Momentum Housing Data · Home Values · Osceola County
CYPRESS SHADOWS (KISSIMMEE, FL): 3 recorded closings in the 12 months ending 2026-08-02, a 6-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 90.6% of original asking; the median sale took 65 days (window ending 2026-08-02).
| Year | Median sold | Median $/sqft | Median DOM | Sold ÷ original ask | Sales |
|---|---|---|---|---|---|
| 2026 | $290,000 | $173 | 65 | 90.6% | 3 |
| 2025 | $344,950 | $192 | 124 | 96.7% | 4 |
| 2024 | $361,000 | $194 | 80 | 97.7% | 10 |
| 2022 | $335,000 | $186 | 5 | 103.1% | 15 |
| 2017 | $181,000 | $102 | 24 | 98.6% | 8 |
| 2016 | $189,500 | $80 | 24 | 95.7% | 4 |
Over the recorded series, CYPRESS SHADOWS’s median sold price moved from $189,500 (2016) to $290,000 (12 months ending 2026-08-02) — +53% over that span, with every year’s figure from recorded closings, not a model.
The recorded series starts in 2016 at $189,500. Against the 2024 peak of $361,000, the current median stands at -20%. Annual sales volume here has ranged from 0 to 15 closings a year (10-yr average 4.2). With roughly 4.2 closings a year, CYPRESS SHADOWS’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: 99% single-family residence, 1% ?, with a median of 1,540 sq ft and a median price per square foot of $173 in the current window.
At CYPRESS SHADOWS’s $290,000 median and Osceola County’s adopted 15.23 mills (FY2025-26), a home assessed at that price carries roughly $4,420 a year in property tax before exemptions, or about $3,820 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Since 2005, 157 CYPRESS SHADOWS listings were withdrawn, canceled, or expired without selling (2 so far in 2026) — overpricing is the recurring cause statewide. Over the recorded years, an average of 71% of CYPRESS SHADOWS listings ended without selling (withdrawn/canceled/expired); in 2026 that rate was 50%. Momentum’s market-heat index for CYPRESS SHADOWS reads 26/100 (computed from DOM, sale-to-list, and absorption; 2020–21 peaked in the 70s here).
Cash bought 33% of recorded CYPRESS SHADOWS 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 CYPRESS SHADOWS 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 CYPRESS SHADOWS 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 |
|---|---|---|---|---|
| CORAL CAY RESORT | $287,000 | $192 | 79 | 7 |
| REGAL OAKS AT OLD TOWN | $295,000 | $203 | 37 | 19 |
| FIESTA KEY | $280,000 | $162 | 37 | 13 |
| STOREY LAKE CONDO | $300,000 | $252 | 91 | 3 |
More CYPRESS SHADOWS: 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 2009 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.