The Historic Buildings Survey photo below from 1936 clearly shows the same house that stands today. The footprint on the 1922 map also matches the current house. The 1877 map shows the dwelling labeled as Capt. M.S. Fletcher. At the time, another structure labeled Capt. T.B. Sherman appears to be attached to the south side of the house on the adjoining lot. Several outbuildings labeled W.W. Sh. & B.S also appear on this lot in 1877. The letters are assumed to stand for Wheelwright Shop and Blacksmith.
A dwelling house and a store house on this property were first mentioned in a newspaper article from 1846. Abraham Ross "died in New Market" in 1822. This was the only property he owned at the time. The house appears to have been built in 1789. The price paid for the lot, 30 pounds, by William Riley in 1789 was consistent with vacant lots sold during that time frame. A year later William Riley sold the property for 100 pounds and one year after that Philip King Sherwood sold the property for 200 pounds. This increase in value in 2 years indicates a structure was built on the property during this time frame.
A tax record from 1898 indicates that Charles W. Meyer improved the house. This is likely the date that the Victorian additions were made to the house.