Homes under $500K in Kissimmee, FL

1,610 for sale · 5,127 homes listed · Updated September 29, 2026 · Page 85 of 103

• 660 celebration avenue 240, Kissimmee 34747 Off market since Sep 2026 $369,000 · 2 bd · 3 ba · 1,360 sqft
• 3609 valleyview drive, Kissimmee 34746 Off market since Sep 2026 $475,000 · 4 bd · 3 ba · 2,530 sqft
• 5149 worchester drive, Kissimmee 34746 Off market since Jul 2026 $477,820 · 4 bd · 3 ba · 2,584 sqft
• 1356 centre court ridge drive 303, Kissimmee 34747 Off market since Sep 2026 $404,000 · 3 bd · 3 ba · 1,590 sqft
• 2211 jessica lane, Kissimmee 34744 Off market since Sep 2026 $499,000 · 4 bd · 2 ba · 2,109 sqft
• 4612 falcon avenue, Kissimmee 34746 Off market since Aug 2026 $375,600 · 4 bd · 2 ba · 1,822 sqft
• 2705 emerald lake court 2705, Kissimmee 34744 Off market since Sep 2026 $240,000 · 2 bd · 2 ba · 1,240 sqft
• 2302 butterfly palm way 301, Kissimmee 34747 Off market since Sep 2026 $229,900 · 3 bd · 2 ba · 1,402 sqft
• 2717 bushman drive, Kissimmee 34746 Off market since Sep 2026 $290,000 · 3 bd · 3 ba · 1,440 sqft
• 1280 south beach circle, Kissimmee 34746 Off market since Sep 2026 $250,000 · 3 bd · 3 ba · 1,468 sqft
• 2452 skyline loop, Kissimmee 34758 Off market since Sep 2026 $290,000 · 3 bd · 3 ba · 1,840 sqft
• 1167 boardwalk place, Kissimmee 34747 Off market since Sep 2026 $349,900 · 3 bd · 3 ba · 1,460 sqft
• 1450 amanda road, Kissimmee 34744 Off market since Sep 2026 $405,000 · 4 bd · 3 ba · 1,998 sqft
• 3151 sunset walk drive 116, Kissimmee 34747 Off market since Sep 2026 $349,900 · 1 bd · 1 ba · 960 sqft
• 4355 summer breeze way, Kissimmee 34744 Off market since Sep 2026 $469,900 · 4 bd · 3 ba · 2,027 sqft
• 2185 antilles club drive, Kissimmee 34747 Off market since Sep 2026 $450,000 · 3 bd · 2 ba · 1,904 sqft
• 3008 red ginger road 3008, Kissimmee 34747 Off market since Sep 2026 $229,000 · 2 bd · 3 ba · 1,161 sqft
• 2112 bunker view court, Kissimmee 34746 Off market since Aug 2026 $394,999 · 3 bd · 3 ba · 2,039 sqft
• 2730 amanda kay way, Kissimmee 34744 Off market since Sep 2026 $415,000 · 4 bd · 3 ba · 2,906 sqft
• 2394 caravelle circle, Kissimmee 34746 Off market since Sep 2026 $285,500 · 4 bd · 3 ba · 1,536 sqft
• 913 san rafael way, Kissimmee 34758 Off market since Sep 2026 $245,999 · 3 bd · 2 ba · 1,329 sqft
• 3004 parkway boulevard 101, Kissimmee 34747 Off market since Sep 2026 $240,000 · 2 bd · 2 ba · 937 sqft
• 8061 vacation avenue 309, Kissimmee 34747 Off market since Sep 2026 $265,000 · 1 bd · 1 ba · 734 sqft
• 4321 bayside drive, Kissimmee 34746 Off market since Sep 2026 $384,900 · 3 bd · 2 ba · 1,426 sqft
• 3119 sun lake court b, Kissimmee 34747 Off market since Sep 2026 $330,000 · 3 bd · 2 ba · 1,484 sqft
• 3003 white orchid road, Kissimmee 34747 Off market since Sep 2026 $225,000 · 2 bd · 3 ba · 1,161 sqft
• 2479 toscolona drive, Kissimmee 34741 Off market since Sep 2026 $316,000 · 3 bd · 3 ba · 1,603 sqft
• 153 club villas lane, Kissimmee 34744 Off market since Sep 2026 $310,000 · 2 bd · 2 ba · 1,306 sqft
• 1125 munster court, Kissimmee 34759 Off market since Sep 2026 $299,000 · 4 bd · 2 ba · 2,004 sqft
• 8923 sydney avenue, Kissimmee 34747 Off market since Sep 2026 $465,000 · 5 bd · 5 ba · 2,263 sqft
• 2868 oconnell drive, Kissimmee 34741 Off market since Sep 2026 $469,900 · 3 bd · 2 ba · 2,180 sqft
• 2903 banana palm drive, Kissimmee 34747 Off market since Sep 2026 $329,990 · 4 bd · 3 ba · 1,902 sqft
• 1857 nice court, Kissimmee 34747 Off market since Sep 2026 $489,000 · 5 bd · 4 ba · 2,492 sqft
• 3202 guana way, Kissimmee 34747 Off market since Sep 2026 $298,000 · 3 bd · 2 ba · 1,300 sqft
• 1177 seaside mist trail, Kissimmee 34747 Off market since Sep 2026 $309,900 · 3 bd · 3 ba · 1,460 sqft
• 2808 mill run boulevard, Kissimmee 34744 Off market since Sep 2026 $399,000 · 3 bd · 2 ba · 1,275 sqft
• 1029 dudley drive, Kissimmee 34758 Off market since Sep 2026 $279,999 · 3 bd · 2 ba · 1,425 sqft
• 7964 hanson bay place, Kissimmee 34747 Off market since Sep 2026 $485,000 · 4 bd · 3 ba · 2,261 sqft
• 4223 little owl lane, Kissimmee 34746 Off market since Sep 2026 $379,000 · 4 bd · 2 ba · 1,843 sqft
• 4882 clock tower drive, Kissimmee 34746 Off market since Sep 2026 $498,000 · 5 bd · 4 ba · 2,128 sqft
• 8546 bay lilly loop, Kissimmee 34747 Off market since Sep 2026 $417,900 · 4 bd · 3 ba · 1,636 sqft
• 1501 angler avenue, Kissimmee 34746 Off market since Sep 2026 $409,000 · 3 bd · 2 ba · 2,670 sqft
• 1722 evergreen street, Kissimmee 34746 Off market since Sep 2026 $374,999 · 5 bd · 3 ba · 2,108 sqft
• 8407 blue lagoon drive, Kissimmee 34747 Off market since Sep 2026 $195,000 · 3 bd · 3 ba · 1,291 sqft
• 2775 red horse drive, Kissimmee 34744 Off market since Aug 2026 $475,000 · 4 bd · 3 ba · 2,463 sqft
• 654 madrid drive, Kissimmee 34758 Off market since Sep 2026 $497,900 · 4 bd · 3 ba · 3,226 sqft
• 3133 enclave court, Kissimmee 34746 Off market since Sep 2026 $239,900 · 2 bd · 3 ba · 1,112 sqft
• 3630 kariba court, Kissimmee 34746 Off market since Sep 2026 $350,000 · 3 bd · 2 ba · 1,949 sqft
• 8529 bay lilly loop, Kissimmee 34747 Off market since Sep 2026 $315,000 · 3 bd · 3 ba · 1,295 sqft
• 8103 coconut palm way 302, Kissimmee 34747 Off market since Sep 2026 $229,000 · 2 bd · 2 ba · 1,022 sqft