Luxury Homes for Sale in Kissimmee, FL
The luxury market in Kissimmee starts at $1,000,000. This page is every active listing at that level, refreshed nightly from the MLS, with what has actually closed, where the inventory sits and how long it takes to sell. For the wider picture see luxury communities in Osceola County.
93 luxury homes are for sale in Kissimmee, FL at $1,000,000 and up — median asking $1,500,000, the top listing at $15,000,000, $300 per square foot. 24 homes closed above $1,000,000 in the last 12 months at a median of $1,500,000. 5% of the luxury inventory is waterfront; 6% is new construction. Median days on market: 91.
Newest luxury listings in Kissimmee
The most expensive homes for sale in Kissimmee
| Listing | Asking | Sq ft | $ / sq ft | Community |
|---|---|---|---|---|
| 7625 Sinclair Road | $15,000,000 | 2,500 | $6,000 | osceola county |
| 8590 Apache Trail | $5,650,000 | 11,138 | $507 | osceola county |
| 1400 Harrelson Lane | $5,500,000 | 1,200 | $4,583 | osceola county |
| High Plains Lane | $5,000,000 | — | — | osceola county |
| 4250 High Plains Lane | $5,000,000 | — | — | osceola county |
| 984 Jack Nicklaus Court | $4,900,000 | 8,407 | $583 | osceola county |
| 4281 Timber Lane | $4,800,000 | — | — | High Plains |
| S Goodman Road | $4,800,000 | — | — | osceola county |
| 1196 Castle Pines Court | $4,300,000 | 6,930 | $620 | Reunion West Village 3A Kissimmee |
| 1770 Business Center Lane | $3,950,000 | 25,200 | $157 | Poinciana Commercenter |
Where the luxury inventory is
| Community | Luxury listings | Median asking |
|---|---|---|
| Veranda Palms | 8 | $1,487,000 |
| Reunion West Village 3A Kissimmee | 4 | $1,369,999 |
| Reunion West Villages North Kissimmee | 3 | $3,185,000 |
| Solara Resort Vacation Villas | 2 | $1,069,450 |
| Reunion West | 2 | $1,500,000 |
| Reunion West | 2 | $1,350,000 |
| Poinciana Commercenter | 1 | $3,950,000 |
| Reunion Bears Den Reunion West | 1 | $1,725,000 |
| South Florida Railroad Co | 1 | $3,200,000 |
| High Plains | 1 | $4,800,000 |
| Encore At Reunion | 1 | $1,239,000 |
| Happy Trails | 1 | $2,495,000 |
Luxury inventory by price
| Band | For sale | Share |
|---|---|---|
| $1,000,000–$1,500,000 | 44 | 47% |
| $1,500,000–$2,000,000 | 21 | 23% |
| $2,000,000–$3,000,000 | 12 | 13% |
| $3,000,000–$5,000,000 | 11 | 12% |
| $5,000,000+ | 5 | 5% |
How to read this
Luxury is defined here as asking prices at or above $1,000,000. Counts, medians and closings come from active and closed MLS listings as of October 24, 2026; closings are the trailing 12 months. Listings appear courtesy of the listing brokerage under IDX rules; information deemed reliable but not guaranteed. See also all 3,104 homes for sale in Kissimmee and what $1M buys across Osceola County.