Homes under $500K in Kissimmee, FL

1,610 for sale · 5,127 homes listed · Updated September 29, 2026 · Page 86 of 103

• 2169 remington pointe boulevard, Kissimmee 34743 Off market since Sep 2026 $379,900 · 3 bd · 2 ba · 1,466 sqft
• 1602 tail feather drive, Kissimmee 34746 Off market since Sep 2026 $367,000 · 3 bd · 3 ba · 2,005 sqft
• 1204 south beach circle, Kissimmee 34746 Off market since Sep 2026 $325,000 · 3 bd · 3 ba · 1,468 sqft
• 1455 eldra drive, Kissimmee 34744 Off market since Sep 2026 $325,000 · 2 bd · 3 ba · 1,288 sqft
• 7593 gathering drive 504, Kissimmee 34747 Off market since Sep 2026 $340,000 · 2 bd · 2 ba · 1,430 sqft
• 4751 clock tower drive 107, Kissimmee 34746 Off market since Sep 2026 $283,900 · 2 bd · 2 ba · 1,186 sqft
• 4069 marina isle drive, Kissimmee 34746 Off market since Sep 2026 $365,000 · 4 bd · 2 ba · 2,184 sqft
• 3875 golden knot drive, Kissimmee 34746 Off market since Jul 2026 $435,000 · 4 bd · 2 ba · 2,165 sqft
• 2253 rita lane, Kissimmee 34744 Off market since Sep 2026 $361,990 · 3 bd · 3 ba · 1,489 sqft
• 5059 worchester drive, Kissimmee 34746 Off market since Jul 2026 $470,820 · 4 bd · 3 ba · 2,584 sqft
• 4365 curacao place, Kissimmee 34758 Off market since Jul 2026 $227,240 · 2 bd · 2 ba · 1,562 sqft
• 984 derbyshire drive, Kissimmee 34758 Off market since Sep 2026 $350,000 · 4 bd · 3 ba · 2,215 sqft
• 1994 spring shower circle, Kissimmee 34744 Off market since Sep 2026 $435,000 · 3 bd · 2 ba · 2,056 sqft
• 4642 tribute trail, Kissimmee 34746 Off market since Sep 2026 $324,900 · 3 bd · 3 ba · 1,797 sqft
• 842 gila way, Kissimmee 34759 Off market since Jul 2026 $270,000 · 3 bd · 2 ba · 1,744 sqft
• 82 lakepointe circle 82, Kissimmee 34743 Off market since Sep 2026 $321,000 · 3 bd · 3 ba · 1,471 sqft
• 3028 camino real drive south, Kissimmee 34744 Off market since Sep 2026 $439,995 · 4 bd · 2 ba · 2,259 sqft
• 1855 egret meadows avenue, Kissimmee 34744 Off market since Sep 2026 $370,000 · 3 bd · 2 ba · 1,672 sqft
• 4840 romeo circle, Kissimmee 34746 Off market since Jul 2026 $458,000 · 4 bd · 3 ba · 1,914 sqft
• 8563 bay lilly loop, Kissimmee 34747 Off market since Sep 2026 $310,000 · 3 bd · 3 ba · 1,295 sqft
• 2256 portrait street, Kissimmee 34758 Off market since Sep 2026 $297,500 · 3 bd · 3 ba · 1,407 sqft
• 3232 herons point circle, Kissimmee 34741 Off market since Sep 2026 $495,000 · 4 bd · 3 ba · 2,085 sqft
• 2249 rita lane, Kissimmee 34744 Off market since Sep 2026 $349,990 · 3 bd · 3 ba · 1,489 sqft
• 7604 stone creek trail, Kissimmee 34747 Off market since Sep 2026 $369,000 · 3 bd · 3 ba · 1,793 sqft
• 1515 carey palm circle, Kissimmee 34747 Off market since Sep 2026 $389,900 · 3 bd · 4 ba · 1,962 sqft
• 4337 quote street, Kissimmee 34746 Off market since Sep 2026 $444,000 · 4 bd · 3 ba · 1,914 sqft
• 202 eden lane b, Kissimmee 34743 Off market since Sep 2026 $214,900 · 2 bd · 3 ba · 1,088 sqft
• 2231 cascades boulevard 304, Kissimmee 34741 Off market since Sep 2026 $134,000 · 1 bd · 1 ba · 635 sqft
• 3603 light port way, Kissimmee 34746 Off market since Sep 2026 $379,000 · 4 bd · 3 ba · 2,156 sqft
• 760 palaiseau court, Kissimmee 34759 Off market since Sep 2026 $280,000 · 4 bd · 2 ba · 2,088 sqft
• 5782 le marin way, Kissimmee 34758 Off market since Sep 2026 $359,900 · 3 bd · 2 ba · 1,451 sqft
• 632 bittern court, Kissimmee 34759 Off market since Sep 2026 $359,900 · 5 bd · 3 ba · 2,530 sqft
• 104 turin way, Kissimmee 34758 Off market since Sep 2026 $249,900 · 3 bd · 2 ba · 1,420 sqft
• 2487 white lilly drive, Kissimmee 34747 Off market since Sep 2026 $350,000 · 4 bd · 2 ba · 1,828 sqft
• 2904 grafton drive, Kissimmee 34741 Off market since Sep 2026 $310,000 · 3 bd · 3 ba · 2,013 sqft
• 2182 fleming mist place, Kissimmee 34747 Off market since Sep 2026 $475,000 · 4 bd · 5 ba · 2,145 sqft
• 7901 putting way, Kissimmee 34747 Off market since Sep 2026 $379,900 · 3 bd · 3 ba · 1,659 sqft
• 1562 carey palm circle, Kissimmee 34747 Off market since Sep 2026 $395,000 · 3 bd · 4 ba · 1,962 sqft
• 1888 gobi drive, Kissimmee 34747 Off market since Sep 2026 $499,900 · 6 bd · 5 ba · 3,142 sqft
• 2918 sunset vista boulevard, Kissimmee 34747 Off market since Sep 2026 $399,000 · 4 bd · 2 ba · 1,701 sqft
• 4779 warrior lane, Kissimmee 34746 Off market since Sep 2026 $304,999 · 2 bd · 2 ba · 1,330 sqft
• 4783 warrior lane, Kissimmee 34746 Off market since Sep 2026 $379,999 · 3 bd · 2 ba · 1,700 sqft
• 2026 estancia circle a, Kissimmee 34741 Off market since Sep 2026 $239,000 · 2 bd · 2 ba · 1,260 sqft
• 7740 sandy ridge drive 228, Kissimmee 34747 Off market since Sep 2026 $390,000 · 5 bd · 5 ba · 2,703 sqft
• 3109 seaview castle drive, Kissimmee 34746 Off market since Sep 2026 $330,000 · 2 bd · 3 ba · 1,112 sqft
• 766 carmel lane, Kissimmee 34759 Off market since Sep 2026 $399,000 · 3 bd · 3 ba · 2,320 sqft
• 610 notre dame way, Kissimmee 34759 Off market since Sep 2026 $307,000 · 4 bd · 3 ba · 2,162 sqft
• 725 robin court, Kissimmee 34759 Off market since Sep 2026 $264,900 · 3 bd · 2 ba · 1,808 sqft
• 3000 laurel park lane 207, Kissimmee 34741 Off market since Sep 2026 $270,000 · 3 bd · 2 ba · 1,779 sqft
• 2806 plymouth place, Kissimmee 34741 Off market since Sep 2026 $367,000 · 3 bd · 3 ba · 1,838 sqft