Harbour Oaks
Homes for Sale in Kissimmee, FL

Harbour Oaks Sub is a 191-home community in Kissimmee with generously sized houses — a median of about 2,840 living square feet — across a wide range of vintages. It reads as an established, owner-occupied enclave rather than a uniform new-build tract.

Stellar MLS sales records identify 61 homes in Harbour Oaks that have changed hands since 2004, built between 1973 and 2002 (median 1980), with a median living area of about 2,094 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.

Harbour Oaks 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 Harbour Oaks specifically. Momentum Research analysis of MLS records.

The defining feature here is age diversity. Homes date from 1928 to 2024, with the midpoint around 1982, so no single era dominates. Practically, that means the physical condition of any given house — roof, systems, kitchens, baths — will drive its value far more than the neighborhood label. Buyers should budget for inspections and read each listing as a distinct project or move-in-ready case, not assume the median describes it.

Size is a consistent strength. A median near 2,840 square feet is substantial, and the older housing stock often comes with layouts and lot proportions you do not find in newer subdivisions. The high homestead share reinforces that this is a lived-in, hold-for-the-long-run community, which tends to translate into steadier upkeep but also fewer homes trading in any given window.

In a market this uneven — few recent closings, a huge vintage spread, and value driven by condition — the median price is a starting point, not an answer. We price and evaluate homes here property by property, weighing what has actually been updated against comparable size and era. That discipline is what protects a buyer from overpaying on an original home and helps a seller capture the premium a genuinely renovated one deserves.

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