Located on Fish Street north of Fryeburg center, the Benjamin Wiley House is two-and-a-half stories, sits on a granite foundation, and has a side-gabled roof and clapboard-sided exterior. The house has many Federal-style features including a central brick chimney and symmetrical facade. The centralized door is framed by simple pilasters, sidelights, and an entablature with a detailed fan in a keyed arch. Attached to the dwelling is a two-story ell that connects to a screened- in porch and barn. Many prominent citizens of Fryeburg have lived on the farmstead including the following.

The Squire Ignatius Haskell House, found along the northern end of a former mill pond, is an example of late-Georgian style architecture with later elements of the Greek Revival style added. The two-and-a-half story dwelling is a rectangular frame construction with clapboard siding and a prominent gambrel roof. It sits on a granite fieldstone foundation and has a central recessed entry accented with Doric entablature and pilasters. Haskell came to Deer Isle from Newburyport, Massachusetts, with his father, Mark, and brother, Solomon, in 1778.

The Martin Kinsley House, located on Main Street, is a two-story Federal-style dwelling with later Italianate-style bracketing under the roof eave. The centrally located door is topped by a fanlight and narrow triangular pediment. The house is one of Hampden's earliest surviving residences and was the home of the first Representative to the United States Congress from the district. Kinsley served as a major in the Massachusetts militia during the American Revolution.

The Libby-MacArthur House is a two-story gambrel-roofed wood frame structure sheathed in weatherboards with brick nogging between the exterior wall studs. The symmetrical facade features a central gabled entrance enclosed in a vestibule and shed roofed dormers on the lower pitch of the roof. It also has a substantial central brick chimney. The dwelling is significant as one of only a few early gambrel roofed buildings remaining in Maine. Philemon and Martha Libby obtained the 100 acre property in 1777.

The Portland Observatory has been a fixture in the Munjoy Hill neighborhood of Maine's largest city since its construction. This unique structure is the only maritime signal tower still standing in the United States, and is as a testament to the city's success in maritime trade.

Located at the end of Church Street in Yarmouth, the North Yarmouth and Freeport Baptist Meeting House was originally constructed in 1796, but its current appearance is the result of changes made in 1825 and 1837. The original building was 46' wide and 50' deep. It originally had ten window openings on each side, which were later enclosed. The building likely had a porch or small steeple in the front as well. In 1825 the building was expanded by 10' in length, the front pedimented projection added with the steeple. In 1837 the window configuration on the side of the building was completed.

Located just north of Route 1 in central Kennebunk, the Bourne Mansion is an excellent example of the Federal style. It is three stories high, wood framed, with a low-pitch hipped roof. The main facade faces south with a secondary entrance on the west, street facing elevation. The south entry, located in the center, is framed by Tuscan pilasters, sidelight windows and topped by an elliptical leaded fanlight.

The Falmouth House is an example of a traditional New England Federal-style tavern. The dwelling is two stories high with a central door, gabled roof, and clapboard exterior. The Falmouth House was moved a few hundred yards to the west when the Grey Road replaced the Old County Road in 1826. The Old County Road alignment is now a walking trail accessed off Hadlock Road near Autumn Way. In the early 1800s this area, set away from the coast and north of Portland, was sparsely settled and travelers had difficulty finding lodging, meals, and accommodations for their horses.

The Blue Hill Historic District comprises the commercial and residential center of the town of Blue Hill at the intersection of Routes 15, 172, and 177. Settlers from Andover, Massachusetts, arrived in this area in 1762. A small town formed, bolstered by lumbering, shipbuilding, and saw, carding, fulling, and grist mills. The historic district includes nine buildings that were constructed prior to 1820.

Located south of Durham Center, the Nathaniel Osgood House is a three-story timber frame farmhouse with a hipped roof, central chimney, and clapboard siding. The symmetrical facade has a central entryway with pilasters supporting a triangular pediment that encloses a six-panel door and transom. The Osgood House is a nicely preserved example of an eighteenth-century rural dwelling in Maine. According to local lore, Nathaniel and his brother Aaron moved to Durham from Deerfield, New Hampshire, after leaving their hometown of Amesbury, Massachusetts, in the early 1780s.