Located on a road that historically led inland from Kittery, the Dennett Garrison is one of the earliest surviving buildings in the state. Constructed using the post-and-beam system, the two-story house is a large rectangle with a steeply pitched side-gabled roof. It is sheathed in clapboards and has a large center chimney. The facade is symmetrical with a center entry door. The interior walls are hand-hewn hemlock on the first floor and oak on the upper floors. John Dennett purchased the property in 1698.

The John Perkins House, located on Perkins Street, is an example of Georgian-style architecture. The house is clad in clapboard siding and has a symmetrical front facade. The front facade's most notable feature is its entry: a paneled front door with sidelights, Doric pilasters, cornice, and a prominent triangular pediment. The framing timbers are hand-hewn and mortised and tenoned with pegs or treenails. John and Phebe Perkins were one of the first families to build a house in Castine.

The Weston Homestead is a large two-story wood-frame building with a side-gabled roof, set on the east bank of and facing the Kennebec River. Clapboard sided with a symmetrical facade and two large interior brick chimneys, the homestead is a well-preserved example of rural Federal-style architecture. The centered entry door is flanked by Doric pilasters and topped by a fanlight and lintel with dentil molding. A two-story ell extends to the rear to connect to the carriage barn. The house was built by Benjamin Weston, whose father settled in the Canaan area in 1771.

The Laura Richards House is a good example of Federal period architecture in the Gardiner area. It is a two-story clapboard sided structure with a hipped roof. The facade is symmetrical with a central entry door framed by sidelights, fanlight, and simple wood pilasters that support a wide entablature. The cornice is denticulated and a shed dormer sits in the center of the roof. Ebenezer Byram built the house after purchasing the land from Robert Hallowell Gardiner. The house's most significant resident was Laura Richards, a renowned author, who lived here from 1878 until her death in 1943.

The Salmon Falls East Historic District is made up of thirteen houses along Route 117 and Simpson Road on the east bank of the Saco River. The area was desirable for its access to water power and fertile farmland. The oldest house (c.1790) was built by Gibeon Elden, a farmer. Clapboard-sided with a symmetrical facade, multi-paned windows, and a central entry door framed by pilasters and an entablature, it is a good example of a Federal era house in a rural setting. The Came-Marshall House (pictured) dates from the early nineteenth century and replaced an earlier wood frame structure.

Located east of the Kennebunk River and centered around Spring Street, Main Street, and School Street, the Kennebunkport Historic District consists of over 175 historic structures, including residences, commercial buildings, churches, and a library and post office. At least a third of the properties date from the early nineteenth century and feature the Federal style. These buildings are typically one or two stories tall, though some are three stories, and feature a central entrance placed on a symmetrical front facade.

The William Colburn House, located on Bennoch Road, is one of a few eighteenth-century Cape dwellings that exist so far north of the coast. This house features a centralized front door framed by sidelights and a decorative louvered fan above. It also has a side-gabled roof with two large interior end brick chimneys. The original owner, William Colburn, moved to Orono with his father and brother one year prior to the American Revolution. When war broke out, they buried their belongings nearby and sought refuge in a fort near the Kennebec River.

The Off-the-Neck Historic District consists of ten farmhouses and a canal located along Route 166 north of Hatch Cove. The northern terminus of the historic district is the former Ferry Road and the southern terminus is the British Canal located on the "neck" between Castine proper and the northern rural part of the town. This area was first settled by European-Americans in the 1760s and was largely dependent on agrarian pursuits that supported the rapidly growing port town to the south.

The Crosby Street Historic District is an L-shaped area consisting of Crosby Street and Crosby Lane, which are located on a hill above downtown Augusta. Its prominent place overlooking the city's historical business district and Kennebec River led several prosperous merchants to construct high style homes here. The George Crosby House is the earliest building in the district, constructed c.1802 and is a two-story house with a hipped roof. It features a one-and-a-half story side ell.

Built by Asa Redington for his son Silas, this house is an example of the Federal style. The house is two stories tall, clad in clapboard siding with a side-gabled roof and narrow footprint. Its most notable feature, likely added before 1850, is its three-quarter length front porch with Ionic columns and an elaborate balustrade on the roof. A second story entry with sidelights exits onto the porch roof. Asa was originally from Boxford, Massachusetts, and joined the Continental Army in 1778.