current Winter Oaks listings →
At Winter Oaks’s $640,000 median and Orange County’s adopted 16.67 mills (FY2025-26), a home assessed at that price carries roughly $10,670 a year in property tax before exemptions, or about $10,000 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 $749,995 against the $640,000 recorded sold median (+17%) — the gap between what sellers hope and what the record shows. The market is carrying about 2.4 months of supply at the current sales pace. Demand check: 0% of Winter Oaks’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 +17% over the recorded sold median, a Winter Oaks 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 Winter Oaks 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 |
|---|---|---|---|---|
| Oaks Brandy Lake O | $485,000 | $244 | 32 | 4 |
| Traditions Sub | $530,000 | $298 | 36 | 4 |
| Townhomes | $172,000 | $213 | 81 | 4 |
| Valencia Shores | $560,000 | $293 | 35 | 3 |
More Winter Oaks: 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 2006 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.