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.

One of the oldest remaining jails in New England, the Wiscasset Jail and its attached Jailer's House (1839) offer an invaluable glimpse into Maines early criminal justice system. First constructed as the local jail for Lincoln County, the building served as Maines primary penitentiary for its first four years of statehood, until the State Prison in Thomaston (no longer in existence) was built in 1824.

The Tarr-Eaton House is a one-and-a-half story cape with a central chimney and a side porch that extends to a gable-roofed shed. The clapboard sheathed house is adjacent to the c.1757 Harpswell Meetinghouse and sits on a concrete foundation with an exposed rubble stone cap. Typical of many cape houses, the symmetrical front facade has a central entrance topped with a narrow transom. The house was constructed by William and Elizabeth (Clark) Tarr. William was a veteran of the American Revolutionary War and was licensed to run an inn or tavern.

Located east of the Kennebec River in rural southern Georgetown, the Stone School House is a small rectangular one-story building with a side-gabled roof. It is a rare example of a stone school house in Maine. The front facade has an entry placed to the left of two small windows. General Joseph Berry oversaw the construction of the school, which was completed by Irish stonemasons. Berry became a prominent shipowner and building in Georgetown and Bath. Georgetown was originally known as Parker's Island, named after John Parker who arrived here in 1668.