Pleasant Hill Trails
Homes for Sale in Kissimmee, FL

Pleasant Hill Trails market snapshot (as of August 2, 2026): the median sale price is about $900K ($307 per sq ft over the trailing 12 months of closed sales), and a median 99 days on market for closed sales.

In ZIP 34746 (KISSIMMEE), 1,615 homes closed in the last 12 months at a median of $405K ($199/sq ft), down 4.5% year over year, with a median 67 days on market. Right now 421 active and 72 pending listings put supply at about 6.7 months — a buyer's market. See the live ZIP 34746 housing market and the Osceola County market.

Pleasant Hill Trails is a community of 35 homes in Kissimmee, Osceola County, built between 1972 and 2023 (median 1990), with a median living area of about 3,724 square feet. 77% of parcels are homesteaded, the owner-occupancy proxy in the Florida DOR assessment roll (2025 roll, public records).

A modest 23-home pocket in Kissimmee distinguished less by its footprint on the map than by the scale of the homes themselves—this is a community of large-format living, not entry-level product.

The defining fact about Pleasant Hill Trails is square footage. A median of 4,265 living square feet is large by almost any resale comparison, and it signals that whatever else varies from house to house—vintage, finish level, lot configuration—buyers here are shopping for space first. That changes the math on everything from carrying costs to renovation scope, and it means two homes in this community can differ substantially in feel even if they're a few doors apart.

Age spread compounds that variation. With construction ranging from 1978 through 2023 and a median year built of 1993, the neighborhood holds both older homes likely due for system updates and newer builds with contemporary construction standards. There is no identified community amenity package in current MLS data, so whatever draws a buyer here is the home itself and its size, not a shared clubhouse or recreational feature. The high homestead share—about 83%—also tells you this is not a community with heavy transient or investment-driven turnover; most owners are settled in for the long run, which tends to keep inventory tight and listings less frequent.

A 23-home community with wide variation in age and no shared amenity baseline is exactly the kind of market where generic comps mislead. We look at each home on its own physical merits—square footage, year built, condition—rather than assume the community label alone tells you what a property is worth.

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