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.

The Alfred Historic District is situated in the center of Alfred Village on Route 202, Route 4 (also known as Oak Street), and along Kennebunk and Saco Roads. The community grew rapidly following the Revolutionary War and maintained a steady population into the early 1900s. Geographically, the area is located at the center of York County. The village became a busy crossroad for traffic between Sanford, Biddeford, and coastal towns, which is also why the York County Courthouse was placed here.

Massachusetts Hall was the first building constructed for Bowdoin College. In 1794 the Massachusetts Legislature approved the creation of the college, and in 1798 the college's board approved construction of this building. Unfortunately, the college did not have enough money to complete the building and the project halted after the construction of brick walls. In 1801 the college sold two of its townships in northern Maine and work resumed on the hall. Completed the following year, Massachusetts Hall originally featured a bell tower that was removed in 1836.

Located in the center of Standish Corner, the Daniel Marrett House is an example of a Federal period building with later Greek Revival-style elements. It is two stories tall, sheathed in clapboards with a side gabled roof and large center chimney. The facade is symmetrical with a central entry located in a projecting vestibule. The entry door is flanked by Tuscan pilasters that support the front gabled roof of the projection. The building corners also feature pilasters. The trim and pilasters are Greek Revival in style and were added later.

Located on Main Street, the Ruggles House is an uncommon example of a Federal-style house that is only one room deep instead of two. The two-story building is most notably known for the distinctive "flying" staircase (one without lateral support) and exterior and interior ornate wood carvings. The staircase splits at a landing between the first and second floors which have windows overlooking the Pleasant River. The front facade is symmetrical and has a central door framed by sidelights, fanlight, and narrow pilasters. A fine Palladian window is located above the entry porch.

Located north of the center of Naples, the Manor House is an unusually fine example of the Federal style in a rural area. Two stories high, the building is sheathed in clapboards on the facade and rear elevation with brick on the side walls. The facade is symmetrical with a central entry. The door is framed by sidelight windows and a large elliptical fanlight. Above the entry on the second floor is a Palladian window (a three-part window with a large center sash bordered by two smaller ones). The cornice line sits just above the second-floor windows and is denticulated.