Caribbean Villas Condo
Condos for Sale in Kissimmee, FL

Caribbean Villas Condo market snapshot (as of September 12, 2026): the median sale price is about $190K ($192 per sq ft over the trailing 12 months of closed sales), and a median 36 days on market for closed sales. The trailing-12-month median is up 2% from the prior 12 months, computed from record-level Stellar MLS closed sales (3 closings in the current window).

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.

Stellar MLS sales records identify 18 homes in Caribbean Villas Condo that have changed hands since 2020, 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; 61% 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.

Caribbean Villas is a small, established condo community of 78 homes in Kissimmee, built in the late 1980s, where most units are similarly sized and priced primarily on interior condition. With homestead use at roughly 27%, a meaningful share of these units are not owner-occupied primary residences.

The building stock here is uniform: late-1980s construction, a tight cluster of living sizes centered near 994 square feet, and a median build year of 1987. That uniformity is useful when you're evaluating value, because it strips size out of the equation and puts the focus on what actually varies — kitchens, baths, flooring, HVAC age, and any updates a prior owner made. The $192.73 median price per square foot is the number to benchmark a specific unit against; well above it should come with visible upgrades, well below it usually signals deferred work.

With only 78 units and a small number of recent closings, comparable data is thin, so a single well- or poorly-priced sale can move the read. That makes hands-on evaluation matter more than usual. Buyers should also weigh the condo association's finances and reserves alongside the unit itself, since building-level costs and assessments affect any 1980s condo more than a headline price does.

In a small community with a shallow pool of recent sales, the price you should pay is a judgment call, not a spreadsheet output. We evaluate the specific unit against the median price per square foot, weigh its condition honestly, and dig into association health before you commit. That's the difference between buying a fairly priced unit and overpaying for someone else's cosmetics.

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