Homes under $500K in Kissimmee, FL

1,610 for sale · 5,127 homes listed · Updated September 29, 2026 · Page 55 of 103

• 1991 key bay trail, Kissimmee 34747 Off market since Sep 2026 $293,000 · 2 bd · 2 ba · 1,437 sqft
• 8061 vacation avenue 108, Kissimmee 34747 Off market since Jul 2026 $445,000 · 2 bd · 2 ba · 1,029 sqft
• 9008 shine drive, Kissimmee 34747 Off market since Sep 2026 $335,000 · 4 bd · 3 ba · 1,694 sqft
• 3174 feltrim place 203, Kissimmee 34747 Off market since Jul 2026 $219,500 · 3 bd · 2 ba · 1,269 sqft
• 2821 almaton loop 301, Kissimmee 34747 Off market since Sep 2026 $340,000 · 3 bd · 2 ba · 1,246 sqft
• 1765 brockridge road, Kissimmee 34744 Off market since Aug 2026 $359,990 · 3 bd · 2 ba · 1,690 sqft
• 7525 bliss way, Kissimmee 34747 Off market since Sep 2026 $308,900 · 3 bd · 3 ba · 1,808 sqft
• 970 amy ridge court, Kissimmee 34747 Off market since Sep 2026 $379,900 · 3 bd · 2 ba · 1,662 sqft
• 4039 navigator way, Kissimmee 34746 Off market since Sep 2026 $359,000 · 4 bd · 3 ba · 2,123 sqft
• 4650 eagle peak drive, Kissimmee 34746 Off market since Aug 2026 $419,000 · 4 bd · 2 ba · 1,822 sqft
• 1037 lake berkley drive, Kissimmee 34746 Off market since Aug 2026 $489,900 · 5 bd · 3 ba · 2,317 sqft
• 2972 salted rim road, Kissimmee 34747 Off market since Sep 2026 $465,000 · 3 bd · 3 ba · 1,564 sqft
• 216 aquamarine lane, Kissimmee 34758 Off market since Sep 2026 $398,000 · 5 bd · 3 ba · 2,271 sqft
• 423 vernon court, Kissimmee 34759 Off market since Sep 2026 $270,000 · 3 bd · 2 ba · 1,163 sqft
• 605 tamarin lane, Kissimmee 34759 Off market since Jul 2026 $252,100 · 2 bd · 2 ba · 1,075 sqft
• 4741 clock tower drive 108, Kissimmee 34746 Off market since Sep 2026 $385,000 · 3 bd · 2 ba · 1,329 sqft
• 25 zinnia lane east, Kissimmee 34759 Off market since Sep 2026 $315,000 · 4 bd · 2 ba · 1,758 sqft
• 189 grand canal drive, Kissimmee 34759 Off market since Aug 2026 $245,000 · 2 bd · 2 ba · 1,240 sqft
• 172 pinewood circle, Kissimmee 34743 Off market since Sep 2026 $404,998 · 4 bd · 3 ba · 1,916 sqft
• 7958 haverhill way, Kissimmee 34747 Off market since Sep 2026 $429,900 · 3 bd · 2 ba · 1,570 sqft
• 3228 running bear way, Kissimmee 34746 Off market since Sep 2026 $379,000 · 3 bd · 2 ba · 1,377 sqft
• 1647 windsor oak court, Kissimmee 34744 Off market since Sep 2026 $245,000 · 3 bd · 3 ba · 1,380 sqft
• 579 kilimanjaro drive, Kissimmee 34758 Off market since Sep 2026 $273,777 · 3 bd · 2 ba · 1,761 sqft
• 2558 east chatman circle, Kissimmee 34746 Off market since Sep 2026 $398,000 · 3 bd · 2 ba · 1,380 sqft
• 3510 beau road, Kissimmee 34746 Off market since Sep 2026 $320,000 · 4 bd · 3 ba · 2,043 sqft
• 507 presido park place, Kissimmee 34759 Off market since Sep 2026 $259,000 · 2 bd · 2 ba · 1,302 sqft
• 2956 salted rim road, Kissimmee 34747 Off market since Sep 2026 $372,999 · 2 bd · 2 ba · 1,188 sqft
• 4741 clock tower drive 102, Kissimmee 34746 Off market since Sep 2026 $294,500 · 2 bd · 2 ba · 1,186 sqft
• 4756 tribute trail, Kissimmee 34746 Off market since Sep 2026 $327,900 · 3 bd · 3 ba · 1,848 sqft
• 8945 shine drive, Kissimmee 34747 Off market since Sep 2026 $299,800 · 3 bd · 2 ba · 1,300 sqft
• 3335 composition street, Kissimmee 34758 Off market since Sep 2026 $275,000 · 2 bd · 3 ba · 1,180 sqft
• 1617 mohegan boulevard, Kissimmee 34744 Off market since Sep 2026 $339,000 · 3 bd · 3 ba · 1,896 sqft
• 331 marquee drive, Kissimmee 34758 Off market since Aug 2026 $319,999 · 3 bd · 2 ba · 1,602 sqft
• 1201 bermuda lakes lane 205, Kissimmee 34741 Off market since Aug 2026 $245,000 · 3 bd · 2 ba · 1,220 sqft
• 2433 caravelle circle, Kissimmee 34746 Off market since Aug 2026 $339,000 · 4 bd · 3 ba · 1,400 sqft
• 3000 maingate lane 327, Kissimmee 34747 Off market since Sep 2026 $41,000 · 1 bd · 1 ba · 304 sqft
• 1686 contentment loop, Kissimmee 34744 Off market since Sep 2026 $340,000 · 3 bd · 3 ba · 1,755 sqft
• 9040 ocean tide way, Kissimmee 34747 Off market since Sep 2026 $329,000 · 3 bd · 3 ba · 1,460 sqft
• 4876 romeo circle, Kissimmee 34746 Off market since Sep 2026 $468,900 · 4 bd · 3 ba · 1,914 sqft
• 410 las fuentes drive, Kissimmee 34746 Off market since Sep 2026 $410,000 · 4 bd · 4 ba · 2,451 sqft
• 2937 banana palm drive, Kissimmee 34747 Off market since Sep 2026 $339,900 · 4 bd · 3 ba · 1,902 sqft
• 7540 sunville avenue, Kissimmee 34747 Off market since Sep 2026 $454,900 · 4 bd · 5 ba · 1,804 sqft
• 1024 chalcedony street, Kissimmee 34744 Off market since Sep 2026 $299,000 · 3 bd · 3 ba · 1,562 sqft
• 2442 sweetwater club circle 41, Kissimmee 34746 Off market since Sep 2026 $204,990 · 3 bd · 2 ba · 1,220 sqft
• 2508 baykal drive, Kissimmee 34746 Off market since Sep 2026 $389,000 · 4 bd · 3 ba · 2,396 sqft
• 4604 southport bay drive, Kissimmee 34759 Off market since Sep 2026 $329,990 · 4 bd · 2 ba · 1,402 sqft
• 7657 recife drive, Kissimmee 34747 Off market since Sep 2026 $430,000 · 4 bd · 5 ba · 2,396 sqft
• 8957 california palm road, Kissimmee 34747 Off market since Aug 2026 $349,000 · 4 bd · 3 ba · 1,902 sqft
• 3587 davenport creek court, Kissimmee 34746 Off market since Sep 2026 $310,000 · 3 bd · 3 ba · 1,373 sqft
• 5794 portico place, Kissimmee 34758 Off market since Sep 2026 $353,514 · 4 bd · 4 ba · 1,989 sqft