Homes under $500K in Kissimmee, FL

1,610 for sale · 5,127 homes listed · Updated September 29, 2026 · Page 89 of 103

• 2024 bearing lane, Kissimmee 34744 Off market since Sep 2026 $459,000 · 4 bd · 3 ba · 2,561 sqft
• 460 martigues drive, Kissimmee 34759 Off market since Sep 2026 $284,900 · 3 bd · 2 ba · 1,559 sqft
• 7602 cabana court 101, Kissimmee 34747 Off market since Sep 2026 $335,000 · 3 bd · 3 ba · 1,755 sqft
• 1018 plantation drive a18, Kissimmee 34741 Off market since Sep 2026 $190,000 · 2 bd · 2 ba · 970 sqft
• 254 amber way, Kissimmee 34758 Off market since Sep 2026 $404,999 · 5 bd · 3 ba · 2,287 sqft
• 1229 bermuda lakes lane 206, Kissimmee 34741 Off market since Sep 2026 $134,900 · 1 bd · 1 ba · 733 sqft
• 2935 theme street, Kissimmee 34746 Off market since Sep 2026 $299,900 · 3 bd · 3 ba · 1,859 sqft
• 135 veracruz avenue, Kissimmee 34743 Off market since Sep 2026 $359,950 · 3 bd · 2 ba · 1,132 sqft
• 2908 banana palm drive, Kissimmee 34747 Off market since Sep 2026 $499,000 · 5 bd · 5 ba · 3,081 sqft
• 663 mesilla drive, Kissimmee 34758 Off market since Sep 2026 $320,000 · 3 bd · 2 ba · 1,856 sqft
• 2361 andrews valley drive, Kissimmee 34758 Off market since Sep 2026 $397,700 · 5 bd · 3 ba · 2,566 sqft
• 280 indian wells avenue, Kissimmee 34759 Off market since Sep 2026 $374,900 · 2 bd · 2 ba · 2,101 sqft
• 2679 corvette lane, Kissimmee 34746 Off market since Sep 2026 $329,900 · 3 bd · 3 ba · 1,474 sqft
• 1576 diamond loop drive, Kissimmee 34744 Off market since Sep 2026 $419,990 · 4 bd · 2 ba · 1,846 sqft
• 3817 golden feather way, Kissimmee 34746 Off market since Sep 2026 $460,000 · 4 bd · 3 ba · 2,724 sqft
• 3191 paradox circle 208, Kissimmee 34746 Off market since Sep 2026 $360,000 · 3 bd · 3 ba · 1,329 sqft
• 119 southampton drive, Kissimmee 34744 Off market since Sep 2026 $360,000 · 3 bd · 2 ba · 1,816 sqft
• 7509 pellham way 0, Kissimmee 34747 Off market since Sep 2026 $264,000 · 3 bd · 3 ba · 1,808 sqft
• 1212 shawnee drive, Kissimmee 34744 Off market since Sep 2026 $390,000 · 4 bd · 2 ba · 1,848 sqft
• 3080 juliet drive, Kissimmee 34746 Off market since Sep 2026 $450,000 · 4 bd · 3 ba · 1,914 sqft
• 1739 good neighbor loop, Kissimmee 34744 Off market since Sep 2026 $445,000 · 3 bd · 2 ba · 2,068 sqft
• 2080 heritage key boulevard, Kissimmee 34744 Off market since Sep 2026 $275,000 · 3 bd · 3 ba · 1,512 sqft
• 2208 antigua place 914, Kissimmee 34741 Off market since Sep 2026 $164,000 · 1 bd · 1 ba · 762 sqft
• 3087 seaview castle drive, Kissimmee 34746 Off market since Sep 2026 $298,500 · 3 bd · 3 ba · 1,394 sqft
• 4806 cumbrian lakes drive, Kissimmee 34746 Off market since Sep 2026 $424,999 · 4 bd · 4 ba · 1,836 sqft
• 2569 folio way, Kissimmee 34741 Off market since Sep 2026 $365,000 · 3 bd · 3 ba · 1,690 sqft
• 3161 paradox circle 304, Kissimmee 34746 Off market since Sep 2026 $308,000 · 2 bd · 2 ba · 1,126 sqft
• 1910 goblet cove street, Kissimmee 34746 Off market since Sep 2026 $359,000 · 3 bd · 2 ba · 1,768 sqft
• 9025 rhodes street, Kissimmee 34747 Off market since Sep 2026 $390,000 · 5 bd · 5 ba · 2,263 sqft
• 2677 rania lane, Kissimmee 34744 Off market since Sep 2026 $440,144 · 4 bd · 2 ba · 1,723 sqft
• 5266 paradise cay circle, Kissimmee 34746 Off market since Sep 2026 $295,000 · 3 bd · 3 ba · 1,595 sqft
• 2417 dubai street, Kissimmee 34747 Off market since Sep 2026 $495,000 · 5 bd · 5 ba · 2,263 sqft
• 3905 bowfin trail, Kissimmee 34746 Off market since Aug 2026 $419,000 · 3 bd · 3 ba · 2,533 sqft
• 672 sterling drive, Kissimmee 34758 Off market since Sep 2026 $375,000 · 4 bd · 3 ba · 2,219 sqft
• 4179 spitfire avenue, Kissimmee 34741 Off market since Sep 2026 $167,200 · 2 bd · 2 ba · 930 sqft
• 2358 old dixie highway, Kissimmee 34744 Off market since Sep 2026 $190,000 · 2 bd · 1 ba · 1,232 sqft
• 4089 navigator way, Kissimmee 34746 Off market since Sep 2026 $365,000 · 4 bd · 3 ba · 2,123 sqft
• 8107 coconut palm way 201, Kissimmee 34747 Off market since Sep 2026 $227,000 · 3 bd · 2 ba · 1,268 sqft
• 1876 cassidy knoll drive, Kissimmee 34744 Off market since Sep 2026 $495,000 · 5 bd · 4 ba · 2,807 sqft
• 1709 golfview drive, Kissimmee 34746 Off market since Sep 2026 $395,000 · 3 bd · 2 ba · 2,302 sqft
• 2281 tradewinds, Kissimmee 34746 Off market since Sep 2026 $380,000 · 3 bd · 2 ba · 2,037 sqft
• 3151 sunset walk drive 1507, Kissimmee 34747 Off market since Sep 2026 $289,000 · 1 bd · 1 ba · 734 sqft
• 3222 brewster drive, Kissimmee 34743 Off market since Sep 2026 $365,000 · 3 bd · 2 ba · 1,392 sqft
• 1608 mohegan boulevard, Kissimmee 34744 Off market since Sep 2026 $359,000 · 3 bd · 3 ba · 2,016 sqft
• 2868 tanzanite terrace, Kissimmee 34758 Off market since Sep 2026 $249,000 · 3 bd · 2 ba · 1,838 sqft
• 3100 parkway boulevard 726, Kissimmee 34747 Off market since Sep 2026 $120,000 · 1 bd · 1 ba · 524 sqft
• 656 cotulla drive, Kissimmee 34758 Off market since Sep 2026 $286,990 · 4 bd · 2 ba · 1,755 sqft
• 3239 sustainable way, Kissimmee 34747 Off market since Sep 2026 $330,000 · 3 bd · 3 ba · 1,361 sqft
• 2193 granger avenue, Kissimmee 34746 Off market since Sep 2026 $399,000 · 4 bd · 3 ba · 2,169 sqft
• 2346 cordova court, Kissimmee 34743 Off market since Sep 2026 $349,000 · 3 bd · 2 ba · 1,102 sqft