You haven’t seen neighborhood pride until you have been to South Boston or Charlestown. Residents of these two corners of Boston love where they live, and with good reason. It’s easy to be loyal to waterfront neighborhoods so walkable, historic, and durable - both only minutes from downtown Boston.
Despite both being so close to town, life in one of these neighborhoods is very different from the other. Both have strong real estate markets and a high quality of life, but they suit contrasting lifestyles. So where should you live — Southie or Charlestown?
South Boston, aka “Southie”
Fans of the movie Good Will Hunting will remember Southie as a scrappy working-class Irish-American enclave. A lot has changed - an influx of young professionals and luxury development have made this area just south of the Seaport District one of the most desirable neighborhoods in Boston. But that Southie pride and local culture remains undiminished.
Southie is a dense, highly-walkable neighborhood with a strong restaurant, nightlife, fitness, and coffeeshop culture. Errands and amenities can easily be accessed on foot, as can gathering points like the Boston Convention & Exhibition Center, Thomas Park, and the Leader Bank Pavilion. The Dorchester Heights Monument overlooking South Boston Harbor commemorates the evacuation of Boston during the Revolutionary War.
Best of all, Southie is a “beach town,” the home of Carson Beach and Pleasure Bay. You don’t always think of Boston as a hotbed of beach bum lifestyle, but in the summer months, Southie residents use the privilege of their geography to tan and frolic in the sand and water.
Young professionals in medicine, tech, and finance love Southie for its street-level energy, access to Carson Beach, and humming social energy.
Charlestown
1628. That’s when Charlestown was settled, making it the oldest settled area in Boston Proper. As such, Charlestown drips with “Old Boston” history at every corner. Quieter than Southie, it’s like a small colonial village only minutes from downtown Boston.
Charlestown is still walkable, but it’s more calm, with commercial activity clustered around Main Street, City Square, and Thompson Square. Neighbors become fast friends here in a family-friendly ambiance defined less by nightlife or coffee shops, and more by deep community roots.
Charlestown is paradise for Revolutionary War buffs. The Battle of Bunker Hill took place here, commemorated by the Bunker Hill Monument and Bunker Hill Museum. Paul Revere Park, the Charlestown Navy Yard, and the 18th-Century warship USS Constitution can also be found in Charlestown. The presence of the Spaulding Rehabilitation Hospital also makes the neighborhood a popular home for medical professionals.
Bottom Line
History, waterfront walkability, and proximity to Boston … both Southie and Charlestown have it. But Southy is better suited for young professionals who love urban density and street-level excitement. Charlestown shines in its residential tranquility, small-town pace, and second-to-none historical pedigree. Whichever fits your vibe, it’s yours for the taking only six minutes from downtown.
FAQ
Q: What kind of homes will I find in South Boston and Charlestown?
A: The meat of the Southie housing stock is converted triple-deckers and historic rowhomes, but luxury waterfront midrises and highrises have asserted their presence in the housing inventory.
In Charlestown you will find a mix of Federal-style townhomes, historic brick rowhomes, Navy Yard condos, and luxury condo conversions, with a limited supply of historic single-family homes ruling the roost.
Q: What are the home prices like in Southie and Charlestown?
A: The median home price in South Boston currently sits just below $1.1 million. The median home price in Charlestown currently sits just above $1.1 million.
Median prices change with market conditions. Reach out to us for the most current prices.
Q: What is the commute like from Southie or Charleston to downtown?
A: Both Southie and Charleston are well-connected to downtown by the T — the Red Line for Southie, the Orange Line for Charleston. Both have easy access to I-93 for six-minute car commutes downtown.
Q: Do I need a car to live in Southie or Charlestown?
A: No, you don’t need a car to live in either Southie or Charlestown. Both enjoy easy, reliable local and regional public transit service.