Oak Leaf Landings
Homes for Sale in Kissimmee, FL

This is a settled Osceola County community of 422 homes, past its build-out phase, where roughly two-thirds of owners hold a homestead exemption — a signal that this leans toward primary residences rather than a churn of short-term turnover.

Stellar MLS sales records identify 52 homes in Oak Leaf Landings that have changed hands since 2015, built between 2000 and 2005 (median 2002), with a median living area of about 2,549 sq ft and a typical 4-bedroom, 3-bath layout; 100% are single-family homes. Source: Stellar MLS closed-sale history compiled by Momentum Research; counts reflect homes with a recorded MLS sale, not every home in the community.

County records show 18 qualified sales in Oak Leaf Landings across 2024–2025 (11 in 2024, 7 in 2025), median $460,000 — the last recorded sale per parcel on the Florida DOR 2025 assessment roll, independent of the MLS.

Pre-construction details are compiled from public records, builder announcements and builder listings, and are subject to change without notice; figures are deemed reliable but not guaranteed. Momentum Research figures are our own analysis. This page describes homes, pricing and community attributes, not residents.

Oak Leaf Landings is too small for its own price trend, so here is the market around it.

In ZIP 34746, 995 homes are on the market and 16% are under contract — a slower corner of Kissimmee.

Across Osceola County, 4,465 homes are active and 1,093 pending (20% under contract).

In ZIP 34746 (Kissimmee), 1,623 homes closed in the last 12 months at a median of $405K ($199/sq ft), down 4.3% year over year, with a median 67 days on market. Right now 435 active and 80 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.

ZIP and county figures describe the wider market, not Oak Leaf Landings specifically. Momentum Research analysis of MLS records.

The defining trait here is size paired with age. A median of 2,713 living square feet is substantial, and with a median build year of 2003, most homes are old enough to be past their first round of major systems replacement. That makes roof age, HVAC, and any updates to kitchens and baths the real story on any given home — the footage is there, the question is what shape it's in.

The homestead share, at just over 65 percent, points to a community held largely by owner-occupants rather than investors. For a buyer, that usually means homes that have been lived in and maintained rather than run as rentals, though it also means inventory can be thinner and slower to turn than in an investor-heavy area.

With no recent closing to anchor value and a wide condition-driven price spread, this is a market where the comps have to be built, not looked up. We walk the home, read the systems and updates against the median-age baseline, and price or negotiate from what's actually in front of us — which is exactly the work that protects you when there's no fresh sale to point to.

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