Homes under $500K in Kissimmee, FL

1,610 for sale · 5,127 homes listed · Updated September 29, 2026 · Page 47 of 103

• 404 quarry rock circle, Kissimmee 34758 Active Under Contract $445,000 · 6 bd · 5 ba · 3,024 sqft
• 3151 paradox circle 103, Kissimmee 34746 Active Under Contract $295,000 · 2 bd · 2 ba · 1,196 sqft
• 774 harland court, Kissimmee 34758 Active Under Contract $185,000 · 3 bd · 2 ba · 1,499 sqft
• 62 bolton court, Kissimmee 34758 Active Under Contract $304,000 · 4 bd · 2 ba · 1,874 sqft
• 3420 fallbrook drive, Kissimmee 34759 Active Under Contract $285,000 · 2 bd · 2 ba · 1,499 sqft
• 709 fredrick place, Kissimmee 34758 Active Under Contract $324,900 · 4 bd · 2 ba · 1,825 sqft
• 2304 lanesboro street, Kissimmee 34746 Active Under Contract $415,000 · 4 bd · 2 ba · 2,253 sqft
• 204 grand canal drive, Kissimmee 34759 Active Under Contract $254,000 · 2 bd · 2 ba · 1,548 sqft
• 9055 treasure trove lane 207, Kissimmee 34747 Active Under Contract $175,000 · 2 bd · 2 ba · 1,445 sqft
• 704 pasteur lane, Kissimmee 34759 Active Under Contract $299,000 · 4 bd · 2 ba · 1,874 sqft
• 2931 paddington way, Kissimmee 34747 Active Under Contract $424,900 · 4 bd · 2 ba · 2,157 sqft
• 2510 west doris street, Kissimmee 34741 Active Under Contract $259,900 · 3 bd · 2 ba · 1,813 sqft
• 8922 zurich lane, Kissimmee 34747 Active Under Contract $499,000 · 6 bd · 5 ba · 3,142 sqft
• 803 wakefield way, Kissimmee 34758 Active Under Contract $329,000 · 5 bd · 3 ba · 2,696 sqft
• 1148 mary frances drive, Kissimmee 34741 Active Under Contract $199,100 · 3 bd · 2 ba · 1,403 sqft
• 965 florida parkway, Kissimmee 34743 Active Under Contract $299,000 · 2 bd · 2 ba · 1,162 sqft
• 4550 jonafree lane 107, Kissimmee 34746 Active Under Contract $259,000 · 4 bd · 3 ba · 1,470 sqft
• 140 juarez drive, Kissimmee 34743 Active Under Contract $385,000 · 4 bd · 3 ba · 1,729 sqft
• 760 del prado drive, Kissimmee 34758 Active Under Contract $310,000 · 3 bd · 2 ba · 1,661 sqft
• 932 halifax drive, Kissimmee 34758 Active Under Contract $285,000 · 4 bd · 2 ba · 2,088 sqft
• 2663 gold dust circle, Kissimmee 34744 Active Under Contract $409,900 · 4 bd · 2 ba · 2,085 sqft
• 212 canterbury court, Kissimmee 34758 Active Under Contract $284,900 · 4 bd · 2 ba · 1,704 sqft
• 2574 sage drive, Kissimmee 34758 Active Under Contract $485,000 · 4 bd · 3 ba · 2,270 sqft
• 3476 forest ridge lane, Kissimmee 34741 Active Under Contract $449,000 · 4 bd · 2 ba · 2,395 sqft
• 338 kingfish drive, Kissimmee 34759 Active Under Contract $235,000 · 4 bd · 2 ba · 1,645 sqft
• 7549 sunflower circle, Kissimmee 34747 Active Under Contract $484,900 · 5 bd · 5 ba · 2,044 sqft
• 4424 silver creek street, Kissimmee 34744 Active Under Contract $449,990 · 5 bd · 3 ba · 2,370 sqft
• 441 danube drive, Kissimmee 34759 Active Under Contract $249,900 · 3 bd · 2 ba · 1,244 sqft
• 953 louvre court, Kissimmee 34759 Active Under Contract $245,000 · 3 bd · 2 ba · 1,409 sqft
• 169 birmingham drive, Kissimmee 34758 Active Under Contract $220,000 · 3 bd · 2 ba · 1,481 sqft
• 2994 big sky boulevard, Kissimmee 34744 Active Under Contract $415,000 · 3 bd · 3 ba · 2,700 sqft
• 1085 jodi ridge court, Kissimmee 34747 Active Under Contract $339,000 · 3 bd · 2 ba · 1,663 sqft
• 7956 formosa valley place, Kissimmee 34747 Active Under Contract $439,000 · 4 bd · 5 ba · 2,112 sqft
• 2217 grand cayman court 1223, Kissimmee 34741 Active Under Contract $189,997 · 2 bd · 2 ba · 1,026 sqft
• 7524 bliss way 7524, Kissimmee 34747 Active Under Contract $319,500 · 3 bd · 3 ba · 1,808 sqft
• 62 lakepointe circle, Kissimmee 34743 Active Under Contract $245,000 · 2 bd · 2 ba · 1,019 sqft
• 2705 chatham circle, Kissimmee 34746 Active Under Contract $329,900 · 3 bd · 2 ba · 1,380 sqft
• 2651 grasmere view parkway north, Kissimmee 34746 Active Under Contract $384,900 · 4 bd · 3 ba · 2,000 sqft
• 642 madrid drive, Kissimmee 34758 Active Under Contract $399,000 · 4 bd · 2 ba · 1,959 sqft
• 4815 lake sheppard street, Kissimmee 34758 Active Under Contract $355,000 · 4 bd · 2 ba · 2,116 sqft
• 5009 laguna bay circle 39, Kissimmee 34746 Active Under Contract $218,900 · 3 bd · 2 ba · 1,220 sqft
• 39 lago mesa way, Kissimmee 34743 Active Under Contract $169,999 · 1 bd · 1 ba · 672 sqft
• 3829 springlake village court, Kissimmee 34744 Active Under Contract $359,000 · 3 bd · 2 ba · 1,661 sqft
• 3571 maple ridge loop, Kissimmee 34741 Active Under Contract $490,000 · 5 bd · 4 ba · 2,636 sqft
• 2244 mallard creek circle, Kissimmee 34743 Active Under Contract $359,888 · 4 bd · 2 ba · 1,972 sqft
• 2740 coupe street, Kissimmee 34746 Active Under Contract $325,000 · 4 bd · 4 ba · 1,852 sqft
• 2528 calla lily cove, Kissimmee 34758 Active Under Contract $499,990 · 4 bd · 3 ba · 2,869 sqft
• 1532 nature trail, Kissimmee 34746 Active Under Contract $335,000 · 3 bd · 3 ba · 2,028 sqft
• 1136 liberty hall drive, Kissimmee 34746 Active Under Contract $359,900 · 4 bd · 2 ba · 1,975 sqft
• 25 lake villa way, Kissimmee 34743 Active Under Contract $219,900 · 3 bd · 2 ba · 992 sqft