Homes under $500K in Kissimmee, FL

1,610 for sale · 5,127 homes listed · Updated September 29, 2026 · Page 48 of 103

• 4971 town terrace southwest, Kissimmee 34758 Active Under Contract $239,999 · 3 bd · 3 ba · 1,504 sqft
• 4733 blue diamond street, Kissimmee 34746 Active Under Contract $465,000 · 4 bd · 3 ba · 1,978 sqft
• 5112 violet lane, Kissimmee 34758 Active Under Contract $379,900 · 3 bd · 2 ba · 1,480 sqft
• 2602 einwood drive, Kissimmee 34758 Active Under Contract $179,000 · 3 bd · 2 ba · 1,507 sqft
• 163 seneca point trail, Kissimmee 34746 Active Under Contract $380,000 · 4 bd · 3 ba · 1,740 sqft
• 412 martigues drive, Kissimmee 34759 Active Under Contract $229,000 · 3 bd · 2 ba · 1,457 sqft
• 8825 coral palms court a, Kissimmee 34747 Active Under Contract $215,000 · 3 bd · 2 ba · 1,168 sqft
• 7748 indian ridge trail south, Kissimmee 34747 Active Under Contract $389,900 · 4 bd · 2 ba · 1,787 sqft
• 2433 white poppy drive, Kissimmee 34747 Active Under Contract $384,900 · 4 bd · 2 ba · 1,830 sqft
• 4005 san sebastian drive 101, Kissimmee 34741 Active Under Contract $265,000 · 4 bd · 3 ba · 1,470 sqft
• 1647 key bay trail, Kissimmee 34747 Active Under Contract $325,000 · 2 bd · 2 ba · 1,557 sqft
• 3341 whitestone circle 203, Kissimmee 34741 Active Under Contract $224,000 · 3 bd · 2 ba · 1,433 sqft
• 962 splash shot place, Kissimmee 33896 Active Under Contract $399,900 · 4 bd · 3 ba · 1,914 sqft
• 120 lindenwood lane, Kissimmee 34743 Active Under Contract $310,000 · 3 bd · 2 ba · 1,610 sqft
• 1915 estuary lane, Kissimmee 34747 Active Under Contract $499,900 · 3 bd · 2 ba · 2,202 sqft
• 4156 key colony place, Kissimmee 34746 Active Under Contract $349,500 · 4 bd · 3 ba · 2,156 sqft
• 2344 caravelle circle, Kissimmee 34746 Active Under Contract $314,990 · 4 bd · 3 ba · 1,636 sqft
• 2680 robin avenue, Kissimmee 34744 Active Under Contract $350,000 · 3 bd · 2 ba · 1,435 sqft
• 4840 lake cecile drive, Kissimmee 34746 Active Under Contract $325,000 · 3 bd · 2 ba · 1,959 sqft
• 1240 windway circle, Kissimmee 34744 Active Under Contract $359,000 · 3 bd · 2 ba · 1,173 sqft
• 1730 neptune road, Kissimmee 34744 Active Under Contract $399,000 · 4 bd · 3 ba · 2,658 sqft
• 336 magical way, Kissimmee 34744 Active Under Contract $395,000 · 4 bd · 3 ba · 1,797 sqft
• 3245 whooping crane run, Kissimmee 34741 Active Under Contract $396,900 · 3 bd · 2 ba · 1,498 sqft
• 1090 jason ridge court, Kissimmee 34747 Active Under Contract $369,900 · 3 bd · 2 ba · 1,679 sqft
• 3285 smoke signal circle, Kissimmee 34746 Active Under Contract $375,000 · 2 bd · 2 ba · 1,123 sqft
• 581 woodlawn terrace, Kissimmee 34744 Active Under Contract $499,900 · 3 bd · 2 ba · 2,467 sqft
• 157 sand piper drive, Kissimmee 34759 Active Under Contract $314,500 · 3 bd · 3 ba · 2,267 sqft
• 3044 slough creek drive, Kissimmee 34744 Active Under Contract $440,000 · 4 bd · 3 ba · 2,016 sqft
• 626 baldwin drive, Kissimmee 34758 Active Under Contract $349,900 · 4 bd · 2 ba · 2,236 sqft
• 3003 limbo lane #103, Kissimmee 34746 Active Under Contract $235,000 · 2 bd · 2 ba · 1,159 sqft
• 4820 love storey lane, Kissimmee 34746 Active Under Contract $449,000 · 4 bd · 3 ba · 1,914 sqft
• 8752 good vibes place, Kissimmee 34747 Active Under Contract $364,900 · 3 bd · 3 ba · 1,372 sqft
• 206 great yarmouth court, Kissimmee 34758 Active Under Contract $299,700 · 4 bd · 2 ba · 1,874 sqft
• 3189 dasha palm drive, Kissimmee 34744 Active Under Contract $354,900 · 3 bd · 2 ba · 1,630 sqft
• 909 san marco drive, Kissimmee 34758 Active Under Contract $279,985 · 3 bd · 2 ba · 1,569 sqft
• 1869 monte cristo lane, Kissimmee 34758 Active Under Contract $349,500 · 3 bd · 2 ba · 1,770 sqft
• 66 herring court, Kissimmee 34759 Active Under Contract $349,000 · 5 bd · 3 ba · 3,170 sqft
• 2220 wyndham palms way, Kissimmee 34747 Active Under Contract $429,900 · 4 bd · 2 ba · 1,567 sqft
• 2260 painter lane, Kissimmee 34741 Active Under Contract $349,990 · 3 bd · 3 ba · 1,838 sqft
• 2608 deck avenue, Kissimmee 34743 Active Under Contract $375,000 · 4 bd · 2 ba · 1,682 sqft
• 1418 bay street, Kissimmee 34744 Active Under Contract $210,000 · 2 bd · 1 ba · 744 sqft
• 2352 old dixie highway, Kissimmee 34744 Active Under Contract $325,000 · 3 bd · 2 ba · 1,438 sqft
• 1934 fairway loop, Kissimmee 34746 Active Under Contract $405,000 · 3 bd · 2 ba · 1,922 sqft
• 925 gillingham court, Kissimmee 34758 Active Under Contract $269,000 · 3 bd · 2 ba · 1,609 sqft
• 619 mayan place, Kissimmee 34758 Active Under Contract $309,000 · 3 bd · 2 ba · 1,730 sqft
• 3107 harris park way, Kissimmee 34758 Active Under Contract $307,990 · 4 bd · 3 ba · 2,175 sqft
• 291 magical way, Kissimmee 34744 Active Under Contract $389,900 · 4 bd · 3 ba · 1,797 sqft
• 8475 oasis key cove, Kissimmee 34747 Active Under Contract $498,000 · 7 bd · 6 ba · 2,881 sqft
• 2414 huron circle, Kissimmee 34746 Active Under Contract $399,000 · 5 bd · 3 ba · 3,124 sqft
• 621 juillac way, Kissimmee 34759 Active Under Contract $289,999 · 3 bd · 3 ba · 2,215 sqft