Homes under $500K in Kissimmee, FL

1,610 for sale · 5,127 homes listed · Updated September 29, 2026 · Page 51 of 103

• 4949 windermere avenue, Kissimmee 34746 Off market since Jul 2026 $495,000 · 4 bd · 3 ba · 1,914 sqft
• 4731 clock tower drive 203, Kissimmee 34746 Off market since Sep 2026 $265,000 · 2 bd · 2 ba · 1,196 sqft
• 5362 diplomat court 103, Kissimmee 34746 Off market since Aug 2026 $321,990 · 3 bd · 2 ba · 1,300 sqft
• 3011 bransbury court, Kissimmee 34747 Off market since Sep 2026 $445,000 · 4 bd · 3 ba · 2,230 sqft
• 8887 geneve court, Kissimmee 34747 Off market since Sep 2026 $395,000 · 5 bd · 5 ba · 2,265 sqft
• 639 mesilla drive, Kissimmee 34758 Off market since Sep 2026 $309,900 · 3 bd · 2 ba · 2,033 sqft
• 4811 brier rose lane, Kissimmee 34746 Off market since Aug 2026 $485,900 · 5 bd · 4 ba · 2,128 sqft
• 4888 romeo circle, Kissimmee 34746 Off market since Sep 2026 $439,900 · 4 bd · 3 ba · 1,914 sqft
• 8100 princess palm lane 203, Kissimmee 34747 Off market since Sep 2026 $213,000 · 3 bd · 2 ba · 1,268 sqft
• 301 bowfin drive, Kissimmee 34759 Off market since Sep 2026 $310,000 · 4 bd · 3 ba · 1,684 sqft
• 735 toulon drive, Kissimmee 34759 Off market since Aug 2026 $240,000 · 4 bd · 2 ba · 1,400 sqft
• 7546 sunville avenue, Kissimmee 34747 Off market since Sep 2026 $409,000 · 4 bd · 5 ba · 1,804 sqft
• 1676 tropical palms circle, Kissimmee 34747 Off market since Sep 2026 $434,900 · 4 bd · 5 ba · 2,145 sqft
• 5014 royal point avenue, Kissimmee 34746 Off market since Sep 2026 $489,000 · 4 bd · 3 ba · 2,532 sqft
• 4613 eaglet lane, Kissimmee 34746 Off market since Jul 2026 $355,000 · 3 bd · 2 ba · 1,802 sqft
• 1285 south south beach circle circle, Kissimmee 34746 Off market since Sep 2026 $201,000 · 3 bd · 3 ba · 1,468 sqft
• 4816 memories lane, Kissimmee 34746 Off market since Jul 2026 $469,900 · 4 bd · 3 ba · 1,914 sqft
• 1648 heart bar road, Kissimmee 34744 Off market since Sep 2026 $374,990 · 3 bd · 2 ba · 1,516 sqft
• 975 gascony court, Kissimmee 34759 Off market since Jul 2026 $279,999 · 3 bd · 2 ba · 1,761 sqft
• 225 starling court, Kissimmee 34759 Off market since Sep 2026 $339,900 · 4 bd · 2 ba · 1,770 sqft
• 663 jaguar court, Kissimmee 34759 Off market since Sep 2026 $254,500 · 3 bd · 2 ba · 1,308 sqft
• 2429 dubai street, Kissimmee 34747 Off market since Sep 2026 $499,000 · 5 bd · 5 ba · 2,263 sqft
• 2988 salted rim road, Kissimmee 34747 Off market since Sep 2026 $475,000 · 3 bd · 3 ba · 1,564 sqft
• 2427 dubai street, Kissimmee 34747 Off market since Sep 2026 $408,000 · 5 bd · 5 ba · 2,265 sqft
• 4504 alberto circle, Kissimmee 34746 Off market since Sep 2026 $289,999 · 3 bd · 3 ba · 1,295 sqft
• 3148 pequod place, Kissimmee 34746 Off market since Sep 2026 $469,900 · 4 bd · 3 ba · 1,914 sqft
• 9061 treasure trove lane 403, Kissimmee 34747 Off market since Sep 2026 $245,000 · 3 bd · 2 ba · 1,700 sqft
• 248 cheshire court, Kissimmee 34758 Off market since Sep 2026 $289,900 · 4 bd · 2 ba · 1,695 sqft
• 4577 alberto circle, Kissimmee 34746 Off market since Sep 2026 $345,000 · 4 bd · 3 ba · 1,636 sqft
• 2609 bright jewel street 2909, Kissimmee 34746 Off market since Sep 2026 $369,000 · 3 bd · 3 ba · 1,699 sqft
• 2433 huron circle, Kissimmee 34746 Off market since Sep 2026 $465,000 · 5 bd · 3 ba · 2,880 sqft
• 440 martigues drive, Kissimmee 34759 Off market since Aug 2026 $229,900 · 3 bd · 2 ba · 1,026 sqft
• 3180 paradox circle 102, Kissimmee 34746 Off market since Sep 2026 $310,000 · 2 bd · 2 ba · 1,186 sqft
• 2901 edenshire way 104, Kissimmee 34746 Off market since Sep 2026 $399,000 · 4 bd · 3 ba · 1,694 sqft
• 3060 pirates retreat court 309, Kissimmee 34747 Off market since Sep 2026 $214,999 · 3 bd · 2 ba · 1,700 sqft
• 4731 clock tower drive 104, Kissimmee 34746 Off market since Sep 2026 $275,000 · 2 bd · 2 ba · 1,126 sqft
• 8944 sydney avenue, Kissimmee 34747 Off market since Sep 2026 $404,900 · 5 bd · 5 ba · 2,263 sqft
• 1201 south beach circle, Kissimmee 34746 Off market since Sep 2026 $274,900 · 3 bd · 3 ba · 1,468 sqft
• 2208 antigua place 932, Kissimmee 34741 Off market since Sep 2026 $190,000 · 2 bd · 2 ba · 1,026 sqft
• 2430 tangier drive, Kissimmee 34747 Off market since Sep 2026 $490,000 · 5 bd · 5 ba · 2,263 sqft
• 3000 maingate lane 228, Kissimmee 34747 Off market since Sep 2026 $47,000 · 1 bd · 1 ba · 304 sqft
• 8502 crystal cove loop, Kissimmee 34747 Off market since Sep 2026 $254,900 · 3 bd · 3 ba · 1,291 sqft
• 1122 spaceport court, Kissimmee 34741 Off market since Jul 2026 $230,000 · 2 bd · 2 ba · 1,052 sqft
• 68 herring court, Kissimmee 34759 Off market since Sep 2026 $240,000 · 4 bd · 3 ba · 1,979 sqft
• 3083 tom sawyer drive, Kissimmee 34746 Off market since Sep 2026 $454,900 · 4 bd · 3 ba · 1,914 sqft
• 2952 beach palm avenue, Kissimmee 34747 Off market since Sep 2026 $464,000 · 6 bd · 5 ba · 3,291 sqft
• 2518 bowmer drive, Kissimmee 34744 Off market since Sep 2026 $359,900 · 3 bd · 2 ba · 1,523 sqft
• 8981 shine drive, Kissimmee 34747 Off market since Sep 2026 $313,000 · 4 bd · 3 ba · 1,694 sqft
• 2663 trafalgar boulevard, Kissimmee 34758 Off market since Sep 2026 $489,999 · 4 bd · 4 ba · 2,423 sqft
• 4963 pall mall street east, Kissimmee 34758 Off market since Sep 2026 $409,999 · 4 bd · 3 ba · 1,469 sqft