This information is taken directly from a brochure prepared by the Quoddy Maritime Museum in 2001. The publication of this brochure was funded by the Maine Community Fund's Washington County Fund. Copies of the brochure, The Eastport Walk-About, which also include maps and pictures are available at the Quoddy Maritime Museum, 70 Washington Street. Some addition have been made to represent the current use of some of the properties.

Architectural styles mirror the development of a town's history. The evolution of the architectural development of Eastport begins with the Colonial period, 1775-1800 and continues with the Federal, 1800-1830, Greek Revival, 1830-1850, Gothic Revival, 1840-1850, Italianate, 1860-1870, Second Empire, 1865-1879, Queen Anne, 1870-1890, Colonial Revival, 1890-1910.

Beginning with the Colonial, there exist five houses with center chimney capes. The Federal style, which is most prevalent for Eastport, is represented by the two-story hipped roof with a five bay symmetrical facade and fanlight, the majority of which are to be found on Boynton Street. Greek Revival structures are found to be mostly side gable capes with applied ornament consisting of door surround, corner pilasters and wide cornice.

The Italianate is mainly expressed in applied ornament. Much of the downtown Water Street Historic District is Italianate. The Aaron Hayden house on Boynton Street best represents the Second Empire. The Gothic Revival is found at the corner of Key and Middle Street (Babb House, 9 Key Street). The Queen Anne style example is 16 Key Street.

Eastport, Maine: Easternmost City in the U.S.A.