Oak Grove East
Homes for Sale in Kissimmee, FL

A compact, largely owner-occupied enclave in Osceola County where a median living area under 1,500 square feet and a build span from 1954 to 2022 mean you're really shopping individual condition, not a uniform product.

Stellar MLS sales records identify 24 homes in Oak Grove East that have changed hands since 2005, built between 1973 and 1976 (median 1974), with a median living area of about 1,365 sq ft and a typical 3-bedroom, 2-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.

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 Grove East is too small for its own price trend, so here is the market around it.

In ZIP 34744, 418 homes are on the market and 21% are under contract — a steady corner of Kissimmee.

Across Osceola County, 4,423 homes are active and 1,079 pending (20% under contract).

In ZIP 34744 (Kissimmee), 785 homes closed in the last 12 months at a median of $406K ($215/sq ft), up 1.8% year over year, with a median 34 days on market. Right now 126 active and 26 pending listings put supply at about 6.6 months — a balanced market. See the live ZIP 34744 housing market and the Osceola County market.

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

The median home here runs about 1,460 square feet — modest by current standards — and the median build year of 1975 means many of these houses have lived through multiple ownership cycles. The value question isn't square footage alone; it's whether the roof, HVAC, electrical, and plumbing have kept pace with the calendar. Homes built closer to 2022 exist in this community, but they're the exception against a mostly mid-century-to-1970s backbone.

Because inventory is thin at 118 homes and roughly seven in ten are homesteaded, well-updated listings tend to draw attention while dated ones sit until the price reflects the work needed. Buyers should budget for the gap between move-in-ready and project. Sellers should invest in the paperwork trail — permits, receipts, dates — because in a market this varied, proof of condition does the heavy lifting.

In a market where price hinges on condition rather than a tidy price band, our job is to read each home on its own terms — pull the permit history, weigh the systems against the 1975-era median, and tell you honestly where a listing sits between project and turnkey. That's how we keep buyers from overpaying for cosmetics and help sellers get credit for the updates that matter.

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