Fisher Hill claims distinction as the largest and best preserved subdivision in the Boston metropolitan area laid out by Frederick Law Olmsted. In 1886 several landowners hired the Olmsted firm to prepare a plan for roads that respected the topography of the hill and featured house lots ranging in size from two to four thousand square feet. The development was from the beginning one of the most successful in Brookline and, unlike other areas of town, managed to resist the pressures to build multifamily housing. The Olmsted plan extended from Fisher Avenue on the top of the hill east to Cypress Street. The neighborhood includes homes designed by many well-known Boston architects built primarily during the period from 1890 to 1910. Particularly outstanding are several early examples of Colonial Revival design. William R. Emerson designed one of the first houses, built in 1885 as a rental property to encourage development, at 195 Fisher Avenue (NRD), a modest interpretation of a symmetrical eighteenth-century house several years before that became the common Colonial Revival form. William Dabney built a garrison-style house (153 Dean Road, NRD) for himself in 1894. Before his death at age forty-two in 1897, Dabney designed the houses at 219 Fisher Avenue (NRD) in 1896 and 260 Fisher Avenue (NRD) in 1896. At 219 Fisher Avenue A. L. Darrow created an early “automobile house” in a Colonial Revival style compatible with the main house and erected in 1902 for the owner's Stanley Steamer, a steam-powered automobile. Fisher Hill has a large number of early garages, especially for the larger homes built in the early twentieth century between Fisher Avenue and Chestnut Hill Avenue.
H. H. Richardson designed his only Brookline house, a Shingle Style residence for Walter Channing, demolished in 1935, on Fisher Hill. In 1935, Richardson's son Philip was the architect for 35 Fisher Avenue, a French provincial stone house that demonstrates what he had learned from his father's facility in stone masonry. Built of random ashlar granite in a variety of colors, the stone is carefully laid up to achieve a balanced polychromatic effect.