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.

Located south of Route 117 on Mountain Road in rural Oxford County, the Churchill Bridge is a rare surviving eighteenth-century span. The bridge is composed of dry laid stone, including five large rectangular slabs laid side to side. It is approximately twenty feet long and ten feet wide and the opening over Bennett Stream is approximately seven feet. The Churchill Bridge exemplifies common bridge building practices in the late eighteenth century, where the abundance of large slabs of stone in New England provided settlers and farmers with material for crossing small to modest waterways.

The Alna Meeting House is a two-story building set on a hillside facing south towards Wiscasset. When constructed it was located in the North Precinct of the larger town of Pownalborough (now Dresden) before Alna was incorporated as New Milford in 1794. Centrally located, it served those living in the villages of Alna Center, Head Tide, Puddle Dock, and points beyond. Constructing a meeting house was one of the most important tasks a burgeoning community would take on.

The Samuel Bucknam House is a Cape form with a side ell and Federal-style details. The most notable Federal-style detail on the house is the ornate carving found around the front entry. The front door is flanked by sidelights, topped with a delicate fanlight, and further emphasized by narrow Doric pilasters. The outermost pilasters support ornate urns carved in relief.

Located south of downtown Hallowell on a hill overlooking the Kennebec River, the Vaughan Homestead was the estate of Benjamin and Charles Vaughan, whose grandfather was Hallowell's namesake. The homestead consists of the main house, summer house, barn, gate, terraced garden, and lawns. The house was originally constructed in 1797 and was a two-story hipped roof building with four rooms on each floor and four chimneys. In the early nineteenth century a front porch and two-story rear ell were added. Later additional wings were added including a two-story octagonal one on the west side.

Located in Kittery Point, the William Pepperrell House was rumored to be the finest house in Maine at the time it was built. The house has been remodeled several times, first in c.1720 and then again in 1848 and no description of its original appearance exists. It is currently two stories high, with clapboard siding and a gambrel roof. The former primary entrance, facing Pepperell Cove, consists of a highly ornate surround of a broken pediment with a wood carved pineapple mounted in the center.

Serving as a general store from its construction until the 1930s, Elden's Store is a rare example of a commercial brick building in a rural area from the early nineteenth century. The building is two-stories high with a side-gable roof. The brick is laid in English bond, a pattern of alternating the long and short sides of the brick. The gable ends are clapboard sided. The windows have multiple small panes and granite sills and lintels. The building sits on the corner of Long Plains Road and Haines Meadow Road and has two street facing sides.