South Boston

Welcome to South Boston

Home to Dorchester Heights and the iconic St. Patrick’s Day Parade, this energetic, urban town has fascinating ties to the Revolutionary War and a rich Irish heritage.


Colloquially known as "Southie" by locals, South Boston is a lively, energetic, waterfront town with a historical legacy. This urban neighborhood nurtures a strong sense of history and tradition that resonates with its predominantly working-class community. Revolutionary War monument, Dorchester Heights, is located here and offers striking views of the downtown skyline and Boston Harbor.


Old-school diners, gastropubs, and cozy pizzerias dot the region, paying homage to the area's robust Irish Catholic heritage. South Boston's vibrant Seaport neighborhood –– with its scenic waterfront, technological innovation, and Fort Point district –– has helped the city develop into a hub for millennial professionals.


What to Love

  • Great range of restaurants
  • Seaport District
  • Dorchester Heights
  • Famous St. Patrick’s Day Parade
  • Strong sense of history and tradition
  • Located on the water

People & Lifestyle

Southie is a classic Boston city with an expansive waterfront and easy downtown commute. From its gritty roots comes an old-school Boston town with lots of heart and a rich history that culminates in the yearly St. Patrick's Day Parade. Southie also boasts more beaches than any other Boston neighborhood and a delightful mixture of traditional homes and new construction. 


On the East Side, you'll find more conventional options, including triple-decker homes divided up into apartments and historic single-family homes. New construction has overtaken the West Side for those who prefer living somewhere with more modern amenities like parking garages and elevators. The easy commute and bounty of natural wonders from beaches to extensive trails make South Boston an excellent place for young millennials and nature lovers alike.


Dining, Entertainment & Shopping

South Boston is full of great restaurants; whether you want to visit a classic pizzeria, a cozy Italian joint, or a tavern, you're sure to find a place suitable to your tastes in the area. Loco is a funky, unique neighborhood watering hole serving tacos and oysters because, why not? Mixing Baja-style Mexican cuisine with creative seafood dishes, Loco is unlike any other eatery. Here you'll find new-wave taco choices and eye-popping choices like root beer-braised chicken and blackened swordfish.


From the same people who brought you Loco comes the classic American tavern Lincoln. Offering reasonably-priced creative pub grub, Lincoln is a traditional saloon with a warm, mahogany interior that feels straight out of the 1940s.


Sometimes all you want is a steaming plate of pasta as big as your face. Luckily for South Boston residents, they have two fantastic Italian eateries to choose from at the Enoteca restaurant Fox and the Knife and Capo.


Fox and the Knife is an award-winning restaurant known for taking risks with its creative Italian dishes. You'll want to try their fried chili chickpeas. Capo boasts delicious pasta, pizza, and more comfort food options within 19th-century inspired rooms. On the lower level, you'll find the glamorous, speakeasy-like supper club.


Things to Do

Castle Island and Dorchester Heights are two of South Boston's most significant attractions. Don't let the name confuse you; Castle Island isn't an island anymore. It's a peninsula on the Boston Harbor with a 22-acre recreation site. Open year-round, Castle Island is also the home of Fort Independence. Anchoring Pleasure Bay Beach, visitors are welcome to swim along the beach, visit the playground, or even take a tour of the fort.


Pleasure Beach, Carson Beach, and M Street Beach form a three-mile segment of parkland along the Dorchester Bay shoreline. Apart from Castle Island, M Street Beach is probably the most popular South Boston beach. Locals affectionately call it "Southie Beach" in homage to South Beach, Miami.


Dorchester Heights is the historic Revolutionary War site where George Washington's army evacuated British forces from Boston. Today the monument is part of the Boston National Historic Park and offers commanding views of the Boston skyline and harbor. It's also the best place in town to watch the fireworks on the Fourth of July.


And speaking of holidays, there is no bigger annual event than the South Boston St. Patrick's Day Parade. This iconic celebration unites thousands of people every year to celebrate the holiday. Boston residents were actually the first to celebrate St. Patty's Day in the country, and the parade is an epic celebration of the iconic Irish saint and Evacuation Day.


Work With Us

Charles King Group has been helping local buyers and sellers just like yourself, locate the finest properties and negotiate the best deals. The team takes great pride in knowing the latest market conditions, government regulations, and upcoming developments — so that you don't have to.