Orlando vs. Kissimmee: what it costs to own
Kissimmee costs less to own. For a single-family home at each city's median sale price, the mortgage, property tax and insurance come to about $2,663 a month there, $419 (14%) less than Orlando at $3,082, under our assumptions. HOA and CDD fees come on top for homes that have them, so a home in a fee-heavy community can flip the answer. This compares the housing payment only, not utilities, groceries or other living costs.
| Orlando | Kissimmee | |
|---|---|---|
| Monthly, before HOA/CDD | $3,082 | $2,663 |
| Median sale price | $439,900 | $380,000 |
| Mortgage | $2,294 | $1,982 |
| Property tax + insurance | $788 | $681 |
| HOA, median if the home has one | +$90/mo | +$111/mo |
| CDD, median if the home has one | +$117/mo | +$159/mo |
| House listings reporting an HOA | 54% | 86% |
| All listings reporting an HOA or condo fee | 68% | 90% |
| Listings with a CDD (of those stating it) | 8% | 32% |
| Price per square foot | $236 | $192 |
| Condo, median | $165,000 | $215,000 |
| Days on market | 31 | 48 |
| Sale vs. original asking | 96% | 96% |
| Homes for sale now | 3,913 | 2,880 |
| Built in the last 2 years | 8% | 12% |
| Private pool | 19% | 31% |
Orlando or Kissimmee?
Is it cheaper to live in Orlando or Kissimmee?
Kissimmee costs less to own. For a single-family home at each city's median sale price, the mortgage, property tax and insurance come to about $2,663 a month there, $419 (14%) less than Orlando at $3,082, under our assumptions. HOA and CDD fees come on top for homes that have them, so a home in a fee-heavy community can flip the answer. This compares the housing payment only, not utilities, groceries or other living costs.
Where do homes sell faster, Orlando or Kissimmee?
Orlando. Recent sales there took a median 31 days, against 48 in Kissimmee.
Which has more HOA and CDD fees?
68% of listings in Orlando report an HOA or condo association fee and 8% a CDD, against 90% and 32% in Kissimmee. Among single-family listings alone, 54% report an HOA in Orlando and 86% in Kissimmee. Newer master-planned communities usually carry both, which can add hundreds a month.
How did you calculate this?
Stellar MLS via Repliers closed sales and listings, one data point per address, updated 2026-10-11. The price is each city's median closed single-family sale. Monthly cost uses the site's standard assumptions: 20% down, 6.8% rate, 30-year loan, and new-owner property tax and insurance as a flat share of price, the same in both cities. Real insurance quotes vary by roof, age and flood zone. HOA and CDD medians are listed separately because only some homes pay them. Utilities and upkeep are not included.
Estimates from MLS data under stated assumptions, not quotes. Other comparisons: Tampa vs. Orlando, Tampa vs. Lakeland, Orlando vs. Lakeland, Kissimmee vs. St Cloud, Clermont vs. Winter Garden, Sanford vs. Deltona, St Petersburg vs. Clearwater, Clearwater vs. Largo.
Talk it through with our team.
Tell us what matters (commute, schools, budget, HOA tolerance) and we'll help you weigh it. Outside Tampa Bay, we'll connect you with a partner team we trust.