Homes under $500K in Kissimmee, FL

1,610 for sale · 5,127 homes listed · Updated September 29, 2026 · Page 53 of 103

• 3111 sun lake court b, Kissimmee 34747 Off market since Sep 2026 $254,900 · 3 bd · 2 ba · 1,484 sqft
• 2300 grasmere view parkway south, Kissimmee 34746 Off market since Jul 2026 $335,000 · 3 bd · 2 ba · 1,542 sqft
• 4721 clock tower drive 108, Kissimmee 34746 Off market since Aug 2026 $399,000 · 3 bd · 2 ba · 1,329 sqft
• 3028 parkway boulevard 308, Kissimmee 34747 Off market since Sep 2026 $249,000 · 2 bd · 2 ba · 937 sqft
• 3308 tranquil trail, Kissimmee 34747 Off market since Aug 2026 $370,000 · 3 bd · 3 ba · 1,365 sqft
• 3824 blue dasher drive, Kissimmee 34744 Off market since Sep 2026 $499,990 · 5 bd · 3 ba · 3,783 sqft
• 4529 alberto circle, Kissimmee 34746 Off market since Sep 2026 $285,000 · 3 bd · 3 ba · 1,295 sqft
• 2820 oakwater drive 2820, Kissimmee 34747 Off market since Sep 2026 $265,000 · 3 bd · 3 ba · 1,808 sqft
• 2737 north poinciana boulevard 92, Kissimmee 34746 Off market since Jul 2026 $219,989 · 3 bd · 2 ba · 1,287 sqft
• 9033 alba lane, Kissimmee 34747 Off market since Sep 2026 $334,500 · 3 bd · 3 ba · 1,530 sqft
• 1792 bull hill road, Kissimmee 34744 Off market since Jul 2026 $417,990 · 3 bd · 2 ba · 1,614 sqft
• 3100 parkway boulevard 521, Kissimmee 34747 Off market since Sep 2026 $160,000 · 1 bd · 1 ba · 648 sqft
• 557 hunter circle, Kissimmee 34758 Off market since Jul 2026 $179,500 · 2 bd · 2 ba · 1,038 sqft
• 3100 parkway boulevard 417, Kissimmee 34747 Off market since Sep 2026 $135,000 · 1 bd · 1 ba · 524 sqft
• 4778 vero beach place, Kissimmee 34746 Off market since Sep 2026 $259,900 · 3 bd · 3 ba · 1,286 sqft
• 1021 golfside court, Kissimmee 34741 Off market since Sep 2026 $327,900 · 3 bd · 2 ba · 1,659 sqft
• 1909 lakeview place, Kissimmee 34759 Off market since Sep 2026 $237,650 · 4 bd · 3 ba · 1,915 sqft
• 404 bar court, Kissimmee 34759 Off market since Sep 2026 $339,900 · 4 bd · 3 ba · 2,630 sqft
• 1406 kissimmee court, Kissimmee 34759 Off market since Sep 2026 $200,000 · 3 bd · 2 ba · 1,819 sqft
• 4840 romeo circle, Kissimmee 34746 Off market since Jul 2026 $468,000 · 4 bd · 3 ba · 1,914 sqft
• 402 quarry rock circle, Kissimmee 34758 Off market since Aug 2026 $405,000 · 5 bd · 3 ba · 2,271 sqft
• 464 danube drive, Kissimmee 34759 Off market since Jul 2026 $295,000 · 3 bd · 2 ba · 1,564 sqft
• 1418 sarasota drive, Kissimmee 34759 Off market since Sep 2026 $309,900 · 4 bd · 3 ba · 2,224 sqft
• 2015 spring shower circle, Kissimmee 34744 Off market since Sep 2026 $412,000 · 3 bd · 2 ba · 2,054 sqft
• 2652 corvette lane, Kissimmee 34746 Off market since Sep 2026 $264,900 · 2 bd · 3 ba · 1,350 sqft
• 1660 tropical palms circle, Kissimmee 34747 Off market since Sep 2026 $435,000 · 5 bd · 5 ba · 2,294 sqft
• 4004 santa maria drive 101, Kissimmee 34741 Off market since Sep 2026 $259,900 · 4 bd · 3 ba · 1,470 sqft
• 3079 tom sawyer drive, Kissimmee 34746 Off market since Sep 2026 $468,000 · 4 bd · 3 ba · 1,914 sqft
• 132 sandalwood drive, Kissimmee 34743 Off market since Sep 2026 $389,793 · 3 bd · 3 ba · 1,706 sqft
• 3240 casa del rey avenue, Kissimmee 34746 Off market since Jul 2026 $389,000 · 4 bd · 2 ba · 1,736 sqft
• 4015 venetian bay drive 104, Kissimmee 34741 Off market since Sep 2026 $229,000 · 3 bd · 2 ba · 1,296 sqft
• 1839 good neighbor loop, Kissimmee 34744 Off market since Sep 2026 $465,000 · 4 bd · 4 ba · 2,717 sqft
• 2422 dubai street, Kissimmee 34747 Off market since Aug 2026 $449,990 · 5 bd · 5 ba · 2,263 sqft
• 1724 ranger highlands road, Kissimmee 34744 Off market since Sep 2026 $363,000 · 4 bd · 2 ba · 1,910 sqft
• 1001 plantation drive c1, Kissimmee 34741 Off market since Jul 2026 $169,900 · 2 bd · 1 ba · 1,008 sqft
• 416 janice kay place, Kissimmee 34744 Off market since Aug 2026 $399,000 · 3 bd · 2 ba · 1,866 sqft
• 3078 shingle creek court, Kissimmee 34746 Off market since Sep 2026 $279,900 · 3 bd · 2 ba · 1,380 sqft
• 2211 san vittorino circle 102, Kissimmee 34741 Off market since Sep 2026 $239,500 · 4 bd · 3 ba · 1,470 sqft
• 1005 lake berkley drive, Kissimmee 34746 Off market since Sep 2026 $459,000 · 4 bd · 2 ba · 1,960 sqft
• 3609 anibal street, Kissimmee 34746 Off market since Sep 2026 $330,000 · 3 bd · 3 ba · 1,555 sqft
• 313 santa barbara lane, Kissimmee 34759 Off market since Sep 2026 $445,000 · 2 bd · 3 ba · 2,343 sqft
• 2665 trafalgar boulevard, Kissimmee 34758 Off market since Sep 2026 $489,999 · 4 bd · 4 ba · 2,423 sqft
• 5367 west irlo bronson memorial highway 4-100, Kissimmee 34746 Off market since Jul 2026 $69,900 · 1 bd · 1 ba · 231 sqft
• 5367 west irlo bronson memorial highway 4-111, Kissimmee 34746 Off market since Jul 2026 $69,900 · 1 bd · 1 ba · 231 sqft
• 1961 sawfish drive, Kissimmee 34759 Off market since Sep 2026 $264,000 · 3 bd · 2 ba · 1,785 sqft
• 1139 cambourne drive, Kissimmee 34758 Off market since Sep 2026 $279,000 · 4 bd · 3 ba · 2,166 sqft
• 4717 flagler beach way, Kissimmee 34746 Off market since Sep 2026 $304,900 · 3 bd · 3 ba · 1,286 sqft
• 1652 cross prairie parkway, Kissimmee 34744 Off market since Sep 2026 $399,900 · 4 bd · 4 ba · 2,537 sqft
• 4459 le reve court, Kissimmee 34746 Off market since Aug 2026 $464,900 · 4 bd · 4 ba · 1,752 sqft
• 2778 almaton loop 203, Kissimmee 34747 Off market since Sep 2026 $329,900 · 3 bd · 2 ba · 1,246 sqft