Momentum Housing Data · Home Values · Osceola County
Buying here? See Crestwynd Bay homes for sale and the Crestwynd Bay community guide (Kissimmee).
Crestwynd Bay (KISSIMMEE, FL): 6 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 87.9% of original asking; the median sale took 123 days (window ending 2026-09-20).
| Year | Median sold | Median $/sqft | Median DOM | Sold ÷ original ask | Sales |
|---|---|---|---|---|---|
| 2026 | $247,450 | $182 | 123 | 87.9% | 6 |
| 2025 | $280,000 | $198 | 42 | 94.6% | 11 |
| 2024 | $285,000 | $232 | 9 | 93.0% | 7 |
| 2023 | $300,000 | $225 | 28 | 96.0% | 7 |
| 2022 | $265,000 | $195 | 6 | 103.0% | 13 |
| 2021 | $204,250 | $157 | 8 | 101.0% | 8 |
| 2016 | $145,000 | $101 | 27 | 93.0% | 14 |
Over the recorded series, Crestwynd Bay’s median sold price moved from $145,000 (2016) to $247,450 (12 months ending 2026-09-20) — +71% over that span, with every year’s figure from recorded closings, not a model.
The recorded series starts in 2016 at $145,000. Against the 2023 peak of $300,000, the current median stands at -18%. Annual sales volume here has ranged from 0 to 14 closings a year (10-yr average 5.2). With roughly 5.2 closings a year, Crestwynd Bay’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 22 recorded Crestwynd Bay closings since 2024, half landed between $251,175 and $287,675 (the middle two quartiles); the lowest recorded sale was $200,000 and the highest $325,000. 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 $225,000 | 1 (5%) | |
| $225,000 – $250,000 | 5 (23%) | |
| $250,000 – $275,000 | 4 (18%) | |
| $275,000 – $300,000 | 9 (41%) | |
| None and up | 3 (14%) |
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 ($232 vs $193) — 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 1,187–1,187 sq ft | $232 | $275,000 | $200,000 – $302,000 | 7 |
| Mid-size homes 1,187–1,362 sq ft | $195 | $265,000 | $235,000 – $290,000 | 7 |
| Larger homes 1,362–1,595 sq ft | $193 | $275,000 | $245,000 – $325,000 | 8 |
From the live MLS feed as of 2026-10-01: 8 active listings (plus 0 pending) asking from $229,000 to $298,999, median $248,950; 5 of 8 have been on the market over 60 days (median 75 days so far); the homes listed or recently sold were built between 2006 and 2007 (median 2006); 15 of 15 listed or recently sold homes report an HOA, median $333/mo; none of the 15 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, Gated Community - No Guard, Playground, Community Mailbox and Park. 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 Crestwynd Bay listings →
At Crestwynd Bay’s $247,450 median and Osceola County’s adopted 15.23 mills (FY2025-26), a home assessed at that price carries roughly $3,770 a year in property tax before exemptions, or about $3,170 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 $262,500 against the $247,450 recorded sold median (+6%) — the gap between what sellers hope and what the record shows. The market is carrying about 13.7 months of supply at the current sales pace. Demand check: 0% of Crestwynd Bay’s listings are under contract, against 12% for ZIP 34747 and 20% for Osceola County as a whole — the community is currently absorbing slower than its surroundings, which is negotiating information.
Asking and recorded sold prices are within a few percent of each other here, so the table above is close to what a Crestwynd Bay 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 Crestwynd Bay 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 |
|---|---|---|---|---|
| Summerville Resort | $417,500 | $235 | 132 | 10 |
| windsor hills | $600,000 | $260 | 26 | 57 |
| Meridian Palms Comm Condo | $42,500 | $140 | 116 | 8 |
| Formosa Gardens | $652,000 | $241 | 94 | 5 |
More Crestwynd Bay: 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.