Homes under $1M in Winchester, TN

131 for sale · 398 homes listed · Updated September 27, 2026 · Page 5 of 8

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
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
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
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
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
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
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
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
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
16 bingham court, Winchester 37398 Off market since Sep 2026 $549,000 · 3 bd · 3 ba · 1,952 sqft
50 maple drive, Winchester 37398 Off market since Sep 2026 $575,000 · 3 bd · 2 ba · 1,493 sqft
154 barefoot way, Winchester 37398 Off market since Jul 2026 $599,900 · 4 bd · 3 ba · 2,224 sqft
0 cascade drive, Winchester 37398 Off market since Jul 2026 $774,900 · 4 bd · 5 ba · 3,090 sqft
111 barefoot way, Winchester 37398 Off market since Jul 2026 $614,900 · 4 bd · 3 ba · 1,981 sqft
49 driftwood court, Winchester 37398 Off market since Sep 2026 $612,086 · 4 bd · 3 ba · 2,893 sqft
59 turtle court, Winchester 37398 Off market since Sep 2026 $695,900 · 4 bd · 4 ba · 2,560 sqft
55 windjammer court, Winchester 37398 Off market since Sep 2026 $799,500 · 4 bd · 4 ba · 3,034 sqft
205 houghton drive, Winchester 37398 Off market since Sep 2026 $349,900 · 4 bd · 3 ba · 2,640 sqft
766 awalt drive, Winchester 37398 Off market since Sep 2026 $649,900 · 3 bd · 4 ba · 3,706 sqft
49 why worry lane, Winchester 37398 Off market since Sep 2026 $998,996 · 4 bd · 4 ba · 3,521 sqft
206 homeward avenue, Winchester 37398 Off market since Sep 2026 $299,900 · 4 bd · 2 ba · 1,999 sqft
6265 lynchburg road, Winchester 37398 Off market since Aug 2026 $309,000 · 2 bd · 2 ba · 1,472 sqft
1400 holders cove road, Winchester 37398 Off market since Sep 2026 $325,000 · 3 bd · 1 ba · 1,490 sqft
74 six mile board road, Winchester 37398 Off market since Aug 2026 $299,000 · 2 bd · 2 ba · 1,472 sqft
117 hammock drive, Winchester 37398 Off market since Sep 2026 $959,000 · 4 bd · 4 ba · 3,034 sqft
802 evans road, Winchester 37398 Off market since Sep 2026 $389,900 · 3 bd · 2 ba · 1,632 sqft
383 strawberry drive, Winchester 37398 Off market since Jul 2026 $296,000 · 3 bd · 2 ba · 1,296 sqft
1200 little street, Winchester 37398 Off market since Jul 2026 $310,000 · 5 bd · 2 ba · 1,600 sqft