Dellwood Park
Homes for Sale in Kissimmee, FL

Dellwood Park's housing stock is compact and older by Kissimmee standards, with a median size of 1,404 square feet and a build date that predates most of the surrounding subdivisions. It reads as a smaller, established corner of the city rather than a planned or amenitized community.

Stellar MLS sales records identify 41 homes in Dellwood Park that have changed hands since 2006, built between 1954 and 2007 (median 1956), with a median living area of about 1,183 sq ft and a typical 3-bedroom, 1.5-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 Dellwood Park across 2024 - 2025 (2 in 2024, 4 in 2025), median $330,000 - 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.

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

• Central Avenue Elem · Elementary
• Denn John Middle · Middle
• Osceola High School · High

Zoned schools reflect the assignments reported on recent Dellwood Park listings and can change; always confirm with Osceola County Public Schools for a specific address.

Buying with schools in mind? We can confirm the exact zoned schools for any Dellwood Park address.

The homes here span more than five decades of construction, from 1953 up through 2007, but the median build year of 1956 tells you where the center of gravity sits. Most of the neighborhood predates the amenity-package subdivisions that define newer Kissimmee construction, and no community amenities are currently identified from MLS listings. This is a neighborhood built around the houses themselves, not a shared clubhouse or pool system.

Just under half of homes here, 46.8 percent, carry a homestead exemption, which points to a mixed base of owner-occupied and non-homestead ownership rather than a neighborhood dominated by one pattern. Combined with a median size of 1,404 square feet, this reads as a market of modest, straightforward homes where renovation history and lot condition drive value more than square footage does.

A 77-home community with a single active listing does not give you room for guesswork. We track closings and supply data closely enough to tell you whether a given price reflects the block or just that one house, and we know how to evaluate an older home's condition against what similar Osceola County properties have actually sold for.

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