Single Family Homes in Winchester, TN

136 for sale · 423 homes listed · Updated September 27, 2026 · Page 5 of 9

• 378 crimson drive, Winchester 37398 Active Under Contract $489,900 · 4 bd · 3 ba · 3,084 sqft
• 167 bluff drive, Winchester 37398 Active Under Contract $1,378,000 · 4 bd · 3 ba · 3,132 sqft
• 410 elm street, Winchester 37398 Active Under Contract $95,000 · 2 bd · 1 ba · 924 sqft
• 167 saddle up lane, Winchester 37398 Active Under Contract $554,000 · 2 bd · 2 ba · 1,650 sqft
• 208 lillian street, Winchester 37398 Active Under Contract $199,500 · 3 bd · 1 ba · 1,326 sqft
• 228 murray lake drive, Winchester 37398 Active Under Contract $1,447,500 · 3 bd · 3 ba · 3,447 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
• 379 hooper road, Winchester 37398 Off market since Jul 2026 $699,000 · 4 bd · 2 ba · 2,793 sqft
• 102 summer lake court, Winchester 37398 Off market since Sep 2026 $675,000 · 4 bd · 4 ba · 2,688 sqft
• 2124 boswell road, Winchester 37398 Off market since Sep 2026 $999,500 · 4 bd · 4 ba · 6,803 sqft
• 1517 paynes church road, Winchester 37398 Sold on Jun 23, 2026 $325,000 · 3 bd · 3 ba · 1,508 sqft
• 18 shady cove lane, Winchester 37398 Off market since Sep 2026 $545,000 · 3 bd · 2 ba · 1,788 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
• 71 slalom circle, Winchester 37398 Off market since Sep 2026 $1,445,000 · 4 bd · 4 ba · 4,500 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
• 220 bryan drive, Winchester 37398 Off market since Sep 2026 $459,000 · 4 bd · 4 ba · 2,209 sqft
• 11 hammock drive, Winchester 37398 Off market since Sep 2026 $974,900 · 4 bd · 5 ba · 3,622 sqft
• 282 owl hollow lane, Winchester 37398 Off market since Sep 2026 $840,900 · 4 bd · 3 ba · 3,484 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
• 171 cypress point drive, Winchester 37398 Off market since Jul 2026 $1,079,000 · 5 bd · 5 ba · 3,191 sqft
• 287 shasteen bend drive, Winchester 37398 Off market since Jul 2026 $850,000 · 3 bd · 3 ba · 1,821 sqft
• 155 cypress point drive, Winchester 37398 Off market since Sep 2026 $869,900 · 3 bd · 3 ba · 2,236 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
• 112 pine bluff court, Winchester 37398 Sold on Jul 20, 2026 $575,000 · 3 bd · 3 ba · 2,500 sqft
• 53 river watch way, Winchester 37398 Off market since Sep 2026 $879,900 · 5 bd · 5 ba · 3,095 sqft
• 3754 aedc road, Winchester 37398 Off market since Sep 2026 $399,000 · 2 bd · 1 ba · 3,560 sqft
• 232 loop drive, Winchester 37398 Off market since Sep 2026 $1,049,000 · 5 bd · 5 ba · 3,670 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
• 236 tims ford drive, Winchester 37398 Off market since Sep 2026 $999,500 · 4 bd · 5 ba · 6,152 sqft
• 323 ridgecrest drive, Winchester 37398 Off market since Jul 2026 $734,900 · 4 bd · 5 ba · 3,960 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
• 369 fanning bend drive, Winchester 37398 Off market since Sep 2026 $899,000 · 4 bd · 5 ba · 2,376 sqft
• 108 lookout drive, Winchester 37398 Off market since Sep 2026 $443,900 · 3 bd · 2 ba · 2,290 sqft
• 914 north jefferson street, Winchester 37398 Off market since Sep 2026 $1,049,000 · 4 bd · 3 ba · 2,714 sqft
• 118 bel aire drive, Winchester 37398 Off market since Jul 2026 $239,900 · 3 bd · 2 ba · 1,476 sqft
• 74 maple drive, Winchester 37398 Off market since Sep 2026 $649,900 · 3 bd · 2 ba · 1,754 sqft
• 645 wildwood trace, Winchester 37398 Off market since Jul 2026 $1,200,000 · 2 bd · 3 ba · 2,460 sqft
• 667 maple bend road, Winchester 37398 Off market since Sep 2026 $320,000 · 2 bd · 2 ba · 1,200 sqft
• 23 skidmore lane, Winchester 37398 Off market since Sep 2026 $499,000 · 3 bd · 3 ba · 2,276 sqft
• 712 fanning bend drive, Winchester 37398 Off market since Jul 2026 $1,275,000 · 4 bd · 5 ba · 3,492 sqft
• 1376 old mansford road, Winchester 37398 Off market since Sep 2026 $2,095,000 · 3 bd · 5 ba · 5,404 sqft