Homes under $500K in Kissimmee, FL

1,610 for sale · 5,127 homes listed · Updated September 29, 2026 · Page 63 of 103

• 1774 good neighbor loop, Kissimmee 34744 Off market since Aug 2026 $445,000 · 3 bd · 2 ba · 2,068 sqft
• 1905 hughey street, Kissimmee 34741 Off market since Sep 2026 $345,000 · 3 bd · 2 ba · 1,294 sqft
• 2244 canyon breeze avenue, Kissimmee 34746 Off market since Sep 2026 $389,500 · 4 bd · 3 ba · 1,960 sqft
• 8411 crystal cove loop, Kissimmee 34747 Off market since Sep 2026 $259,000 · 3 bd · 3 ba · 1,277 sqft
• 53 west marbrisa way, Kissimmee 34743 Off market since Sep 2026 $224,900 · 2 bd · 2 ba · 875 sqft
• 3226 fox squirrel drive, Kissimmee 34741 Off market since Sep 2026 $189,890 · 2 bd · 2 ba · 1,100 sqft
• 3831 nautical way 203, Kissimmee 34741 Off market since Sep 2026 $156,990 · 2 bd · 2 ba · 910 sqft
• 3176 tamarind circle 19, Kissimmee 34747 Off market since Aug 2026 $255,000 · 2 bd · 2 ba · 1,012 sqft
• 8458 secret key cove, Kissimmee 34747 Off market since Sep 2026 $495,000 · 4 bd · 3 ba · 2,217 sqft
• 2607 corvette lane, Kissimmee 34746 Off market since Sep 2026 $274,000 · 2 bd · 3 ba · 1,350 sqft
• 3139 britannia boulevard c, Kissimmee 34747 Off market since Sep 2026 $230,000 · 3 bd · 2 ba · 1,357 sqft
• 303 alencon way, Kissimmee 34759 Off market since Sep 2026 $399,000 · 4 bd · 2 ba · 1,872 sqft
• 3814 bay club circle 204, Kissimmee 34741 Off market since Sep 2026 $158,990 · 2 bd · 2 ba · 910 sqft
• 2048 cypress bay boulevard, Kissimmee 34743 Off market since Sep 2026 $300,000 · 3 bd · 3 ba · 1,807 sqft
• 8550 crystal cove loop, Kissimmee 34747 Off market since Sep 2026 $289,900 · 3 bd · 3 ba · 1,277 sqft
• 4417 canopy court, Kissimmee 34758 Off market since Sep 2026 $367,700 · 4 bd · 3 ba · 2,847 sqft
• 7568 sunflower circle, Kissimmee 34747 Off market since Sep 2026 $419,000 · 3 bd · 3 ba · 1,530 sqft
• 2909 theme street, Kissimmee 34746 Off market since Jul 2026 $339,660 · 3 bd · 3 ba · 1,869 sqft
• 2546 sage drive, Kissimmee 34758 Off market since Sep 2026 $359,900 · 3 bd · 2 ba · 1,434 sqft
• 2822 moultrie creek drive, Kissimmee 34743 Off market since Sep 2026 $359,990 · 3 bd · 2 ba · 1,450 sqft
• 2620 lodi circle 101, Kissimmee 34746 Off market since Sep 2026 $270,000 · 4 bd · 3 ba · 1,470 sqft
• 2661 ames haven road, Kissimmee 34744 Off market since Sep 2026 $425,830 · 4 bd · 2 ba · 1,866 sqft
• 2680 mayaguana street, Kissimmee 34747 Off market since Sep 2026 $252,000 · 3 bd · 3 ba · 1,362 sqft
• 2620 santosh cove, Kissimmee 34746 Off market since Sep 2026 $440,000 · 4 bd · 4 ba · 2,038 sqft
• 710 bluebill place, Kissimmee 34759 Off market since Sep 2026 $235,000 · 3 bd · 2 ba · 1,252 sqft
• 7498 sunville avenue, Kissimmee 34747 Off market since Sep 2026 $489,155 · 5 bd · 6 ba · 2,169 sqft
• 1317 anchor bend way, Kissimmee 34746 Off market since Jul 2026 $315,000 · 3 bd · 3 ba · 1,365 sqft
• 4721 clock tower drive 306, Kissimmee 34746 Off market since Sep 2026 $300,000 · 2 bd · 2 ba · 1,196 sqft
• 1404 dusty stone lane, Kissimmee 34744 Off market since Sep 2026 $312,990 · 3 bd · 3 ba · 1,624 sqft
• 354 dundee drive, Kissimmee 34759 Off market since Sep 2026 $245,000 · 3 bd · 2 ba · 1,071 sqft
• 1057 universal rest place, Kissimmee 34744 Off market since Sep 2026 $240,000 · 3 bd · 2 ba · 1,728 sqft
• 2776 club cortile circle a, Kissimmee 34746 Off market since Sep 2026 $215,000 · 3 bd · 2 ba · 1,202 sqft
• 3032 parkway boulevard 305, Kissimmee 34747 Off market since Sep 2026 $160,000 · 2 bd · 2 ba · 937 sqft
• 4419 azure isle way, Kissimmee 34744 Off market since Jul 2026 $479,990 · 3 bd · 2 ba · 1,941 sqft
• 3958 carrick bend drive, Kissimmee 34746 Off market since Sep 2026 $430,000 · 4 bd · 2 ba · 2,055 sqft
• 3016 madelia lane, Kissimmee 34744 Off market since Jul 2026 $405,000 · 4 bd · 2 ba · 1,784 sqft
• 2405 lincolnshire court, Kissimmee 34743 Off market since Sep 2026 $339,000 · 3 bd · 2 ba · 1,424 sqft
• 1495 skyline drive, Kissimmee 34744 Off market since Sep 2026 $435,000 · 3 bd · 2 ba · 2,094 sqft
• 2925 satire street, Kissimmee 34746 Off market since Aug 2026 $384,500 · 3 bd · 3 ba · 1,859 sqft
• 5313 barefoot path, Kissimmee 34746 Off market since Jul 2026 $339,900 · 3 bd · 2 ba · 1,377 sqft
• 7519 bliss way 7519, Kissimmee 34747 Off market since Sep 2026 $298,000 · 3 bd · 2 ba · 1,255 sqft
• 605 cadillac boulevard, Kissimmee 34741 Off market since Aug 2026 $269,000 · 4 bd · 2 ba · 1,404 sqft
• 468 acacia tree way, Kissimmee 34758 Off market since Jul 2026 $359,900 · 4 bd · 3 ba · 2,308 sqft
• 4774 cumbrian lakes drive, Kissimmee 34746 Off market since Sep 2026 $399,999 · 4 bd · 4 ba · 1,830 sqft
• 4815 south love storey lane, Kissimmee 34746 Off market since Sep 2026 $475,000 · 4 bd · 3 ba · 1,914 sqft
• 1914 manatee court, Kissimmee 34759 Off market since Sep 2026 $238,000 · 3 bd · 2 ba · 1,368 sqft
• 4327 lighterknot trace, Kissimmee 34746 Off market since Sep 2026 $434,000 · 4 bd · 3 ba · 2,581 sqft
• 1023 spring meadow drive 1023, Kissimmee 34741 Off market since Jul 2026 $165,000 · 2 bd · 2 ba · 1,012 sqft
• 2280 avian loop, Kissimmee 34741 Off market since Sep 2026 $494,900 · 4 bd · 3 ba · 2,351 sqft
• 1534 carey palm circle, Kissimmee 34747 Off market since Sep 2026 $469,980 · 4 bd · 5 ba · 2,090 sqft