Boston, Massachusetts

Wicked Pissah

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Some of the towns and cities—including Waltham, Sudbury, Winchester, and Stoneham—are downright pastoral, with widely spaced single-family homes amid lush yards and down long driveways. Some—including Boston proper Quincy, Medford, and Cambridge—are mostly densely urban and come with all the bustle you would expect to find in a big city.

Downtown Boston is expensive, but so are those farther-flung pastoral areas, where single-family houses with yards can quickly run into the seven figures each.

If you’re used to sizable yards and lots of elbow room, you should probably forget it. There will be crowds and unless you move to the region’s farther reaches, you will hear your neighbors from time to time.

Picking a neighborhood you like is supremely important. They are often distinct in terms of retail, parkland, and transit options and as such, the neighborhood you pick will become a neighborhood you spend a lot of time in—as opposed to many cities, where one amorphously bleeds into another.


College Students

It is a bit ridiculous trying to narrow down Boston to a few neighborhoods for college kids. There are colleges everywhere so what’s the point to some degree. That said, there are a few that draw bigger volumes due to proximity to the biggest schools. Fenway/Kenmore has the greatest concentration due to Boston University, Emmanuel College, Simmons, Wentworth, Mass College of Art, and Harvard Medical School all in the area.

Allston/Brighton is another big option. It is home to Harvard Business School and part of Boston College is here. It’s also just a short train ride to Boston U. Both of these areas are filled with cheap (for Boston) apartments, plenty of bars and restaurants and some of the best public transportation in the country.

  • Fenway/Kenmore
  • Allston/Brighton

Back Bay

Young Professionals

The Fenway/Kenmore area remains popular with young professionals when they graduate due to tons of housing options, and the bounty of restaurants, cheap (and nice) bars and tons of shopping. Right next door and nicer and more expensive is Back Bay. Those making the big bucks can afford to live here and even those who save a few living farther up Comm Ave still come here to hobnob and socialize. In more recent years South Boston, or “Southie” as Mark Wahlberg likes to call it, has become hot due to continued gentrification of the surrounding communities.

  • Fenway/Kenmore
  • Back Bay
  • Allston
  • South Boston



One of the common behaviors in Boston is to move between neighborhoods every year or two as your station and patience for city life waxes and wanes. Young professionals will shift from Allston/Brighton to Back Bay or South End or Brookline when they want to remain in the city but get a bit more refined lifestyle.

  • Back Bay
  • South End
  • Brookline

Jamaica Plain


Jamaica Plain is a diverse neighborhood that attracts the LGBTQ+ community in general and queer/trans people of color in particular. Centre Street is the “center” of the commercial district for the community with plenty of queer-friendly restaurants and shops lining the streets.

  • Jamaica Plain
  • South End
  • Dorchester

West Roxbury


As with most cities a lot of families hit the ‘burbs when the kids come and they feel the need for room and great public schools. Boston has some strongholds though for families that want to hold onto city life and seek neighborhoods with some of the benefits of suburbs. West Roxbury and Roxbury are two of these neighborhoods with West Roxbury historically being the Irish and white side of the dividing line, and Roxbury the predominantly black family community. Gentrification and demographic shifts have changed things some but these remain heavily family neighborhoods. Beacon Hill is the fanciest of Boston neighborhoods and families who crave a blue blood lifestyle with a short walk downtown set up shop here.

  • West Roxbury
  • Roxbury
  • Beacon Hill
  • Charlestown
  • East Boston