Facing south on Pepperell Road towards the Piscataqua River, the First Congregational Church, the Parsonage, and Old Burying Ground are significant landmarks associated with Kittery's early development. The church, completed in 1730, is a wood-frame building with a gable-front roof and a square tower with a domed roof. An entrance is located in the center of the facade and is flanked by large windows composed of many small panes of glass. The original parsonage, built in 1729, is located north of the church and is a narrow two-story building with a side-gabled roof and long rear ell.

Built by Francis Tufts, a brickmaker, the Tufts House is a finely detailed example of a brick Federal-style house in a rural setting. The house is two stories with a side-gabled roof and chimneys on either end. The facade is symmetrically arranged with the entry in the center. The wood paneled door is framed by delicately carved woodwork and topped by a semi-oval fanlight. The windows contain double-hung sashes with numerous small panes. The cornice line of the roof is finished with dentil molding.

One of the earliest surviving structures in the state, the Hunniwell House is a low posted wood-frame cape dwelling (a side-gabled house, typically only one room deep). It stands one story high on a fieldstone foundation. The facade is composed of an off-center door with a window on each side. The door is topped by a four-pane transom window which lit the small hallway inside. The windows were replaced in the nineteenth century. The house has a central square brick chimney, rebuilt after the house was moved, which feeds the fireplaces in both front rooms.

The General Peleg Wadsworth House, located on a hill west of the Saco River, is a two-story dwelling with a side-gabled roof that sits on a granite foundation. Unlike many Federal-style buildings, the front facade is longer than typical. Although the entryway is central with a portico, General Wadsworth built the house to a larger specification to accommodate a sizeable centralized room with high ceilings to host town meetings, civic and social functions, and drill local militia during inclement weather and in the winter months.

Currently the Portland Club, the Hunnewell-Shepley House was designed by prominent early American architect Alexander Parris. Three stories high, the building is constructed of brick on the sides and wood frame with clapboards on the front and rear. The facade is symmetrical with a centered entry door. The door is flanked by sidelights and topped by an elliptical fanlight window. The second floor window above the entry is a Palladian window, a large arch-topped center window framed by two smaller rectangular windows.

The Old Morrell House is a two-story Federal-style dwelling with a clapboard exterior, gable roof, and central chimney. The front facade is symmetrical with a central doorway framed by simple pilasters and topped with a transom and projecting cornice. The house is on a tract of land once known as Kittery Common. The original owner of the house was Winthrop Morrell. The Morrell family were one of the first settlers in the area. Winthrop's great-grandfather, John Morrell, was given the land by his father-in-law. A log house was built by John Morrell, Jr., here in 1640. Morrell, Jr.

Found on Chadbourne Ridge Road, the Elder Grey Meeting House was originally built at the foot of the Ossippee Pond in North Waterboro and served as a Union church with Baptist affiliations. Elder James Grey was one of the early pastors here who served as the spiritual leader until his death in 1856. He was so loved by the congregation that the Meeting House was moved four miles to its current location in 1832 to be nearer to the aging pastor's house. With a decline in the congregation in the 1880s the Meeting House began to fall into disrepair.

The John Watson House, located in a rural area east of the Saco River, is a two-story wood framed building with a hipped roof, large central chimney, and clapboard siding. The Federal-style house sits on a granite foundation and has a central entrance. The door is flanked by sidelights with a recessed rectangular panel below each. A broad louvered fan extends over both the door and its adjoining sidelights. Later, two one-story Colonial Revival-style wings were added on both sides of the dwelling. One wing connects the house to a one-and-a-half story shed.

Constructed for the storage of gun powder, armaments, and field supplies, the Powder House is a small brick gable-sided structure. It sits on a high ridge, providing an expansive view of the Kennebec River. It has no windows and the brick is laid in American or common-bond pattern, with a course of short end bricks laid between several courses of long sided bricks. The Powder House is one of three surviving early-nineteenth-century magazines in the state, though the other two were constructed in response to the War of 1812.

Located on Jones Road, the Abel Jones House is a two-story structure that was originally oriented south. Thus, the house when first completed reflected Federal-style elements, such as a side-gabled roof and a symmetrical front facade with a central entry and a long rear ell. In the late nineteenth century, the house was remodeled to reflect the popularity of the Italianate style by changing the orientation towards Jones Road and constructing a hood supported by heavy brackets over the new entry. The original entry was removed.