The shopping center contains 640,090 sq ft (59,466 m2) of fashion retailers, restaurants, and entertainment options.

[1] The architecture and design of the new shopping center mimics modern village-like streetscapes and overlooks neighboring Hammond Pond.

In 1950, a development team from C&R Management, headed by Daniel Rothenberg and Julien Cohen, built a shopping center in Chestnut Hill, six miles (9.7 km) from Boston.

Chestnut Hill Shopping Center began with a variety of shops, such as Filene's, Franklin Simon & Co., and London Harness Company, adjacent to a Star Market at the intersection of Route 9 and Hammond Street.

On July 27,[year needed] R.H. Stearns and S.S. Pierce opened in a separate building.