While many of Pittsburgh’s hillsides and valleys were becoming developed in the late 1800s, Squirrel Hill remained lush and rural as the city grew up around it. Because electric trolleys connected Squirrel Hill to the rest of the city, the verdant tracts of land were attractive to the millionaires of Pittsburgh’s industrial age. In 1914, the Sterrett family, who at the time owned a large swath of land in the community, built one such impressive manse at 5558 Aylesboro Ave. in Squirrel Hill North. The powerful local family included Pennsylvania Supreme Court Justice James Patterson Sterrett; Pittsburgh Sterrett 6-8, a neighborhood school and partial Classical Academy Magnet school in Point Breeze, still bears his name. They focused their search on Squirrel Hill because of its proximity to Downtown and walkability to restaurants, schools and Schenley Park.