Momentum Housing Data · Home Values · Orange County
WINTER OAKS (WINTER GARDEN, FL): 3 recorded closings in the 12 months ending 2026-08-02, an 8-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 96.1% of original asking; the median sale took 42 days (window ending 2026-08-02).
| Year | Median sold | Median $/sqft | Median DOM | Sold ÷ original ask | Sales |
|---|---|---|---|---|---|
| 2026 | $715,000 | $240 | 42 | 96.1% | 3 |
| 2025 | $511,875 | $262 | 21 | 96.4% | 7 |
| 2024 | $540,000 | $248 | 6 | 97.2% | 7 |
| 2023 | $499,000 | $271 | 7 | 96.0% | 3 |
| 2022 | $499,000 | $226 | 4 | 105.2% | 5 |
| 2017 | $305,000 | $138 | 5 | 98.4% | 7 |
| 2016 | $233,000 | $162 | 4 | 97.2% | 3 |
| 2015 | $210,000 | $113 | 8 | 95.9% | 3 |
Over the recorded series, WINTER OAKS’s median sold price moved from $210,000 (2015) to $715,000 (12 months ending 2026-08-02) — +240% over that span, with every year’s figure from recorded closings, not a model.
The recorded series starts in 2015 at $210,000. Annual sales volume here has ranged from 0 to 7 closings a year (10-yr average 3.4). With roughly 3.4 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.
What actually trades here: 100% single-family residence, with a median of 3,000 sq ft and a median price per square foot of $240 in the current window.
From the live MLS feed as of 2026-09-03: The homes listed or recently sold were built between 2003 and 2005 (median 2004); 6 of 6 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 Community Mailbox, Deed Restrictions, Playground, Pool and Golf Carts OK. See the current WINTER OAKS listings →
At WINTER OAKS’s $715,000 median and Orange County’s adopted 16.67 mills (FY2025-26), a home assessed at that price carries roughly $11,920 a year in property tax before exemptions, or about $11,250 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.
Demand check: 100% of WINTER OAKS’s listings are under contract, against 28% for ZIP 34787 and 26% for Orange County as a whole — the community is absorbing faster than its surroundings. Since 2005, 70 WINTER OAKS listings were withdrawn, canceled, or expired without selling — overpricing is the recurring cause statewide. Over the recorded years, an average of 47% of WINTER OAKS listings ended without selling (withdrawn/canceled/expired); in 2025 that rate was 0%. Momentum’s market-heat index for WINTER OAKS reads 44/100 (computed from DOM, sale-to-list, and absorption; 2020–21 peaked in the 70s here).
Cash bought 33% of recorded WINTER OAKS sales in the window ending 2026-06 (1 of 3) — a fact worth knowing before assuming every buyer needs an appraisal to close. The table above is the closed-sale record to price a WINTER OAKS home against; asking prices are an opening position, recorded closings are the value.
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 | $552,500 | $244 | 30 | 4 |
| TRADITIONS SUB | $562,500 | $311 | 11 | 4 |
| TOWNHOMES WINTER GARDEN | $157,000 | $226 | 48 | 5 |
| LAKEVIEW RESERVE 46/149 | $594,000 | $270 | 4 | 4 |
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.