Homes under $300K in Kissimmee, FL

584 for sale · 1,843 homes listed · Updated September 27, 2026 · Page 15 of 37

• 263 cranbrook drive, Kissimmee 34758 Pending $269,000 · 3 bd · 2 ba · 1,554 sqft
• 763 rolfe street, Kissimmee 34741 Pending $135,950 · 3 bd · 2 ba · 1,088 sqft
• 4367 curacao place, Kissimmee 34758 Pending $228,490 · 2 bd · 2 ba · 1,562 sqft
• 5531 pimenta court, Kissimmee 34758 Pending $298,420 · 3 bd · 2 ba · 1,424 sqft
• 7732 water oak court, Kissimmee 34747 Pending $299,000 · 2 bd · 2 ba · 1,220 sqft
• 5121 heatherstone court, Kissimmee 34758 Pending $279,995 · 3 bd · 2 ba · 1,604 sqft
• 2413 ruddenstone way, Kissimmee 34744 Pending $299,900 · 3 bd · 2 ba · 1,560 sqft
• 740 shore drive, Kissimmee 34744 Pending $250,000 · 3 bd · 2 ba · 1,628 sqft
• 15 west country cove, Kissimmee 34743 Pending $240,000 · 2 bd · 2 ba · 1,200 sqft
• 1013 park ridge circle, Kissimmee 34746 Pending $279,900 · 4 bd · 4 ba · 1,645 sqft
• 1374 boulder drive, Kissimmee 34744 Pending $290,000 · 2 bd · 2 ba · 1,063 sqft
• 2457 lynx court, Kissimmee 34744 Pending $290,000 · 3 bd · 2 ba · 1,387 sqft
• 4006 san gallo drive 108, Kissimmee 34741 Pending $235,000 · 4 bd · 3 ba · 1,470 sqft
• 920 patrick street, Kissimmee 34741 Pending $129,900 · 1 bd · 1 ba · 528 sqft
• 3341 whitestone circle 108, Kissimmee 34741 Pending $229,900 · 3 bd · 2 ba · 1,433 sqft
• 84 lakepointe circle, Kissimmee 34743 Pending $240,000 · 2 bd · 2 ba · 1,019 sqft
• 8908 legacy court 16-104, Kissimmee 34747 Pending $240,000 · 3 bd · 2 ba · 1,249 sqft
• 190 east miami terrace, Kissimmee 34741 Pending $175,000 · 2 bd · 2 ba · 959 sqft
• 3453 sugar mill road, Kissimmee 34741 Pending $299,900 · 3 bd · 2 ba · 1,184 sqft
• 2801 marshfield preserve way, Kissimmee 34746 Pending $289,900 · 3 bd · 2 ba · 1,597 sqft
• 111 dorchester court, Kissimmee 34758 Pending $269,450 · 4 bd · 2 ba · 1,872 sqft
• 2651 sherry circle, Kissimmee 34744 Pending $275,000 · 3 bd · 3 ba · 1,998 sqft
• 2216 grand cayman court 1415, Kissimmee 34741 Active Under Contract $192,900 · 2 bd · 2 ba · 1,026 sqft
• 4731 clock tower drive 105, Kissimmee 34746 Active Under Contract $275,000 · 2 bd · 2 ba · 1,194 sqft
• 4315 lake avenue, Kissimmee 34746 Active Under Contract $193,000 · 3 bd · 1 ba · 1,012 sqft
• 2618 roadster lane, Kissimmee 34746 Active Under Contract $265,000 · 2 bd · 3 ba · 1,350 sqft
• 306 aylesbury court, Kissimmee 34758 Active Under Contract $222,000 · 3 bd · 2 ba · 1,174 sqft
• 8816 dunes court 303, Kissimmee 34747 Active Under Contract $179,999 · 2 bd · 2 ba · 1,048 sqft
• 1207 atlantic court, Kissimmee 34759 Active Under Contract $230,000 · 3 bd · 2 ba · 1,624 sqft
• 3017 bonfire beach drive 203, Kissimmee 34746 Active Under Contract $260,000 · 3 bd · 2 ba · 1,667 sqft
• 8558 crystal cove loop, Kissimmee 34747 Active Under Contract $258,900 · 3 bd · 3 ba · 1,291 sqft
• 521 big black way, Kissimmee 34759 Active Under Contract $225,000 · 3 bd · 2 ba · 1,629 sqft
• 1137 shawnee drive, Kissimmee 34744 Active Under Contract $234,700 · 2 bd · 1 ba · 684 sqft
• 3000 maingate lane 218, Kissimmee 34747 Active Under Contract $45,000 · 1 bd · 1 ba · 304 sqft
• 3111 rio grande trail 3111, Kissimmee 34741 Active Under Contract $185,000 · 3 bd · 2 ba · 1,375 sqft
• 2788 almaton loop 402, Kissimmee 34747 Active Under Contract $240,000 · 2 bd · 2 ba · 1,081 sqft
• 851 assembly court, Kissimmee 34747 Active Under Contract $249,000 · 3 bd · 3 ba · 1,688 sqft
• 3141 paradox circle 404, Kissimmee 34746 Active Under Contract $287,000 · 2 bd · 2 ba · 1,194 sqft
• 4617 sparkling shell avenue, Kissimmee 34746 Active Under Contract $275,000 · 3 bd · 3 ba · 1,683 sqft
• 8842 grand palms circle b, Kissimmee 34747 Active Under Contract $229,000 · 3 bd · 2 ba · 1,245 sqft
• 214 taranto way, Kissimmee 34758 Active Under Contract $250,000 · 4 bd · 4 ba · 2,871 sqft
• 431 cart court, Kissimmee 34759 Active Under Contract $215,900 · 3 bd · 2 ba · 1,252 sqft
• 4004 san gallo drive 107, Kissimmee 34741 Active Under Contract $220,000 · 4 bd · 3 ba · 1,470 sqft
• 114 cassino way, Kissimmee 34758 Active Under Contract $280,000 · 3 bd · 2 ba · 1,416 sqft
• 2624 lodi circle 12-105, Kissimmee 34746 Active Under Contract $230,000 · 3 bd · 2 ba · 1,286 sqft
• 2756 big timber drive, Kissimmee 34758 Active Under Contract $299,000 · 3 bd · 2 ba · 1,493 sqft
• 1617 perdido court, Kissimmee 34759 Active Under Contract $230,000 · 3 bd · 2 ba · 1,368 sqft
• 4723 marcos circle, Kissimmee 34758 Active Under Contract $250,000 · 3 bd · 2 ba · 1,525 sqft
• 538 lakeview court, Kissimmee 34759 Active Under Contract $220,000 · 3 bd · 2 ba · 1,349 sqft
• 2002 royal bay boulevard 135, Kissimmee 34746 Active Under Contract $225,000 · 3 bd · 2 ba · 1,350 sqft