The Spring Street Historic District encompasses portions of the West End and the Arts District in Portland. It is a predominantly residential area with multiple churches and schools. The area was historically where many of Portland's wealthy citizens made their homes. Structures existing by 1820 are Federal-style brick townhomes, such as the Prentiss Mellen House dating from 1807 (pictured). The earliest settlement on the peninsula was established in 1632-33. Portland, like many early Maine settlements, experienced numerous conflicts with the Native American inhabitants of the area.

Situated on the east side of the Presumpscot River, the Great Falls Historic District consists of three residences and several industrial ruins. All three buildings are of frame construction and represent either the Federal style or the Greek Revival style. The oldest building is the Federal-style Trickey-John White House (pictured) that features a low-pitched hipped roof, clapboard siding, and a central entry topped with a louvered fan and flanked by sidelights.

This single-story Cape Cod style house is thought to be the oldest in Damariscotta. The structure is a good representation of the types of homes European settlers would construct after the initial wave of settlement. The Chapman-Hall House is thought to have been built by Nathaniel Chapman, half-brother of Anthony Chapman who is believed to be the first permanent European settler in Damariscotta. Nathaniel, an established housewright, was persuaded to leave Ipswich, Massachusetts, to construct proper homes to replace the rudimentary structures first constructed.

This Gothic Revival-style house is an unusual example from the early nineteenth century. Located on Whiskeag Road, this two-and-a-half story rectangular dwelling is constructed of granite blocks with wood trim and a gable roof. The facade has a centralized door with granite steps flanked by large floor to ceiling windows with many small lights topped with pointed arches. Known as the "stone house," this dwelling was built by one of the founding fathers of Maine and the state's first governor.

The Dyer-Hutchinson farm is one of the few eighteenth-century farms still in active use. The farmhouse, a one-story Federal period cape, was built by William Dyer in the western part of Cape Elizabeth. The property served as his homestead, where he and his wife raised two children and owned forty-five acres of land, twenty of which were used for farming.

The oldest part of the Squire Tarbox House, the current one-and-a-half story rear ell, was built in 1763 and located on a hill to the north. In 1806 Squire Tarbox purchased the house and moved it in 1819 to where it now resides. The next year, he constructed the two-story part of the house. This two-story main block is characterized by the Federal style with a low-pitched hipped roof and symmetrically placed window and door openings on the front facade.

Located on the Pemaquid Peninsula on Harrington Road, the Harrington Meeting House overlooks the Eastern Branch of the Johns River and the Harrington Burial Ground. The frame of the Georgian-style meeting house was originally constructed in 1772 in the geographic center of Bristol, but after much discussion about where the town's meeting house should be constructed it was moved to another location and completed in 1775. The meeting house was moved again in the 1840s to its current location, facing the Old Harrington Road.

The Ebenezer Alden House, located off of Route 131, is notable as a late example of Georgian architecture in Maine. The two-and-a-half story dwelling is topped with a side-gabled roof with two symmetrically placed chimneys. It is constructed with brick nogging between wooden timbers and sheathed with clapboards. The Georgian style is typically unadorned except for quoins at the corners, denticulation at the cornice, and detailing at the door surround. In this case, the surround consists of pilasters and a triangular pediment, while the fanlight is more indicative of the Federal style.

Located near the village center, the Captain Nathaniel Lord House is an excellent example of the Federal style. It is three stories tall, clad in clapboard siding, and topped by a flat roof with an octagonal cupola. The facade is symmetrical with the entrance located in the center. An entry porch, a later addition, shelters the front door, which is framed by sidelight windows and topped by an elliptical fanlight. Above the entrance on the second floor is a flat topped Palladian window (a three-part window with a large central sash bordered by two narrower ones).

Located just south of Main Street, the Baxter House is a two-story, clapboard-sided, Federal-style building. The facade is symmetrical and the centered entry is framed by sidelight windows and an elliptical fanlight. The windows are grouped in pairs except for the single second floor window directly above the entry. The upper windows are smaller than the first floor's and placed just below the eaves which are supported by paired brackets. The roof is side-gabled with two gable front dormer windows.