Homes under $500K in Winchester, TN
92 homes for sale · Updated August 12, 2026 · Page 1 of 2
- 6004 lynchburg road, Winchester 37398 $143,000 · 2 bd · 2 ba · 880 sqft
- 103 north shephard street, Winchester 37398 $307,900 · 3 bd · 2 ba · 1,213 sqft
- 2077 holders cove road, Winchester 37398 $150,000 · 4 bd · 1 ba · 1,580 sqft
- 220 bryan drive, Winchester 37398 $459,000 · 4 bd · 4 ba · 2,209 sqft
- 69 anderton drive, Winchester 37398 $489,900 · 3 bd · 3 ba · 2,564 sqft
- 270 wood bluff road, Winchester 37398 $451,500 · 4 bd · 3 ba · 2,228 sqft
- 103 anderton drive, Winchester 37398 $476,800 · 5 bd · 3 ba · 2,160 sqft
- 25 lookout drive, Winchester 37398 $454,900 · 4 bd · 2 ba · 1,887 sqft
- 203 campfire court, Winchester 37398 $450,000 · 4 bd · 3 ba · 2,141 sqft
- 3754 aedc road, Winchester 37398 $399,000 · 2 bd · 1 ba · 3,560 sqft
- 124 lookout drive, Winchester 37398 $429,900 · 4 bd · 2 ba · 1,890 sqft
- 0 mansford road, Winchester 37398 $429,900 · 3 bd · 2 ba · 1,706 sqft
- 108 lookout drive, Winchester 37398 $443,900 · 3 bd · 2 ba · 2,290 sqft
- 667 maple bend road, Winchester 37398 $320,000 · 2 bd · 2 ba · 1,200 sqft
- 23 skidmore lane, Winchester 37398 $499,000 · 3 bd · 3 ba · 2,276 sqft
- 38 murray lake drive, Winchester 37398 $339,999 · 2 bd · 2 ba · 1,683 sqft
- 205 houghton drive, Winchester 37398 $364,500 · 4 bd · 3 ba · 2,640 sqft
- 206 homeward avenue, Winchester 37398 $299,900 · 4 bd · 2 ba · 1,999 sqft
- 1400 holders cove road, Winchester 37398 $325,000 · 3 bd · 1 ba · 1,490 sqft
- 74 six mile board road, Winchester 37398 $299,000 · 2 bd · 2 ba · 1,472 sqft
- 802 evans road, Winchester 37398 $399,900 · 3 bd · 2 ba · 1,632 sqft
- 6063 mansford road, Winchester 37398 $369,900 · 3 bd · 3 ba · 1,833 sqft
- 1010 north high street, Winchester 37398 $249,900 · 3 bd · 2 ba · 1,866 sqft
- 58 island way, Winchester 37398 $439,000 · 4 bd · 3 ba · 2,660 sqft
- 61 brookfield circle, Winchester 37398 $340,000 · 3 bd · 2 ba · 2,038 sqft
- 172 lookout drive, Winchester 37398 $469,900 · 3 bd · 2 ba · 1,817 sqft
- 67 lake lane, Winchester 37398 $359,900 · 3 bd · 2 ba · 1,886 sqft
- 205 8th avenue northwest, Winchester 37398 $205,000 · 3 bd · 2 ba · 1,333 sqft
- 71 david crockett highway, Winchester 37398 $450,000 · 5 bd · 3 ba · 2,420 sqft
- 70 island way, Winchester 37398 $499,900 · 4 bd · 3 ba · 2,578 sqft
- 173 country club terrace, Winchester 37398 $324,000 · 3 bd · 3 ba · 2,047 sqft
- 309 2nd avenue northwest, Winchester 37398 $470,000 · 5 bd · 2 ba · 3,922 sqft
- 111 campfire court, Winchester 37398 $480,000 · 3 bd · 3 ba · 2,230 sqft
- 314 4th avenue northwest, Winchester 37398 $450,000 · 3 bd · 3 ba · 2,629 sqft
- 1508 clark street, Winchester 37398 $213,999 · 3 bd · 2 ba · 1,104 sqft
- 253 brookfield circle, Winchester 37398 $344,900 · 3 bd · 2 ba · 1,300 sqft
- 267 brookfield circle, Winchester 37398 $344,900 · 3 bd · 2 ba · 1,338 sqft
- 208 lillian street, Winchester 37398 $209,900 · 3 bd · 1 ba · 1,326 sqft
- 90 owl hollow lane, Winchester 37398 $429,900 · 3 bd · 3 ba · 2,431 sqft
- 615 lakeview way, Winchester 37398 $475,000 · 3 bd · 3 ba · 3,067 sqft
- 44 houghton drive, Winchester 37398 $399,900 · 4 bd · 4 ba · 2,197 sqft
- 145 murray lake drive, Winchester 37398 $364,500 · 3 bd · 2 ba · 1,797 sqft
- 99 north shephard street, Winchester 37398 $299,999 · 3 bd · 2 ba · 1,213 sqft
- 1687 georgia crossing road, Winchester 37398 $319,900 · 2 bd · 2 ba · 1,080 sqft
- 6606 old tullahoma road, Winchester 37398 $359,000 · 3 bd · 2 ba · 1,972 sqft
- 106 chattin street, Winchester 37398 $455,000 · 3 bd · 3 ba · 1,800 sqft
- 805 north jefferson street, Winchester 37398 $499,900 · 4 bd · 4 ba · 2,260 sqft
- 647 golf shores drive, Winchester 37398 $489,900 · 3 bd · 2 ba · 2,116 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