By 1884 there were a few part-time and year round residents like the Lees and the Pierces, but Fisher Hill remained largely undeveloped. The Boston and Albany Railroad (now the MBTA Green Line) circumvented the hill on the north and east, effectively cutting off development from that direction. On the west side Fisher Avenue began at what is now Hyslop Street next to the Pierce estate on Chestnut Hill Avenue and extended up the hill past the covered reservoir established by the town in 1875. The largest estate on the south side of the hill was built by dry goods magnate Joseph H.White in 1881-82 (541-45 Boylston St.). White's house and carriage barn, though still standing, are surrounded by recent development. It was designed by the prominent Boston firm of Peabody & Stearns and was pictured in L'Architecture Americaine. published in Paris in 1886. Frederick Law Olmsted was hired to plan the landscaping for this estate, although little evidence remains of his work.

Both White and Pierce were among the landowners who, in 1884, hired the Olmsted firm to prepare a development plan for Fisher Hill. The others were Arthur Rotch, one of Boston's leading architects, Thomas Lee, the son of Henry, and the Goddard Land Company, which owned a large parcel on the hill. Pierce had already begun to develop his land and it was said that he was careful about who he sold to, "lest he might sell it to someone who would not respect his desire that Fisher Hill remain unblemished by any structure not in harmony with the high character he wished the neighborhood to maintain/7 One can presume these sentiments reflected those of the other large landholders as well.

It was not until the late 1880s that the development of house lots really got under way. With Buckminster already completed most of the new houses were built on that road. Between 1888-1892 there were eleven houses built on Buckminster, including a large stone mansion at 62 Buckminster for Jonathan White, the brother of Joseph White, designed by Peabody & Stearns. Clarence Blackall, writing in an architectural journal in 1889, commented on the Jonathan White House that it was "... pleasing not only for its well-studied details and good general effect, but also for the manner in which Mr. Olmsted's landscape work and the architect's design are so united that the house seems to be just as thoroughly in place, and a part of the surroundings, as though it had grown there."

At the same time Jonathan's brother Joseph began to develop Seaver Street on the hill above his house. He hired Shepley, Rutan & Coolidge to design a large brick Tudor style house at 80 Seaver St. which he rented to his daughter and son-in-law for many years. While these houses were being built other roads planned by the Olmsted firm were under construction, opening up house lots on Leicester, Hyslop, Holland, Clinton, and Dean, as well as an extension of Fisher Avenue north of Buckminster.

With standards for new construction having been established in the 1890s the largest undeveloped section of the hill was purchased in 1903 by a very unusual couple, John and Mary Longyear. These wealthy mid-westerners and devotees of Mary Baker Eddy and the Christian Science religion assembled a parcel so large that they absorbed a section of Hyslop Road where it originally extended to Leicester (Hayden Road is a remnant of that extension). Incredibly, the Longyears dismantled their stone house in Marquette, Michigan, which had been built in 1890, and had it reassembled at 120 Seaver St, making a large addition as well. The landscaped grounds originally extended down to the intersection of Seaver and Buckminster Road where a portion of their stone and iron fence still stands. The houses on the hill above Seaver were built by Mrs. Longyear for members of her church in the 1910s.

Notwithstanding the fact that by the early 1900s Fisher Hill was clearly a neighborhood of "high class" houses, a number of property owners were concerned about the need to protect their investments in the face of the rapid increase in demand for multi-family homes elsewhere in Brookline. Areas which only a few years before had been dominated by single family homes were giving way to the construction of apartment blocks. Accordingly, in 1914, a covenant was entered into by 165 property owners to protect their holdings against "deterioration through the construction of apartment houses, two family houses, public garages, stores and hospitals." This covenant expired in 1940, by which time zoning regulations had been established by the town to restrict high density residential construction.