Oak Run
Homes for Sale in Kissimmee, FL

Oak Run market snapshot (as of September 20, 2026): the median sale price is about $350K ($240 per sq ft over the trailing 12 months of closed sales), and a median 31 days on market for closed sales. The trailing-12-month median is down 5% from the prior 12 months and up 306% since 2012, computed from record-level Stellar MLS closed sales (13 closings in the current window).

In ZIP 34744 (Kissimmee), 789 homes closed in the last 12 months at a median of $406K ($215/sq ft), up 1.2% year over year, with a median 33 days on market. Right now 128 active and 26 pending listings put supply at about 6.7 months — a balanced market. See the live ZIP 34744 housing market and the Osceola County market.

County records show 29 qualified sales in Oak Run across 2024–2025 (23 in 2024, 6 in 2025), median $365,000 — the last recorded sale per parcel on the Florida DOR 2025 assessment roll, independent of the MLS.

Oak Run is a community of 588 homes in Kissimmee, Osceola County, built between 1959 and 2009 (median 1988.0), with a median living area of about 1,818 square feet. 75% of parcels are homesteaded, the owner-occupancy proxy in the Florida DOR assessment roll (2025 roll, public records).

This is an established, mid-size community of 205 homes in Osceola County, with a housing stock that spans four decades and centers on roughly 1,842 square feet of living space. The high owner-occupancy share — about 72% homesteaded — points to a stable, lived-in enclave rather than a rental-heavy corridor.

The defining feature of Oak Run Unit 9 is variance. A build range from 1959 to 2002 means you'll find genuinely older homes next to ones from the turn of the millennium, and the gap shows up in floor plans, systems, and update history. There is no single 'typical' house — there is a median size near 1,842 square feet and a wide condition spread around it. Value tracks what's been done to each property, so comps require judgment, not arithmetic.

The ownership profile reinforces the character. With roughly 72% of homes homesteaded, this reads as an owner-occupied community where properties tend to be held rather than flipped. That can mean fewer listings and slower turnover — good for stability, less good if you want a broad menu of options at any given moment. Combined with a light recent closing count, patience is part of the strategy on both sides of the table.

In a low-volume, condition-driven market like this, the wrong comp leads to the wrong number. We underwrite each home individually — roof, systems, and updates against its build year — instead of leaning on a thin sales record. That protects sellers from mispricing and gives buyers a clear-eyed read on what they're actually buying.

Confirm the current HOA dues, exactly what they cover, and any CDD bond or special assessment for a specific address before you offer.