So You Want to Live in Charlestown, Massachusetts?

Looking for a small-town feel in the city? This waterfront enclave in Boston might be for you.

Photo via Getty Images

1. Pick Your Price Point

With its cobblestone ways and gas-lamp-lit streets, Charlestown oozes Colonial charm. Appealing 18th- and 19th-century clapboards and brick row houses make up much of the housing stock, while full-amenity condo buildings are clustered around the waterfront. Charlestown’s median condo sale price last year was $842,000, with single-families going for much higher. Homes don’t stay on the market long, so if you see a place listed for $700,000 or below—and there are some two-bedrooms in that range—act fast.

See all »

2. Plot Your Commute

Traffic to and from Charlestown right now is bad. Here’s why: The North Washington Street Bridge that spans the Charles River and connects Charlestown with the North End has been under construction since 2018, forcing traffic to be confined to a narrow temporary bridge. Delays have pushed out the completion of the new bridge to early 2025. Until then, commuters should consider riding the Orange Line from Sullivan Square during peak times.

Photo via Getty Images

3. Take in the Vibe

While Charlestown has evolved considerably from its Irish working-class roots—remember Ben Affleck’s 2010 movie The Town ?—it remains a close-knit community. Unlike some other parts of the city, you’ll know your neighbors here. There’s a Whole Foods and a Starbucks, along with a slew of stellar independent eateries—dig in to brunch at Waverly Kitchen & Bar.

Photo via Getty Images

4. Check out the Culture

Incorporated in 1639, history abounds in Charlestown. The famed Battle of Bunker Hill took place here during the American Revolution in 1775; Paul Revere began his famous ride to Lexington from the neighborhood, too. In fact, one of Revere’s favorite watering holes was the circa-1780 Warren Tavern, which is still a beloved local establishment.

5. Scope out the Schools

Most young kids attend one of Charlestown’s two local elementary schools, Warren-Prescott and Harvard-Kent. Others enroll at the Eliot in the North End, a Boston Public Innovation School with an enhanced curriculum that focuses not just on academics but also on students’ physical, social, and emotional needs. The nearly 800-student Charlestown High School, meanwhile, gets mixed reviews, spurring some parents to go private.

Photo via Getty Images

First published in the print edition of the December 2023/January 2024 issue with the headline, “So You Want to Live In…Charlestown.”