Homes under $500K in Winchester, TN

89 for sale · 265 homes listed · Updated September 27, 2026 · Page 4 of 6

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
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
205 houghton drive, Winchester 37398 Off market since Sep 2026 $349,900 · 4 bd · 3 ba · 2,640 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
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
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
58 island way, Winchester 37398 Off market since Sep 2026 $429,000 · 4 bd · 3 ba · 2,660 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
71 david crockett highway, Winchester 37398 Off market since Sep 2026 $435,000 · 5 bd · 3 ba · 2,420 sqft
70 island way, Winchester 37398 Off market since Sep 2026 $479,900 · 4 bd · 3 ba · 2,578 sqft
173 country club terrace, Winchester 37398 Off market since Sep 2026 $299,000 · 3 bd · 3 ba · 2,047 sqft
309 2nd avenue northwest, Winchester 37398 Off market since Sep 2026 $470,000 · 5 bd · 2 ba · 3,922 sqft
111 campfire court, Winchester 37398 Off market since Sep 2026 $480,000 · 3 bd · 3 ba · 2,578 sqft
314 4th avenue northwest, Winchester 37398 Off market since Sep 2026 $450,000 · 3 bd · 3 ba · 2,629 sqft
240 myers road, Winchester 37398 Off market since Aug 2026 $338,000 · 4 bd · 3 ba · 1,960 sqft
1508 clark street, Winchester 37398 Off market since Sep 2026 $213,999 · 3 bd · 2 ba · 1,104 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
5630 mansford road, Winchester 37398 Off market since Aug 2026 $329,900 · 3 bd · 1 ba · 1,600 sqft
3896 lynchburg road, Winchester 37398 Off market since Sep 2026 $355,000 · 3 bd · 2 ba · 1,509 sqft
90 owl hollow lane, Winchester 37398 Off market since Aug 2026 $429,900 · 3 bd · 3 ba · 2,431 sqft
17 smith road, Winchester 37398 Sold on Jul 21, 2026 $80,000 · 2 bd · 1 ba · 672 sqft
204 homeward avenue, Winchester 37398 Off market since Aug 2026 $375,000 · 3 bd · 3 ba · 1,988 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
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
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
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
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
466 willow oak drive, Winchester 37398 Off market since Sep 2026 $464,000 · 3 bd · 4 ba · 4,244 sqft