Homes over $1M in Winchester, TN

15 for sale · 49 homes listed · Updated September 27, 2026

• 914 north jefferson street, Winchester 37398 $1,049,000 · 4 bd · 3 ba · 2,714 sqft
• 1485 water tank road, Winchester 37398 $1,475,000 · 3 bd · 5 ba · 6,300 sqft
• 61 joy circle, Winchester 37398 $1,399,900 · 6 bd · 6 ba · 6,176 sqft
• 368 chandler drive, Winchester 37398 $3,499,000 · 4 bd · 7 ba · 8,447 sqft
• 5630 mansford road, Winchester 37398 $1,179,000 · 3 bd · 1 ba · 1,600 sqft
• 221 hammock drive, Winchester 37398 $1,199,000 · 4 bd · 6 ba · 3,812 sqft
• 645 wildwood trace, Winchester 37398 $1,150,000 · 2 bd · 3 ba · 2,460 sqft
• 0 leatherwood drive, Winchester 37398 $1,999,000 · 3 bd · 5 ba · 3,438 sqft
• 71 fanning bend drive, Winchester 37398 $1,075,000 · 4 bd · 3 ba · 2,583 sqft
• 160 wakeboard way, Winchester 37398 $1,199,900 · 4 bd · 4 ba · 3,720 sqft
• 136 bay cove trail, Winchester 37398 $1,499,000 · 4 bd · 4 ba · 4,035 sqft
• 107 brandi way, Winchester 37398 $1,500,000 · 3 bd · 2 ba · 2,962 sqft
• 318 north porter street, Winchester 37398 $2,110,900 · 4 bd · 6 ba · 6,160 sqft
• 322 north porter street, Winchester 37398 $1,799,000 · 4 bd · 5 ba · 5,019 sqft
• 3539 liberty road, Winchester 37398 $1,775,000 · 6 bd · 4 ba · 3,617 sqft
• 644 fanning bend drive, Winchester 37398 Active Under Contract $1,295,000 · 4 bd · 4 ba · 3,922 sqft
• 86 simmons circle, Winchester 37398 Active Under Contract $1,475,000 · 4 bd · 6 ba · 4,080 sqft
• 169 joy circle, Winchester 37398 Active Under Contract $1,249,000 · 3 bd · 4 ba · 3,183 sqft
• 90 wildwood court, Winchester 37398 Active Under Contract $1,275,000 · 3 bd · 2 ba · 2,184 sqft
• 135 fanning bend drive, Winchester 37398 Active Under Contract $1,060,000 · 4 bd · 4 ba · 2,919 sqft
• 155 hammock drive, Winchester 37398 Active Under Contract $1,049,994 · 4 bd · 5 ba · 3,375 sqft
• 412 east petty lane, Winchester 37398 Active Under Contract $1,399,900 · 4 bd · 4 ba · 6,500 sqft
• 323 sunset cove lane, Winchester 37398 Active Under Contract $2,999,999 · 3 bd · 5 ba · 4,637 sqft
• 167 bluff drive, Winchester 37398 Active Under Contract $1,378,000 · 4 bd · 3 ba · 3,132 sqft
• 228 murray lake drive, Winchester 37398 Active Under Contract $1,447,500 · 3 bd · 3 ba · 3,447 sqft
• 71 slalom circle, Winchester 37398 Off market since Sep 2026 $1,445,000 · 4 bd · 4 ba · 4,500 sqft
• 171 cypress point drive, Winchester 37398 Off market since Jul 2026 $1,079,000 · 5 bd · 5 ba · 3,191 sqft
• 232 loop drive, Winchester 37398 Off market since Sep 2026 $1,049,000 · 5 bd · 5 ba · 3,670 sqft
• 914 north jefferson street, Winchester 37398 Off market since Sep 2026 $1,049,000 · 4 bd · 3 ba · 2,714 sqft
• 645 wildwood trace, Winchester 37398 Off market since Jul 2026 $1,200,000 · 2 bd · 3 ba · 2,460 sqft
• 712 fanning bend drive, Winchester 37398 Off market since Jul 2026 $1,275,000 · 4 bd · 5 ba · 3,492 sqft
• 1376 old mansford road, Winchester 37398 Off market since Sep 2026 $2,095,000 · 3 bd · 5 ba · 5,404 sqft
• 208 loop drive, Winchester 37398 Off market since Sep 2026 $1,050,000 · 4 bd · 4 ba · 2,906 sqft
• 100 barefoot way, Winchester 37398 Off market since Sep 2026 $1,249,900 · 4 bd · 5 ba · 2,800 sqft
• 1485 water tank road, Winchester 37398 Off market since Sep 2026 $1,475,000 · 3 bd · 5 ba · 6,300 sqft
• 71 fanning bend drive, Winchester 37398 Off market since Sep 2026 $1,075,000 · 4 bd · 3 ba · 2,583 sqft
• 61 joy circle, Winchester 37398 Off market since Sep 2026 $1,399,900 · 6 bd · 6 ba · 6,176 sqft
• 3539 liberty road, Winchester 37398 Off market since Sep 2026 $1,775,000 · 6 bd · 4 ba · 3,617 sqft
• 160 wakeboard way, Winchester 37398 Off market since Aug 2026 $1,229,900 · 4 bd · 4 ba · 3,720 sqft
• 318 north porter street, Winchester 37398 Off market since Sep 2026 $2,110,900 · 4 bd · 6 ba · 6,160 sqft
• 368 chandler drive, Winchester 37398 Off market since Sep 2026 $3,499,000 · 4 bd · 7 ba · 8,447 sqft
• 221 hammock drive, Winchester 37398 Off market since Sep 2026 $1,199,000 · 4 bd · 6 ba · 3,812 sqft
• 645 wildwood trace, Winchester 37398 Off market since Sep 2026 $1,150,000 · 2 bd · 3 ba · 2,460 sqft
• 322 north porter street, Winchester 37398 Off market since Sep 2026 $1,799,000 · 4 bd · 5 ba · 5,019 sqft
• 5630 mansford road, Winchester 37398 Off market since Sep 2026 $1,179,000 · 3 bd · 1 ba · 1,600 sqft
• 136 bay cove trail, Winchester 37398 Off market since Sep 2026 $1,499,000 · 4 bd · 4 ba · 4,035 sqft
• 0 leatherwood drive, Winchester 37398 Off market since Sep 2026 $1,999,000 · 3 bd · 5 ba · 3,438 sqft
• 160 wakeboard way, Winchester 37398 Off market since Sep 2026 $1,199,900 · 4 bd · 4 ba · 3,720 sqft
• 107 brandi way, Winchester 37398 Off market since Sep 2026 $1,500,000 · 3 bd · 2 ba · 2,962 sqft