Homes under $500K in Winchester, TN
92 homes for sale · Updated August 12, 2026 · Page 2 of 2
- 109 oak park, Winchester 37398 $449,000 · 3 bd · 2 ba · 2,157 sqft
- 84 meadowood lane, Winchester 37398 $430,000 · 3 bd · 2 ba · 1,814 sqft
- 201 lookout drive, Winchester 37398 $455,000 · 3 bd · 3 ba · 2,543 sqft
- 466 willow oak drive, Winchester 37398 $479,000 · 5 bd · 4 ba · 4,244 sqft
- 131 charlotte drive, Winchester 37398 $349,999 · 3 bd · 2 ba · 1,548 sqft
- 6933 winchester highway, Winchester 37398 $399,900 · 5 bd · 3 ba · 2,632 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
- 79 charlotte drive, Winchester 37398 $355,000 · 3 bd · 2 ba · 1,340 sqft
- 56 deer valley circle, Winchester 37398 $429,900 · 2 bd · 2 ba · 1,664 sqft
- 1102 north high street, Winchester 37398 $229,500 · 3 bd · 2 ba · 1,353 sqft
- 342 chase circle, Winchester 37398 $359,900 · 2 bd · 2 ba · 1,801 sqft
- 1563 paynes church road, Winchester 37398 $325,000 · 3 bd · 2 ba · 1,508 sqft
- 1605 paynes church road, Winchester 37398 $325,000 · 3 bd · 2 ba · 1,508 sqft
- 1585 paynes church road, Winchester 37398 $325,000 · 3 bd · 2 ba · 1,508 sqft
- 1543 paynes church road, Winchester 37398 $325,000 · 3 bd · 2 ba · 1,508 sqft
- 129 meredith lane, Winchester 37398 $479,000 · 3 bd · 2 ba · 2,149 sqft
- 23 woods edge road, Winchester 37398 $298,000 · 3 bd · 2 ba · 1,400 sqft
- 512 cline ridge road, Winchester 37398 $499,999 · 3 bd · 2 ba · 1,388 sqft
- 2607 old tullahoma road, Winchester 37398 $464,900 · 4 bd · 3 ba · 2,645 sqft
- 1200 little street, Winchester 37398 $299,000 · 5 bd · 2 ba · 1,600 sqft
- 0 sisk road, Winchester 37398 $349,000 · 3 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
- 219 old mill road, Winchester 37398 $349,000 · 3 bd · 2 ba · 3,050 sqft
- 101 royal oak drive, Winchester 37398 $310,999 · 3 bd · 2 ba · 1,510 sqft
- 95 luttrell drive, Winchester 37398 $374,900 · 3 bd · 2 ba · 1,657 sqft
- 383 strawberry drive, Winchester 37398 $296,000 · 3 bd · 2 ba · 1,296 sqft
- 924 cline ridge road, Winchester 37398 $399,900 · 2 bd · 2 ba · 1,450 sqft
- 801 south high street, Winchester 37398 $279,900 · 3 bd · 2 ba · 1,697 sqft
- 266 woods edge road, Winchester 37398 $305,000 · 3 bd · 2 ba · 1,500 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
- 1111 holders cove road, Winchester 37398 $369,900 · 3 bd · 2 ba · 1,508 sqft
- 207 melody lane, Winchester 37398 $194,900 · 3 bd · 2 ba · 1,755 sqft
- 262 crimson drive, Winchester 37398 $459,999 · 3 bd · 2 ba · 2,355 sqft
- 345 franklin heights drive, Winchester 37398 $399,000 · 3 bd · 2 ba · 2,333 sqft
- 206 country club road, Winchester 37398 $484,000 · 4 bd · 2 ba · 1,710 sqft
- 401 east petty lane, Winchester 37398 $359,900 · 3 bd · 3 ba · 2,653 sqft
- 171 raspberry drive, Winchester 37398 $285,000 · 3 bd · 2 ba · 1,544 sqft