Originally built in Portland, the Thomas Skelton House was slated for demolition to enlarge a parking lot, but was moved to Falmouth in 1971. Skelton was a housewright who soon after construction was completed sold the dwelling to a Portland mariner, John Rackleff. Afterward, it changed hands and appearance numerous times. The structure was originally one-and-a-half stories high, but another floor was added roughly ten years later, c.1810.

The Harpswell Meetinghouse, located on State Route 123, is a two-story building with a side-gabled roof and numerous multi-paned windows. Sheathed in clapboard siding, the structure is rectangular, but nearly square, with an exterior stair-hall. Building began in the late 1750s but was not completed until the mid-1770s. Elisha Eaton, the son of the first meeting house parish pastor of the same name, was likely the original builder. After his death in 1764, the elder Eaton's son Samuel took over duties as pastor.

The Elisha Purington House is a two-story structure with a gable roof and central chimney. The dwelling is sheathed with clapboard siding and has small paned windows. The central six panel door is framed by molded architrave trim and capped by a transom, and entablature. This structure is a well-preserved example of mid-eighteenth-century rural Maine architecture. The builder was Elisha Purington. Originally from New Hampshire, Purington is considered one of the finest colonial New England clockmakers. He also earned a reputation as a gunsmith and blacksmith.

The Matthew Cottrill House, with its symmetrical front facade and central entry flanked by two sets of windows, is a good example of the Federal style. Its rounded portico with deep entablature supported by fluted columns is notable. The door is topped by a wide elliptical fanlight and sidelights. Its early date is partially demonstrated by the raised granite foundation, often referred to a water table, and more typically seen with the earlier Georgian style. The rear ell is thought to have been associated with the Chapman family, thought to be the first European settlers in Damariscotta.

The Samuel Weston Homestead is a high-quality example of transitional Georgian-Federal period architecture. Located on a rural stretch of US 201, southeast of the center of Skowhegan, the house is a two-story clapboard-sided wood-frame structure in an L-shape. The facade is irregularly arranged, with the main entrance located off center slightly to the west. The door is sheltered by a pedimented entry porch supported by Doric columns. A second door that served as the entrance to Samuel Weston's office is located on the eastern end of the facade and obscured by heavy vegetation.

The Philip Leach House is a well-preserved example of a Federal-style Cape house. It is a one-and one-half-story, clapboard-sided building with a side-gable roof. The faade is symmetrical with a central entry door. The door is framed by sidelight windows. The house is remarkable for the stencil work and floor painting in its parlor. Floral and abstract designs in green, red, and yellow adorn the walls, preserved after being covered by wallpaper. The floorboards are also painted, with freehand leaf patterns.

Found on Port Road, the Gates House is a Federal-style home with early nineteenth-century characteristics, such as the low-pitched hipped roof and windows consisting of small panes of glass. Situated on a steep slope near the edge of the Machias River, the house is two stories at the road and three at the river. The building has a narrow L-shaped footprint. It has clapboard siding and a main entrance framed by pilasters, a 5-paned fanlight, and projecting cornice.

Settled by four brothers, the Paine Neighborhood Historic District represents a typical settlement pattern in eighteenth-century Maine. Joseph Paine moved to the area in 1780 from Eastham, Massachusetts. His four sons built homes along Route 113 and established a family cemetery. One of the houses burned in the 1980s but the Myrick, Richard, and Joseph Paine, Jr. Houses survive and make up the district. Myrick's is the largest with two stories, a hipped roof, and four interior chimneys.

The Paul Family Farm, located on Route 101, has a two-story Federal- and Greek Revival-style farmhouse that rests on a fieldstone foundation. It is covered in clapboards and has a symmetrical facade with a central door framed by sidelights, pilasters, and a wide entablature. It has a massive central brick chimney. Outbuildings on the site include a gabled barn, woodshed, chicken coop, tool shop, and a garage all built later on the nineteen-acre property. Moses Paul initially settled in the area in 1780, living with his wife Jane in a different two-story structure.

The Cushing and Hannah Prince House is located on Greely Road and demonstrates the architectural trends associated with a late eighteenth-century farmhouse. Constructed in the Federal style, the Prince House is two stories tall and features a thick central chimney in a side-gabled roof. The building largely lacks exterior ornamentation, except for the front entry with a paneled wood door flanked by sidelights and topped with a molded fan. It is clad in clapboard siding and has wood windows composed of many small panes of glass.