Originally including a larger plot of land that extended north along Pleasant Street, this property was purchased in the late 1700s by Squire Daniel Mitchell, a "gentleman farmer." Around 1795, he built this Federal-style home that retains many of its original elements: twin brick chimneys, entrance enframed with an elliptical fan light and narrow sidelights, and a Tuscan columned and balustraded porch.
Daniel's son, Bela, inherited the home, which he shared with his son, James, and his daughter, Mary. Mary wed Edward A. Hewitt, a prominent local businessman who owned a jewelry and clock shop on Central Square (roughly where the Nail & Spa Club currently sits).
At some point in the mid 1800s, a large, two-story addition was added to the rear of the house. In 1879, Edward and Mary carved off a piece of the lot to build a new house at 39 Pleasant Street, and James later sold the family's home at 101 South Street to Edward M. Alden. Edward worked at his father's coal business in Boston, which he later took over in his own name.
During the Alden company's years of prosperity, Edward added a screened-in porch to the side of the house (now used a laundry room). Porches like these were popular in the early 20th century, due not only to a lack of air conditioning, but also to a relatively new belief that fresh air brought health benefits.
Alden's coal business filed for bankruptcy in 1928, and the home has passed through several families since. At some point in the late 20th century, it was converted to a multi-family home. Although it lost its elaborate second-floor window, the listing at Prisco's Real Estate shows that it maintains beautiful interior fireplace surrounds, a split staircase, and a 1700s stone basement.