| Name | Styles | Significance | Periods |
|---|
ADVENTURE (schooner) (State Fish Pier, Gloucester Inner Harbor) | | architecture, engineering, maritime history, industry | 1950-1974, 1925-1949 |
| Annisquam Bridge | No Style Listed | engineering, other, commerce, transportation | 1850-1874, 1950-1974, 1925-1949, 1875-1899, 1900-1924 |
Annisquam Harbor Light Station (Wigwam Pt.) | | engineering, architecture, maritime history, transportation | 1875-1899, 1850-1874, 1825-1849, 1800-1824 |
Beauport (Eastern Point Blvd.) | Shingle Style, No Style Listed | architecture, art | 1925-1949, 1900-1924 |
Davis - Freeman House (302 Essex St.) | Colonial | architecture | 1700-1749 |
Dyke - Wheeler House (144 Wheeler St.) | Colonial | architecture | 1700-1749 |
Eastern Point Light Station (Eastern Pt.) | Queen Anne, Gothic | maritime history, architecture, engineering, transportation | 1875-1899, 1925-1949, 1900-1924 |
Edward Harraden House (12--14 Leonard St.) | Colonial | architecture, historic - non-aboriginal | 1650-1699 |
Ella Proctor Herrick House (189 Concord St.) | Colonial | architecture | 1650-1699 |
Fitz Hugh Lane House (Harbor side of Rogers St.) | Gothic Revival | architecture, art, landscape architecture | 1825-1849, 1850-1874 |
Hammond Castle (80 Hesperus Ave.) | Mixed (More Than 2 Styles From Different Periods) | invention, science, communications, military, architecture, performing arts | 1925-1949 |
Oak Grove Cemetery (Bounded by Derby, Washington, and Grove Sts., and Maplewood Ave.) | Romanesque | landscape architecture, community planning and development | 1850-1874 |
| PORTLAND (Shipwreck and Remains) | | historic - non-aboriginal, engineering, transportation, architecture, commerce, maritime history | 1875-1899 |
Ten Pound Island Light (Gloucester Harbor) | | transportation, architecture, maritime history, engineering | 1875-1899, 1825-1849, 1850-1874, 1800-1824 |
White - Ellery House (244 Washington St.) | Colonial | architecture | 1700-1749 |
Whittemore House (179 Washington St.) | Colonial | historic - non-aboriginal, architecture | 1700-1749 |
William Haskell House (11 Lincoln St.) | Colonial | historic - non-aboriginal, architecture | 1700-1749 |