Your boutique residential real estate consultancy and brokerage specializing in Boston’s most highly sought addresses.
NEIGHBORHOODS
Chester Square
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.
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No Exclusive listings in this area are available.
$2M+ LUXURY MARKET DATA
Only one sale occurred this year over $2M: a restored, oversized parlor-level duplex at 531 Massachusetts Avenue, Unit 1, which sold for $2,200,000 after 106 days on the market, down from an asking price of $2,350,000. The three-bedroom, one-and-a-half-bath residence featured direct-access parking, private outdoor space, and open views overlooking Chester Square Park, all within close proximity to Symphony Hall and the South End’s renowned dining scene.By comparison, 2024 also recorded just one sale in the sub-neighborhood—a grand Victorian at 542 Massachusetts Avenue that closed for $2,580,000—while 2023 saw no sales above $2 million, reinforcing the scarcity and exclusivity of transactions in this pocket of the South End.
$2,200,000
TOTAL SALES VOLUME
$886
AVG. PRICE PER SQ. FOOT
1
NUMBER OF $2M+ PROPERTIES SOLD
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