Heritage Key Villas
Homes for Sale in Kissimmee, FL

Heritage Key Villas 2 in Kissimmee, Osceola County, is a smaller-footprint villa community where typical living space runs around 1,537 square feet and construction dates span nearly two decades.

Stellar MLS sales records identify 82 homes in Heritage Key Villas that have changed hands since 2008, built between 2006 and 2007 (median 2007), with a median living area of about 1,512 sq ft and a typical 3-bedroom, 2.5-bath layout; 91% are townhomes. 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.

Heritage Key Villas 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 Heritage Key Villas specifically. Momentum Research analysis of MLS records.

With 153 homes built between 2006 and 2024, this is not a single-phase, single-vintage community. A median year built of 2007 tells you the bulk of the original construction is now nearly two decades old, but the presence of homes built as recently as 2024 means newer construction has been added into the same footprint over time. Anyone shopping here should treat build year as a primary filter, not an afterthought, since two homes a few doors apart may have almost nothing in common structurally.

No community amenities are currently identified from MLS listings, which means the appeal here is the villa itself and its immediate lot, not a shared clubhouse, pool, or recreation package. At a median living area of roughly 1,537 square feet, these are compact homes suited to buyers prioritizing a smaller, lower-maintenance footprint over expansive interior space or resort-style community features.

In a community spanning nearly two decades of construction with no listed amenity package to fall back on, the home itself carries the entire evaluation. We walk each listing on its own construction era and condition rather than leaning on community-wide assumptions, and we factor in what the low homestead share signals about how the surrounding units are actually being used before you make an offer.

Listings in this community report association dues of about $284 per month ($3,408 a year) — the median AssociationFee across 18 MLS records, normalised to a monthly figure; most are billed monthly. Dues change with budgets and can differ by section or product type; confirm the current figure with the association before you offer. Source: MLS listing records, 2026-09.

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