Homes under $500K in Kissimmee, FL

1,610 for sale · 5,127 homes listed · Updated September 29, 2026 · Page 50 of 103

• 275 chadworth drive, Kissimmee 34758 Active Under Contract $379,999 · 4 bd · 4 ba · 2,948 sqft
• 4303 summer breeze way, Kissimmee 34744 Active Under Contract $475,000 · 4 bd · 3 ba · 2,297 sqft
• 1165 seasons boulevard, Kissimmee 34746 Active Under Contract $465,000 · 5 bd · 4 ba · 2,286 sqft
• 8816 corcovado drive, Kissimmee 34747 Active Under Contract $408,000 · 5 bd · 6 ba · 2,622 sqft
• 1593 heritage crossing court, Kissimmee 34747 Active Under Contract $344,900 · 3 bd · 3 ba · 2,069 sqft
• 1809 king edward drive, Kissimmee 34744 Active Under Contract $419,000 · 3 bd · 2 ba · 1,919 sqft
• 429 fountainhead circle 121, Kissimmee 34741 Active Under Contract $175,000 · 2 bd · 2 ba · 967 sqft
• 8831 geneve court, Kissimmee 34747 Active Under Contract $409,000 · 5 bd · 5 ba · 2,263 sqft
• 1989 spring shower circle, Kissimmee 34744 Active Under Contract $399,000 · 3 bd · 2 ba · 2,087 sqft
• 233 magical way, Kissimmee 34744 Active Under Contract $395,000 · 4 bd · 3 ba · 2,132 sqft
• 2971 banana palm drive, Kissimmee 34747 Active Under Contract $334,900 · 4 bd · 3 ba · 1,902 sqft
• 7661 sand pierre court, Kissimmee 34747 Active Under Contract $399,000 · 2 bd · 2 ba · 1,437 sqft
• 8816 dunes court 103, Kissimmee 34747 Active Under Contract $187,500 · 2 bd · 2 ba · 1,048 sqft
• 247 competition drive, Kissimmee 34743 Active Under Contract $395,995 · 3 bd · 2 ba · 1,790 sqft
• 21 lind avenue, Kissimmee 34744 Active Under Contract $249,900 · 3 bd · 2 ba · 1,210 sqft
• 275 azalea drive, Kissimmee 34743 Active Under Contract $259,900 · 2 bd · 1 ba · 759 sqft
• 3002 limbo lane 103, Kissimmee 34746 Active Under Contract $245,000 · 2 bd · 2 ba · 1,159 sqft
• 74 lake villa way, Kissimmee 34743 Active Under Contract $145,000 · 1 bd · 1 ba · 595 sqft
• 1861 pine needle trail, Kissimmee 34746 Active Under Contract $499,990 · 4 bd · 3 ba · 2,904 sqft
• 4731 clock tower drive #203, Kissimmee 34746 Active Under Contract $265,000 · 2 bd · 2 ba · 1,196 sqft
• 8827 grand palms circle #b, Kissimmee 34747 Active Under Contract $219,800 · 3 bd · 2 ba · 1,222 sqft
• 4754 vero beach place, Kissimmee 34746 Active Under Contract $229,900 · 3 bd · 3 ba · 1,286 sqft
• 2908 banana palm drive, Kissimmee 34747 Active Under Contract $499,000 · 5 bd · 5 ba · 3,081 sqft
• 1150 indian ridge trail east, Kissimmee 34747 Active Under Contract $349,900 · 3 bd · 2 ba · 1,636 sqft
• 3050 china berry court, Kissimmee 34746 Active Under Contract $235,000 · 4 bd · 2 ba · 2,013 sqft
• 2735 summer retreat lane, Kissimmee 34744 Active Under Contract $325,000 · 2 bd · 2 ba · 1,559 sqft
• 352 blue lake circle, Kissimmee 34758 Active Under Contract $399,900 · 5 bd · 3 ba · 2,836 sqft
• 2777 green meadow circle, Kissimmee 34741 Active Under Contract $350,000 · 3 bd · 2 ba · 1,738 sqft
• 1805 michigan avenue #d, Kissimmee 34744 Active Under Contract $124,000 · 2 bd · 2 ba · 1,118 sqft
• 3108 landsend court, Kissimmee 34743 Active Under Contract $220,000 · 3 bd · 2 ba · 1,277 sqft
• 1708 casuarina lane, Kissimmee 34744 Active Under Contract $355,000 · 3 bd · 2 ba · 1,502 sqft
• 2487 white lilly drive, Kissimmee 34747 Active Under Contract $350,000 · 4 bd · 2 ba · 1,828 sqft
• 419 allspice court, Kissimmee 34759 Active Under Contract $189,800 · 3 bd · 2 ba · 1,951 sqft
• 1495 skyline drive, Kissimmee 34744 Active Under Contract $460,000 · 3 bd · 2 ba · 2,094 sqft
• 2606 lodi circle 105, Kissimmee 34746 Off market since Sep 2026 $225,000 · 3 bd · 2 ba · 1,296 sqft
• 2166 fleming mist place, Kissimmee 34747 Off market since Aug 2026 $469,800 · 5 bd · 5 ba · 2,294 sqft
• 4546 alberto circle, Kissimmee 34746 Off market since Sep 2026 $325,000 · 3 bd · 3 ba · 1,295 sqft
• 602 mesilla drive, Kissimmee 34758 Off market since Sep 2026 $289,900 · 3 bd · 2 ba · 1,771 sqft
• 2302 silver palm drive 301, Kissimmee 34747 Off market since Sep 2026 $245,000 · 3 bd · 2 ba · 1,402 sqft
• 947 emerald green court, Kissimmee 34746 Off market since Sep 2026 $419,000 · 4 bd · 4 ba · 2,246 sqft
• 1310 seasons boulevard, Kissimmee 34746 Off market since Sep 2026 $485,000 · 4 bd · 3 ba · 1,940 sqft
• 1696 tropical palms circle, Kissimmee 34747 Off market since Sep 2026 $475,000 · 4 bd · 5 ba · 2,145 sqft
• 210 majors lane b, Kissimmee 34743 Off market since Sep 2026 $265,000 · 3 bd · 3 ba · 1,270 sqft
• 7663 recife drive, Kissimmee 34747 Off market since Sep 2026 $405,000 · 3 bd · 4 ba · 2,268 sqft
• 3208 oyster lane, Kissimmee 34747 Off market since Sep 2026 $312,500 · 4 bd · 3 ba · 1,694 sqft
• 4211 little owl lane, Kissimmee 34746 Off market since Sep 2026 $395,000 · 4 bd · 2 ba · 1,854 sqft
• 8711 rockingham terrace a, Kissimmee 34747 Off market since Aug 2026 $237,000 · 3 bd · 2 ba · 1,357 sqft
• 7947 golden pond circle, Kissimmee 34747 Off market since Sep 2026 $459,000 · 4 bd · 2 ba · 1,643 sqft
• 2955 banana palm drive, Kissimmee 34747 Off market since Sep 2026 $379,000 · 4 bd · 3 ba · 1,902 sqft
• 3180 paradoux circle 205, Kissimmee 34746 Off market since Sep 2026 $279,000 · 2 bd · 2 ba · 1,126 sqft