Homes under $500K in Kissimmee, FL

1,610 for sale · 5,127 homes listed · Updated September 29, 2026 · Page 58 of 103

• 1158 saint tropez court, Kissimmee 34759 Off market since Sep 2026 $240,000 · 3 bd · 2 ba · 1,825 sqft
• 2050 east irlo bronson memorial highway 108, Kissimmee 34744 Off market since Sep 2026 $55,000 · 1 bd · 1 ba · 324 sqft
• 409 fountainhead circle 236, Kissimmee 34741 Off market since Sep 2026 $165,000 · 2 bd · 2 ba · 932 sqft
• 8419 crystal cove loop, Kissimmee 34747 Off market since Sep 2026 $245,500 · 3 bd · 3 ba · 1,291 sqft
• 8174 coconut place, Kissimmee 34747 Off market since Aug 2026 $407,000 · 2 bd · 3 ba · 1,440 sqft
• 2915 blooming alamanda loop, Kissimmee 34747 Off market since Aug 2026 $474,995 · 5 bd · 4 ba · 2,677 sqft
• 3172 river branch circle, Kissimmee 34741 Off market since Sep 2026 $316,000 · 3 bd · 2 ba · 1,512 sqft
• 8919 shine drive, Kissimmee 34747 Off market since Sep 2026 $307,000 · 3 bd · 2 ba · 1,300 sqft
• 4802 love storey lane, Kissimmee 34746 Off market since Sep 2026 $474,900 · 4 bd · 3 ba · 1,914 sqft
• 2729 north poinciana boulevard 117, Kissimmee 34746 Off market since Sep 2026 $215,000 · 3 bd · 2 ba · 1,301 sqft
• 8834 coral palms court a, Kissimmee 34747 Off market since Sep 2026 $220,000 · 4 bd · 2 ba · 1,220 sqft
• 305 chelmsford court, Kissimmee 34758 Off market since Sep 2026 $275,000 · 4 bd · 2 ba · 1,808 sqft
• 265 gladiola court, Kissimmee 34759 Off market since Jul 2026 $287,890 · 4 bd · 2 ba · 1,861 sqft
• 8969 majesty palm road, Kissimmee 34747 Off market since Sep 2026 $310,000 · 4 bd · 3 ba · 1,884 sqft
• 3150 paradox circle 302, Kissimmee 34746 Off market since Sep 2026 $295,000 · 2 bd · 2 ba · 1,186 sqft
• 1007 siena park boulevard east, Kissimmee 34747 Off market since Sep 2026 $469,000 · 3 bd · 2 ba · 1,465 sqft
• 2472 palm tree drive, Kissimmee 34759 Off market since Sep 2026 $289,900 · 3 bd · 2 ba · 1,539 sqft
• 2505 coral avenue, Kissimmee 34741 Off market since Sep 2026 $230,000 · 2 bd · 2 ba · 1,074 sqft
• 2163 copper bell place, Kissimmee 34747 Off market since Aug 2026 $499,900 · 4 bd · 5 ba · 2,090 sqft
• 2930 polynesian isle boulevard 245, Kissimmee 34746 Off market since Jul 2026 $65,000 · 1 bd · 1 ba · 300 sqft
• 2360 eagle talon court, Kissimmee 34746 Off market since Sep 2026 $492,000 · 4 bd · 3 ba · 2,604 sqft
• 2031 cascades boulevard 103, Kissimmee 34741 Off market since Sep 2026 $135,000 · 1 bd · 1 ba · 618 sqft
• 3964 carrick bend drive, Kissimmee 34746 Off market since Sep 2026 $484,900 · 4 bd · 3 ba · 2,424 sqft
• 699 glendora road, Kissimmee 34759 Off market since Jul 2026 $430,000 · 3 bd · 3 ba · 2,450 sqft
• 3028 parkway boulevard 105, Kissimmee 34747 Off market since Sep 2026 $230,000 · 2 bd · 2 ba · 937 sqft
• 3180 paradox circle 108, Kissimmee 34746 Off market since Sep 2026 $379,000 · 3 bd · 2 ba · 1,329 sqft
• 3827 bay club circle 204, Kissimmee 34741 Off market since Sep 2026 $182,000 · 2 bd · 2 ba · 910 sqft
• 4626 eagle peak drive, Kissimmee 34746 Off market since Sep 2026 $409,000 · 4 bd · 2 ba · 1,822 sqft
• 3115 fox squirrel drive 3115, Kissimmee 34741 Off market since Sep 2026 $159,900 · 3 bd · 2 ba · 1,250 sqft
• 84 east marbrisa way, Kissimmee 34743 Off market since Sep 2026 $179,000 · 2 bd · 1 ba · 750 sqft
• 7681 sir kaufmann court, Kissimmee 34747 Off market since Sep 2026 $410,000 · 3 bd · 3 ba · 1,440 sqft
• 236 aquamarine lane, Kissimmee 34758 Off market since Sep 2026 $366,000 · 4 bd · 2 ba · 1,845 sqft
• 5367 west irlo bronson memorial highway 1-209, Kissimmee 34746 Off market since Jul 2026 $65,000 · 1 bd · 1 ba · 231 sqft
• 5367 west irlo bronson memorial highway 1-210, Kissimmee 34746 Off market since Sep 2026 $65,000 · 1 bd · 1 ba · 231 sqft
• 3007 white orchid road, Kissimmee 34747 Off market since Sep 2026 $220,000 · 2 bd · 3 ba · 1,161 sqft
• 3154 tamarind circle, Kissimmee 34747 Off market since Aug 2026 $415,000 · 2 bd · 2 ba · 1,012 sqft
• 8070 unwind way 5211, Kissimmee 34747 Off market since Sep 2026 $199,900 · 1 bd · 1 ba · 501 sqft
• 8070 unwind way 5314, Kissimmee 34747 Off market since Sep 2026 $279,900 · 1 bd · 1 ba · 745 sqft
• 8070 unwind way 5416, Kissimmee 34747 Off market since Sep 2026 $377,900 · 2 bd · 2 ba · 1,029 sqft
• 2540 blowing breeze avenue, Kissimmee 34744 Off market since Sep 2026 $370,000 · 3 bd · 3 ba · 1,700 sqft
• 2444 varenna loop, Kissimmee 34741 Off market since Sep 2026 $425,000 · 3 bd · 2 ba · 1,706 sqft
• 8061 vacation avenue 2307, Kissimmee 34747 Off market since Sep 2026 $275,000 · 1 bd · 1 ba · 501 sqft
• 9025 rhodes street, Kissimmee 34747 Off market since Jul 2026 $435,000 · 5 bd · 5 ba · 2,263 sqft
• 8061 vacation avenue 2313, Kissimmee 34747 Off market since Sep 2026 $275,000 · 1 bd · 1 ba · 501 sqft
• 1861 houston street, Kissimmee 34743 Off market since Sep 2026 $299,900 · 3 bd · 3 ba · 1,452 sqft
• 4652 tribute trail, Kissimmee 34746 Off market since Sep 2026 $320,000 · 3 bd · 3 ba · 1,674 sqft
• 2634 corvette lane, Kissimmee 34746 Off market since Sep 2026 $285,000 · 2 bd · 3 ba · 1,350 sqft
• 4338 finch lane, Kissimmee 34746 Off market since Jul 2026 $369,990 · 4 bd · 2 ba · 1,843 sqft
• 8815 grand palms circle b, Kissimmee 34747 Off market since Sep 2026 $209,999 · 3 bd · 2 ba · 1,222 sqft
• 1822 foxhall circle 1822, Kissimmee 34741 Off market since Aug 2026 $150,000 · 2 bd · 2 ba · 1,074 sqft