Homes under $500K in Winchester, TN

89 for sale · 265 homes listed · Updated September 27, 2026 · Page 5 of 6

• 131 charlotte drive, Winchester 37398 Off market since Sep 2026 $349,999 · 3 bd · 2 ba · 1,548 sqft
• 409 4th avenue southwest, Winchester 37398 Off market since Sep 2026 $65,000 · 2 bd · 1 ba · 672 sqft
• 424 laura avenue, Winchester 37398 Off market since Sep 2026 $174,900 · 2 bd · 1 ba · 824 sqft
• 79 charlotte drive, Winchester 37398 Off market since Sep 2026 $355,000 · 3 bd · 2 ba · 1,340 sqft
• 56 deer valley circle, Winchester 37398 Off market since Aug 2026 $429,900 · 2 bd · 2 ba · 1,664 sqft
• 342 chase circle, Winchester 37398 Off market since Sep 2026 $359,900 · 2 bd · 2 ba · 1,801 sqft
• 1563 paynes church road, Winchester 37398 Off market since Sep 2026 $315,000 · 3 bd · 2 ba · 1,508 sqft
• 1605 paynes church road, Winchester 37398 Off market since Sep 2026 $315,000 · 3 bd · 2 ba · 1,508 sqft
• 1585 paynes church road, Winchester 37398 Off market since Sep 2026 $315,000 · 3 bd · 2 ba · 1,508 sqft
• 1543 paynes church road, Winchester 37398 Off market since Sep 2026 $315,000 · 3 bd · 2 ba · 1,508 sqft
• 23 woods edge road, Winchester 37398 Off market since Sep 2026 $298,000 · 3 bd · 2 ba · 1,400 sqft
• 109 carter farris lane, Winchester 37398 Off market since Sep 2026 $490,000 · 6 bd · 4 ba · 3,158 sqft
• 44 hammock drive, Winchester 37398 Off market since Sep 2026 $499,000 · 3 bd · 3 ba · 2,266 sqft
• 2607 old tullahoma road, Winchester 37398 Off market since Sep 2026 $464,900 · 4 bd · 3 ba · 2,645 sqft
• 1200 little street, Winchester 37398 Off market since Sep 2026 $289,000 · 5 bd · 2 ba · 1,600 sqft
• 0 sisk road, Winchester 37398 Off market since Sep 2026 $349,000 · 3 bd · 2 ba · 1,600 sqft
• 102 oak park, Winchester 37398 Off market since Sep 2026 $269,900 · 2 bd · 1 ba · 1,373 sqft
• 128 bel aire drive, Winchester 37398 Off market since Sep 2026 $299,900 · 4 bd · 2 ba · 1,923 sqft
• 219 old mill road, Winchester 37398 Off market since Sep 2026 $349,000 · 3 bd · 2 ba · 3,050 sqft
• 95 luttrell drive, Winchester 37398 Off market since Sep 2026 $374,900 · 3 bd · 2 ba · 1,657 sqft
• 924 cline ridge road, Winchester 37398 Off market since Sep 2026 $399,900 · 2 bd · 2 ba · 1,450 sqft
• 801 south high street, Winchester 37398 Off market since Sep 2026 $279,900 · 3 bd · 2 ba · 1,697 sqft
• 1361 joyce lane, Winchester 37398 Off market since Sep 2026 $175,000 · 3 bd · 2 ba · 1,644 sqft
• 1325 joyce lane, Winchester 37398 Off market since Sep 2026 $225,000 · 3 bd · 3 ba · 2,146 sqft
• 46 woods edge road, Winchester 37398 Off market since Jul 2026 $289,900 · 3 bd · 2 ba · 1,470 sqft
• 266 woods edge road, Winchester 37398 Off market since Sep 2026 $299,900 · 3 bd · 2 ba · 1,500 sqft
• 605 gin street, Winchester 37398 Off market since Sep 2026 $110,000 · 4 bd · 3 ba · 2,052 sqft
• 525 sharp springs road, Winchester 37398 Off market since Sep 2026 $230,000 · 2 bd · 2 ba · 1,600 sqft
• 145 edgewood lane, Winchester 37398 Off market since Sep 2026 $209,900 · 3 bd · 2 ba · 1,000 sqft
• 1111 holders cove road, Winchester 37398 Off market since Sep 2026 $354,900 · 3 bd · 2 ba · 1,508 sqft
• 207 melody lane, Winchester 37398 Off market since Sep 2026 $179,900 · 3 bd · 2 ba · 1,755 sqft
• 262 crimson drive, Winchester 37398 Off market since Sep 2026 $449,000 · 3 bd · 2 ba · 2,355 sqft
• 206 country club road, Winchester 37398 Off market since Sep 2026 $484,000 · 4 bd · 2 ba · 1,710 sqft
• 401 east petty lane, Winchester 37398 Off market since Aug 2026 $359,900 · 3 bd · 3 ba · 2,653 sqft
• 1522 holders cove road, Winchester 37398 Off market since Sep 2026 $385,000 · 3 bd · 2 ba · 1,700 sqft
• 218 charlotte drive, Winchester 37398 Off market since Sep 2026 $488,000 · 4 bd · 3 ba · 2,116 sqft
• 406 2nd avenue northwest, Winchester 37398 Off market since Sep 2026 $125,000 · 3 bd · 1 ba · 1,150 sqft
• 204 homeward avenue, Winchester 37398 Off market since Sep 2026 $355,000 · 3 bd · 3 ba · 1,988 sqft
• 401 east petty lane, Winchester 37398 Off market since Sep 2026 $360,000 · 3 bd · 3 ba · 3,960 sqft
• 80 tanya terrace, Winchester 37398 Off market since Sep 2026 $349,900 · 3 bd · 2 ba · 1,400 sqft
• 416 colonial drive, Winchester 37398 Off market since Sep 2026 $335,000 · 3 bd · 2 ba · 1,587 sqft
• 56 deer valley circle, Winchester 37398 Off market since Sep 2026 $419,000 · 2 bd · 2 ba · 1,664 sqft
• 203 west petty lane, Winchester 37398 Off market since Sep 2026 $199,900 · 3 bd · 1 ba · 1,271 sqft
• 69 anderton drive, Winchester 37398 Off market since Sep 2026 $479,900 · 3 bd · 3 ba · 2,564 sqft
• 76 chase circle, Winchester 37398 Off market since Sep 2026 $369,900 · 2 bd · 2 ba · 1,818 sqft
• 115 7th avenue northeast, Winchester 37398 Off market since Sep 2026 $319,000 · 3 bd · 2 ba · 1,308 sqft
• 124 lookout drive, Winchester 37398 Off market since Sep 2026 $424,900 · 4 bd · 2 ba · 1,890 sqft
• 108 lookout drive, Winchester 37398 Off market since Sep 2026 $443,900 · 3 bd · 2 ba · 2,290 sqft
• 1790 old estill springs road, Winchester 37398 Off market since Sep 2026 $299,000 · 3 bd · 2 ba · 1,675 sqft
• 206 homeward avenue, Winchester 37398 Off market since Sep 2026 $299,900 · 4 bd · 2 ba · 1,999 sqft