Hillside Street, running between Randolph Avenue and the Blue Hills Reservation, forms the spine of Scott's Woods Historic District (NRD), an unusual concentration of farmhouses and barns that are part of the agricultural history of Milton. The McIntyre Farm represents several important aspects of the town's farming history. The house was built in the early nineteenth century for a tenant farmer. In 1872 Peter McIntyre, primarily a cattle dealer who took his livestock to the Brighton market, acquired the house with 127 acres. He probably built the large barn with the entrance in the narrow gable end around the time he acquired the property.
McIntyre retired in 1907, and around 1914 his farm became a gentleman's country estate for Hugh Gallagher, president of the Baker Chocolate Factory in Dorchester. Gallagher built a Colonial Revival residence for himself at 303 Hillside Street in 1915. At the same time he remodeled the McIntyre Farm for use by a caretaker and to serve as the entrance to the estate. Accordingly, the two buildings were remodeled and enlarged to form a picturesque ensemble in the spirit of a New England connected farm. Neither the architect for the remodeling nor for the Gallagher House has been identified. Gallagher's property, called Notlim Farm (Milton spelled backwards), also included other buildings in the vicinity.