Prior to 1850, the area today known as the Longwood neighborhood of Brookline remained largely farmland on the banks of the Muddy River, the border of Boston. In the first half of the 19th century David Sears (1787-1871) and Amos Lawrence (1814-1886), both prominent Boston businessmen, bought up large tracts of what had been Sewall’s estate. The arrival of the Brookline Branch Railroad (now the MBTA Green Line D branch) served as an impetus to develop the area more fully. Some of the houses built by Lawrence and Sears became homes to friends and business associates, but neither lived in the area. One of the rented houses built and rented by David Sears is this Second Empire cottage likely built in the 1860s. The house was long-rented to wealthy families until the Sears heirs sold the house to Nathan Leo Amster and his wife, Estelle Dreyfus who was raised in Boston. Nathan L. Amster was a railroad executive who eventually became president of the Manhattan Railway Company. When the purchased the cottage, the Amster’s hired Boston architect Clarence Blackall to renovate and “modernize” the home, which added the Classically inspired elements. The couple did not appear to live in the house long, as they spent most of their years in their Fifth Avenue NYC residence. The Sears-Amster Cottage remains an important early house in the Longwood development of Brookline.