Single Family Homes in Winchester, TN

136 for sale · 423 homes listed · Updated September 27, 2026 · Page 6 of 9

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
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
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
1485 water tank road, Winchester 37398 Off market since Sep 2026 $1,475,000 · 3 bd · 5 ba · 6,300 sqft
6063 mansford road, Winchester 37398 Off market since Sep 2026 $369,900 · 3 bd · 3 ba · 1,833 sqft
1010 north high street, Winchester 37398 Off market since Sep 2026 $249,900 · 3 bd · 2 ba · 1,866 sqft
347 campfire court, Winchester 37398 Off market since Sep 2026 $600,000 · 4 bd · 3 ba · 2,930 sqft
319 campfire court, Winchester 37398 Off market since Sep 2026 $595,000 · 3 bd · 4 ba · 2,579 sqft
61 brookfield circle, Winchester 37398 Off market since Sep 2026 $340,000 · 3 bd · 2 ba · 2,038 sqft
172 lookout drive, Winchester 37398 Off market since Sep 2026 $469,900 · 3 bd · 2 ba · 1,817 sqft
128 bel aire drive, Winchester 37398 Off market since Jul 2026 $309,900 · 4 bd · 2 ba · 1,923 sqft
67 lake lane, Winchester 37398 Off market since Sep 2026 $350,000 · 3 bd · 2 ba · 1,886 sqft
794 river watch way, Winchester 37398 Off market since Sep 2026 $584,000 · 3 bd · 2 ba · 1,909 sqft
106 clearview circle, Winchester 37398 Off market since Sep 2026 $799,000 · 3 bd · 3 ba · 2,395 sqft
71 david crockett highway, Winchester 37398 Off market since Sep 2026 $435,000 · 5 bd · 3 ba · 2,420 sqft
173 country club terrace, Winchester 37398 Off market since Sep 2026 $299,000 · 3 bd · 3 ba · 2,047 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
309 2nd avenue northwest, Winchester 37398 Off market since Sep 2026 $470,000 · 5 bd · 2 ba · 3,922 sqft
356 ridgecrest drive, Winchester 37398 Off market since Aug 2026 $689,900 · 4 bd · 4 ba · 3,705 sqft
110 south porter street, Winchester 37398 Off market since Aug 2026 $695,000 · 5 bd · 4 ba · 3,187 sqft
314 4th avenue northwest, Winchester 37398 Off market since Sep 2026 $450,000 · 3 bd · 3 ba · 2,629 sqft
1508 clark street, Winchester 37398 Off market since Sep 2026 $213,999 · 3 bd · 2 ba · 1,104 sqft
260 lookout drive, Winchester 37398 Off market since Jul 2026 $649,000 · 4 bd · 3 ba · 3,115 sqft
253 brookfield circle, Winchester 37398 Off market since Sep 2026 $344,900 · 3 bd · 2 ba · 1,300 sqft
208 lillian street, Winchester 37398 Off market since Sep 2026 $209,900 · 3 bd · 1 ba · 1,326 sqft
423 shasteen bend drive, Winchester 37398 Off market since Aug 2026 $997,500 · 3 bd · 2 ba · 1,890 sqft
5630 mansford road, Winchester 37398 Off market since Aug 2026 $329,900 · 3 bd · 1 ba · 1,600 sqft
0 ridgecrest drive, Winchester 37398 Off market since Sep 2026 $794,500 · 4 bd · 4 ba · 3,165 sqft
3896 lynchburg road, Winchester 37398 Off market since Sep 2026 $355,000 · 3 bd · 2 ba · 1,509 sqft
25 dry fork drive, Winchester 37398 Off market since Sep 2026 $745,000 · 3 bd · 3 ba · 2,592 sqft
90 owl hollow lane, Winchester 37398 Off market since Aug 2026 $429,900 · 3 bd · 3 ba · 2,431 sqft