Shenandoah
Homes for Sale in Kissimmee, FL

This is a compact, single-era community in Kissimmee where homes share a common build period and a modest footprint. With just 93 homes, turnover is limited, so serious buyers should be ready to move when the right condition comes available.

Stellar MLS sales records identify 56 homes in Shenandoah that have changed hands since 2004, built between 1980 and 2004 (median 1980), with a median living area of about 1,188 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.

County records show 6 qualified sales in Shenandoah across 2024–2025 (4 in 2024, 2 in 2025), median $295,000 — 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.

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

In ZIP 34744, 447 homes are on the market and 19% are under contract — a steady corner of Kissimmee.

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

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.

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

Homes here were built between 1979 and 1982, with the median year landing at 1980. Four-plus decades in, the meaningful questions are about the roof, the HVAC, the electrical panel, and whether major updates have been done. Two homes of nearly identical size can price very differently based purely on how they've been maintained and modernized.

The owner-occupancy signal is notable: roughly 68% of homes carry a homestead exemption. That points to a community held largely by people living in their homes rather than a heavy investor or rental concentration, which tends to correlate with steadier upkeep and a more stable resale environment. At 1,483 median living square feet, these are right-sized homes rather than sprawling ones.

In a 93-home community where price is driven by condition rather than size, our job is to read the difference between a home that's been genuinely updated and one that's been staged to look that way. We walk the systems, price against the specific median profile of this neighborhood, and tell you plainly when an asking price assumes work that hasn't been done.

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