Chester Square

South End


Chester Square’s brownstones may seem more stately than other buildings around the South End at first glance. But, this is mostly due to perspective. Massachusetts Avenue’s four lanes across plus two symmetrical parks (squares)offset the Chester Square brownstones from the busy street, giving onlookers the sense that these buildings are larger than their counterparts on the smaller side streets within the neighborhood. . What Mass Ave gives up in charm, it makes up for in name recognition. Northeastern University and other major institutions like the Boston Symphony Orchestra and Christian Science Church headquarters make up the landscape.


Chester Square sits tucked around one of the southernmost sections of Massachusetts Avenue, with Chester Park marking its center. The neighborhood includes parts of Tremont, West Springfield, Northampton, Shawmut, Comet, and Washington—and the square’s residents walk just fifteen minutes to reach the Prudential Center or less than 5 minutes to get on the MBTA Orange Line at Mass Ave Station.


Chester Square sees just four sales every year that are over $1M. Homes that are new to the market wait for 25 days, on average, before an offer is made. The typical square footage value in Chester Square tops off at just around $900.


Chester Square’s residents take advantage of myriad parks and accessibility with regards to the Museum of Fine Arts, Northeastern University, Fenway Park, and more. Inhabitants of this distinctive square enjoy pastries and coffee at Flour, Caribbean and Venezuelan cuisine at Orinoco, and tapas at Toro – all just a few blocks south. Ramsay Park offers a sprawling respite from city life, and Boston University’s Medical Center is within easy reach.

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