Homes under $500K in Kissimmee, FL

1,580 for sale · 5,069 homes listed · Updated September 29, 2026 · Page 42 of 102

• 5111 staniard drive, Kissimmee 34746 Active Under Contract $235,000 · 2 bd · 3 ba · 1,304 sqft
• 3016 parkway boulevard 303, Kissimmee 34747 Active Under Contract $158,000 · 2 bd · 2 ba · 937 sqft
• 3001 laurel park lane 207, Kissimmee 34741 Active Under Contract $259,900 · 3 bd · 2 ba · 1,779 sqft
• 7675 comrow street 402, Kissimmee 34747 Active Under Contract $249,900 · 2 bd · 2 ba · 1,081 sqft
• 4943 royal point avenue, Kissimmee 34746 Active Under Contract $445,000 · 5 bd · 3 ba · 2,660 sqft
• 2924 caribbean soul drive, Kissimmee 34747 Active Under Contract $353,000 · 3 bd · 3 ba · 1,545 sqft
• 2780 rialto court, Kissimmee 34746 Active Under Contract $434,000 · 4 bd · 3 ba · 2,430 sqft
• 705 harland court, Kissimmee 34758 Active Under Contract $259,900 · 4 bd · 2 ba · 1,592 sqft
• 1980 summer court, Kissimmee 34744 Active Under Contract $499,999 · 3 bd · 3 ba · 2,687 sqft
• 3154 yellow lantana lane, Kissimmee 34747 Active Under Contract $290,000 · 3 bd · 3 ba · 1,295 sqft
• 3410 oakmont court, Kissimmee 34746 Active Under Contract $484,000 · 3 bd · 3 ba · 2,741 sqft
• 3196 stonehurst circle, Kissimmee 34741 Active Under Contract $415,000 · 3 bd · 2 ba · 1,814 sqft
• 1813 daniels street, Kissimmee 34746 Active Under Contract $225,000 · 2 bd · 4 ba · 1,428 sqft
• 3390 bellezza court, Kissimmee 34746 Active Under Contract $299,000 · 3 bd · 3 ba · 2,019 sqft
• 2634 autumn creek circle, Kissimmee 34747 Active Under Contract $474,900 · 4 bd · 2 ba · 1,778 sqft
• 138 madiera beach boulevard, Kissimmee 34746 Active Under Contract $399,900 · 4 bd · 3 ba · 1,940 sqft
• 3231 cupid pl place, Kissimmee 34747 Active Under Contract $299,999 · 4 bd · 3 ba · 1,694 sqft
• 4770 tribute trail, Kissimmee 34746 Active Under Contract $295,900 · 3 bd · 3 ba · 1,674 sqft
• 15201 indian creek drive b, Kissimmee 34759 Active Under Contract $139,900 · 2 bd · 2 ba · 981 sqft
• 1309 lombardi court, Kissimmee 34759 Active Under Contract $280,000 · 2 bd · 2 ba · 1,366 sqft
• 1807 good neighbor loop, Kissimmee 34744 Active Under Contract $440,000 · 4 bd · 3 ba · 2,151 sqft
• 635 lake marion golf resort, Kissimmee 34759 Active Under Contract $120,000 · 2 bd · 2 ba · 784 sqft
• 545 genoa drive, Kissimmee 34759 Active Under Contract $375,000 · 2 bd · 2 ba · 2,038 sqft
• 3104 stonehurst circle, Kissimmee 34741 Active Under Contract $389,900 · 3 bd · 2 ba · 1,650 sqft
• 4409 blackbird street, Kissimmee 34746 Active Under Contract $310,000 · 3 bd · 2 ba · 1,560 sqft
• 4518 alaqua trail, Kissimmee 34746 Active Under Contract $374,900 · 4 bd · 2 ba · 1,546 sqft
• 136 puelba lane, Kissimmee 34743 Active Under Contract $310,000 · 4 bd · 3 ba · 1,856 sqft
• 2781 almaton loop 401, Kissimmee 34747 Active Under Contract $289,500 · 3 bd · 2 ba · 1,246 sqft
• 1838 tohoqua boulevard, Kissimmee 34744 Active Under Contract $309,900 · 3 bd · 3 ba · 1,600 sqft
• 5316 coral vine lane, Kissimmee 34758 Active Under Contract $365,000 · 4 bd · 3 ba · 2,384 sqft
• 7624 sand pierre court, Kissimmee 34747 Active Under Contract $319,000 · 2 bd · 2 ba · 1,437 sqft
• 1491 august gray drive, Kissimmee 34744 Active Under Contract $394,900 · 4 bd · 3 ba · 2,070 sqft
• 1692 tropical palms circle, Kissimmee 34747 Active Under Contract $499,999 · 5 bd · 5 ba · 2,294 sqft
• 9017 alba lane, Kissimmee 34747 Active Under Contract $279,995 · 3 bd · 3 ba · 1,530 sqft
• 620 las fuentes drive, Kissimmee 34746 Active Under Contract $378,000 · 4 bd · 3 ba · 1,907 sqft
• 3843 golden knot drive, Kissimmee 34746 Active Under Contract $399,987 · 3 bd · 2 ba · 1,827 sqft
• 8602 wellington loop, Kissimmee 34747 Active Under Contract $399,900 · 3 bd · 2 ba · 1,482 sqft
• 244 largo drive, Kissimmee 34759 Active Under Contract $339,500 · 2 bd · 2 ba · 2,057 sqft
• 3195 whooping crane run, Kissimmee 34741 Active Under Contract $369,000 · 3 bd · 2 ba · 1,579 sqft
• 1895 spring shower circle, Kissimmee 34744 Active Under Contract $320,000 · 3 bd · 2 ba · 1,559 sqft
• 8912 rhodes street, Kissimmee 34747 Active Under Contract $490,000 · 7 bd · 6 ba · 3,314 sqft
• 2660 sunrise shores drive, Kissimmee 34747 Active Under Contract $399,900 · 4 bd · 5 ba · 1,804 sqft
• 2675 candied apple alley, Kissimmee 34744 Active Under Contract $339,000 · 3 bd · 3 ba · 1,615 sqft
• 2300 butterfly palm way 203, Kissimmee 34747 Active Under Contract $275,000 · 3 bd · 2 ba · 1,268 sqft
• 1451 taos avenue, Kissimmee 34744 Active Under Contract $390,000 · 4 bd · 2 ba · 1,846 sqft
• 1825 big oak lane lane, Kissimmee 34746 Active Under Contract $499,000 · 3 bd · 2 ba · 2,742 sqft
• 1003 dorking way, Kissimmee 34758 Active Under Contract $254,900 · 3 bd · 2 ba · 1,411 sqft
• 381 aldershot court, Kissimmee 34758 Active Under Contract $265,000 · 4 bd · 3 ba · 2,763 sqft
• 2604 summer clouds way, Kissimmee 34744 Active Under Contract $419,000 · 3 bd · 2 ba · 2,214 sqft
• 4881 lake cecile drive, Kissimmee 34746 Active Under Contract $448,000 · 3 bd · 2 ba · 1,999 sqft