Homes under $500K in Kissimmee, FL

1,580 for sale · 5,069 homes listed · Updated September 29, 2026 · Page 41 of 102

• 2468 caravelle circle, Kissimmee 34746 Active Under Contract $314,000 · 4 bd · 3 ba · 1,512 sqft
• 8017 king palm circle, Kissimmee 34747 Active Under Contract $470,000 · 5 bd · 4 ba · 2,255 sqft
• 2926 foraker way, Kissimmee 34758 Active Under Contract $340,000 · 3 bd · 2 ba · 1,825 sqft
• 3000 maingate lane 218, Kissimmee 34747 Active Under Contract $45,000 · 1 bd · 1 ba · 304 sqft
• 1433 riverboat drive, Kissimmee 34744 Active Under Contract $365,000 · 4 bd · 2 ba · 1,846 sqft
• 3111 rio grande trail 3111, Kissimmee 34741 Active Under Contract $185,000 · 3 bd · 2 ba · 1,375 sqft
• 2788 almaton loop 402, Kissimmee 34747 Active Under Contract $240,000 · 2 bd · 2 ba · 1,081 sqft
• 851 assembly court, Kissimmee 34747 Active Under Contract $249,000 · 3 bd · 3 ba · 1,688 sqft
• 3141 paradox circle 404, Kissimmee 34746 Active Under Contract $287,000 · 2 bd · 2 ba · 1,194 sqft
• 7838 spectrum drive, Kissimmee 34747 Active Under Contract $347,000 · 3 bd · 3 ba · 1,704 sqft
• 4617 sparkling shell avenue, Kissimmee 34746 Active Under Contract $275,000 · 3 bd · 3 ba · 1,683 sqft
• 591 highlands hammock drive, Kissimmee 34759 Active Under Contract $375,000 · 2 bd · 2 ba · 2,078 sqft
• 2944 sunset vista boulevard, Kissimmee 34747 Active Under Contract $415,000 · 4 bd · 2 ba · 1,701 sqft
• 8842 grand palms circle b, Kissimmee 34747 Active Under Contract $229,000 · 3 bd · 2 ba · 1,245 sqft
• 2420 painter lane, Kissimmee 34741 Active Under Contract $335,000 · 3 bd · 2 ba · 1,900 sqft
• 214 taranto way, Kissimmee 34758 Active Under Contract $250,000 · 4 bd · 4 ba · 2,871 sqft
• 7979 magnolia bend court, Kissimmee 34747 Active Under Contract $430,000 · 4 bd · 3 ba · 1,975 sqft
• 415 francisco way, Kissimmee 34758 Active Under Contract $318,000 · 4 bd · 2 ba · 1,872 sqft
• 677 via corso court, Kissimmee 34759 Active Under Contract $429,999 · 3 bd · 3 ba · 2,235 sqft
• 405 balboa drive, Kissimmee 34759 Active Under Contract $365,000 · 3 bd · 3 ba · 2,350 sqft
• 8881 rhodes street, Kissimmee 34747 Active Under Contract $499,000 · 6 bd · 5 ba · 3,142 sqft
• 8979 california palm road, Kissimmee 34747 Active Under Contract $305,000 · 4 bd · 3 ba · 1,902 sqft
• 1998 key bay trail 524, Kissimmee 34747 Active Under Contract $365,000 · 2 bd · 2 ba · 1,583 sqft
• 4914 windermere avenue, Kissimmee 34746 Active Under Contract $479,000 · 4 bd · 3 ba · 1,914 sqft
• 8033 acadia estates court, Kissimmee 34747 Active Under Contract $489,000 · 6 bd · 5 ba · 2,681 sqft
• 115 toluca drive, Kissimmee 34743 Active Under Contract $327,000 · 3 bd · 2 ba · 1,175 sqft
• 2620 palisade boulevard, Kissimmee 34741 Active Under Contract $375,000 · 3 bd · 3 ba · 2,120 sqft
• 431 cart court, Kissimmee 34759 Active Under Contract $215,900 · 3 bd · 2 ba · 1,252 sqft
• 4004 san gallo drive 107, Kissimmee 34741 Active Under Contract $220,000 · 4 bd · 3 ba · 1,470 sqft
• 114 cassino way, Kissimmee 34758 Active Under Contract $280,000 · 3 bd · 2 ba · 1,416 sqft
• 2624 lodi circle 12-105, Kissimmee 34746 Active Under Contract $230,000 · 3 bd · 2 ba · 1,286 sqft
• 2619 peace of mind avenue, Kissimmee 34744 Active Under Contract $460,000 · 4 bd · 3 ba · 2,109 sqft
• 2950 lucayan harbour circle 105, Kissimmee 34746 Active Under Contract $309,900 · 4 bd · 3 ba · 1,694 sqft
• 271 la paz drive, Kissimmee 34743 Active Under Contract $316,990 · 3 bd · 2 ba · 1,065 sqft
• 2756 big timber drive, Kissimmee 34758 Active Under Contract $299,000 · 3 bd · 2 ba · 1,493 sqft
• 1617 perdido court, Kissimmee 34759 Active Under Contract $230,000 · 3 bd · 2 ba · 1,368 sqft
• 2947 langdon lane south, Kissimmee 34741 Active Under Contract $305,000 · 3 bd · 3 ba · 1,749 sqft
• 3113 brasilia avenue, Kissimmee 34747 Active Under Contract $399,000 · 3 bd · 4 ba · 2,181 sqft
• 2908 eldiente way, Kissimmee 34758 Active Under Contract $310,000 · 4 bd · 3 ba · 2,099 sqft
• 1941 partin terrace road, Kissimmee 34744 Active Under Contract $499,777 · 4 bd · 4 ba · 2,787 sqft
• 4723 marcos circle, Kissimmee 34758 Active Under Contract $250,000 · 3 bd · 2 ba · 1,525 sqft
• 2058 rome drive, Kissimmee 34747 Active Under Contract $435,000 · 5 bd · 5 ba · 2,263 sqft
• 1381 del mar drive, Kissimmee 34759 Active Under Contract $340,000 · 3 bd · 3 ba · 2,002 sqft
• 4633 fairy tale circle, Kissimmee 34746 Active Under Contract $419,000 · 3 bd · 3 ba · 1,950 sqft
• 2346 silver palm drive, Kissimmee 34747 Active Under Contract $329,900 · 3 bd · 3 ba · 1,440 sqft
• 410 rosland drive, Kissimmee 34741 Active Under Contract $344,900 · 4 bd · 2 ba · 1,829 sqft
• 538 lakeview court, Kissimmee 34759 Active Under Contract $220,000 · 3 bd · 2 ba · 1,349 sqft
• 231 strathmore circle, Kissimmee 34744 Active Under Contract $459,900 · 4 bd · 2 ba · 2,262 sqft
• 2002 royal bay boulevard 135, Kissimmee 34746 Active Under Contract $225,000 · 3 bd · 2 ba · 1,350 sqft
• 7955 magnolia bend court, Kissimmee 34747 Active Under Contract $499,000 · 5 bd · 4 ba · 2,618 sqft