Located on Main Street in Bucksport, the Jed Prouty Tavern and Inn is a three-story building overlooking the Penobscot River. It has a side-gabled roof and a one-story veranda that runs the entire length of the building. It has two entrances, both framed by sidelights and a transom. The oldest section of the building, the eastern end, was built by Asa Peabody and was only two stories with a hipped roof. In 1820 a man named Sparhawk opened a tavern and inn in the building and changed the roof to side-gabled.

Positioned on top of a slight hill overlooking the outlet of the Ducktrap River into Penobscot Bay, the George Ulmer House is a two-story timber-framed residence with a hipped roof and two interior brick chimneys. The house demonstrates the Federal style with its symmetrical front facade and delicate inverted cove brackets under the cornice . George Ulmer, a Revolutionary War veteran, arrived in Lincolnville in 1784 with his brother Philip, also a veteran. The Ulmers, through a variety of endeavors, amassed substantial wealth in a short amount of time, but subsequently lost most of it.

Lt. Robert Andrews commissioned his house from John Kilborn, Jr. a local master builder in 1805. The house, located south of downtown Bridgton in a rural area, is two stories with a side gabled roof and clapboard siding. The facade is symmetrical with a central entry. The entry door is framed by tapered pilasters supporting a finely denticulated cornice. Above the door is a leaded fanlight. The windows are made up of multiple small panes and have simple frames. The main cornice is also denticulated, identical to the one over the door.

The Paris Hill Historic District boasts a rare concentration of early nineteenth-century buildings in its compact village center. Much of Paris Hill's charm is due to its cohesive appearance as a collection of Federal and Greek Revival buildings; the built landscape remains largely-unaltered, with all but a few original buildings still standing. The arrival of the Atlantic & St.

Thought to be the oldest known house in Deer Isle, the Peter Powers House is located between Deer Isle and South Deer Isle and faces Long Cove. It was built at a time when maritime travel was more prominent than overland routes. The gambrel roof was a rare architectural feature in Maine, especially on a Cape form, which is traditionally side-gabled. The one-and-one-half story structure is sheathed in clapboard siding and sits on a fieldstone foundation. The house retains windows with small panes of glass. This modest house has a centered entrance with a paneled door.

The Archibald-Adams House, located on Route 193, is considered one the oldest and most intact Federal period houses within the area. Built during the 1790s, the house is a 2-story home nearly square in shape. It sits on a granite foundation and has a hipped roof and clapboard siding. The house is removed from the town center and has two entrances: one facing south towards the business district and one facing east. The east facade, facing the road, feature windows with multiple small panes of glass and the original center door surmounted by a triangular pediment.

The Barrows-Steadman Homestead, located on Main Street, is a two-and-a-half story Federal-style house. The frame is a post-and-beam construction with a side-gabled roof and two large chimneys. It sits on a fieldstone foundation and is sheathed in clapboard siding. The facade has a central entrance flanked by Doric pilasters and sidelights and surmounted by an entablature. A two-and-a-half story ell was added in 1910. The unique feature of the dwelling is the "Tree Room." In 1830, frescoes were painted in the room by Rufus Porter and Jonathan D. Poor. Porter was a Renaissance man.

Thomas Hobbs, Jr. built this house on Wells Street near the junction with Elm Street near the center of town. The two-story structure sits on a fieldstone foundation, has a side-gabled roof and a central brick chimney. Sheathed in clapboard siding, it has a centralized door covered by hipped-roof entry porch. It is an excellent example of simple mid-eighteenth-century New England architecture and design. Also known as the "Hostelry," this building was considered a social center in the former mill town and a popular stop for travelers.

Set on a hill in South Windham, the Parson Smith House is an intact example of Georgian-style architecture best evidenced by its large and bulky massing especially compared to its small windows, which are comprised of many small panes. It is two stories tall with clapboard siding and a side-gabled roof with two large interior end chimneys. There is little ornamentation on the exterior. The facade is symmetrical with a central entry, flanked by sidelight windows and outlined in molded trim which were likely additions as styles changed.

Located on the southern end of downtown Kennebunk, Wallingford Hall is particularly striking example of the Federal style of residential architecture., The house is two stories high, sheathed in clapboards, and topped by a low-pitched hip roof. The facade is nearly symmetrical with a centered entry. The entry door is framed by sidelight windows and topped by an elliptical leaded fanlight. Above the entry on the second floor is a flat-topped Palladian window (a three-sash window configuration with a large center window flanked by two narrow windows).