Momentum Housing Data · Home Values · Osceola County
CYPRESS CAY (KISSIMMEE, FL): 3 recorded closings in the 12 months ending 2026-08-02, a 4-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 83.5% of original asking; the median sale took 291 days (window ending 2026-08-02).
| Year | Median sold | Median $/sqft | Median DOM | Sold ÷ original ask | Sales |
|---|---|---|---|---|---|
| 2026 | $330,000 | $185 | 291 | 83.5% | 3 |
| 2025 | $370,990 | $214 | 36 | 95.9% | 29 |
| 2024 | $374,990 | $219 | 14 | 98.9% | 73 |
| 2023 | $377,190 | $218 | 0 | 100.0% | 17 |
Over the recorded series, CYPRESS CAY’s median sold price moved from $377,190 (2023) to $330,000 (12 months ending 2026-08-02) — -13% over that span, with every year’s figure from recorded closings, not a model.
What actually trades here: 100% townhouse, with a median of 1,782 sq ft and a median price per square foot of $185 in the current window.
Of the 79 recorded CYPRESS CAY closings since 2024, half landed between $361,495 and $388,290 (the middle two quartiles); the lowest recorded sale was $312,000 and the highest $422,590. 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 $350,000 | 5 (6%) | |
| $350,000 – $366,667 | 21 (27%) | |
| $366,667 – $383,333 | 30 (38%) | |
| $383,333 – $400,000 | 13 (16%) | |
| None and up | 10 (13%) |
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. Price per square foot is nearly flat across sizes here ($217 to $221), so square footage alone explains most of the price spread.
| Size group | Median $/sqft | Median sold | Sold range | Sales |
|---|---|---|---|---|
| Smaller homes 1,699–1,699 sq ft | $217 | $369,490 | $312,000 – $392,990 | 26 |
| Mid-size homes 1,699–1,782 sq ft | $212 | $364,495 | $330,000 – $399,290 | 26 |
| Larger homes 1,782–1,782 sq ft | $221 | $393,290 | $364,990 – $422,590 | 27 |
From the live MLS feed as of 2026-09-03: 6 active listings (plus 1 pending) asking from $314,900 to $369,000, median $349,188; 3 of 6 have been on the market over 60 days (median 78 days so far); the homes listed or recently sold were built between 2022 and 2024 (median 2022); 11 of 11 listed or recently sold homes report an HOA, median $300/mo; none of the 11 geocoded listed or recently sold homes sits in a FEMA special flood hazard zone (median elevation 80 ft); the features listings here most often name are Playground, Pool, Dog Park, Park and Basketball Court. For a seller this is the competition a buyer will tour alongside your home; for a buyer, the stale share is where negotiating room usually is. See the current CYPRESS CAY listings →
At CYPRESS CAY’s $330,000 median and Osceola County’s adopted 15.23 mills (FY2025-26), a home assessed at that price carries roughly $5,030 a year in property tax before exemptions, or about $4,430 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.
Current asking prices run a median $349,000 against the $330,000 recorded sold median (+6%) — the gap between what sellers hope and what the record shows. The market is carrying about 21 months of supply at the current sales pace. Demand check: 0% of CYPRESS CAY’s listings are under contract, against 21% for ZIP 34746 and 21% for Osceola County as a whole — the community is currently absorbing slower than its surroundings, which is negotiating information. Since 2022, 58 CYPRESS CAY listings were withdrawn, canceled, or expired without selling (6 so far in 2026) — overpricing is the recurring cause statewide. Over the recorded years, an average of 46% of CYPRESS CAY listings ended without selling (withdrawn/canceled/expired); in 2026 that rate was 75%.
Cash bought 67% of recorded CYPRESS CAY sales in the window ending 2026-06 (2 of 3) — a fact worth knowing before assuming every buyer needs an appraisal to close. Asking and recorded sold prices are within a few percent of each other here, so the table above is close to what a CYPRESS CAY buyer will actually pay; the spread on any single home comes down to size, condition and timing.
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 CAY 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 |
|---|---|---|---|---|
| VERANDA PALMS | $495,000 | $170 | 165 | 11 |
| CLUB CORTILE | $275,000 | $149 | 91 | 7 |
| HAMLETS | $385,000 | $172 | 133 | 3 |
| MONTEGO BAY | $345,000 | $226 | 37 | 4 |
More CYPRESS CAY: 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.