Immediately north of Jones House on Atkinson Street stand two small, unassuming dwellings. These are the Cotton Tenant Houses, built about 1835, and the last of the extant houses to be constructed in the Strawbery Banke neighborhood.

Leonard Cotton bought this property in 1834, and shortly thereafter had these two modest houses erected. Cotton, born in Portsmouth in 1800, was descended from a family that had been in the town since 1650. As a young man he tried his hand at the cooper's trade, first in Portsmouth and then in Trinidad in the West Indies, but Cotton was looking for more lucrative work. Following the example of many others in Portsmouth, he turned to a mercantile career.

By the 1830s Cotton was a retail grocer on Pleasant Street. He probably dealt mostly in spices, tea, coffee and sugar, and possibly some alcoholic beverages. He employed at least one clerk and a bookkeeper. Apparently Cotton's business was successful, for he began purchasing investment properties such as this one on Atkinson Street in Strawbery Banke.

Cotton was already capitalizing on the economic changes in Portsmouth in the 1830s. With trade in a definite decline, the level of wealth in the area was falling. Fewer people could afford to buy homes; more and more were renting. Thus, Leonard Cotton bought a piece of land in a prime location, near Puddle Dock, and built two functional rental dwellings on it.

Cotton must have been pleased with his investment and with his role as landlord. He continued to buy lots and houses, and by the time of his death in 1872 he owned more than forty properties in this neighborhood and throughout the city. Cotton could oversee many of his holdings from his own windows, for he lived in an elegant Georgian mansion that still sits atop a small knoll directly across Washington Street from Strawbery Banke's Webster House.

The Cotton Tenant Houses are strikingly similar, not only in dimensions and framing members, but also in doors, trim, and original hardware. Both houses exhibit more modern frames than most other Strawbery Banke houses. They also have rafter roofs without purlins, a common feature of houses constructed after 1830. The main difference between them is the shed that runs along the back of the north house, the building that faces Atkinson Street. But as examples of housing built for investment, rather than for personal use, they lack much of the simplest decoration that even lower income owners had traditionally put into their own homes.