Like many of the island’s other Victorian cottages of its era, the Sheffield House was designed and constructed by local architect J. Frank Hayes. It was commissioned by the island’s doctor, Frank Bennett, who moved in with his family when it was completed in 1888. Bennett was described as “a man of generous heart and noble impulses, a skillful physician and a true friend.” Dr. Bennett’s obituary stated that nearly every resident mourned that “sweet smiling and noble face,” and it was opined that he died of heart trouble, possibly precipitated by overwork during an influx of summer visitors.
Dr. Bennett owned the home but a short time. It was known as Flynn Cottage from 1901 through 1911, when it was inhabited by another notable islander, Captain John Smith. Captain Smith was part of a group of island men that won Carnegie Medals for their roles in the rescue of survivors of the Larchmont, which sank off Block Island in horrific winter conditions in 1907.
In l911 the wrap-around porch was enclosed and converted into a master bedroom by the next owner, George Sheffield, whose name stayed with the house long after it passed to the Rose family in 1967. The Roses converted it from a private home into a bed-and-breakfast.
A history of the house compiled by former owners, Steve and Claire McQueeny, and Nancy Sarah, with information from contributor Robert Downie.