The Alfred Historic District is situated in the center of Alfred Village on Route 202, Route 4 (also known as Oak Street), and along Kennebunk and Saco Roads. The community grew rapidly following the Revolutionary War and maintained a steady population into the early 1900s. Geographically, the area is located at the center of York County. The village became a busy crossroad for traffic between Sanford, Biddeford, and coastal towns, which is also why the York County Courthouse was placed here.

Massachusetts Hall was the first building constructed for Bowdoin College. In 1794 the Massachusetts Legislature approved the creation of the college, and in 1798 the college's board approved construction of this building. Unfortunately, the college did not have enough money to complete the building and the project halted after the construction of brick walls. In 1801 the college sold two of its townships in northern Maine and work resumed on the hall. Completed the following year, Massachusetts Hall originally featured a bell tower that was removed in 1836.

Located in the center of Standish Corner, the Daniel Marrett House is an example of a Federal period building with later Greek Revival-style elements. It is two stories tall, sheathed in clapboards with a side gabled roof and large center chimney. The facade is symmetrical with a central entry located in a projecting vestibule. The entry door is flanked by Tuscan pilasters that support the front gabled roof of the projection. The building corners also feature pilasters. The trim and pilasters are Greek Revival in style and were added later.

Located on Main Street, the Ruggles House is an uncommon example of a Federal-style house that is only one room deep instead of two. The two-story building is most notably known for the distinctive "flying" staircase (one without lateral support) and exterior and interior ornate wood carvings. The staircase splits at a landing between the first and second floors which have windows overlooking the Pleasant River. The front facade is symmetrical and has a central door framed by sidelights, fanlight, and narrow pilasters. A fine Palladian window is located above the entry porch.

Located north of the center of Naples, the Manor House is an unusually fine example of the Federal style in a rural area. Two stories high, the building is sheathed in clapboards on the facade and rear elevation with brick on the side walls. The facade is symmetrical with a central entry. The door is framed by sidelight windows and a large elliptical fanlight. Above the entry on the second floor is a Palladian window (a three-part window with a large center sash bordered by two smaller ones). The cornice line sits just above the second-floor windows and is denticulated.

Hezekiah Hutchins, a Revolutionary War veteran who moved to Rumford in 1801 with his wife and four children, built this house. The facade is symmetrical with a central entry door and windows made up of multiple small panes. Two large brick chimneys are symmetrically placed on each side of the entrance. The only decorative elements are reserved for the entry door, which is flanked by wood pilasters supporting a wide cornice that projects over the paneled door and its transom. The interior is remarkable for its Rufus Porter murals added c.1840.

The Godfrey Ludwig House, located north of Waldoboro proper, is a cape dwelling that sits on a granite foundation. The brick house has a side-gabled roof with two chimneys and a central door framed by recessed sidelights. Unlike other brick homes of the same period, the Ludwig House exterior walls are covered with stucco. Unique features of the dwelling include a row of dentils located under the eaves across the length of the front facade, and in the interior hinged panel walls that could be opened to one large meeting room.

The Federal Street Historic District is comprised of 138 buildings, mostly residential, that represent a wide array of architectural styles spanning over two centuries. The area extends over seven streets near downtown Brunswick. Included in the district are thirty-six educational and nine fraternal buildings located on the Bowdoin College campus, four churches, and numerous commercial and public use structures. There are many buildings demonstrating the Federal, Greek Revival, and Colonial Revival styles within the district.

Situated in a field near the location of the original town hall, the Buxton Powder House is one of only three surviving powder houses from the War of 1812 period in the state. It is a square, one-story brick structure with a hipped roof. The only door is placed on the east elevation and is attached with wrought iron hinges. The powder house was constructed in response to the breakout of the War of 1812, a conflict between the United States and Great Britain over what the U.S. saw as economic threats by Great Britain through the restriction of trade and interference with westward expansion.

Tucked away on 180 acres south of Freeport, the Pettengill House and Farm is a good example of a saltwater farm and is removed from the modern word, thus nearly preserving its original setting. Open fields, woodlands, and salt marshes surround the two-story saltbox farmhouse, which is sheathed in clapboard siding with a central chimney supported by granite foundation. This saltbox dwelling, a form rarely built in Maine, has a door located left of center. The property served as a farm until 1960. The house remains without electricity, heating, or plumbing.