1."Tally-Ho" (private home) - 1859
2. Fleisher House (private home) - 1901
3. Montvalle Lodge (Montvallee Motel) - 1890
4. Monterey United Methodist Church - 1851
5. Monterey Hotel (The Highland Inn) - 1904
6. Trimble's Store (High's Restaurant) - 1900
7. Seig House (private home) - 1850
8. Lundsford & Sons Store (Gallery of Mountain Secrets)
9. Campbell House (The Corner Room) - 1852
10. Highland Mercantile (Highland County Crafts) - 1909
11. Landmark House (The Attic) - 1790
12. Original name unknown (Blanchard's Woodwork) - 1900
13. Highland County Jail - 1900
14. Jones-McCoy House (private home) - 1900
15. C.P. Jones Law Office - 1874
16. Highland County Court House - 1948
(standing on site of original structure built in 1850)
17. Peterson's Store (H & H Cash Store) - 1903
18. Virgil Bishop House (private home) - 1896
19. Whitelaw House (Cherry Hill B&B) - 1900

 

20. Monterey Cemetery
21. Gibson House (private home) - 1901
22. First National Bank of Highland (Evelyn's Pantry) - 1908
23. Masonic Temple - 1910
24. C.G. Cross House (private home) - 1885
25. Monterey School (Maple Street Guest House) - 1900
26. Prichard House (private home) - 1900
27. "The Crow's Nest" (private home) - 1908
28. Arbogast House (Mountain Laurel Inn B&B) - 1900
29. Monterey Presbyterian Church - 1873
30. See House (private home) - 1875
31. "Hitching Post" (private home) - 1890
32. Kincaid House (private home) - 1856
33. J. Brown Lightner House (private home) - 1919
34. Trimble Acres (private home) - 1898
35. Metheny- Hansel House (private home) - 1909
36. Sullenberger House (private home) - 1906
37. Beverage House (private home) - 1902
38. Highland Elementary School (The Highland Center) - 1922