Homes in Highlands, Winchester, TN

6 for sale · 9 homes listed · Updated September 27, 2026

• 25 lookout drive, Winchester 37398 $454,900 · 4 bd · 2 ba · 1,887 sqft
• 172 lookout drive, Winchester 37398 $469,900 · 3 bd · 2 ba · 1,817 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
• 101 edgefield court, Winchester 37398 $369,000 · 2 bd · 2 ba · 1,615 sqft
• 0 edgefield court, Winchester 37398 $399,000 · 2 bd · 2 ba · 1,716 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
• 260 lookout drive, Winchester 37398 Off market since Jul 2026 $649,000 · 4 bd · 3 ba · 3,115 sqft