The area north of High Street has been listed as the Olde Towne Historic District and is mainly residential. The style of the buildings vary by time period, with many Federal and Greek Revival houses located south and just north of High Street. At the turn of the 20th century, the Revival styles, such as Classical Renaissance, Gothic and Romanesque were incorporated into the construction of homes. However, it is during the Reconstruction period that Portsmouth built its grand churches, which dominate its skyline.

An early building of note is the House & Commercial Building located at 300 High Street. This building dates from the late 18th century and is characterized by an elevated basement and progressively shorter stories from the first to third story. This building is the oldest building in the Olde Towne district and is significant in Portsmouth's history because it was headquarters for Benedict Arnold's occupation of Portsmouth. It has a plain facade but an elaborate Doric porch and is really not representative of the Federal style architecture. It has one of the few remaining elevated basements.

Another early antebellum house is a California Gold Rush house located at the corner of Dinwiddie and South streets. According to local history, house parts were manufactured in Portsmouth during the 1850s and shipped via barge to California to house the burgeoning population that migrated there in search of wealth. At the end of the Gold Rush, there were three houses that were not shipped and instead assembled in Portsmouth - this house being one of them.

Two interesting early Reconstruction houses are at 604 Court Street and 721 South Street. Both have Second Empire elements, but the dwelling on South Street is more true to a Second Empire rowhouse.

There are too many wonderful homes to mention them all, but two dwellings of note in the Queen Anne style are located at 434 South Street and 711 Washington Street. Both of these homes boast so many decorative elements that it is almost overwhelming - a true feast for connoisseurs of Queen Anne architecture.

The Hill House at 221 North Street has been a museum since 1961 when the last of the Hill sisters deeded the property to the Portsmouth Historical Society. It is open to the public and truly represents a slice of early 1800's life.

A beautiful book, entitled "Historic Olde Towne" published by the Olde Towne Civic League is available at many area locations. The book contains photographs and a history of many of the homes in Olde Towne.