Homes under $500K in Kissimmee, FL

1,610 for sale · 5,127 homes listed · Updated September 29, 2026 · Page 76 of 103

• 162 harwood circle, Kissimmee 34744 Off market since Sep 2026 $429,900 · 4 bd · 3 ba · 2,516 sqft
• 340 chiquita court, Kissimmee 34758 Off market since Sep 2026 $265,000 · 3 bd · 2 ba · 1,053 sqft
• 402 ohio way, Kissimmee 34759 Off market since Sep 2026 $289,990 · 3 bd · 2 ba · 1,548 sqft
• 2609 mill run boulevard, Kissimmee 34744 Off market since Sep 2026 $394,990 · 3 bd · 2 ba · 1,280 sqft
• 2461 avian loop, Kissimmee 34741 Off market since Jul 2026 $499,900 · 3 bd · 3 ba · 1,860 sqft
• 2901 sweetspire circle, Kissimmee 34746 Off market since Sep 2026 $429,000 · 4 bd · 3 ba · 2,220 sqft
• 2788 almaton loop 202, Kissimmee 34747 Off market since Sep 2026 $275,000 · 2 bd · 2 ba · 1,081 sqft
• 2959 banana palm drive, Kissimmee 34747 Off market since Sep 2026 $338,300 · 4 bd · 3 ba · 1,902 sqft
• 3022 white orchid road, Kissimmee 34747 Off market since Sep 2026 $414,900 · 4 bd · 3 ba · 1,636 sqft
• 7651 amazonas street, Kissimmee 34747 Sold on Aug 31, 2026 $445,990 · 4 bd · 5 ba · 2,396 sqft
• 2743 sun key place, Kissimmee 34747 Off market since Sep 2026 $265,000 · 3 bd · 3 ba · 1,291 sqft
• 2515 nouveau way, Kissimmee 34741 Off market since Sep 2026 $419,990 · 4 bd · 2 ba · 1,706 sqft
• 447 hunter circle, Kissimmee 34758 Off market since Jul 2026 $259,999 · 3 bd · 3 ba · 1,586 sqft
• 1200 wahneta drive, Kissimmee 34759 Off market since Sep 2026 $299,995 · 3 bd · 2 ba · 1,445 sqft
• 3050 white orchid road, Kissimmee 34747 Off market since Sep 2026 $279,000 · 2 bd · 3 ba · 1,161 sqft
• 7674 otterspool street, Kissimmee 34747 Off market since Sep 2026 $425,000 · 3 bd · 3 ba · 1,440 sqft
• 121 south roma way, Kissimmee 34746 Off market since Sep 2026 $345,000 · 4 bd · 2 ba · 1,740 sqft
• 4878 coral castle drive, Kissimmee 34746 Off market since Sep 2026 $294,000 · 3 bd · 3 ba · 1,762 sqft
• 1255 wispy cypress drive, Kissimmee 34746 Off market since Sep 2026 $375,000 · 4 bd · 3 ba · 1,918 sqft
• 4602 cumbrian lakes drive, Kissimmee 34746 Off market since Sep 2026 $499,900 · 5 bd · 5 ba · 2,636 sqft
• 3 country club court, Kissimmee 34759 Off market since Sep 2026 $250,000 · 3 bd · 2 ba · 1,218 sqft
• 2948 crest drive, Kissimmee 34744 Off market since Sep 2026 $445,000 · 4 bd · 3 ba · 1,923 sqft
• 2784 almaton loop 301, Kissimmee 34747 Off market since Sep 2026 $304,000 · 3 bd · 2 ba · 1,246 sqft
• 8819 grand palms circle a, Kissimmee 34747 Off market since Sep 2026 $260,000 · 3 bd · 2 ba · 1,245 sqft
• 336 montgomery court, Kissimmee 34758 Off market since Sep 2026 $220,000 · 3 bd · 2 ba · 1,346 sqft
• 4121 cannon court, Kissimmee 34746 Off market since Sep 2026 $302,500 · 3 bd · 2 ba · 1,436 sqft
• 252 fig court, Kissimmee 34759 Off market since Sep 2026 $240,000 · 4 bd · 2 ba · 1,414 sqft
• 5043 royal point avenue, Kissimmee 34746 Off market since Jul 2026 $437,000 · 4 bd · 3 ba · 2,248 sqft
• 2778 almaton loop 303, Kissimmee 34747 Off market since Sep 2026 $345,000 · 3 bd · 2 ba · 1,246 sqft
• 5179 royal point avenue, Kissimmee 34746 Off market since Aug 2026 $395,000 · 3 bd · 2 ba · 1,639 sqft
• 7657 somersworth drive, Kissimmee 34747 Off market since Sep 2026 $478,900 · 4 bd · 3 ba · 2,051 sqft
• 2581 marshfield preserve way, Kissimmee 34746 Off market since Sep 2026 $355,000 · 3 bd · 2 ba · 2,235 sqft
• 2705 willow glen circle, Kissimmee 34744 Off market since Sep 2026 $415,999 · 4 bd · 3 ba · 1,679 sqft
• 4712 terra esmeralda drive, Kissimmee 34746 Off market since Sep 2026 $330,000 · 3 bd · 3 ba · 1,591 sqft
• 2922 willow creek lane, Kissimmee 34741 Off market since Sep 2026 $450,000 · 3 bd · 2 ba · 1,796 sqft
• 7667 otterspool street, Kissimmee 34747 Off market since Sep 2026 $449,000 · 3 bd · 3 ba · 1,440 sqft
• 2 lake villa way, Kissimmee 34743 Off market since Sep 2026 $219,900 · 3 bd · 2 ba · 992 sqft
• 2900 edenshire way 107, Kissimmee 34746 Off market since Sep 2026 $280,000 · 3 bd · 2 ba · 1,300 sqft
• 140 guaymas drive, Kissimmee 34743 Off market since Sep 2026 $329,900 · 3 bd · 2 ba · 1,444 sqft
• 4562 jonafree lane 106, Kissimmee 34746 Off market since Sep 2026 $215,000 · 3 bd · 2 ba · 1,296 sqft
• 661 elbridge drive, Kissimmee 34758 Off market since Sep 2026 $352,000 · 4 bd · 3 ba · 2,308 sqft
• 8932 sydney avenue, Kissimmee 34747 Off market since Sep 2026 $449,000 · 5 bd · 5 ba · 2,265 sqft
• 2606 roadster lane, Kissimmee 34746 Off market since Sep 2026 $240,000 · 2 bd · 3 ba · 1,350 sqft
• 760 siena palm drive 205, Kissimmee 34747 Off market since Sep 2026 $385,000 · 3 bd · 2 ba · 1,544 sqft
• 17 south flag drive, Kissimmee 34759 Off market since Sep 2026 $229,999 · 3 bd · 2 ba · 1,218 sqft
• 3145 stonehurst circle, Kissimmee 34741 Off market since Sep 2026 $395,000 · 3 bd · 2 ba · 1,806 sqft
• 8904 sydney avenue, Kissimmee 34747 Off market since Sep 2026 $429,000 · 5 bd · 5 ba · 2,263 sqft
• 3070 yellow lantana lane, Kissimmee 34747 Off market since Sep 2026 $265,900 · 2 bd · 3 ba · 1,161 sqft
• 1068 lake berkley drive, Kissimmee 34746 Off market since Sep 2026 $435,000 · 4 bd · 2 ba · 1,782 sqft
• 422 lakeview road, Kissimmee 34759 Off market since Sep 2026 $350,000 · 4 bd · 3 ba · 2,790 sqft