Heritage Key Villas
Homes for Sale in Kissimmee, FL

Heritage Key Villas is a compact, gated enclave of eight villas built in a single year, positioned in Osceola County's Kissimmee submarket with guard access and shared recreational amenities rather than standalone yards.

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.

Every home in Heritage Key Villas dates to 2007, so there is no mix of eras to sort through - the housing stock is uniform in age and, at a median of 1,650 square feet, fairly uniform in size as well. That consistency simplifies comparisons between units but also means the community's appeal rests almost entirely on condition, updates, and how each owner has maintained their villa, since floor plans and vintage are not differentiators.

The amenity package - guarded gate, clubhouse, fitness center, playground, and association-owned recreation space - points to a resort-style, deed-restricted setup rather than a conventional neighborhood. Reclaimed-water irrigation and buyer-approval requirements are worth flagging early to anyone underwriting a purchase, since they carry HOA process and cost implications that a standard single-family resale would not.

With only eight homes in the entire community and no active listings at the moment, timing and off-market awareness matter more here than in a typical subdivision - we track this niche closely enough to flag a listing, or a motivated seller, before it becomes a public search result. We also walk buyers through the HOA's buyer-approval and deed-restriction process up front, since a rental-oriented, gated community like this one has more moving parts than a standard resale.

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