Caribbean Villas
Homes for Sale in Kissimmee, FL

A small, uniformly aged pocket of 219 modestly sized homes in Kissimmee, Osceola County, where the story is condition and ownership mix rather than square footage.

Stellar MLS sales records identify 123 homes in Caribbean Villas that have changed hands since 2004, built between 1982 and 1993 (median 1984), with a median living area of about 991 sq ft and a typical 2-bedroom, 2-bath layout; 68% are condominiums. 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.

Caribbean Villas is too small for its own price trend, so here is the market around it.

In ZIP 34741, 299 homes are on the market and 15% are under contract — a slower corner of Kissimmee.

Across Osceola County, 4,423 homes are active and 1,079 pending (20% under contract).

In ZIP 34741 (Kissimmee), 745 homes closed in the last 12 months at a median of $411K ($205/sq ft), down 2.2% year over year, with a median 44 days on market. Right now 201 active and 47 pending listings put supply at about 6.0 months — a balanced market. See the live ZIP 34741 housing market and the Osceola County market.

ZIP and county figures describe the wider market, not Caribbean Villas specifically. Momentum Research analysis of MLS records.

With homes clustered between 1982 and 1993 and a median living area near 994 square feet, Caribbean Villas offers little variation in footprint. That uniformity pushes value discovery onto the things you can see and touch: roof, HVAC, plumbing, and the quality of any interior updates. Expect a wide spread in asking positions across otherwise similar layouts, and expect the gap to reflect deferred maintenance more than location within the community.

The ownership profile — with homestead occupancy at about 26.5% — points to a market where a meaningful share of homes are held as rentals or seasonal properties. Practically, that means comparable sales can be uneven and inventory turnover reflects investor timing. Do the diligence on association rules, rental policies, and reserve health before you commit, because those factors influence carrying costs and resale liquidity here as much as the home itself.

In a community this small and this condition-sensitive, the number that matters is the one attached to the specific unit in front of you, not a neighborhood average. We read each listing on its systems and updates, pressure-test the comps, and help you understand how the ownership mix and association rules affect both carrying costs and resale before you write or accept an offer.

Listings in this community report association dues of about $285 per month ($3,420 a year) — the median AssociationFee across 3 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.