Caribbean Villas
Homes for Sale in Kissimmee, FL
All 2,887 homes for sale in Kissimmee, FL · median $374,999 · 255 homes for sale in 34741 · Osceola County homes for sale
True comps, carrying-cost math, and listings before the portals.
Photo via Stellar MLS
As of October 2026, Caribbean Villas in Kissimmee, FL has 2 homes for sale. As of October 2026, the MLS records 41 closed sales in Caribbean Villas in Kissimmee, FL since 2005, the most recent in April 2024. Recorded prices since 2024 ran from $183,705 to $250,000 (median $240,000), on homes of 991 to 1,191 sq ft. Across Kissimmee as a whole, 2,523 homes closed in the last 12 months at a median of $387,990, 62 median days on market, with 1,265 homes for sale today. At that median and Osceola County's FY2025-26 rate of 15.23 mills, annual property tax runs about $3,660 ($3,050 with the full homestead exemption).
Sections of Caribbean Villas in the MLS
Caribbean Villas in Kissimmee, FL is recorded as 4 separate subdivisions/phases in the MLS; 2 homes are for sale across them today. Each section has its own page:
- Caribbean Villas Condo · 2 for sale
- Caribbean Villas Condo Ph A-F · 3 sold/12 mo
- Caribbean Villas Condo Ph F
- Caribbean Villas Condo Phs A-F
| Location | Kissimmee, Osceola County, FL · ZIP 34741 |
|---|---|
| Homes in the community | 219 (FL DOR 2025 assessment roll) |
| Years built | 1982–1993 (median 1984) |
| Typical living area | 994 sq ft (median) |
| Amenities listed by sellers | None, Pool |
| For sale right now | 2 active, 0 pending · median asking $189,500 |
| Owner-occupied (homestead) share | 26% |
Data as of September 20, 2026. Based on Stellar MLS data distributed by MLS GRID for the period 2005 through 2024; housing-stock figures from Florida Department of Revenue public records. Market figures describe homes, not residents. Cite as: Momentum Realty, “Caribbean Villas key facts,” movewithmomentum.com/neighborhoods/caribbean-villas, data as of September 20, 2026.
Last 30 days in Caribbean Villas: 2 new listings (median asking $189,500). As of October 5, 2026, Listings courtesy of Stellar MLS as distributed by MLS GRID.
Caribbean Villas is a compact community of 219 homes built in a tight window from 1982 to 1993, with a median build year of 1984. At a median living area right around 994 square feet, these are small, single-story-scaled floor plans, and price here is driven far more by condition and updates than by size differences. Two units of similar footprint can trade well apart depending on roof age, systems, and interior renovation, so buyers should underwrite the specific unit, not the community average.
The homestead share sits at roughly a quarter of homes, which tells you this leans heavily toward non-owner-occupants. That posture matters: it signals an investor- and second-home-oriented market, which tends to move on rental math and carrying costs as much as on lifestyle. For sellers, presentation and turnkey condition carry outsized weight; for buyers, there is room to negotiate on units that need work.
The 60-Second Overview
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.
County records show 16 qualified sales in Caribbean Villas across 2024–2025 (12 in 2024, 4 in 2025), median $195,000 — the last recorded sale per parcel on the Florida DOR 2025 assessment roll, independent of the MLS.
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.
Who Caribbean Villas is best for.
Best for
- Investors running rental math who want a compact, condition-priced entry point in Osceola County
- Buyers seeking a small, single-level-scaled floor plan without a large maintenance burden
- Value-minded buyers willing to renovate a dated unit and price their offer to the work required
Probably not for
- Buyers who need significantly more than roughly 1,000 square feet of living space
- Buyers who want a predominantly owner-occupied community
- Buyers seeking newer construction or homes built well after the early 1990s
The market around Caribbean Villas
Caribbean Villas is too small for its own price trend, so here is the market around it.
In ZIP 34741, 290 homes are on the market and 14% are under contract — a slower corner of Kissimmee.
Across Osceola County, 4,465 homes are active and 1,093 pending (20% under contract).
In ZIP 34741 (Kissimmee), 754 homes closed in the last 12 months at a median of $411K ($205/sq ft), down 0.8% year over year, with a median 44 days on market. Right now 207 active and 46 pending listings put supply at about 6.1 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.
Housing distress & ownership in Caribbean Villas, Kissimmee
Who owns here, how much is not owner-occupied, and how much for-sale inventory is under distress.
Source: Momentum Realty Research. Ownership & parcels from the FL DOR 2025 tax roll; distress from MLS active-listing status/remarks; price from MLS closed sales. Based on Stellar MLS data distributed by MLS GRID for the period September 2026 through September 2026. Deemed reliable but not guaranteed.
Homes For Sale Right Now in Caribbean Villas
Live MLS inventory for Caribbean Villas. Every active listing, what is under contract right now, and the last 12 months of closed sales, refreshed twice a day. Closed comps beat an algorithm's guess every time.
Active and pending Caribbean Villas listings as of 2026-10-01, priced high to low. Based on Stellar MLS data distributed by MLS GRID for the period 2005 through 2024. Tap any home to ask about it.
Every Home for Sale in Caribbean Villas Right Now (2)
All 2 active and pending Caribbean Villas listings with a detail page, newest first, refreshed twice a day from the MLS.
- 2305 Trinidad Court · $184,000 · 2 bd / 2 ba · listed Sep 20, 2026 · listed by Viva Orlando Realty Inc.
- 2207 Caribbean Drive · $195,000 · 2 bd / 2 ba · listed Sep 10, 2026 · listed by Agent Trust Realty Corporation
Schools
- Osceola County Public Schools
- Verify the zoned schools by address
- Magnet and choice options may be available
- Kissimmee Elem · Elementary
- Kissimmee Middle · Middle
- Osceola High School · High
Zoned schools reflect the assignments reported on recent Caribbean Villas listings and can change; always confirm with Osceola County Public Schools for a specific address.
Buying with schools in mind? We can confirm the exact zoned schools for any Caribbean Villas address.
The Caribbean Villas buying strategy.
If we were buying in Caribbean Villas today, this is the order of operations we would run for our clients.
Underwrite the condition first. Price the roof, HVAC, and systems honestly before judging any list price; condition swings value here more than square footage alone.
Match the home to real comps. Recent sales of similar condition and lot, not the asking price, tell you what a home is worth.
Move deliberately, not desperately. Neither side has a decisive edge, so a well-prepared, fairly-priced offer wins without overpaying.
Line up financing and inspection early. A pre-approval and an inspection plan let you act fast and negotiate from evidence.
Keep an agent in your corner. The listing agent works for the seller; we represent you and prepare a hand-built valuation before any offer in Caribbean Villas.
A condition-driven market
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.
The location and the amenities are priced into every listing in Caribbean Villas. The deal is won or lost on condition, the comps, and the renovation math.
Why work with Momentum here
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.
Caribbean Villas in 15 seconds.
HOA, CDD & Fees
- HOA dues reported around $285/month (about $3,420/yr) · median of 37 MLS listings, most billed monthly
- Any club/amenity membership is billed separately
Listings in this community report association dues of about $285 per month ($3,420 a year) — the median AssociationFee across 37 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, 2026-10.
Confirm the current HOA dues, exactly what they cover, and any CDD bond or special assessment for a specific address before you offer.
Tools for a Caribbean Villas buy.
Free calculators to pressure-test the real cost before you tour.
Selling here is won on condition and pricing to real comps, not an automated estimate. The right number comes from closed Caribbean Villas sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Caribbean Villas, the right list price comes from recent comparable sales matched to your home's condition and location, not an automated estimate.
What is your Caribbean Villas home worth?
Get a no-obligation home value based on real comparable sales in Caribbean Villas, not an automated guess. Tell us about your home and we will personally prepare your numbers and a pricing strategy. No obligation, no spam.
See all homes for sale in Kissimmee →
11% of homes for sale in ZIP 34741 are already under contract (under contract ÷ under contract + active listings) — a read on how much of the available inventory buyers have already claimed. Source: MLS data (2026-10-04).
Frequently Asked Questions
How many homes are in Caribbean Villas?
What share of Caribbean Villas is owner-occupied?
When were the homes in Caribbean Villas built?
Who is the best real estate agent for Caribbean Villas?
How do I find a top Kissimmee real estate agent who knows Caribbean Villas?
Can Momentum Realty connect me with an agent for Caribbean Villas?
Where is Caribbean Villas, and what county is it in?
Should you buy in Caribbean Villas?
An honest fit check. We will tell you when it is not your community.
Data sources & freshness
| Live listings | Stellar MLS, refreshed twice daily (last: October 1, 2026) |
| Housing stock & ownership | Florida DOR assessment roll (street-list match (7 streets, ZIP 34741)) |
| Under-contract shares | Stellar MLS records, as of 2026-09-20 |
| Historical depth | Closed-sale records back to 2005 (41 transactions analyzed) |
Verify the primary sources yourself: Florida DOR · U.S. Census · FEMA flood maps · Citizens Property Insurance.
Momentum Research figures are our own analysis of Stellar MLS records; MLS data is deemed reliable but not guaranteed. Methodology: how Momentum market scores are computed. Market metrics describe homes for sale and recent sales, not residents.
Own a home here?
You just read the data. Now see what your home is worth.
The numbers on this page move markets in the aggregate. The number that matters to you is what a buyer pays for your address. Momentum sells for 1.25% above the Stellar MLS member average and 8 days faster, and we’ll price yours against live local comps.
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See how Caribbean Villas fits the bigger picture — live prices, inventory, and Momentum Scores:
Nearby Communities
Explore more neighborhoods near Caribbean Villas with Momentum Realty’s local guides.