Homes under $500K in Kissimmee, FL

1,610 for sale · 5,127 homes listed · Updated September 29, 2026 · Page 44 of 103

• 766 maderia court, Kissimmee 34758 Active Under Contract $197,500 · 3 bd · 2 ba · 1,293 sqft
• 1329 windsor drive, Kissimmee 34741 Active Under Contract $130,000 · 2 bd · 3 ba · 1,290 sqft
• 3078 sangria street, Kissimmee 34744 Active Under Contract $380,000 · 3 bd · 2 ba · 1,770 sqft
• 2658 mayaguana street, Kissimmee 34747 Active Under Contract $259,000 · 3 bd · 3 ba · 1,362 sqft
• 8958 sugar palm road, Kissimmee 34747 Active Under Contract $449,900 · 5 bd · 5 ba · 3,081 sqft
• 7997 formosa valley place, Kissimmee 34747 Active Under Contract $439,000 · 4 bd · 5 ba · 2,112 sqft
• 9055 treasure trove lane 105, Kissimmee 34747 Active Under Contract $219,900 · 3 bd · 2 ba · 1,700 sqft
• 8869 bengal court, Kissimmee 34747 Active Under Contract $489,000 · 5 bd · 4 ba · 2,492 sqft
• 2403 silver palm drive, Kissimmee 34747 Active Under Contract $269,900 · 3 bd · 3 ba · 1,440 sqft
• 2101 painter lane, Kissimmee 34741 Active Under Contract $355,000 · 3 bd · 3 ba · 1,820 sqft
• 3212 oyster lane, Kissimmee 34747 Active Under Contract $290,000 · 3 bd · 2 ba · 1,300 sqft
• 268 acadia drive, Kissimmee 34759 Active Under Contract $285,000 · 2 bd · 2 ba · 1,387 sqft
• 3234 river branch circle, Kissimmee 34741 Active Under Contract $325,000 · 3 bd · 2 ba · 1,526 sqft
• 131 westmoreland circle, Kissimmee 34744 Active Under Contract $399,999 · 4 bd · 3 ba · 2,285 sqft
• 3078 juliet drive, Kissimmee 34746 Active Under Contract $459,000 · 4 bd · 3 ba · 1,914 sqft
• 8928 cuban palm road, Kissimmee 34747 Active Under Contract $438,000 · 4 bd · 3 ba · 1,902 sqft
• 9051 treasure trove lane 303, Kissimmee 34747 Active Under Contract $218,000 · 3 bd · 2 ba · 1,700 sqft
• 4900 sausalito lane, Kissimmee 34746 Active Under Contract $379,990 · 3 bd · 2 ba · 1,380 sqft
• 2074 rio grande canyon loop, Kissimmee 34759 Active Under Contract $345,000 · 4 bd · 3 ba · 2,154 sqft
• 261 autumn lane 3, Kissimmee 34743 Active Under Contract $200,000 · 2 bd · 3 ba · 990 sqft
• 1105 indian ridge trail east, Kissimmee 34747 Active Under Contract $329,000 · 4 bd · 2 ba · 1,656 sqft
• 4807 worchester drive, Kissimmee 34746 Active Under Contract $410,000 · 4 bd · 3 ba · 2,186 sqft
• 710 east jackson street, Kissimmee 34744 Active Under Contract $320,000 · 3 bd · 2 ba · 1,338 sqft
• 1550 regal oak drive, Kissimmee 34744 Active Under Contract $460,000 · 4 bd · 2 ba · 2,312 sqft
• 74 south marbrisa way, Kissimmee 34743 Active Under Contract $184,900 · 1 bd · 1 ba · 672 sqft
• 1205 teton drive, Kissimmee 34744 Active Under Contract $334,000 · 4 bd · 3 ba · 1,935 sqft
• 4751 clock tower drive 204, Kissimmee 34746 Active Under Contract $265,000 · 2 bd · 2 ba · 1,126 sqft
• 2367 silver palm drive, Kissimmee 34747 Active Under Contract $349,000 · 3 bd · 3 ba · 1,440 sqft
• 4004 san gallo drive 106, Kissimmee 34741 Active Under Contract $200,000 · 3 bd · 2 ba · 1,296 sqft
• 134 coralwood circle, Kissimmee 34743 Active Under Contract $349,900 · 3 bd · 2 ba · 1,462 sqft
• 2739 north poinciana boulevard 71, Kissimmee 34746 Active Under Contract $175,000 · 3 bd · 2 ba · 1,287 sqft
• 3222 whooping crane run, Kissimmee 34741 Active Under Contract $350,000 · 3 bd · 2 ba · 1,498 sqft
• 8810 grand palms circle a, Kissimmee 34747 Active Under Contract $230,000 · 3 bd · 2 ba · 1,245 sqft
• 3009 sea plane lane, Kissimmee 34747 Active Under Contract $394,999 · 2 bd · 3 ba · 1,283 sqft
• 254 cranbrook drive, Kissimmee 34758 Active Under Contract $249,900 · 3 bd · 2 ba · 1,329 sqft
• 2331 peppercorn street, Kissimmee 34741 Active Under Contract $409,900 · 3 bd · 2 ba · 1,769 sqft
• 375 aldershot court, Kissimmee 34758 Active Under Contract $335,450 · 4 bd · 3 ba · 2,308 sqft
• 635 gazelle drive, Kissimmee 34759 Active Under Contract $239,900 · 4 bd · 2 ba · 1,188 sqft
• 4928 worchester drive, Kissimmee 34746 Active Under Contract $389,000 · 4 bd · 2 ba · 1,922 sqft
• 3060 rockefeller way 156, Kissimmee 34747 Active Under Contract $489,999 · 4 bd · 5 ba · 2,356 sqft
• 332 gait court, Kissimmee 34743 Active Under Contract $349,000 · 3 bd · 2 ba · 1,390 sqft
• 4827 coral castle drive, Kissimmee 34746 Active Under Contract $275,000 · 3 bd · 3 ba · 1,762 sqft
• 105 harness lane, Kissimmee 34743 Active Under Contract $445,000 · 4 bd · 2 ba · 1,730 sqft
• 1598 whitewood court, Kissimmee 34747 Active Under Contract $445,000 · 3 bd · 2 ba · 2,066 sqft
• 2386 ruth lane, Kissimmee 34744 Active Under Contract $465,000 · 4 bd · 2 ba · 1,836 sqft
• 2654 hawthorne lane, Kissimmee 34743 Active Under Contract $465,000 · 4 bd · 2 ba · 2,081 sqft
• 5385 dahlia reserve drive, Kissimmee 34758 Active Under Contract $499,000 · 6 bd · 3 ba · 2,658 sqft
• 106 vista drive, Kissimmee 34759 Active Under Contract $269,900 · 3 bd · 2 ba · 1,786 sqft
• 2799 club cortile circle 2799, Kissimmee 34746 Active Under Contract $259,000 · 4 bd · 3 ba · 1,873 sqft
• 2746 patrician circle, Kissimmee 34746 Active Under Contract $410,000 · 5 bd · 3 ba · 2,794 sqft