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.
63 luxury homes are for sale in Kissimmee, FL at $1,000,000 and up — median asking $1,420,000, the top listing at $4,300,000, $309 per square foot. 24 homes closed above $1,000,000 in the last 12 months at a median of $1,500,000. 11% 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 |
|---|---|---|---|---|
| 1196 Castle Pines Court | $4,300,000 | 6,930 | $620 | osceola county |
| 2780 Vickie Court | $3,200,000 | 9,881 | $324 | osceola county |
| 580 Muirfield Loop | $3,185,000 | 6,756 | $471 | Reunion West Villages North Kissimmee |
| 7829 Palmilla Court | $3,185,000 | 6,900 | $462 | Reunion West Villages North Kissimmee |
| 550 Muirfield Loop | $2,999,000 | 8,580 | $350 | Reunion West Villages North Kissimmee |
| 9054 Paolos Place | $2,950,000 | 6,811 | $433 | osceola county |
| 8398 Happy Trail | $2,495,000 | 3,667 | $680 | Happy Trails |
| 1063 Jack Nicklaus Court | $2,425,000 | 5,944 | $408 | Reunion West Fairways |
| 1051 Jack Nicklaus Court | $2,299,000 | 5,831 | $394 | Reunion West Fairways |
| 2794 Holiday Woods Drive | $2,250,000 | 2,970 | $758 | osceola county |
Where the luxury inventory is
| Community | Luxury listings | Median asking |
|---|---|---|
| Veranda Palms | 8 | $1,487,000 |
| Reunion West Villages North Kissimmee | 5 | $2,999,000 |
| Reunion West | 3 | $1,500,000 |
| Solara Resort Vacation Villas | 2 | $1,064,450 |
| Encore At Reunion | 1 | $1,239,000 |
| Moss Oaks | 1 | $1,400,000 |
| Happy Trails | 1 | $2,495,000 |
| Solara | 1 | $1,119,000 |
| Reunion West | 1 | $1,200,000 |
| Reunion West Village 3A Kissimmee | 1 | $1,225,000 |
| Formosa Gardens | 1 | $1,100,000 |
| Bellalago | 1 | $1,099,000 |
Luxury inventory by price
| Band | For sale | Share |
|---|---|---|
| $1,000,000–$1,500,000 | 36 | 57% |
| $1,500,000–$2,000,000 | 15 | 24% |
| $2,000,000–$3,000,000 | 8 | 13% |
| $3,000,000–$5,000,000 | 4 | 6% |
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 November 14, 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 3,127 homes for sale in Kissimmee and what $1M buys across Osceola County.