The Limerick Upper Village Historic District consists of twenty-eight properties including three constructed prior to statehood. Composed of the Upper Village located on top of a high ridge where a gap contains roughly 200 acres of flat land. The district mostly sits on Main Street and includes numerous businesses, residences, three churches, a former academy, library, town hall, multiple cemeteries, band stand, park, and a memorial marker. All three houses built before 1820 are multi-storied Federal-style houses with clapboard exteriors and known as the Rev. Edmund Eastman House (c.

Few of Maine's early schoolhouses still in existence hold so similarly to their original exterior design as the Alna School (also known as the Center School), located in Alna Center about a half-mile south of the Alna Meeting House (which is also listed in the National Register of Historic Places). It is believed to be the second-oldest schoolhouse still standing in Maine; the Old Schoolhouse in York predates it by 40 years. The Alna Schoolhouse is a one-story, nearly square building that maintained its educational function into the twentieth century.

The Belfast Historic District encompasses a large area of the city center and includes a variety of residential, commercial, religious, and governmental buildings. There are 287 properties listed in the district, and many of them were constructed before 1900. The district includes buildings on eighteen different streets. Various architectural styles were employed by its citizens including Federal, Greek Revival, Gothic Revival, Italianate, Queen Anne, and Renaissance Revival designs. Belfast was first settled in the late-eighteenth century.

The Holmes-Craft Homestead sits on a hill north of Jay proper at the fork of Route 17 and Old Jay Road. Original owner and early settler, John Starr was a representative to the Massachusetts General Court, first elected in 1804. Starr was a jack-of-all trades, working as a lawyer, judge, accomplished land surveyor, owner of a tavern with a stagecoach stop in the village, and postmaster. Later, Starr's son-in-law and talented cabinet maker, Aruna Holmes, purchased the property. The timber-framed Federal-style house is two stories high with a hipped roof.

Located in a rural area west of the town center, the James Smith Homestead is a Georgian era farmhouse. It is two stories tall with clapboard siding, a side gable roof, and large central chimney. The facade is symmetrical with a central entry. The entry door is framed by pilasters and topped by a broken pediment. A one-story ell extends to the southeast. James Smith purchased the land on which the house stands in 1753 and it remained in his family for many years.

Facing south on Pepperell Road towards the Piscataqua River, the First Congregational Church, the Parsonage, and Old Burying Ground are significant landmarks associated with Kittery's early development. The church, completed in 1730, is a wood-frame building with a gable-front roof and a square tower with a domed roof. An entrance is located in the center of the facade and is flanked by large windows composed of many small panes of glass. The original parsonage, built in 1729, is located north of the church and is a narrow two-story building with a side-gabled roof and long rear ell.

Built by Francis Tufts, a brickmaker, the Tufts House is a finely detailed example of a brick Federal-style house in a rural setting. The house is two stories with a side-gabled roof and chimneys on either end. The facade is symmetrically arranged with the entry in the center. The wood paneled door is framed by delicately carved woodwork and topped by a semi-oval fanlight. The windows contain double-hung sashes with numerous small panes. The cornice line of the roof is finished with dentil molding.

One of the earliest surviving structures in the state, the Hunniwell House is a low posted wood-frame cape dwelling (a side-gabled house, typically only one room deep). It stands one story high on a fieldstone foundation. The facade is composed of an off-center door with a window on each side. The door is topped by a four-pane transom window which lit the small hallway inside. The windows were replaced in the nineteenth century. The house has a central square brick chimney, rebuilt after the house was moved, which feeds the fireplaces in both front rooms.

The General Peleg Wadsworth House, located on a hill west of the Saco River, is a two-story dwelling with a side-gabled roof that sits on a granite foundation. Unlike many Federal-style buildings, the front facade is longer than typical. Although the entryway is central with a portico, General Wadsworth built the house to a larger specification to accommodate a sizeable centralized room with high ceilings to host town meetings, civic and social functions, and drill local militia during inclement weather and in the winter months.

Currently the Portland Club, the Hunnewell-Shepley House was designed by prominent early American architect Alexander Parris. Three stories high, the building is constructed of brick on the sides and wood frame with clapboards on the front and rear. The facade is symmetrical with a centered entry door. The door is flanked by sidelights and topped by an elliptical fanlight window. The second floor window above the entry is a Palladian window, a large arch-topped center window framed by two smaller rectangular windows.