The Parker House located southwest of Blue Hill proper, is a two-story, hipped roof, Federal-style structure. The symmetrical dwelling is clad in narrow clapboard siding and with a central door set under a slim entablature and framed by narrow pilasters and sidelights. The house sits on a granite foundation and has windows composed of numerous panes of glass. At the turn of the twentieth century, the house was remodeled by Blue Hill native, architect George Clough.

Located in a rural area between Hartford and Buckfield, the David Warren House is a rare early nineteenth-century example in this area of a large Federal-style house. The building is two stories with a side-gabled roof and two interior end brick chimneys. The house has a centrally placed front entry with a classical door surround consisting of wide pilasters supporting an entablature and projecting cornice. A four-light transom sits above the door. A side ell connects the house with a gable-front barn.

Union, Maine, was settled between 1772 and 1776 and incorporated in 1786. Like many inland towns in the region, the population steadily grew after the Revolutionary War and into the early decades of the nineteenth century as people moved to the rural areas of Maine for the opportunity to build homesteads and establish livelihoods. The Common in Union is a town-owned green space that became a community space. The first record of the Common dates to 1790, but the land was not deeded to the town until 1809.

After his sea captain father died, young Nathaniel Hawthorne, his mother, Elizabeth, and siblings moved from Salem, Massachusetts, to Raymond where his uncle Richard Manning had also relocated to manage his family's land holdings. Manning built this house for Elizabeth and her children just down the street from his own home. The wood framed house is two stories tall, with clapboard siding and a side-gabled roof. The facade is symmetrical with a central entry.

The Boynton Street Historic District, in Eastport, includes three Federal style homes dating from 1810-1822: Weston House (1810), Kilby House (1820), and Stetson-Starboard House (1822). Each are similar in materials and layout: two stories high with low-pitched hipped roofs and clapboard siding. Each front facade has a central entry with distinctive doors. Federal-style residences are not common in Eastport, and this represents the finest concentration of this style east of Machias.

During the early nineteenth century settlements in Maine began to lose their frontier characteristics as civic improvements created more structured communities. These improvements included the regulation of livestock. During early settlement, many areas in Maine were largely agricultural and animals including swine, horses, cattle, and sheep were allowed to roam free. As infrastructure improved, it became a health hazard and a nuisance to allow this practice to continue.

Roughly encompassing sixty-three acres, the East Machias Historic District starts at the Pope Memorial Bridge and includes structures, both residential and commercial, on Bridge, High, and Water Streets. East Machias was settled in 1763, but trading posts existed in the area as early as 1633. After incorporation, East Machias became a shipbuilding and lumbering community with the first sawmill built in 1765. As the industries grew many prominent citizens, including veterans of the American Revolution and the War of 1812, built homes within the district.

Located on a rural road, the Stephen Longfellow House is a large Georgian-style side-gabled dwelling. The house is two stories high with a massive center chimney and a symmetrical facade. Located in the center, the door is topped by a transom and the entry is framed by a triangular pediment supported by pilasters. The windows are multi-paned and on the first floor are topped with wood molding. The second-floor windows sit directly below the eaves, which overhang slightly. On the interior, the house retains its original woodwork which includes floor to ceiling paneling in several rooms.

Located on Foreside Road, the Randall-Hildreth House is a two-story dwelling in the Georgian style with a low-pitched hipped roof with two symmetrically placed interior chimneys. The front faade has a prominent entryway with a six-paneled door surrounded by a transom and sidelights. Above the doorway is a compound-roof pediment supported by ornate columns, likely added by the late nineteenth century. Other unique features include detailed wooden quoins (mimicking stone block) at all four corners of the house and dentils under the roofline.

Originally located in York Corner, the school house is a small wood frame structure with a side gabled roof. The entry sits at the north side of the facade, with a small window just off center. The other elevations contain small windows and a chimney is located on the north elevation. The windows were originally covered in oiled brown paper, producing a dull, yellow light in the interior. Built by the residents of York, the school served the local children. It operated as a school for more than 100 years.