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.

The First Parish Meeting House is the oldest public building in Biddeford and one of the oldest meeting houses in Maine. It is a single story, gable front structure, sheathed in clapboards. Its symmetrical facade contains two entry doors on the ground floor and a sash window in the gable. Both the window and doors are topped by a louvered pointed arch. It was built by Nathaniel Perkins, a local master builder, using hand hewn timbers. The building originally had a belfry and side galleries on the interior. These were removed along with the soundboard and the pulpit lowered in 1840.

Located south of US Route 202 and Route 137 on Main Street, Water Street, Neck Road, and Canton Street and west of China Lake, the China Village Historic District consists of 47 structures. Most of these structures are residential, but the district also includes a post office, church, commercial building, library, and two fraternal buildings. The Town of China was first surveyed in 1773 and 1774. It was originally known as Jones Plantation but incorporated in 1796 as Harlem. The town boundaries were refined to its current borders in 1818.

Located on State Highway 201, the Peacock Tavern is a timber and plank framed, two-story structure with a hipped roof and clapboard siding. The center doorway is flanked by sidelights and pilasters supporting a detailed entablature. The original facade consisted of an entryway framed by two windows on either side. Sometime during the nineteenth century an addition was added to the north side of the building with two more windows and a two-story ell. The tavern has long been a local landmark.

Found on Main Street near its intersection with Union Street, the U.S. Customs House is currently known as the Louis T. Graves Memorial Public Library. The Federal-style two-story brick building is rectangular in shape and has a low-pitched hipped roof. It sits on a granite foundation and has arched window and door openings. Originally built by the Kennebunk Bank of Arundel, the first floor housed the bank and beginning in 1815 the second floor held offices for U.S. customs agents.

Overlooking Greenland Cove in Muscongus Bay, the Daniel Weston Homestead consists of a house with a side ell connected to an attached barn and a detached barn. The house is a two-story dwelling with a side-gabled roof. The house is unusually long for its date of construction. It has a central entry flanked by multi-paned sidelights and topped with an entablature and projecting cornice. The house is clad in clapboard siding. Weston's father and uncle bought 320 acres here in 1772. Weston inherited the land from his father and built this house after his first marriage in 1805.

Valley Lodge, located in the rural interior of Cumberland County, survives as an example of the growth of early homestead houses. Ephraim Brown settled in Baldwin in 1788, building a small one-story cape and naming it Valley Lodge. That original cape is now enveloped in a two-story Federal-style structure, which Brown built around his pre-existing house in the early 1800s to accommodate the needs of his growing family.

A National Historic Landmark, Fort Western was built by the Proprietors of the Kennebec Purchase as a fortified trading post. The fort is a rare surviving example of a eighteenth-century military outpost in Maine. Lieutenant James Howard and twenty men were assigned to the fort. In the 1750s local Native Americans actively defended their lands from European settlement and Fort Western was established to provide safe travel along the Kennebec River. Fort Western remained an active military post until 1767. Howard later bought the fort and used it has a residence and store.

Moses Carleton, scion of the region, built this Federal-style house for his daughter, Elizabeth Dole. Located on a farm, overlooking the Sheepscot River valley, the property also contains two period barns, a carriage shed, and associated orchards and fields, and has changed little since its construction. It reflects the wealth accumulated by Moses Carleton and others as early settlers, shipbuilders, speculators, and businessmen.