Homes under $500K in Winchester, TN

89 for sale · 265 homes listed · Updated September 27, 2026 · Page 3 of 6

• 614 fairview circle, Winchester 37398 Active Under Contract $285,000 · 3 bd · 2 ba · 1,412 sqft
• 38 murray lake drive, Winchester 37398 Active Under Contract $339,999 · 2 bd · 2 ba · 1,683 sqft
• 367 carol circle, Winchester 37398 Active Under Contract $275,000 · 3 bd · 2 ba · 1,420 sqft
• 267 brookfield circle, Winchester 37398 Active Under Contract $344,900 · 3 bd · 2 ba · 1,338 sqft
• 135 bel aire drive, Winchester 37398 Active Under Contract $239,000 · 4 bd · 2 ba · 1,889 sqft
• 1466 bible crossing road, Winchester 37398 Active Under Contract $229,000 · 2 bd · 1 ba · 1,116 sqft
• 1687 georgia crossing road, Winchester 37398 Active Under Contract $319,900 · 2 bd · 2 ba · 1,080 sqft
• 74 pine bluff road, Winchester 37398 Active Under Contract $469,000 · 3 bd · 3 ba · 2,308 sqft
• 30 west paradise drive, Winchester 37398 Active Under Contract $299,900 · 3 bd · 2 ba · 1,798 sqft
• 185 favre circle, Winchester 37398 Active Under Contract $435,000 · 3 bd · 2 ba · 1,971 sqft
• 6933 winchester highway, Winchester 37398 Active Under Contract $389,900 · 5 bd · 3 ba · 2,632 sqft
• 1102 north high street, Winchester 37398 Active Under Contract $224,900 · 3 bd · 2 ba · 1,353 sqft
• 102 cannonball court, Winchester 37398 Active Under Contract $435,000 · 2 bd · 3 ba · 1,425 sqft
• 129 meredith lane, Winchester 37398 Active Under Contract $479,000 · 3 bd · 2 ba · 2,149 sqft
• 512 cline ridge road, Winchester 37398 Active Under Contract $499,999 · 3 bd · 2 ba · 1,388 sqft
• 417 plattenburg street, Winchester 37398 Active Under Contract $139,999 · 2 bd · 1 ba · 1,018 sqft
• 135 chickamauga trail, Winchester 37398 Active Under Contract $328,500 · 3 bd · 2 ba · 1,898 sqft
• 101 royal oak drive, Winchester 37398 Active Under Contract $299,999 · 3 bd · 2 ba · 1,510 sqft
• 404 south jefferson street, Winchester 37398 Active Under Contract $228,000 · 2 bd · 2 ba · 1,370 sqft
• 204 8th avenue southeast, Winchester 37398 Active Under Contract $325,000 · 3 bd · 3 ba · 2,248 sqft
• 345 franklin heights drive, Winchester 37398 Active Under Contract $399,000 · 3 bd · 2 ba · 2,333 sqft
• 171 raspberry drive, Winchester 37398 Active Under Contract $285,000 · 3 bd · 2 ba · 1,544 sqft
• 146 holly drive, Winchester 37398 Active Under Contract $459,900 · 3 bd · 3 ba · 2,348 sqft
• 125 hazelwood lane, Winchester 37398 Active Under Contract $289,000 · 3 bd · 2 ba · 1,456 sqft
• 378 crimson drive, Winchester 37398 Active Under Contract $489,900 · 4 bd · 3 ba · 3,084 sqft
• 410 elm street, Winchester 37398 Active Under Contract $95,000 · 2 bd · 1 ba · 924 sqft
• 208 lillian street, Winchester 37398 Active Under Contract $199,500 · 3 bd · 1 ba · 1,326 sqft
• 335 myers road, Winchester 37398 Active Under Contract $289,900 · 3 bd · 2 ba · 1,768 sqft
• 107 highland drive, Winchester 37398 Active Under Contract $200,000 · 2 bd · 1 ba · 1,348 sqft
• 6004 lynchburg road, Winchester 37398 Off market since Aug 2026 $143,000 · 2 bd · 2 ba · 880 sqft
• 1517 paynes church road, Winchester 37398 Sold on Jun 23, 2026 $325,000 · 3 bd · 3 ba · 1,508 sqft
• 111 dogwood lane, Winchester 37398 Off market since Jul 2026 $300,000 · 3 bd · 1 ba · 1,822 sqft
• 102 dogwood lane, Winchester 37398 Off market since Aug 2026 $419,900 · 3 bd · 3 ba · 2,688 sqft
• 204 8th avenue southeast, Winchester 37398 Off market since Jul 2026 $373,500 · 3 bd · 3 ba · 2,476 sqft
• 2077 holders cove road, Winchester 37398 Off market since Sep 2026 $150,000 · 4 bd · 1 ba · 1,580 sqft
• 25 billy goat hill road, Winchester 37398 Off market since Aug 2026 $375,000 · 3 bd · 2 ba · 1,803 sqft
• 65 campfire court, Winchester 37398 Off market since Aug 2026 $474,900 · 4 bd · 3 ba · 2,564 sqft
• 220 bryan drive, Winchester 37398 Off market since Sep 2026 $459,000 · 4 bd · 4 ba · 2,209 sqft
• 69 anderton drive, Winchester 37398 Off market since Aug 2026 $489,900 · 3 bd · 3 ba · 2,564 sqft
• 270 wood bluff road, Winchester 37398 Off market since Sep 2026 $451,500 · 3 bd · 3 ba · 2,228 sqft
• 107 highland drive, Winchester 37398 Off market since Jul 2026 $210,000 · 3 bd · 1 ba · 1,348 sqft
• 401 east petty lane, Winchester 37398 Off market since Aug 2026 $369,900 · 3 bd · 3 ba · 2,653 sqft
• 103 anderton drive, Winchester 37398 Off market since Sep 2026 $449,900 · 5 bd · 3 ba · 2,160 sqft
• 25 lookout drive, Winchester 37398 Off market since Sep 2026 $454,900 · 4 bd · 2 ba · 1,887 sqft
• 203 campfire court, Winchester 37398 Off market since Sep 2026 $450,000 · 4 bd · 3 ba · 2,141 sqft
• 3754 aedc road, Winchester 37398 Off market since Sep 2026 $399,000 · 2 bd · 1 ba · 3,560 sqft
• 124 lookout drive, Winchester 37398 Off market since Sep 2026 $424,900 · 4 bd · 2 ba · 1,890 sqft
• 101 royal oak drive, Winchester 37398 Off market since Jul 2026 $315,000 · 3 bd · 2 ba · 1,510 sqft
• 525 sharp springs road, Winchester 37398 Off market since Jul 2026 $239,000 · 2 bd · 2 ba · 1,600 sqft
• 0 mansford road, Winchester 37398 Off market since Sep 2026 $429,900 · 3 bd · 2 ba · 1,706 sqft