Then and Now: Chester Square
When engineers for the City of Boston laid out plans for the newly-created Back Bay and South End, they drew inspiration from Europe: long Parisian boulevards and narrow parks dominate Back Bay, while narrow streets and London-style neighborhood parks dominate South End. In 1852, Ezra Lincoln designed Chester Square, a park to lure the wealthy from Beacon Hill to the South End.
According to the Chester Square Area Neighborhood Association:
[T]he park was landscaped lavishly by the city while developers and property owners began building the seventy townhouses that surround the park. The handsome houses are a combination of flat fronted central buildings and stepped forward, bow fronted buildings at the curved ends and “are more grant and opulent in style and influence” than any other South End houses.
The plan worked for a while, but by 1950, the South End had fallen into sad shape:
Within a few decades, the handsome houses of the South End became successively homes for small artisans, rooming houses and the residential entry point for waves of immigrants. Many fell into disrepair and were boarded up and abandoned. In the 1950’s, in the worst excesses of urban renewal, whole square blocks of the South End and Lower Roxbury were torn down as slums. Although none of the buildings that constitute the architectural framework of Chester Square were razed, in 1952 when the Southeast Expressway was completed, funneling thousands of cars into Boston from the South every day, the city took the center of Chester Park for four lanes of traffic. On its 100th birthday, the center of the historic residential square became a flowing river of traffic.
Have you ever seen the narrow fenced-in lawn on both sides of Mass Ave between Tremont Street and Shawmut Avenue? That’s all that remains of Chester Square: two narrow strips of sod.
Want to see homes near the square? I listed the following apartments in Boston instead of their respective neighborhoods because nobody can tell me whether they’re in Roxbury or the South End. I’m reasonably confident it’s the South End, but I’m afraid to make that my final answer.
570 Mass Ave, #1
Boston,02118
Beds: 2/Baths: 2
SQ.FT.: 1182
$479,900
582 Mass Ave, #2
Boston, 02118
Beds: 2/Baths: 1
SQ.FT.: 1010
$585,000
520 Mass Ave, #3
Boston, 02118
Beds: 2/Baths: 2
SQ.FT.: 1106
$579,000
And this one is directly on Chester Square:
534 Mass Ave, #2
Boston, 02118
Beds: 1/ Baths: 1
SQ.FT.: 740
$430,000
Top Five: The Most Expensive Homes in the South End
