Chatham Park
Homes for Sale in Kissimmee, FL

This is a settled early-1990s neighborhood in Osceola County with a median living area just under 2,000 square feet, so the product is consistent and the variables that move value are condition, systems age, and updates rather than radically different home sizes.

Stellar MLS sales records identify 131 homes in Chatham Park that have changed hands since 2005, built between 1991 and 1995 (median 1994), with a median living area of about 1,677 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 21 qualified sales in Chatham Park across 2024–2025 (12 in 2024, 9 in 2025), median $374,000 — 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.

Chatham Park 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 Chatham Park specifically. Momentum Research analysis of MLS records.

With homes clustered between 1991 and 1995, this is a community where the big-ticket components — roofs, HVAC, water heaters, windows — are all reaching or past the point where replacement matters. That is not a negative; it is a checklist. The homes that have already had those items addressed will command a premium, and the ones that haven't should price to reflect the work ahead.

The median living area of roughly 1,956 square feet gives you real, usable space in a plan type that has aged well. Because the sizes are broadly similar across the 251 homes, buyers can compare apples to apples and focus their attention where it belongs: finishes, mechanical condition, and lot specifics rather than guessing at value from square footage alone.

In a neighborhood this uniform, the money is made or lost on condition, and that is exactly where a local read pays off. We walk the systems, price the deferred work honestly, and position an updated home to capture the premium it has earned — or help a buyer avoid overpaying for cosmetics laid over a home that still needs its bones addressed.

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