4 Bedroom Homes in Winchester, TN

40 for sale · 123 homes listed · Updated September 27, 2026 · Page 2 of 3

142 barefoot way, Winchester 37398 Active Under Contract $575,000 · 4 bd · 4 ba · 2,150 sqft
379 bell drive west, Winchester 37398 Active Under Contract $530,000 · 4 bd · 4 ba · 3,579 sqft
798 haddon lane, Winchester 37398 Active Under Contract $650,000 · 4 bd · 4 ba · 2,723 sqft
426 maple bend road, Winchester 37398 Active Under Contract $619,900 · 4 bd · 3 ba · 2,981 sqft
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
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
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
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
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
124 lookout drive, Winchester 37398 Off market since Sep 2026 $424,900 · 4 bd · 2 ba · 1,890 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
369 fanning bend drive, Winchester 37398 Off market since Sep 2026 $899,000 · 4 bd · 5 ba · 2,376 sqft
914 north jefferson street, Winchester 37398 Off market since Sep 2026 $1,049,000 · 4 bd · 3 ba · 2,714 sqft
712 fanning bend drive, Winchester 37398 Off market since Jul 2026 $1,275,000 · 4 bd · 5 ba · 3,492 sqft
208 loop drive, Winchester 37398 Off market since Sep 2026 $1,050,000 · 4 bd · 4 ba · 2,906 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
100 barefoot way, Winchester 37398 Off market since Sep 2026 $1,249,900 · 4 bd · 5 ba · 2,800 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
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
117 hammock drive, Winchester 37398 Off market since Sep 2026 $959,000 · 4 bd · 4 ba · 3,034 sqft
58 island way, Winchester 37398 Off market since Sep 2026 $429,000 · 4 bd · 3 ba · 2,660 sqft
347 campfire court, Winchester 37398 Off market since Sep 2026 $600,000 · 4 bd · 3 ba · 2,930 sqft
128 bel aire drive, Winchester 37398 Off market since Jul 2026 $309,900 · 4 bd · 2 ba · 1,923 sqft
70 island way, Winchester 37398 Off market since Sep 2026 $479,900 · 4 bd · 3 ba · 2,578 sqft
73 cypress point drive, Winchester 37398 Off market since Jul 2026 $879,000 · 4 bd · 4 ba · 2,684 sqft
71 fanning bend drive, Winchester 37398 Off market since Sep 2026 $1,075,000 · 4 bd · 3 ba · 2,583 sqft
356 ridgecrest drive, Winchester 37398 Off market since Aug 2026 $689,900 · 4 bd · 4 ba · 3,705 sqft
240 myers road, Winchester 37398 Off market since Aug 2026 $338,000 · 4 bd · 3 ba · 1,960 sqft
260 lookout drive, Winchester 37398 Off market since Jul 2026 $649,000 · 4 bd · 3 ba · 3,115 sqft
0 ridgecrest drive, Winchester 37398 Off market since Sep 2026 $794,500 · 4 bd · 4 ba · 3,165 sqft
44 houghton drive, Winchester 37398 Off market since Sep 2026 $399,900 · 4 bd · 4 ba · 2,197 sqft
160 wakeboard way, Winchester 37398 Off market since Aug 2026 $1,229,900 · 4 bd · 4 ba · 3,720 sqft
318 north porter street, Winchester 37398 Off market since Sep 2026 $2,110,900 · 4 bd · 6 ba · 6,160 sqft
805 north jefferson street, Winchester 37398 Off market since Sep 2026 $474,900 · 4 bd · 4 ba · 2,260 sqft
210 cascade drive, Winchester 37398 Off market since Sep 2026 $774,900 · 4 bd · 5 ba · 3,090 sqft