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.

The Sproul Homestead is located on a peninsula between the outlet of the Damariscotta River and the Johns River. The Sproul House consists of two separate houses joined in 1833. The oldest portion of the house was constructed at this location in 1749 and is a one-story Cape form with a side-gabled roof. It now functions as a rear ell. The 1815 house was moved from across the road and is two stories tall. It demonstrates the Federal style with a low-pitched hipped roof, substantial chimneys, and a symmetrical facade.

This stately home is one of the most ornately detailed Federal-style houses in Maine. It was built in 1803 by Nathan Codd (who also built the nearby St. Patrick's Catholic Church) for James Kavanaugh, who along with Matthew Cottrill, were among the first Irish settlers in this area. James arrived in Boston with Cottrill around 1780 from County Wexford, Ireland - ten years later both were in Newcastle. James invested in land and soon became a prominent lumber and shipbuilding baron.

Located on the northern edge of the village center, the Old Red Church is a well-preserved Federal period meeting house painted in an unusual color for a church of this period. The wood frame building is two stories tall with a gable front roof. The facade is symmetrical with an entrance on each side. Above the cornice in the gable end is a large louvered fan. A square tower sits just behind the front of the church. The belfry is open and the top of the tower is lined with a balustrade with finial posts.

The Old Walpole Meeting House was constructed by the residents of the Town of Bristol in the area known as Walpole. Nearly unaltered from its original appearance the Meeting House continues to serve as a place of worship during the summer months. It is believed that the original, hand shaved shingles clad the building to this day. The building has a well-documented history and it is known that the hardware was all handmade and that the glass windowpanes were imported from England. Local lore is that each window cost the price of a cow.

The Temple Intervale School is a one-story, single-room building with a gable roof and clapboard siding. An open cupola on the roof ridge holds a bell which was rung by pulling a rope in the schoolhouse. A stove was located at the opposite end of the room, providing heat for students and the teacher. The ell and woodshed were added in the early twentieth century, likely around the time the state began requiring privies (or bathrooms) at schools.