Momentum Housing Data · Home Values · Osceola County
REGAL OAKS AT OLD TOWN (KISSIMMEE, FL): 19 recorded closings in the 12 months ending 2026-08-02, a 10-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 95.5% of original asking; the median sale took 37 days (window ending 2026-08-02).
| Year | Median sold | Median $/sqft | Median DOM | Sold ÷ original ask | Sales |
|---|---|---|---|---|---|
| 2026 | $295,000 | $203 | 37 | 95.5% | 19 |
| 2025 | $330,000 | $232 | 35 | 96.3% | 30 |
| 2024 | $333,750 | $242 | 20 | 97.7% | 28 |
| 2023 | $322,250 | $231 | 8 | 99.4% | 17 |
| 2022 | $285,000 | $194 | 3 | 103.5% | 63 |
| 2021 | $243,500 | $169 | 3 | 101.6% | 6 |
| 2019 | $200,000 | $142 | 42 | 95.5% | 5 |
| 2018 | $159,500 | $121 | 328 | 84.5% | 4 |
| 2017 | $162,000 | $107 | 193 | 89.4% | 23 |
| 2016 | $161,250 | $102 | 43 | 91.2% | 6 |
Over the recorded series, REGAL OAKS AT OLD TOWN’s median sold price moved from $161,250 (2016) to $295,000 (12 months ending 2026-08-02) — +83% over that span, with every year’s figure from recorded closings, not a model.
The recorded series starts in 2016 at $161,250. The 2020–22 run-up did what it did everywhere — REGAL OAKS AT OLD TOWN’s median moved +42% from 2019 to 2022. Against the 2024 peak of $333,750, the current median stands at -12%. Annual sales volume here has ranged from 0 to 63 closings a year (10-yr average 19.5).
What actually trades here: 99% townhouse, 1% condominium, 1% ?, with a median of 1,440 sq ft and a median price per square foot of $203 in the current window.
Of the 66 recorded REGAL OAKS AT OLD TOWN closings since 2024, half landed between $300,000 and $343,000 (the middle two quartiles); the lowest recorded sale was $267,500 and the highest $379,000. 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 $300,000 | 16 (24%) | |
| $300,000 – $316,667 | 13 (20%) | |
| $316,667 – $333,333 | 14 (21%) | |
| $333,333 – $350,000 | 9 (14%) | |
| None and up | 14 (21%) |
The same recorded closings, split into thirds by living area. Find the row your home falls in: the $/sqft figure times your square footage is the recorded-sales bracket for homes like yours here — a starting range from real closings, not a valuation of your specific property. Smaller homes here have been selling at a higher price per square foot than larger ones ($238 vs $224) — the usual pattern, since lot, kitchen and baths do not scale with floor area.
| Size group | Median $/sqft | Median sold | Sold range | Sales |
|---|---|---|---|---|
| Smaller homes 1,290–1,435 sq ft | $238 | $315,000 | $267,500 – $352,000 | 22 |
| Mid-size homes 1,435–1,440 sq ft | $209 | $301,250 | $267,500 – $379,000 | 22 |
| Larger homes 1,474–1,852 sq ft | $224 | $347,500 | $285,000 – $375,000 | 22 |
At REGAL OAKS AT OLD TOWN’s $295,000 median and Osceola County’s adopted 15.23 mills (FY2025-26), a home assessed at that price carries roughly $4,490 a year in property tax before exemptions, or about $3,890 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 Osceola County tax page.
Since 2008, 162 REGAL OAKS AT OLD TOWN listings were withdrawn, canceled, or expired without selling (20 so far in 2026) — overpricing is the recurring cause statewide. Over the recorded years, an average of 62% of REGAL OAKS AT OLD TOWN listings ended without selling (withdrawn/canceled/expired); in 2026 that rate was 62%. Momentum’s market-heat index for REGAL OAKS AT OLD TOWN reads 28/100 (computed from DOM, sale-to-list, and absorption; 2020–21 peaked in the 70s here).
Cash bought 27% of recorded REGAL OAKS AT OLD TOWN sales in the window ending 2026-06 (6 of 22) — a fact worth knowing before assuming every buyer needs an appraisal to close. The table above is the closed-sale record to price a REGAL OAKS AT OLD TOWN 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 REGAL OAKS AT OLD TOWN are also weighing (same ZIP), 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 |
|---|---|---|---|---|
| CYPRESS SHADOWS | $290,000 | $173 | 65 | 3 |
| STOREY LAKE CONDO | $300,000 | $252 | 91 | 3 |
| CORAL CAY RESORT | $287,000 | $192 | 79 | 7 |
| FIESTA KEY | $280,000 | $162 | 37 | 13 |
More REGAL OAKS AT OLD TOWN: 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 2011 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.