During the early European-American settlement of Maine's towns, many areas were largely agricultural and animals including swine, horses, cattle, and sheep were allowed to roam free. As infrastructure improved and towns formed, the wandering animals became a health hazard and a nuisance. As a result, many towns constructed small pounds or enclosures to confine loose animals. The owner of the lost animal could then reclaim it from the pound for a small fee.

The Harraseeket Historic District is a large and amorphous district containing three villages, South Freeport, Porter's Landing, and Mast Landing, and outlying areas, such as Wolfe's Neck. The villages are situated on the Harraseeket River which river flows into Casco Bay. European settlers arrived in Freeport in the 1600s, but development did not increase until the latter part of the 1700s. Mast Landing developed first at the river's head of tide. As early as 1753 the British and local colonists had shipped lumber from here, particularly timber cut for ship masts.

The two-story, timber-framed, saltbox-plan, Pote House, located on Wolfe's Neck, faces an open field towards the Harraseeket River. Sheathed in split cedar shingles, the front facade has an odd number of windows and a right-of-center door-unusual for the time period and style. Originally built near Portland, the house was relocated to its current location c.1765 by its first owner Captain Greenfield Pote. Folklore notes that Captain Pote, a Yankee skipper, waited multiple days for a favorable breeze to set out to sea.

Located on Stearns Hill to the southeast of West Paris proper, the Stearns Hill Farm consists of over 130 acres and a house, several barns, blacksmith shop, and sap house. Originally built prior to 1797 in the Cape form, the farmhouse was expanded sometime between 1818 and 1830 to its current configuration as a side-gabled house with a rectangular footprint. The barn and blacksmith shop also date to c.1818, though the size and shape of the barn was expanded several times in the nineteenth and twentieth centuries.

Positioned on top of a small hill east of the Kennebec River, the Colburn School is a modest side-gabled building and a rare example of an early brick school. It has an asymmetrical facade with the front entry placed to the left of three windows. Each window is topped with a granite lintel. The wood shingled ell was constructed to hold two privies. The school is one-room, typical of nineteenth-century rural educational buildings where one teacher taught all grades in a single space.

The Nutting Homestead is an example of the adaptability of a rural Maine farmstead which evolved through the late-eighteenth century to the early-nineteenth century. Initially constructed as a cape with a later, grand attached Federal period house, the farm grew to include a barn, carriage house, and corn crib. The cape, built by Nathan Nutting shortly after moving to Otisfield in 1796, is a one-story dwelling that sits on a granite foundation with clapboards siding, but has lost its original central entry.

The Dr. Samuel Quimby House is sited overlooking a valley of farmland. Dr. Quimby bought 100 acres of land here in 1793 or 1794 and he and his wife Lydia remained here until 1836. The house, constructed in the Federal style by a talented though unknown builder, has elaborate and unusual decorative finishes. The most notable decorative features are the entrance and the ornate Palladian window centered over it. The front entry is unusual with a six-part door topped by an elliptical transom with three round panes.

Located in a rural area northwest of Norway proper, the Nathaniel and Elizabeth Bennett House is a large two-story building with interior end chimneys in a side-gabled roof. The house has symmetrically placed windows and doors on the front facade. Local tradition holds that the house was originally only one room deep and that it was expanded to two rooms deep in 1812. Around 1830 Greek Revival-style elements were added, including a substantial door surround with pilasters and entablature to the front entry. At this time, unique floral stencils were added to a first floor room.

Sitting atop a rocky hill near the center of York Village, the Old York Gaol (pronounced "jail"), a National Historic Landmark, was constructed in stages. The first prison on the site, a plank structure, was finished in 1656 and demolished around 1720. By the early eighteenth century, freestanding buildings of the prison complex included a House of Correction (1707, for debtors and minor criminals), the new Stone Prison (1720), and Gaoler's Residence (1729). The buildings were sited around an open-air prison yard.

A rare example of an early eighteenth-century house in Maine, the John Tarr House sits on the south side of the Saco River. It is a one story, side-gabled structure, originally clapboard sided. The facade faces the river and contains a central entry door with two windows on either side. Typical of the Cape form, it was built with a large center chimney (since removed). A side ell extends to the north and a secondary entrance is located on the south elevation.