Homes under $500K in Kissimmee, FL

1,610 for sale · 5,127 homes listed · Updated September 29, 2026 · Page 45 of 103

• 407 para avenue, Kissimmee 34741 Active Under Contract $280,000 · 3 bd · 2 ba · 1,118 sqft
• 708 duffer lane, Kissimmee 34759 Active Under Contract $275,990 · 3 bd · 2 ba · 1,254 sqft
• 3849 carrick bend drive, Kissimmee 34746 Active Under Contract $399,990 · 4 bd · 2 ba · 2,050 sqft
• 1933 bellknoll lane, Kissimmee 34744 Active Under Contract $399,000 · 4 bd · 2 ba · 1,846 sqft
• 3838 nautical way 104, Kissimmee 34741 Active Under Contract $139,990 · 2 bd · 2 ba · 910 sqft
• 1906 lakeview way, Kissimmee 34759 Active Under Contract $242,000 · 3 bd · 2 ba · 1,526 sqft
• 404 manitoba drive, Kissimmee 34759 Active Under Contract $304,990 · 4 bd · 3 ba · 2,222 sqft
• 2905 summer green trail, Kissimmee 34744 Active Under Contract $448,000 · 4 bd · 3 ba · 2,344 sqft
• 5017 laguna bay circle 97, Kissimmee 34746 Active Under Contract $242,000 · 3 bd · 2 ba · 1,220 sqft
• 156 barefoot beach way, Kissimmee 34746 Active Under Contract $425,000 · 4 bd · 3 ba · 1,549 sqft
• 8807 dunes court 308, Kissimmee 34747 Active Under Contract $170,000 · 1 bd · 1 ba · 747 sqft
• 5356 harmony place, Kissimmee 34758 Active Under Contract $361,900 · 3 bd · 2 ba · 1,606 sqft
• 2827 shadow wood court, Kissimmee 34746 Active Under Contract $499,990 · 3 bd · 4 ba · 2,736 sqft
• 3024 bransbury court, Kissimmee 34747 Active Under Contract $394,999 · 3 bd · 2 ba · 1,712 sqft
• 205 owenshire circle, Kissimmee 34744 Active Under Contract $359,900 · 4 bd · 2 ba · 1,560 sqft
• 2842 berkshire circle, Kissimmee 34743 Active Under Contract $399,900 · 3 bd · 2 ba · 1,492 sqft
• 602 cotulla drive, Kissimmee 34758 Active Under Contract $270,700 · 3 bd · 2 ba · 1,451 sqft
• 8001 formosa valley, Kissimmee 34747 Active Under Contract $438,900 · 4 bd · 5 ba · 2,112 sqft
• 1959 cacutta way, Kissimmee 34744 Active Under Contract $350,000 · 4 bd · 2 ba · 1,846 sqft
• 2600 shortleaf, Kissimmee 34746 Active Under Contract $400,000 · 4 bd · 2 ba · 1,959 sqft
• 165 toluca drive, Kissimmee 34743 Active Under Contract $318,000 · 3 bd · 2 ba · 1,260 sqft
• 3005 red ginger road, Kissimmee 34747 Active Under Contract $220,000 · 2 bd · 3 ba · 1,161 sqft
• 1321 arisha drive, Kissimmee 34746 Active Under Contract $375,000 · 4 bd · 4 ba · 2,376 sqft
• 340 edgewood court, Kissimmee 34759 Active Under Contract $259,900 · 3 bd · 2 ba · 1,176 sqft
• 816 adour drive, Kissimmee 34759 Active Under Contract $220,000 · 3 bd · 2 ba · 1,302 sqft
• 8132 fan palm way, Kissimmee 34747 Active Under Contract $475,000 · 4 bd · 3 ba · 1,834 sqft
• 2210 granger avenue, Kissimmee 34746 Active Under Contract $339,900 · 3 bd · 2 ba · 1,869 sqft
• 2356 royale oaks boulevard, Kissimmee 34744 Active Under Contract $399,900 · 4 bd · 3 ba · 2,079 sqft
• 4808 rockvale drive, Kissimmee 34758 Active Under Contract $364,900 · 4 bd · 2 ba · 1,972 sqft
• 3214 rio grande trail 00, Kissimmee 34741 Active Under Contract $205,000 · 3 bd · 3 ba · 1,414 sqft
• 2481 winchester boulevard, Kissimmee 34743 Active Under Contract $249,900 · 3 bd · 2 ba · 1,023 sqft
• 2535 fassona drive, Kissimmee 34741 Active Under Contract $299,998 · 3 bd · 3 ba · 1,603 sqft
• 665 regency way, Kissimmee 34758 Active Under Contract $374,990 · 6 bd · 3 ba · 2,417 sqft
• 4852 coral castle drive, Kissimmee 34746 Active Under Contract $269,990 · 3 bd · 3 ba · 1,762 sqft
• 308 big sioux lane, Kissimmee 34759 Active Under Contract $235,000 · 4 bd · 2 ba · 2,262 sqft
• 2103 limestone trail, Kissimmee 34747 Active Under Contract $486,500 · 3 bd · 2 ba · 2,066 sqft
• 2602 lola lane, Kissimmee 34744 Active Under Contract $487,451 · 4 bd · 2 ba · 2,059 sqft
• 611 jura lane, Kissimmee 34759 Active Under Contract $339,000 · 3 bd · 2 ba · 1,444 sqft
• 4250 lake avenue, Kissimmee 34746 Active Under Contract $364,500 · 4 bd · 3 ba · 1,850 sqft
• 3058 bay laurel circle north, Kissimmee 34744 Active Under Contract $394,000 · 4 bd · 2 ba · 2,059 sqft
• 323 alegriano court, Kissimmee 34758 Active Under Contract $309,900 · 3 bd · 2 ba · 2,239 sqft
• 1974 majorca drive, Kissimmee 34747 Active Under Contract $440,000 · 5 bd · 5 ba · 2,265 sqft
• 111 nicholas court, Kissimmee 34758 Active Under Contract $168,300 · 3 bd · 2 ba · 1,329 sqft
• 261 autumn lane 4, Kissimmee 34743 Active Under Contract $197,000 · 2 bd · 3 ba · 990 sqft
• 3150 paradox circle 405, Kissimmee 34746 Active Under Contract $300,000 · 2 bd · 2 ba · 1,196 sqft
• 2788 club cortile circle a, Kissimmee 34746 Active Under Contract $190,000 · 3 bd · 2 ba · 1,204 sqft
• 8065 lost shaker lane, Kissimmee 34747 Active Under Contract $380,000 · 3 bd · 3 ba · 1,410 sqft
• 300 kingfish drive, Kissimmee 34759 Active Under Contract $249,900 · 3 bd · 2 ba · 1,810 sqft
• 2717 eagle canyon drive south, Kissimmee 34746 Active Under Contract $390,000 · 4 bd · 3 ba · 2,383 sqft
• 1723 hughey street, Kissimmee 34741 Active Under Contract $299,900 · 3 bd · 2 ba · 1,071 sqft