In the years just before and after the turn of the century, a number of subdivisions were created on the periphery of Madison, enabled by the expansion of the street car line. One of these was the Highland Park subdivision, which opened in May 1906. It lay a few blocks outside the Madison city limits just west of University Heights, bounded on the south by University Avenue, on the north by a park and pleasure drive (now Regent Street), on the east by Highland Avenue, and on the west by Farley Avenue. Originally the 42-acre Scheler farm, it was carved into 252 lots. The lots cost between $300 and $350, though the price was scheduled to increase by $50 on July 1.
The main thoroughfare was Grand Avenue, running north and south halfway between Highland and Farley. The cross streets (from south to north) were Park Place, Mason, Harper (now Van Hise), Vroman (now Chamberlain), McKinley (now Kendall), and Stevens.
The company that created the subdivision was led by C. A. Harper, president; Vroman Mason, secretary; and August Paunack, treasurer. Other major investors included J. M. Boyd, M. S. Rowley, future Wisconsin Supreme Court justice Burr Jones, UW professor Richard T. Ely, Judge E. Ray Stevens, Charles Hudson, Leslie Rowley, George Westerfield, and Frank Curren.
The subdivision was convenient, accessible via the street car line that terminated by the Forest Hill Cemetery gate at its southeast corner. Eventually, that corner was occupied by the Rentschler greenhouse (where the West athletic fields are today). A small commercial district arose on University Avenue just west of Highland Avenue, which also remains.