Momentum Housing Data · Home Values · Osceola County
WINDSOR POINT (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 95.6% of original asking; the median sale took 123 days (window ending 2026-08-02).
| Year | Median sold | Median $/sqft | Median DOM | Sold ÷ original ask | Sales |
|---|---|---|---|---|---|
| 2026 | $430,000 | $212 | 123 | 95.6% | 3 |
| 2025 | $400,000 | $232 | 31 | 100.0% | 3 |
| 2022 | $385,000 | $191 | 7 | 99.6% | 10 |
| 2019 | $270,800 | $131 | 83 | 95.0% | 3 |
| 2016 | $221,200 | $112 | 47 | 96.2% | 6 |
| 2015 | $208,000 | $100 | 16 | 95.6% | 5 |
Over the recorded series, WINDSOR POINT’s median sold price moved from $208,000 (2015) to $430,000 (12 months ending 2026-08-02) — +107% over that span, with every year’s figure from recorded closings, not a model.
The recorded series starts in 2015 at $208,000. The 2020–22 run-up did what it did everywhere — WINDSOR POINT’s median moved +42% from 2019 to 2022. Annual sales volume here has ranged from 0 to 10 closings a year (10-yr average 2.2). With roughly 2.2 closings a year, WINDSOR POINT’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 1,942 sq ft and a median price per square foot of $212 in the current window.
From the live MLS feed as of 2026-09-03: 4 active listings (plus 0 pending) asking from $369,900 to $450,000, median $409,500; 1 of 4 have been on the market over 60 days (median 45 days so far); the homes listed or recently sold were built between 2003 and 2004 (median 2004); 8 of 8 listed or recently sold homes report an HOA, median $76/mo; none of the 8 geocoded listed or recently sold homes sits in a FEMA special flood hazard zone (median elevation 87 ft); the features listings here most often name are Pool, Playground, Gated, Gated Community - No Guard and Street Lights. 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 WINDSOR POINT listings →
At WINDSOR POINT’s $430,000 median and Osceola County’s adopted 15.23 mills (FY2025-26), a home assessed at that price carries roughly $6,550 a year in property tax before exemptions, or about $5,950 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 $424,500 against the $430,000 recorded sold median (-1%) — the gap between what sellers hope and what the record shows. The market is carrying about 12 months of supply at the current sales pace. Demand check: 20% of WINDSOR POINT’s listings are under contract, against 17% for ZIP 34741 and 21% for Osceola County as a whole — roughly in line with its surroundings. Since 2005, 100 WINDSOR POINT 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 65% of WINDSOR POINT listings ended without selling (withdrawn/canceled/expired); in 2026 that rate was 50%. Momentum’s market-heat index for WINDSOR POINT reads 33/100 (computed from DOM, sale-to-list, and absorption; 2020–21 peaked in the 70s here).
Cash bought 25% of recorded WINDSOR POINT sales in the window ending 2026-06 (1 of 4) — 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 WINDSOR POINT 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 WINDSOR POINT 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 |
|---|---|---|---|---|
| Townhomes Of Flora Ridge Kissimmee | $312,500 | $161 | 99 | 10 |
| AVILLA | $715,000 | $269 | 30 | 3 |
| HERONS LANDING PH 3 | $460,000 | $234 | 43 | 4 |
| TAPESTRY | $430,000 | $204 | 106 | 27 |
More WINDSOR POINT: 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 2007 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.