Single Family Homes in Winchester, TN

136 for sale · 423 homes listed · Updated September 27, 2026 · Page 7 of 9

61 joy circle, Winchester 37398 Off market since Sep 2026 $1,399,900 · 6 bd · 6 ba · 6,176 sqft
292 ridgecrest drive, Winchester 37398 Off market since Sep 2026 $649,000 · 5 bd · 4 ba · 3,695 sqft
204 homeward avenue, Winchester 37398 Off market since Aug 2026 $375,000 · 3 bd · 3 ba · 1,988 sqft
3539 liberty road, Winchester 37398 Off market since Sep 2026 $1,775,000 · 6 bd · 4 ba · 3,617 sqft
615 lakeview way, Winchester 37398 Off market since Sep 2026 $473,000 · 3 bd · 3 ba · 3,067 sqft
171 raspberry drive, Winchester 37398 Off market since Jul 2026 $295,000 · 3 bd · 2 ba · 1,544 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
112 rogers avenue, Winchester 37398 Off market since Aug 2026 $699,999 · 3 bd · 2 ba · 1,300 sqft
145 murray lake drive, Winchester 37398 Off market since Sep 2026 $354,500 · 3 bd · 2 ba · 1,797 sqft
99 north shephard street, Winchester 37398 Off market since Sep 2026 $295,999 · 3 bd · 2 ba · 1,213 sqft
1717 georgia crossing road, Winchester 37398 Off market since Sep 2026 $99,900 · 3 bd · 2 ba · 1,500 sqft
6606 old tullahoma road, Winchester 37398 Off market since Sep 2026 $359,000 · 3 bd · 2 ba · 1,972 sqft
106 chattin street, Winchester 37398 Off market since Sep 2026 $455,000 · 3 bd · 3 ba · 1,800 sqft
59 walnut drive, Winchester 37398 Off market since Sep 2026 $740,000 · 3 bd · 3 ba · 2,075 sqft
805 north jefferson street, Winchester 37398 Off market since Sep 2026 $474,900 · 4 bd · 4 ba · 2,260 sqft
647 golf shores drive, Winchester 37398 Off market since Sep 2026 $489,900 · 3 bd · 2 ba · 2,116 sqft
88 meadow lane, Winchester 37398 Off market since Aug 2026 $299,999 · 3 bd · 2 ba · 1,708 sqft
150 edie mae lane, Winchester 37398 Off market since Jul 2026 $825,000 · 3 bd · 3 ba · 2,411 sqft
109 oak park, Winchester 37398 Off market since Sep 2026 $429,000 · 3 bd · 2 ba · 2,157 sqft
84 meadowood lane, Winchester 37398 Off market since Sep 2026 $425,000 · 3 bd · 2 ba · 1,814 sqft
210 cascade drive, Winchester 37398 Off market since Sep 2026 $774,900 · 4 bd · 5 ba · 3,090 sqft
114 bel aire drive, Winchester 37398 Off market since Sep 2026 $259,900 · 3 bd · 2 ba · 1,875 sqft
201 lookout drive, Winchester 37398 Off market since Sep 2026 $460,000 · 3 bd · 3 ba · 2,543 sqft
22 hammock drive, Winchester 37398 Off market since Sep 2026 $775,000 · 4 bd · 3 ba · 3,104 sqft
466 willow oak drive, Winchester 37398 Off market since Sep 2026 $464,000 · 3 bd · 4 ba · 4,244 sqft
92 freeman court, Winchester 37398 Off market since Sep 2026 $525,000 · 3 bd · 3 ba · 2,494 sqft
131 charlotte drive, Winchester 37398 Off market since Sep 2026 $349,999 · 3 bd · 2 ba · 1,548 sqft
0 deer valley, Winchester 37398 Off market since Aug 2026 $580,458 · 3 bd · 2 ba · 2,274 sqft
409 4th avenue southwest, Winchester 37398 Off market since Sep 2026 $65,000 · 2 bd · 1 ba · 672 sqft
424 laura avenue, Winchester 37398 Off market since Sep 2026 $174,900 · 2 bd · 1 ba · 824 sqft
0 golf shore drive, Winchester 37398 Off market since Sep 2026 $688,000 · 3 bd · 3 ba · 2,313 sqft
8 latitude drive, Winchester 37398 Off market since Sep 2026 $587,900 · 5 bd · 4 ba · 2,753 sqft
368 chandler drive, Winchester 37398 Off market since Sep 2026 $3,499,000 · 4 bd · 7 ba · 8,447 sqft
79 charlotte drive, Winchester 37398 Off market since Sep 2026 $355,000 · 3 bd · 2 ba · 1,340 sqft
56 deer valley circle, Winchester 37398 Off market since Aug 2026 $429,900 · 2 bd · 2 ba · 1,664 sqft
342 chase circle, Winchester 37398 Off market since Sep 2026 $359,900 · 2 bd · 2 ba · 1,801 sqft
1563 paynes church road, Winchester 37398 Off market since Sep 2026 $315,000 · 3 bd · 2 ba · 1,508 sqft
1605 paynes church road, Winchester 37398 Off market since Sep 2026 $315,000 · 3 bd · 2 ba · 1,508 sqft
1585 paynes church road, Winchester 37398 Off market since Sep 2026 $315,000 · 3 bd · 2 ba · 1,508 sqft
1543 paynes church road, Winchester 37398 Off market since Sep 2026 $315,000 · 3 bd · 2 ba · 1,508 sqft
23 woods edge road, Winchester 37398 Off market since Sep 2026 $298,000 · 3 bd · 2 ba · 1,400 sqft
221 hammock drive, Winchester 37398 Off market since Sep 2026 $1,199,000 · 4 bd · 6 ba · 3,812 sqft
44 hammock drive, Winchester 37398 Off market since Sep 2026 $499,000 · 3 bd · 3 ba · 2,266 sqft
2607 old tullahoma road, Winchester 37398 Off market since Sep 2026 $464,900 · 4 bd · 3 ba · 2,645 sqft
1200 little street, Winchester 37398 Off market since Sep 2026 $289,000 · 5 bd · 2 ba · 1,600 sqft
0 sisk road, Winchester 37398 Off market since Sep 2026 $349,000 · 3 bd · 2 ba · 1,600 sqft
102 oak park, Winchester 37398 Off market since Sep 2026 $269,900 · 2 bd · 1 ba · 1,373 sqft
92 hammock drive, Winchester 37398 Off market since Sep 2026 $834,000 · 4 bd · 4 ba · 2,986 sqft