Homes under $500K in Winchester, TN
98 for sale · 176 homes listed · Updated September 27, 2026 · Page 2 of 4
- 1200 little street, Winchester 37398 $289,000 · 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 $269,900 · 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
- 95 luttrell drive, Winchester 37398 $374,900 · 3 bd · 2 ba · 1,657 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
- 1361 joyce lane, Winchester 37398 $175,000 · 3 bd · 2 ba · 1,644 sqft
- 1325 joyce lane, Winchester 37398 $225,000 · 3 bd · 3 ba · 2,146 sqft
- 266 woods edge road, Winchester 37398 $299,900 · 3 bd · 2 ba · 1,500 sqft
- 605 gin street, Winchester 37398 $110,000 · 4 bd · 3 ba · 2,052 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 $354,900 · 3 bd · 2 ba · 1,508 sqft
- 207 melody lane, Winchester 37398 $179,900 · 3 bd · 2 ba · 1,755 sqft
- 262 crimson drive, Winchester 37398 $449,000 · 3 bd · 2 ba · 2,355 sqft
- 1522 holders cove road, Winchester 37398 $400,000 · 3 bd · 2 ba · 1,700 sqft
- 406 2nd avenue northwest, Winchester 37398 $125,000 · 3 bd · 1 ba · 1,150 sqft
- 204 homeward avenue, Winchester 37398 $355,000 · 3 bd · 3 ba · 1,988 sqft
- 401 east petty lane, Winchester 37398 $360,000 · 3 bd · 3 ba · 3,960 sqft
- 80 tanya terrace, Winchester 37398 $349,900 · 3 bd · 2 ba · 1,400 sqft
- 416 colonial drive, Winchester 37398 $335,000 · 3 bd · 2 ba · 1,587 sqft
- 56 deer valley circle, Winchester 37398 $419,000 · 2 bd · 2 ba · 1,664 sqft
- 203 west petty lane, Winchester 37398 $199,900 · 3 bd · 1 ba · 1,271 sqft
- 69 anderton drive, Winchester 37398 $479,900 · 3 bd · 3 ba · 2,564 sqft
- 76 chase circle, Winchester 37398 $369,900 · 2 bd · 2 ba · 1,818 sqft
- 115 7th avenue northeast, Winchester 37398 $319,000 · 3 bd · 2 ba · 1,308 sqft
- listing-10647930021, Winchester 37398 $299,000 · 5 bd · 2 ba · 1,588 sqft
- 124 lookout drive, Winchester 37398 $424,900 · 4 bd · 2 ba · 1,890 sqft
- 108 lookout drive, Winchester 37398 $443,900 · 3 bd · 2 ba · 2,290 sqft
- 1790 old estill springs road, Winchester 37398 $299,000 · 3 bd · 2 ba · 1,675 sqft
- 206 homeward avenue, Winchester 37398 $299,900 · 4 bd · 2 ba · 1,999 sqft
- 0 style street, Winchester 37398 $239,000 · 3 bd · 2 ba · 1,100 sqft
- 117 carol circle, Winchester 37398 $340,000 · 3 bd · 2 ba · 1,750 sqft
- 810 cumberland drive, Winchester 37398 $399,900 · 3 bd · 2 ba · 2,260 sqft
- 338 royal oak drive, Winchester 37398 $339,900 · 3 bd · 2 ba · 1,916 sqft
- 319 chase circle, Winchester 37398 $389,000 · 2 bd · 2 ba · 1,711 sqft
- 101 edgefield court, Winchester 37398 $369,000 · 2 bd · 2 ba · 1,615 sqft
- 1557 rowe gap road, Winchester 37398 $349,900 · 3 bd · 2 ba · 1,460 sqft
- 0 edgefield court, Winchester 37398 $399,000 · 2 bd · 2 ba · 1,716 sqft
- 0 south high street, Winchester 37398 $229,900 · 3 bd · 2 ba · 1,014 sqft
- 735 shadowbrook road, Winchester 37398 $499,000 · 3 bd · 3 ba · 2,530 sqft
- 260 union road, Winchester 37398 $299,900 · 3 bd · 2 ba · 1,288 sqft
- 220 union road, Winchester 37398 $299,900 · 3 bd · 2 ba · 1,288 sqft
- 36 meadowwood lane, Winchester 37398 $376,300 · 3 bd · 2 ba · 1,420 sqft
- 814 south high street, Winchester 37398 $285,000 · 3 bd · 1 ba · 1,154 sqft
- 222 orchard lane, Winchester 37398 $249,000 · 3 bd · 2 ba · 1,344 sqft
- 188 wiseman lane, Winchester 37398 Pending $464,900 · 4 bd · 2 ba · 2,269 sqft
- 205 8th avenue northwest, Winchester 37398 Pending $205,000 · 3 bd · 2 ba · 1,333 sqft