Chester Square

South End


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.


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 Area managed one sale in 2021. 561 Massachusetts Avenue, #1 sold for $2,900,000 and clocked a price per square foot of $753.25. This is up from zero sales in both 2019 and 2020. Let us be the ones to tell you the triplex home that sold at 561 Mass Ave was one of the most impressive brownstone condo units that we’ve seen! The scale and layout of this unit would have easily commanded a price into the mid $3M’s or even $4M had it been in the Pilot Block or Golden Triangle. Alas, to the point above, homes like this simply do not exist in those sub-neighborhoods but they can be found within the bounds of Chester Square.


Sadly, the saga that is the redevelopment of the Hotel Alexandra at the corner of Mass Ave and Washington Street continued through 2021. This signature property has, devastatingly, languished as a so called “vacant” since at least the early 1970’s. Its majestic architecture has slowly but surely deteriorated into a neighborhood eyesore that is begging for new life. While plans had come together back in 2020 to reposition the property to a boutique hotel, the capital markets were not conducive to making actual progress. Alas, we’re back where we started with this vibrant gateway to the sub-neighborhood waiting for its knight in shining armor.

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For more sales data and details on it’s sub-neighborhoods check out our Boston Luxury Real Estate Review >