Chester Square

South End

Overview

Not all brownstone properties were created equal and it just so happens that the brownstones that were built around the Chester Square area of the South End were grander than many of the others in the area. Generally, we expect South End brownstones to average 19’ of width and 40’ of depth. This “standard” floor plate affords around 700 SF of livable area on each floor after removing space for common halls and stairs. Well, for those who call Chester Square home, they are fortunate to have more like 24’ of width and 50’ of depth in their homes. The floor plates on Chester Square are routinely north of 1,000 SF and provide residents an extra large canvas to create their perfect home. Having said that, it’s no secret that there is a pricing discount for living on or near Massachusetts Avenue where “Methadone Mile” continues to be a blight on the community.

Location

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.

$2M+ Luxury Market Data

In contrast to last year’s lack of sales above $2M in Chester Square, 2024 brought about one sale for $2,580,000 – 99.42% of ask achieved! Totaling 0.79% of the South End’s total sales volume above $2M, Chester Square made it onto the list in 2024. 

We believe when real estate consumers are presented with a complete and robust spread of data, in conjunction with their personal preferences, decisions can be reached with the most confidence.

To learn more about changing market dynamics moving into 2025 check out our Perspective on the Boston Luxury Housing Market>