Homes under $500K in Kissimmee, FL

1,610 for sale · 5,127 homes listed · Updated September 29, 2026 · Page 64 of 103

• 4752 blue diamond street, Kissimmee 34746 Off market since Sep 2026 $399,900 · 3 bd · 3 ba · 2,420 sqft
• 4978 strand street 0, Kissimmee 34758 Off market since Sep 2026 $399,000 · 4 bd · 4 ba · 2,182 sqft
• 1823 spring shower circle, Kissimmee 34744 Off market since Sep 2026 $394,900 · 3 bd · 2 ba · 1,579 sqft
• 2834 eagle eye court, Kissimmee 34746 Off market since Sep 2026 $392,500 · 3 bd · 3 ba · 2,301 sqft
• 4764 ormond beach way, Kissimmee 34746 Off market since Sep 2026 $285,500 · 3 bd · 3 ba · 1,286 sqft
• 1066 park ridge circle, Kissimmee 34746 Off market since Sep 2026 $236,400 · 3 bd · 3 ba · 1,291 sqft
• 3000 maingate lane 319, Kissimmee 34747 Off market since Sep 2026 $48,500 · 1 ba · 304 sqft
• 7605 recife drive, Kissimmee 34747 Off market since Sep 2026 $385,000 · 3 bd · 4 ba · 2,181 sqft
• 3589 anibal street, Kissimmee 34746 Off market since Sep 2026 $300,000 · 3 bd · 3 ba · 1,373 sqft
• 2024 cypress bay boulevard, Kissimmee 34743 Off market since Sep 2026 $294,999 · 3 bd · 3 ba · 1,807 sqft
• 2139 balboa way, Kissimmee 34741 Off market since Sep 2026 $258,900 · 2 bd · 3 ba · 1,418 sqft
• 3204 sabal palms court b, Kissimmee 34747 Off market since Sep 2026 $168,900 · 2 bd · 2 ba · 1,087 sqft
• 1150 south beach circle, Kissimmee 34746 Off market since Sep 2026 $214,000 · 3 bd · 3 ba · 1,468 sqft
• 4569 corsa lane, Kissimmee 34746 Off market since Sep 2026 $289,900 · 3 bd · 3 ba · 1,295 sqft
• 418 marlberry leaf court, Kissimmee 34758 Off market since Sep 2026 $380,000 · 4 bd · 3 ba · 2,571 sqft
• 3533 somerset circle, Kissimmee 34746 Off market since Sep 2026 $489,000 · 4 bd · 3 ba · 2,452 sqft
• 200 aquamarine lane, Kissimmee 34758 Off market since Sep 2026 $385,000 · 4 bd · 2 ba · 1,845 sqft
• 8056 dreamsicle drive, Kissimmee 34747 Off market since Sep 2026 $390,000 · 2 bd · 3 ba · 1,283 sqft
• 813 glendora road, Kissimmee 34759 Off market since Sep 2026 $489,000 · 3 bd · 3 ba · 2,454 sqft
• 5350 diplomat court 104, Kissimmee 34746 Off market since Sep 2026 $315,000 · 4 bd · 3 ba · 1,694 sqft
• 3001 laurel park lane 105, Kissimmee 34741 Off market since Sep 2026 $244,995 · 3 bd · 2 ba · 1,433 sqft
• 522-524 imperial place, Kissimmee 34758 Off market since Sep 2026 $455,000 · 6 bd · 4 ba · 2,310 sqft
• 1822 bering road, Kissimmee 34759 Off market since Sep 2026 $325,000 · 3 bd · 2 ba · 1,496 sqft
• 14 glendale drive, Kissimmee 34744 Off market since Sep 2026 $475,000 · 4 bd · 3 ba · 2,510 sqft
• 2003 kelley avenue, Kissimmee 34744 Off market since Jul 2026 $437,000 · 6 bd · 3 ba · 2,568 sqft
• 2009 kelley avenue, Kissimmee 34744 Off market since Jul 2026 $437,000 · 6 bd · 3 ba · 2,568 sqft
• 305 medina court, Kissimmee 34758 Off market since Sep 2026 $270,000 · 3 bd · 2 ba · 1,948 sqft
• 3201 gold lane, Kissimmee 34747 Off market since Sep 2026 $318,000 · 4 bd · 3 ba · 1,694 sqft
• 9055 treasure trove lane 208, Kissimmee 34747 Off market since Sep 2026 $195,000 · 2 bd · 2 ba · 1,445 sqft
• 352 clermont drive, Kissimmee 34759 Off market since Aug 2026 $310,000 · 3 bd · 2 ba · 1,810 sqft
• 1174 seaside mist trail, Kissimmee 34747 Off market since Sep 2026 $328,400 · 3 bd · 3 ba · 1,654 sqft
• 1001 la mirada court, Kissimmee 34744 Off market since Sep 2026 $355,000 · 4 bd · 3 ba · 1,626 sqft
• 8931 shine drive, Kissimmee 34747 Off market since Sep 2026 $271,500 · 3 bd · 2 ba · 1,300 sqft
• 217 ellsworth drive, Kissimmee 34758 Off market since Sep 2026 $269,900 · 4 bd · 3 ba · 1,951 sqft
• 1842 egret meadows avenue, Kissimmee 34744 Off market since Sep 2026 $399,900 · 4 bd · 2 ba · 1,846 sqft
• 3839 golden feather way, Kissimmee 34746 Off market since Sep 2026 $499,900 · 4 bd · 4 ba · 3,032 sqft
• 2342 barbados court, Kissimmee 34741 Off market since Sep 2026 $230,000 · 2 bd · 2 ba · 991 sqft
• 2611 gala road north 106, Kissimmee 34746 Off market since Sep 2026 $229,900 · 3 bd · 2 ba · 1,296 sqft
• 4607 kalispell road, Kissimmee 34758 Off market since Sep 2026 $324,000 · 3 bd · 2 ba · 1,680 sqft
• 4554 alberto circle, Kissimmee 34746 Off market since Sep 2026 $315,000 · 3 bd · 3 ba · 1,295 sqft
• 2821 scenic lane, Kissimmee 34744 Off market since Sep 2026 $499,900 · 4 bd · 3 ba · 2,538 sqft
• 2832 osprey cove place 202, Kissimmee 34746 Off market since Sep 2026 $190,000 · 3 bd · 2 ba · 1,136 sqft
• 2737 cranmoor drive, Kissimmee 34758 Off market since Sep 2026 $240,000 · 3 bd · 2 ba · 1,104 sqft
• 1112 roan court, Kissimmee 34759 Off market since Sep 2026 $294,000 · 4 bd · 2 ba · 1,804 sqft
• 3167a brasilia avenue, Kissimmee 34747 Off market since Sep 2026 $420,000 · 3 bd · 4 ba · 2,181 sqft
• 3171a brasilia avenue, Kissimmee 34747 Sold on Jul 15, 2026 $429,000 · 4 bd · 5 ba · 2,396 sqft
• 2215 san vittorino circle 102, Kissimmee 34741 Off market since Sep 2026 $255,000 · 4 bd · 3 ba · 1,470 sqft
• 1764 stamen drive, Kissimmee 34744 Off market since Sep 2026 $444,990 · 3 bd · 3 ba · 1,985 sqft
• 2801 oakwater drive 2801, Kissimmee 34747 Off market since Sep 2026 $305,000 · 3 bd · 2 ba · 1,255 sqft
• 2040 royal bay boulevard 30, Kissimmee 34746 Off market since Sep 2026 $214,500 · 3 bd · 2 ba · 1,326 sqft