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Homes for Sale in South Boston, MA

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Living in South Boston (colloquially Southie), is an experience unlike any other. In contrast with the historically gritty portrayal of the neighborhood – notably in films like Martin Scorsese’s The Departed – modern South Boston is a contemporary metropolis, comfortably standing toe-to-toe with any neighborhood in the nation. With roots as old as America itself, South Boston’s persistently rugged personality, upscale sophistication, and passionate sense of community combine to make a potent cocktail with a unique flavor all its own.

About South Boston, MA

Homes for Sale in South Boston, MA

Living in South Boston (colloquially Southie), is an experience unlike any other. In contrast with the historically gritty portrayal of the neighborhood – notably in films like Martin Scorsese’s The Departed – modern South Boston is a contemporary metropolis, comfortably standing toe-to-toe with any neighborhood in the nation. With roots as old as America itself, South Boston’s persistently rugged personality, upscale sophistication, and passionate sense of community combine to make a potent cocktail with a unique flavor all its own.

While it has weathered storms in the past, the two words that best define modern South Boston are “explosive growth.” No longer a best-kept secret, this hidden gem of the east coast shines brightly for all to see. In South Boston, posh cafes, vegan restaurants, and locally owned coffee houses sit shoulder to shoulder with old-school pubs, vintage shops, and historical sites. Over the past few years, South Boston’s real estate market has come into full bloom. From immaculately restored Victorians to transforming reclaimed warehouse space into stylish lofts, the homes for sale in South Boston, MA seamlessly blend timeless sophistication with the amenities and comforts that define modern living.

As South Boston moves from hidden gem to crown jewel, an influx of new construction rises to keep pace with the neighborhood’s historic buildings. Overall, it is a great time to look at homes for sale in South Boston, MA.

An Overview of South Boston

Boston is a city that sparks intense local pride in its residents, but the reality of establishing a permanent residence in Boston and the greater Boston area is often difficult at best. South Boston presents a plugged-in, connected option, making it incredibly attractive for anyone looking to set down roots in the area. With quick access to major highways, downtown Boston, the airport, and the Atlantic Ocean, homes for sale in South Boston, MA offer a bit of something for everyone. There has never been a better time to move in.

Points of Interest in South Boston

From bars and restaurants to museums, parks, and waterfront, South Boston has no shortage of interesting destinations to explore.

Children’s Wharf

Formerly known as Museum Wharf, this district owes its name to the Boston Children’s Museum

which is on its shore. Well over a century old, the museum got its start in 1909, when a collection of Boston’s science teachers came together to improve the surrounding area. This group, appropriately titled the Science Teacher’s Bureau, immediately started planning a museum to enrich the minds of young Bostonians. Planning for four years alongside the Women’s Education Association, they opened the Children’s Museum’s doors on August 1 , 1913, making it the second oldest museum of its kind in the nation.

Originally located in Jamaica Plain, the Boston Children’s Museum moved to a former wool storage warehouse – along the Fort Point channel in 1979. Notable exhibits include the Japanese House – a genuine two-story townhome, sent to Boston from its sister city Kyoto in Japan, a three-story climbing structure, and the Science Playground, where visitors can learn about the world through various activities.

Nearby on the wharf, you will find the Boston Tea Party Ship, where you can take a guided tour with colonial reenactors, toss tea into the harbor, and hear period correct music as you learn about Boston’s history.

South Boston Candlepin

Also known as, Southie Bowl, this traditional candlepin bowling alley is a South Boston community institution for sixty years and counting. Family run for the past two decades, Candlepin is a genuine throwback and a bona fide Southie tradition, which is perfect for anyone looking to while away an afternoon with some uniquely retro fun.

Trillium Brewing Company

Head by South Boston’s Trillium Brewing Company at 369 Congress Street, and you are likely to see a line that stretches out the door, thus illustrating the popularity of this local microbrewery. Founded by Esther & JD Tetreault a self-described “young dumb couple in love,” Trillium is a haven for beer geeks and a way to foster community with like-minded souls. That community has an increasingly wide reach: the 2018 Rate Beer rankings list them as the third best brewery, not just in the USA, but the entire world.

GrandTen Distilling

If your taste in beverages runs towards cocktails, GrandTen bar and distillery is another South Boston spot that deserves your attention. Creative cocktails, inventive mixologists, top-shelf spirits, and the authentic atmosphere can only come from spirits distilled on-site. Swing by the tasting room and sample their single run, small batch artisanal spirits that are all lovingly crafted on site in Southie.

Districts with Homes for Sale in South Boston, MA

Technically, South Boston is a neighborhood of Boston proper. That has not stopped it from developing its own distinct, city-sized personality. South Boston has its own distinct feel, with plenty of variety within its borders. Boston proudly blends the traditional and the modern, the historic and avant-garde.

South Boston’s different districts embody Beantown’s unique fusion of these elements. Seemingly contradictory elements come together to create these neighborhoods-within-a-neighborhood, resulting in one of Boston’s most intriguing locations.

Andrew Square / Columbus Park

Situated around Andrew Station, homes in this district have quick, convenient access to the Red Line, as well as a number of buses. Joe Moakley Park and Carson Beach are just down the street, as is the excellent GrandTen Distilling, which is a must-see for fans of craft spirits.

Contrasted with other homes for sale in South Boston, MA, properties in Andrew Square are more affordable, making them attainable to more people and a range of budgets. Homeowners in this district enjoy all the benefits of living in a tight-knit South Boston community without paying the premium that some neighborhoods carry.

Andrew Square is also home to the South Boston Bark Park, a great place for dog walking or dog watching.

City Point

If you like bustling, vibrant neighborhoods, you are going to love City Point. With 28,000+ residents per square mile, City Point is in the top three percent (well, 3.1% anyway) of the most densely populated neighborhoods in America. Sophisticated and urbane, City Point is a quintessential South Boston neighborhood. Expertly renovated Victorian homes share the view with locally owned pizza shops. The old-school coziness of the L Street Tavern (featured prominently in Good Will Hunting) is a few short blocks away from a trio of upscale yacht clubs, Medal of Honor Park, Marine Park, and the aptly named Pleasure Beach.

Like the rest of South Boston’s East Side, City Point favors classic architecture over the West Side’s more modern offerings. Vintage Brownstones and Victorians dominate the landscape, though new construction occasionally brings something genuinely new to market. Given the desirability of the neighborhood, it is no surprise that some of South Boston’s most impressive real estate carries a City Point address.

D Street/West Broadway

Primarily known for apartments, this district frequently sees condominiums hitting the real estate market. Home to Coppersmith, a converted warehouse that combines a restaurant, rooftop bar, and public dining room serviced by an array of food trucks, the D Street/West Broadway area is a real hidden gem. Downtown Boston and the South Bay Shopping Center are easily accessible via the Red Line or by bus, and interstates 90 and 93 are just a stone’s throw away.

Anyone looking at homes for sale in South Boston, MA who is not thrilled with the cost and commitment of buying a house in the area would do well to look here.

Fort Point

Formerly an industrial district, Fort Point is emerging as a hip, trendy destination dotted with lofts, housing studios, and art galleries, as well as the Boston Children’s Museum and the Boston Tea Party Ships & Museum. The district also boasts an array of trendy new shops, bars, cafes, and restaurants, highlighted by Sportello, celebrity chef Barbara Lynch’s excellent trattoria-inspired Italian diner.

From smart homes in vintage brick & beam lofts, to the tall ceilings of condominiums in a refurbished factory space, many homes in Fort Point blend vintage authenticity with modern sensibility for excellent results. In addition, with residences ranging from studio apartment space all the way up to multi-million dollar penthouses, the impressive range of available homes speaks to the universal appeal of this emerging district.

Of course, some will counter that Fort Point is a neighborhood in its own right, separate from South Boston. While many longtime residents still consider it a part of South Boston, the distinction is ultimately academic. But wherever you stand on the topic, there’s no denying that Fort Point is one of, if not the biggest artist communities in the greater Boston metropolitan area Therefore, it is unquestionably one of its most attractive neighborhoods.

Telegraph Hill

Telegraph Hill has a rich history predating the founding of the nation. During the American Revolution, George Washington’s forces drove the British army out of Boston with cannons looming from this site. Known as Dorchester Heights at the time, the name Telegraph Hill would come into use around 1801. These hills dotted the Massachusetts landscape acting as a sort of mechanical internet and communicating information between ships.

This early system had advantages and disadvantages in equal measure. By the 1850s, Samuel Morse’s electric telegraph had risen to prominence, negating the need for vision-based semaphore communication from hilltop to hilltop. Today, Telegraph Hill is home to Thomas Park, where the Dorchester Heights Monument commemorates the liberation of Boston.
The northern edge of Telegraph Hill is overflowing with bars, restaurants, and coffee shops. Residents are rarely more than a five-minute jaunt from food and drink; Both public transit and bike infrastructure make it easy to get around.

Just as Telegraph Hill nestles between Andrew Square and City Point, so too do its housing options fit neatly between its two neighbors. While it has its share of breathtaking seven-figure homes, it also contains more affordable options, most of which blend the region’s historic charm effectively with modern amenities.

Population of South Boston

As of this writing, the most recent census data estimates that approximately 33,700 residents call South Boston home. With a population density of 11,511 people per square mile, things are a little less crowded when compared to Boston as a whole (13,894 people per square mile). That said, this is unquestionably a thriving urban center. Those seeking a quiet, spacious suburb might want to look elsewhere. However, those who enjoy the energy and community of an active urban center should feel right at home.

History of South Boston

The history of South Boston interweaves with the very fabric of the neighborhood. To write about South Boston without mentioning its historical roots would be like omitting the Atlantic Ocean in the description. Both loom large and influence every waking moment of life in South Boston.

From Humble Beginnings to Revolutionary Fire

The year was 1635. Reverend Richard Mather, accompanied by a hundred followers and dozens of cattle, arrived at Dorchester on the Mattapan peninsula, located just south of contemporary Boston. North across the water, a narrow peninsula housed a fresh water spring, shaded by a grove of weeping willows. Mather and company just had to see this place for themselves.
They first came ashore at what is now the bottom of K Street in South Boston, landing at the place called Mattapannock by the native population. Tragically, the native citizens were devastated by a plague just prior to the pilgrims’ arrival, but the community that replaced them provided the bedrock of American patriotism. From the Boston Massacre and Boston Tea Party, to the eventual evacuation of the British forces, the Mattapannock/South Boston area played a key role in the liberation, and foundation, of the United States.

Fast-forward almost a hundred years to 1804. The city of Boston annexed Mattapannock, also called Dorchester Neck, which was primarily pastoral grazing land. Famine overseas and fires in Boston forced large portions of the population seeking refuge to immigrate to South Boston. By coming together to overcome adversity, the early residents of South Boston set the tone of rugged determination that would come to define the region.

Saint Patrick’s Day

Most are aware that March 14 is a day of celebration in Boston, as the famous Saint Patrick’s Day Parade commemorates the city’s special relationship with the holiday. Starting from West Broadway and winding its way through South Boston down to Dorchester Avenue, the annual festivities never fail to delight attendees. t South Boston’s love for the holiday has deep, deep roots, tied with the very foundation of the city as well as the nation itself.

The Feast of Saint Patrick in Occupied Boston

The celebration of the Saint Patrick’s Day Parade is a time-honored Boston tradition dating back to 1724 when Massachusetts was still one of several British colonies. Though the celebrations predate the founding of America, Saint Patrick’s Day would play an integral role in securing Boston’s and the nation’s freedom.

As noted above, modern-day Telegraph Hill was the site of a turning point in the American Revolution. The former Dorchester Heights troops hoisted a fearsome assortment of cannons to the hill and aimed them at the British military occupying Boston. Under the command of Colonel Henry Knox, the revolutionaries relocated 59 cannons from the recently captured Fort Ticonderoga to South Boston. In keeping with the unorthodox methods that the revolutionary army would become famous for, this display also included countless cannon-sized logs, felled and fire-blackened to create the illusion of a truly terrifying amount of artillery.

With British troops and sympathizers present en masse, the Continental troops could not risk infiltration at this crucial juncture. They needed a password, something uniquely Bostonian that the Redcoats would never guess. Since the maneuver took place on March 17, 1776, the same day that South Boston residents had celebrated as Saint Patrick’s feast day, George Washington opted to use “Saint Patrick” as the password allowing soldiers to move back and forth through continental lines.

Security held tight and the gambit worked. Miraculously, the American forces never fired a single shot. Seeing the fearsome display of artillery (and frankly, reading the proverbial writing on the wall), the British troops and sympathizers boarded their ships and left. They liberated Boston without inflicting casualties on either side. Washington would later call it a “most remarkable interposition by providence”. Needless to say, there was some celebrating afterwards.

Evacuation Day

In 1902, city leaders declared the event, now known as Evacuation Day, a holiday in the City of Boston. They instituted a parade commemorating the event. In 1928, the state of Massachusetts recognized it as an official holiday in Suffolk County. The city itself sponsored the parade until 1947, at which point the South Boston Allied War Veterans Council took the reins. Over the years, many notable guests, including several sitting presidents, have attended the parade. The modern incarnation sees roughly half a million people flock to South Boston to take in the spectacle.

James Brendan Connolly, the First Olympic Champion

Around the world, a select group of communities can say that an Olympic gold medalist calls their neighborhood home. However, only one neighborhood gets to be first and that honor goes to South Boston. In 1896, at the first modern incarnation of the Olympic Games, James Brendan Connolly took home the gold in the triple jump competition (known as the “hop, step, and jump competition” back then). He also competed, and took second place, in the high jump competition.

If you head to South Boston’s Moakly Park, you can take in Connolly’s 1987 memorial, dedicated 101 years after his historic victory.

Real Estate Data on Homes for Sale in South Boston, MA

South Boston is a booming real estate market. As of this writing, the average sale price of homes for sale in South Boston, MA is $859,749, an increase of +5.76% over the previous year, and an increase of +140% from four years prior. So while things might have steadied in the past year or so, they are still very much on the upswing. The median price of homes for sale in South Boston, MA is currently $884,000, most of which are condominiums. With an average of 15.41 homes sold each month, listings typically last just shy of two months. While prospective homeowners are unlikely to be flooded with available options, there remains a steady stream of homes for sale in South Boston, MA.

Transportation near Homes for Sale in South Boston, MA

With the Red Line subway, Fairmount and Haverhill Line commuter rail, and the MBTA’s extensive busing service, South Boston residents have a multitude of choices when it comes to public transportation. Located a stone’s throw away from the South Station Train Terminal, residents have access to multiple transportation options. Whether by land, sea, or air, South Boston residents can get just about anywhere using public transportation.

South Boston Parking

While not as crowded as downtown Boston and still nowhere near New York City levels of congestion, parking a car in South Boston can be an exercise in patience. Simply put, there is only so much space to go around, and this causes cramped on-street parking. . Parking a block away, two at most, from your home is a common occurrence. If that sounds like a deal breaker, make sure that you include garage access as you search through the various homes for sale in South Boston, MA. Though relatively uncommon, having your own garage can transform a promising home into the residence of your dreams.

Education near Homes for Sale in South Boston, MA

Greater Boston is one of the intellectual centers of the United States. South Boston likewise reaps the benefits of having such prestigious universities call the metropolis home.

University Education in South Boston

While South Boston itself contains no institutes of higher learning, it offers easy access to Greater Boston’s numerous world-class universities by way of public transportation. From Harvard and MIT, to Berklee College of Music, to any of the dozens of top-rate colleges in the greater Boston metropolis, some of the best houses of learning in the world are in South Boston’s backyard.

Public and Private Schools in South Boston

Like all Boston neighborhoods, Boston Public High Schools are available for all students regardless of their neighborhoods. Some of the best schools in the state, like the magnet high school Boston Latin Academy, are available to qualified students. South Boston is home to some excellent charter schools, with the Up Academy Charter School of Boston and Boston Middle School Academy both achieving high standards.

South Boston boasts a pair of excellent private schools in the PK-6 South Boston Catholic Academy and the PK-8 St. Peter Academy. While the latter focuses on small class sizes with a maximum of 20 students per class, the former has roughly three times the total students, making admission far less competitive while keeping a 9:1 student-teacher ratio. Both have an emphasis on STEM education.

Daily Life in South Boston

When evaluating homes for sale in South Boston, MA, it pays to know what residents love about the area; Southie residents are passionate about their neighborhood. Combining historic districts and trend-setting new development is a big plus. Residents get to enjoy the full Boston lifestyle while enjoying an easy commute and pain-free access not just to downtown, but to their favorite local hot spots as well. Ready access to rail, bus, and air travel makes life easy for everyone from adventurous backpackers to busy business travelers.

South Boston’s strong sense of community permeates the local culture, granting the neighborhood its distinctly old-school Bostonian vibe. Whenever the Bruins, Celtics, Patriots or Red Sox are playing, neighborhood pubs overflow with passionate fans cheering up a storm. It is the sort of place where a working artist and a real estate tycoon might chat over a shared love of spuckies (Boston’s iconic sub sandwich) while enjoying the ocean breeze.

Local Traditions in South Boston

Finally, whether you are looking at homes for sale in South Boston, MA or simply visiting, you will want to keep a few things in mind.

First, and perhaps most importantly, when referring to South Boston use the local-approved colloquial “Southie,” rather than the New York-coined “SoBo.” Bostonians typically hold strong opinions about their neighborhoods, and are rarely shy about how different they are from New York. Second, if you come in from out of town for a home viewing or just to check out the neighborhood, locals strongly advise leaving the car behind and getting a feel for the city the old-fashioned way. How you feel about public transportation can play a big role in whether or not the homes for sale in South Boston, MA will be right for you. If car ownership is a more reasonable proposition, you might be happier living in a nearby suburb.

However, to the residents of South Boston, the idea of living anywhere else can seem downright absurd. Those who take up residence in South Boston will always have a home there.

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