Built for Joseph McCobb and Jacob Auld, this double house is thought to be the oldest brick residence in Boothbay Harbor. The two men, initially independent merchants, merged into the firm of McCobb and Auld by 1797. Shortly after, McCobb married Auld's sister Margaret and Auld married Sarah Reed. It is believed that soon after their marriages the men hired John Leishman, Jr. to construct a house worthy of their new status. The house, at two stories tall with a hipped roof and full basement, is larger than many others in Boothbay Harbor constructed at the same time.

The Stephen Coffin House is unique as a rare example of a Federal period store attached to the merchant's house. Along with the Matthew Cottrill House (also in Damariscotta), the house is among the best examples of the Federal style in the area. The store was in the west wing, partially visible above, and was likely simplistic when compared to the fine interior of the house. The house features four rooms per floor, two on either side of a central hall and a rectangular kitchen at the back, through which the store was accessed.

Located on the north side of Russell Farm Road, the Lower Alewive Historic District consists of four farms and over two hundred acres. All of the farms are oriented to the south towards Emmons Road with three of the four farms extending northerly to the Kennebunk River. The four farmhouses are similarly constructed: a rectangular main block, two stories high, and a long ell extending from the east end. All of the farms have at least one barn as well. Historically, northwest Kennebunk was settled in the 1750s and became known as Alewive.

Fort Edgecomb was constructed to protect Wiscasset - a critical port community and one of the busiest in New England in the early nineteenth century. Built at the south end of Davis Island, it overlooked both the Sheepscot River and Back River and provided an excellent vantage point to keep watch on approaching maritime traffic. The octagonal fort is modelled after English forts and is two stories tall. The walls of the first story, 27' feet high, are pierced by narrow openings so that muskets could be fired from the interior.

The Parson Fisher House is an uncommon example of the Federal style with its asymmetrical front facade with an off-centered entry. The two-story dwelling has a hipped roof with a substantial brick interior chimney. The full width beltcourse of flush boards above the second story windows is a rare feature for the time. This house is the second built by Parson Johnathan Fisher, but the gabled-barn behind the house likely dates from the construction of the original house in the late-eighteenth century.

A National Historic Landmark, the Parker Cleaveland House is a two-story frame dwelling with a low-pitched hipped roof and four tall brick interior end chimneys. It features a central entry on the front facade with a paneled door topped with an elliptical fanlight and flanked by pilasters and surmounted by a frieze and cornice. The residence is significant for its association with Parker Cleaveland, a nationally recognized mineralogist. Cleaveland lived here from 1806 to 1858 and was a professor at Bowdoin College.

Built for Nathaniel Dyer, a shipbuilder and merchant, the house is unusual as a modest brick home on the Portland peninsula. Other brick houses in Portland from this period were typically more elaborate. The front of the house is laid in Flemish bond, a pattern that alternates the long and short sides of the brick, while the other elevations are English bond, which alternates rows of the long and short sides of the brick. The facade is symmetrical with a central entry. The door is framed by wooden pilasters supporting a projecting piece of molding above a fanlight window.

Originally located on the other side of Main Street and further to the south, the Squire Chase House was built in the Federal style but was later remodeled in the nineteenth century with Italianate-style characteristics. The dwelling is two stories high with clapboard siding and a hipped roof. Attached is a long ell connecting to a barn-both with gabled roofs. The front facade is symmetrical with a central entrance framed by red glass sidelights and topped with a fanlight. The Italianate-style elements include the bracketed cornice and ornate rectangular cupola.

This McCobb-Hill-Minott House, located on Parker Head Road, is an exquisite Georgian style house with a hip-roof and central cupola sitting between two chimneys. The two-story dwelling has clapboard siding with central doors on both the southwest and northwest facades. Both entryways are framed by Doric pilasters and topped by a triangular pediment. Originally from Ireland, James McCobb came to the area in 1731. He gained considerable wealth in both lumber and commerce and built the house after acquiring roughly 1,000 acres.

Though currently located in the central business district of Portland, when first completed, the Wadsworth-Longfellow House had nearly unobstructed views of the Portland Harbor and the Back Cove. The building sits back from the street behind a cast-iron fence and a brick courtyard. It is three stories high, constructed of brick. The symmetrical facade contains little ornamentation except the arched windows on the first and second floors and the entry porch sheltering the door. Doric columns support a projecting pediment that covers a simple wood paneled door.