Cedar Fairmount, the residential and commercial neighborhood where eastbound Cedar Road forks into Cedar to the left and Fairmount to the right, emerged as the "gateway to the Heights" as early as 1918 when the Tudor-style Heights Center Building opened on the north side of Cedar Road between Lennox and Surrey roads. Taking advantage of its streetcar connection to Cleveland via Cedar Glen, the district grew rapidly in the 1920s, with new storefronts and apartment buildings erected throughout the decade. For many years Heights Medical Building and Doctors' Hospital (which stood slightly southeast of the Buckingham Condominiums where Euclid Heights Boulevard intersects with Cedar Road) made the area a medical hub.
Cedar Fairmount's growth was further buoyed by Barton Deming's development of Euclid Golf, an upscale neighborhood bounded roughly by the Cedar-Fairmount intersection to the west, Cedar Road to the north, North Park Boulevard to the south, and Coventry Road to the east. A large percentage of Deming's development was previously occupied by the Euclid Golf Club, whose property (owned in part by John D. Rockefeller) also stretched west into the Cedar Heights neighborhood, whose streets include Grandview and Bellfield Avenues. Euclid Golf Club closed in 1912. Not surprisingly, Demington Drive takes its name from Barton Deming.
Concerns about the "aging" of Cleveland Heights led to plans for a massive redevelopment of Cedar Fairmount in 1969. The renewal's cornerstone was to be called Surrey Place, a combination of high-rise and garden-type apartments, connected to a proposed Cleveland Transit System (CTS) rapid transit spur to Severance Center. The plan failed, but a half century later, following lengthy public debate, the "Top of the Hill" project got underway in 2021.