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.

The Main Street Historic District is located on the district's namesake from Portland Street to roughly Swans Falls Road. The district is a narrow elongated rectangular area located down the town's principal street and is approximately fifty-five acres in size. It consists of mostly residential buildings, but does include three commercial properties, a religious building, a park, and a private academy. There are thirty-five contributing buildings (with nine properties dating before statehood) and five non-contributing buildings.

Located on a ridge between the Back River and Sasanoa River, the Heal Family House faces former agricultural fields and Robinhood Cove. The house is a good example of Federal-style architecture and it stands two-stories tall with a large central brick chimney. Its windows and doors are symmetrically placed along the front facade. The central entry has a wood paneled door that is accented with pilasters, a four-pane transom, and a projecting cornice. The house has a side ell with another entry that has a classical door surround.

Set back on a hill overlooking University of Southern Maine (USM) Gorham campus, the Academy Building is a two-story wood frame building topped by a cupola. The Academy Building was built as a college preparatory school for boys. It went through several changes before becoming home to the coeducational Gorham Seminary in 1856. This school closed in 1877 and the building was leased to the state for use as part of the normal college (now USM) that had been built around it. The facade features an elaborate entry porch supported by four Doric columns and topped by a railing.

Oriented towards Robinhood Cove, the Benjamin Riggs House is located in rural Georgetown. The Federal-style house is two-stories tall with a low-pitched hipped roof and a large central brick chimney. Its front facade is symmetrical with a central entry evenly placed between two windows. It has a rear ell that extends to a carriage barn (a nineteenth century addition). The paneled front door is topped with a fanlight and accented with pilasters and projecting cornice. Benjamin Riggs was born in Gloucester, Massachusetts, and arrived in Georgetown in 1776.