Homes under $300K in Winchester, TN

26 homes for sale · Updated August 12, 2026

6004 lynchburg road, Winchester 37398 $143,000 · 2 bd · 2 ba · 880 sqft
2077 holders cove road, Winchester 37398 $150,000 · 4 bd · 1 ba · 1,580 sqft
206 homeward avenue, Winchester 37398 $299,900 · 4 bd · 2 ba · 1,999 sqft
74 six mile board road, Winchester 37398 $299,000 · 2 bd · 2 ba · 1,472 sqft
1010 north high street, Winchester 37398 $249,900 · 3 bd · 2 ba · 1,866 sqft
205 8th avenue northwest, Winchester 37398 $205,000 · 3 bd · 2 ba · 1,333 sqft
1508 clark street, Winchester 37398 $213,999 · 3 bd · 2 ba · 1,104 sqft
208 lillian street, Winchester 37398 $209,900 · 3 bd · 1 ba · 1,326 sqft
99 north shephard street, Winchester 37398 $299,999 · 3 bd · 2 ba · 1,213 sqft
88 meadow lane, Winchester 37398 $299,999 · 3 bd · 2 ba · 1,708 sqft
30 west paradise drive, Winchester 37398 $299,900 · 3 bd · 2 ba · 1,798 sqft
409 4th avenue southwest, Winchester 37398 $65,000 · 2 bd · 1 ba · 672 sqft
424 laura avenue, Winchester 37398 $174,900 · 2 bd · 1 ba · 824 sqft
1102 north high street, Winchester 37398 $229,500 · 3 bd · 2 ba · 1,353 sqft
23 woods edge road, Winchester 37398 $298,000 · 3 bd · 2 ba · 1,400 sqft
1200 little street, Winchester 37398 $299,000 · 5 bd · 2 ba · 1,600 sqft
102 oak park, Winchester 37398 $284,900 · 2 bd · 1 ba · 1,373 sqft
128 bel aire drive, Winchester 37398 $299,900 · 4 bd · 2 ba · 1,923 sqft
383 strawberry drive, Winchester 37398 $296,000 · 3 bd · 2 ba · 1,296 sqft
801 south high street, Winchester 37398 $279,900 · 3 bd · 2 ba · 1,697 sqft
605 gin street, Winchester 37398 $115,000 · 4 bd · 3 ba · 2,052 sqft
404 south jefferson street, Winchester 37398 $238,000 · 2 bd · 2 ba · 1,370 sqft
525 sharp springs road, Winchester 37398 $230,000 · 2 bd · 2 ba · 1,600 sqft
145 edgewood lane, Winchester 37398 $209,900 · 3 bd · 2 ba · 1,000 sqft
207 melody lane, Winchester 37398 $194,900 · 3 bd · 2 ba · 1,755 sqft
171 raspberry drive, Winchester 37398 $285,000 · 3 bd · 2 ba · 1,544 sqft