Columbus & Over Group

Pill Hill, also known as “High Street Hill,” is a neighborhood nicknamed for the large numbers of doctors who moved to this area of Brookline –  and it’s no surprise they chose to live here as it’s close to Brookline Village, which gives the Historic District a walkable commercial center, and Longwood where they work. 

The local homeowners association works hard to maintain the area’s 19th-century charm. Many residences feature intricate woodwork, large porches, and beautifully maintained gardens.