Neighborhood Guide - South Boston: Boston, MA

Neighborhood Guide - South Boston: Boston, MA
Getting to know the South Boston – From talking about the different areas that make up the South Boston and what they have to offer from restaurants to schools to parks.


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With its rich history and strong sense of community, South Boston is an evolving, vibrant neighborhood located in Boston, MA.

From the Departed to Good Will Hunting, South Boston (colloquially known as ‘Southie’) has been the setting of many well-known movies over the years. However, you’ll find that South Boston is quite different from the neighborhoods these movies have often portrayed.

This traditional community is one of the city's most storied and historically rich areas, but don’t make the mistake of thinking it’s stuck in the past! Over the past few years, South Boston has been changing and reinventing itself. The community has seen new life with the opening of new restaurants, hotels and markets all over, as well as new housing developments, from stunning condos to the refurbishment of many of the original Victorian-era style buildings.

Neighborhoods here are filled with life and character. And, with the influx of working professionals and families streaming into the area, it’s no secret that South Boston has become one of the city’s most sought-after areas.

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History of South Boston

Previously fertile farmland, the first formal settlement in South Boston dates back more than 350 years, with the Anglo-Saxon Protestant Puritans’ arrival in 1635. This piece of the neighborhood's history is quite ironic since South Boston would later become famous as a haven for Irish Catholic immigrants in the following centuries.

After being annexed in 1804, South Boston became a center of rapidly growing industrial development. As factories producing everything from glassworks to chemicals became the economic focus of the area, many immigrant workers, and their families, made their way to South Boston.

By the 1820s, Irish immigrants made up most of the area’s population. And following Ireland's infamous potato famine in the 1840’s and Bostons ‘Great Fire’ in 1872, the number of Irish settlers in ‘Southie’ rose even more!

Despite being dominantly populated by the Irish for the majority of the nineteenth and twentieth centuries, a substantial number of Canadians and Germans were also attracted to the neighborhoods of South Boston both before and after the Civil War. From the twentieth century onwards, an infusion of new European immigrants began arriving, including groups of Polish, Lithuanian, Italians, and even Russian Jews. By the end of WW1, the population of South Boston was numbered at roughly 70 000- which is more than double what it is today!

This infusion of people and culture has led South Boston to be the vibrant community it is today - still attracting people from all over the world to call it home.

South Boston Today

Since undergoing its revival, South Boston is a very different place from what it was in the past. Today ‘Southie’ is one of the most interesting, vibrant, and friendly places to live in the city. Plus, with its convenient location and easy access to public transportation, a trip to downtown Boston will take you less than fifteen minutes! Other popular commute destinations are equally quick to get to:

  • South Station 15m by train, 5m by car
  • North Station 30m by train, 12m by car
  • Boston Commons 18m by train, 10m by car
  • Harvard Square 18m by train, 10m by car

Many are also attracted to the area by its miles of beaches, lovely parks, and of course, the waterfront- so it’s no wonder why South Boston is one of the top listed neighborhoods of Boston.

Residential Areas in South Boston

Considering moving to South Boston? There are many smaller communities that make up the greater community. When first evaluating South Boston, people generally start with the East Side, West Side, or the Seaport District. These areas of South Boston are all very different and provide a person that is buying a home in South Boston with different types of value.

The Seaport District has been home to a lot of development in the last couple of years. You would not recognize it today if it has been 5 years since you were last there. The Seaport District today gives you a much greater “city feel” with tall 20+ story buildings that are home to some of Boston’s biggest companies as well as some of the most premier condos the city has to offer. It is important to note that much of the building in the Seaport District of Boston has been for Office Spaces as well as luxury rentals.

When people generally refer to the “East Side” or “West Side” of South Boston, they are generally referring to the areas that go along the intersection of where East and West Broadway meet. The East Side is considered the Eastern side of this point with the West Side being the Western side of this point… With some gray areas mixed in!

Both Sides have different feels and personalities. The East Side of South Boston is home to more of the traditional Single Family Victorians or the two or three family homes that have been condo converted. That is not to say that you can’t find some bigger developments on the East Side, however, they are more the exception instead of the rule.

In contrast, the West Side has seen larger developments over the last couple of years. And, this is because historically the larger tracts of land that housed manufacturing and industrial businesses were here. They are now being developed into high-end condo buildings. But don’t worry, you will also still find quite a few of the Triple deckers that have been condo converted over the years.

South Boston Neighborhoods

There are quite a few neighborhoods within the neighborhood of South Boston. These neighborhoods include Fort Point, City Point, Telegraph Hill, Andrew Square, and the Seaport District.

Andrew Square was originally named Washington Village (Fun fact on how they got the name for the new HUGE development in this neighborhood). It was named to honor the 25th Governor of Massachusetts, John Albion Andrew. The Red Line T Stop, Andrew Square is located in the neighborhood which spans from the Columbus Avenue line where South Boston and Dorchester meet up Old Colony and along Dorchester. It jets out to about Gates Street and Dorchester Street. It is home to some of the biggest development in not only the neighborhood but also the city. Washington Village is a 5 acre, 1 million square foot project that will include 656 residential units. The development will consist of 8 buildings ranging from 6 to 22 stories in height. The project will also include 45,000 square feet of outdoor space. 

City Point is on the east...east side of South Boston! It spans from L Street over to Farragut Road covering all in between. It also spans E 1st through E 3rd Street going down to Dorchester Street. People looking to buy a South Boston condo often look to City Point because of the close proximity to the best beaches in Boston and Castle Island. The mix of living options in City Point consists of more traditional triple deckers that have been condo converted with some new development mixed in.

Telegraph Hill is a neighborhood that consists roughly from Gates Street to L Street and from E Broadway down to Columbia Road. Telegraph Hill is home to Dorchester Heights Park as well as L Street Beach. Telegraph Hill’s section of East Broadway is more commercial with some restaurants and local storefronts. It is also home to one of South Boston's most desirable streets, K Street.

Seaport District is one of Boston’s fastest-growing neighborhoods. The Seaport has grown at a breakneck speed being nearly transformed in the last decade. A fun fact is that Robert Kraft actually tried to build the Patriots Stadium here in what seems like a lifetime ago! Today the Seaport District is home to some of the most expensive real estate in the entire city as well as some of the most premier companies in the state… and World! The Seaport District is also home to some of Boston’s best restaurants and most vibrant nightlife.

Fort Point neighborhood boundaries are not exactly defined but includes the land a few blocks on either side of the Fort Point Channel. It is tucked in between the Seaport District, South Boston, and the Fort Point Channel. Do you remember 344 Washington Street in the movie “The Departed”? That was in Fort Point! Here you will find a mixture of housing and commercial space with big plans of development that will further enhance the area for residents and visitors alike.

Click Here to see all available South Boston Condos For Sale

Finding your dream home

When it comes to South Boston Real Estate, there is a lot to take in. South Boston has it all for all different types of homebuyers. From first-time homebuyers to people looking to downsize there is an option for everyone. Its proximity to downtown as well as the highways make it a great place for people to live.

There are plenty of things to do and love about each of these micro-communities, but finding the perfect one for you depends on your personal needs and style preferences.

Houses for sale in South Boston MA offer something for every need and lifestyle. From family homes and townhouses to apartments and lavish condos, plus its ‘mix-and-match’ of traditional and modern architecture styles, there is plenty to choose from.

Future Developments

Development in South Boston has been in full swing for a number of years. The blocked-off sidewalks and sound of the swinging hammer is pretty much been a constant in South Boston for the last decade.

One of the biggest projects to adorn South Boston is Washington Village which is a 5-acre site that will consist of a million square feet of mixed-use space. The development will consist of 8 buildings ranging from 6 to 22 stories in height with 45,000 square feet of outdoor space. The mixed-use community will consist of 656 residential units with 110 of the units being affordable housing. The area is expected to also house a grocery store, restaurants, and cafes as well as a pharmacy.

The Edison Power Plant in South Boston has officially been given the stamp of re-development approval by the Boston Planning & Development Agency. This large-scale redevelopment will be consisted of new building construction as well as renovating four historic turbine halls.

The 15.2 acre development will consist of 760,000 square feet of Commercial and R&D space, 80,000 square feet of retail space, 240 hotel rooms, and 636 housing units. 5.7 acres of the 15.2 acre development will be designated public open space with the largest chunk being a 2.5 acre waterfront park while other green spaces will include a basketball court and at least one other recreational area. This will be the single biggest development project in South Boston’s history.

Plans were also announced to make the area a frontier for new-age industries - an ‘innovation district’. This has led to the establishment of many companies and in turn, the creation of thousands of jobs- another reason why more people are moving into the area.

Then there is the Seaport District which is constantly and rapidly changing. WSDevelopment is in charge of unlocking this 33 acre, 7.6 million square feet of space development. Today (so far), the Seaport District is home to 350 companies that span from global leaders to startups.

Fort Point Development Plan is still in its beginning stages but would transform another section of Boston. As proposed, it is 88.7 acres currently occupied by office space and parking lots. The vision is to turn this space into a blend of public space and new private developments. The public open space would include two large parks, pocket parks, a promenade, and even an amphitheater.

South Boston Restaurants

South Boston is home to some of the city's finest restaurants and cafes. These are our top 3 restaurants to start off your culinary adventure in Southie.


Jeffrey Chubb & The Chubb Homes Team is one of the top agents in South Boston. Contact our team today for professional service, trusted advice, and the best open houses South Boston MA has to offer. We’re ready to show you exclusive real estate in one of our favorite places - South Boston MA.

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