Momentum Housing Data · Home Values · Osceola County

PINEHURST AT CYPRESS WOODS Home Values: What Homes Actually Sell For

PINEHURST AT CYPRESS WOODS (KISSIMMEE, FL): 3 recorded closings in the 12 months ending 2026-08-02, a 5-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 93.6% of original asking; the median sale took 145 days (window ending 2026-08-02).

The 5-year recorded price history

Over the recorded series, PINEHURST AT CYPRESS WOODS’s median sold price moved from $152,500 (2016) to $420,000 (12 months ending 2026-08-02) — +175% over that span, with every year’s figure from recorded closings, not a model.

What actually trades here: 100% single-family residence, with a median of 2,778 sq ft and a median price per square foot of $151 in the current window.

The PINEHURST AT CYPRESS WOODS housing stock, from the live feed

From the live MLS feed as of 2026-09-03: The homes listed or recently sold were built between 1997 and 1998 (median 1997); 4 of 4 listed or recently sold homes report an HOA, median $95/mo; 1 of 4 geocoded listed or recently sold homes sit inside a FEMA special flood hazard zone (A/V), which buyers’ lenders will price into insurance; median elevation 70 ft. See the current PINEHURST AT CYPRESS WOODS listings →

At PINEHURST AT CYPRESS WOODS’s $420,000 median and Osceola County’s adopted 15.23 mills (FY2025-26), a home assessed at that price carries roughly $6,400 a year in property tax before exemptions, or about $5,800 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.

Selling in PINEHURST AT CYPRESS WOODS right now: what the record says

Current asking prices run a median $330,000 against the $420,000 recorded sold median (-21%) — the gap between what sellers hope and what the record shows. The market is carrying about 4 months of supply at the current sales pace. Demand check: 0% of PINEHURST AT CYPRESS WOODS’s listings are under contract, against 29% for ZIP 34758 and 21% for Osceola County as a whole — the community is currently absorbing slower than its surroundings, which is negotiating information. Since 2006, 21 PINEHURST AT CYPRESS WOODS listings were withdrawn, canceled, or expired without selling — overpricing is the recurring cause statewide. Over the recorded years, an average of 50% of PINEHURST AT CYPRESS WOODS listings ended without selling (withdrawn/canceled/expired); in 2025 that rate was 67%.

Cash bought 33% of recorded PINEHURST AT CYPRESS WOODS sales in the window ending 2026-06 (1 of 3) — a fact worth knowing before assuming every buyer needs an appraisal to close. Asking prices here currently sit -21% under the recorded sold median — sellers are pricing to move, and the closed record above is the number a buyer's appraiser will see.

How PINEHURST AT CYPRESS WOODS compares with its neighbors

Communities buyers shopping PINEHURST AT CYPRESS WOODS 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.

More PINEHURST AT CYPRESS WOODS: 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 2014 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