Homes under $500K in Kissimmee, FL

1,610 for sale · 5,127 homes listed · Updated September 29, 2026 · Page 49 of 103

• 833 oglethorpe court, Kissimmee 34758 Active Under Contract $140,000 · 3 bd · 2 ba · 1,422 sqft
• 4148 big valley boulevard, Kissimmee 34746 Active Under Contract $345,000 · 3 bd · 3 ba · 1,583 sqft
• 1513 indian oaks trail, Kissimmee 34747 Active Under Contract $380,000 · 4 bd · 2 ba · 1,536 sqft
• 2529 jasmine trace drive, Kissimmee 34758 Active Under Contract $449,000 · 4 bd · 3 ba · 2,384 sqft
• 145 dorchester court, Kissimmee 34758 Active Under Contract $216,900 · 3 bd · 2 ba · 1,072 sqft
• 2135 balboa way, Kissimmee 34741 Active Under Contract $254,900 · 2 bd · 3 ba · 1,418 sqft
• 124 citrine loop, Kissimmee 34758 Active Under Contract $334,500 · 4 bd · 2 ba · 1,725 sqft
• 1795 partin terrace road south, Kissimmee 34744 Active Under Contract $389,000 · 4 bd · 2 ba · 1,730 sqft
• 815 assembly court, Kissimmee 34747 Active Under Contract $299,900 · 3 bd · 3 ba · 1,553 sqft
• 2440 sweetwater club circle 40, Kissimmee 34746 Active Under Contract $229,900 · 3 bd · 2 ba · 1,220 sqft
• 3500 suzette drive, Kissimmee 34746 Active Under Contract $224,950 · 3 bd · 2 ba · 1,285 sqft
• 36 bradford court, Kissimmee 34758 Active Under Contract $300,000 · 4 bd · 2 ba · 1,828 sqft
• 2848 oconnell drive, Kissimmee 34741 Active Under Contract $339,000 · 3 bd · 2 ba · 2,245 sqft
• 1896 flora pass place, Kissimmee 34747 Active Under Contract $420,000 · 2 bd · 2 ba · 1,557 sqft
• 2714 sample street, Kissimmee 34744 Active Under Contract $175,000 · 2 bd · 1 ba · 648 sqft
• 2313 pebble brook road, Kissimmee 34741 Active Under Contract $309,000 · 3 bd · 2 ba · 1,233 sqft
• 2560 amati drive, Kissimmee 34741 Active Under Contract $295,000 · 3 bd · 3 ba · 1,528 sqft
• 1124 dara cay drive, Kissimmee 34741 Active Under Contract $290,000 · 4 bd · 2 ba · 1,980 sqft
• 138 hollyhock court, Kissimmee 34743 Active Under Contract $349,900 · 3 bd · 2 ba · 1,642 sqft
• 9011 murano mews court, Kissimmee 34747 Active Under Contract $400,000 · 4 bd · 3 ba · 1,581 sqft
• 1016 lester ridge court, Kissimmee 34747 Active Under Contract $330,000 · 3 bd · 2 ba · 1,779 sqft
• 2658 tranquility way, Kissimmee 34746 Active Under Contract $445,000 · 4 bd · 4 ba · 2,095 sqft
• 8803 parliament court, Kissimmee 34747 Active Under Contract $290,000 · 3 bd · 2 ba · 1,363 sqft
• 1346 dunbarton court, Kissimmee 34758 Active Under Contract $259,990 · 3 bd · 2 ba · 1,600 sqft
• 2817 almaton loop 402, Kissimmee 34747 Active Under Contract $275,000 · 2 bd · 2 ba · 1,081 sqft
• 4833 romeo circle, Kissimmee 34746 Active Under Contract $439,900 · 4 bd · 3 ba · 1,914 sqft
• 8060 santee drive, Kissimmee 34747 Active Under Contract $499,000 · 5 bd · 4 ba · 2,136 sqft
• 2212 grand cayman court 1617, Kissimmee 34741 Active Under Contract $189,900 · 2 bd · 2 ba · 1,026 sqft
• 906 assembly court, Kissimmee 34747 Active Under Contract $315,000 · 4 bd · 3 ba · 1,862 sqft
• 2721 cecile street, Kissimmee 34741 Active Under Contract $327,000 · 3 bd · 2 ba · 1,656 sqft
• 3805 laurel view drive, Kissimmee 34744 Active Under Contract $350,000 · 3 bd · 2 ba · 1,722 sqft
• 918 brack street, Kissimmee 34744 Active Under Contract $235,000 · 2 bd · 2 ba · 1,008 sqft
• 110 tangerine court, Kissimmee 34743 Active Under Contract $260,000 · 2 bd · 1 ba · 899 sqft
• 126 dahlia drive, Kissimmee 34743 Active Under Contract $270,000 · 3 bd · 2 ba · 1,434 sqft
• 3266 peace pipe drive, Kissimmee 34746 Active Under Contract $269,000 · 2 bd · 2 ba · 1,123 sqft
• 2746 tropical lake drive, Kissimmee 34741 Active Under Contract $144,900 · 3 bd · 2 ba · 1,152 sqft
• 1096 carrie lane, Kissimmee 34741 Active Under Contract $199,000 · 3 bd · 2 ba · 1,296 sqft
• 380 buttonwood drive, Kissimmee 34743 Active Under Contract $415,000 · 3 bd · 2 ba · 1,593 sqft
• 5370 diplomat court 108, Kissimmee 34746 Active Under Contract $324,900 · 4 bd · 3 ba · 1,694 sqft
• 2721 eagle cliff drive, Kissimmee 34746 Active Under Contract $334,900 · 3 bd · 2 ba · 1,904 sqft
• 8849 candy palm road, Kissimmee 34747 Active Under Contract $355,000 · 4 bd · 3 ba · 1,902 sqft
• 8060 white crane court, Kissimmee 34747 Active Under Contract $454,900 · 4 bd · 2 ba · 1,782 sqft
• 1506 jenni lee court, Kissimmee 34744 Active Under Contract $459,000 · 4 bd · 3 ba · 2,050 sqft
• 664 brockton drive, Kissimmee 34758 Active Under Contract $300,000 · 5 bd · 3 ba · 2,206 sqft
• 2782 roccella court, Kissimmee 34747 Active Under Contract $480,000 · 4 bd · 2 ba · 1,694 sqft
• 2608 lodi circle 104, Kissimmee 34746 Active Under Contract $205,000 · 3 bd · 2 ba · 1,296 sqft
• 4470 seymour street, Kissimmee 34744 Active Under Contract $324,900 · 2 bd · 2 ba · 1,248 sqft
• 2666 willow glen circle, Kissimmee 34744 Active Under Contract $429,000 · 4 bd · 3 ba · 2,415 sqft
• 3026 bransbury court, Kissimmee 34747 Active Under Contract $460,000 · 3 bd · 2 ba · 1,712 sqft
• 3137 bear path, Kissimmee 34746 Active Under Contract $425,000 · 3 bd · 2 ba · 1,377 sqft