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Homes for Sale in Charlestown, MA

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As one of the oldest cities in America, Charlestown, MA has undergone plenty of changes across its nearly four centuries of history. While revolutionary meetings and powdered wigs have given way to coffeehouse chats and undercuts, Charlestown retains a serious old-world charm through it all.

If you love the feel of historic bricks and gas lamps, but are less thrilled with the cost of real estate in neighborhoods like Beacon Hill or the Back Bay, the homes for sale in Charlestown, MA could be exactly what you are looking for. Want to know more? Come with us on a guided tour through one of America’s oldest neighborhoods.

About Charlestown, MA

Homes for Sale in Charlestown, MA

As one of the oldest cities in America, Charlestown, MA has undergone plenty of changes across its nearly four centuries of history. While revolutionary meetings and powdered wigs have given way to coffeehouse chats and undercuts, Charlestown retains a serious old-world charm through it all.

If you love the feel of historic bricks and gas lamps, but are less thrilled with the cost of real estate in neighborhoods like Beacon Hill or the Back Bay, the homes for sale in Charlestown, MA could be exactly what you are looking for. Want to know more? Come with us on a guided tour through one of America’s oldest neighborhoods.

An Overview of Charlestown, MA

The oldest neighborhood in Boston, Charlestown, MA occupies the city’s northern peninsula across the Charles River from downtown. Borders are Somerville to the west, Chelsea to the north across the Mystic River, Downtown Boston to the south across the Charles River, and East Boston just across Boston Harbor to the east.

Like much of Boston, the homes for sale in Charlestown, MA are a vibrant mix of historic and modern. You can find cutting-edge luxury condominiums glistening in the sunrise alongside the harbor, refined, elegant, sturdy brick townhouses in the lamp lit streets they have occupied for generations, and many other architectural styles. The homes for sale in Charlestown, MA live comfortably between these two worlds, drawing on the best aspects of both to create a uniquely excellent neighborhood.

Areas of Interest in Charlestown, MA

Home to some of Boston’s most treasured historic landmarks, Charlestown also boasts its share of lively neighborhood hangouts to go with the national parks, Freedom Trail stops, and breathtaking views of the harbor.

Bunker Hill Monument

One of the first monuments built in the United States, and the final stop on the Freedom Trail, the 221-foot impressive granite structure is a constant reminder of the heroism and ingenuity displayed at the battle of Bunker Hill. Constructed over a period of 18 years beginning in 1825 and finally completed in 1843, the monument and its companion museum are open to the public free of charge.

The impressive, Quincy granite-built monument is, interestingly enough, not on Bunker Hill. The monument is actually located on Breed’s Hill, which is where most of the fighting in the legendary battle occurred. The original Bunker Hill monument, an 18-foot wooden column in memory of the fallen hero Dr. Joseph Warren, was located there. The 62-foot hill hosts not only Monument Square where the Bunker Hill Monument is located, but also some of the most sought-after homes for sale in Charlestown, MA.

Charlestown Navy Yard

Open 24 hours a day, this national park celebrates Boston’s history as a major shipyard, and a pivotal player in keeping America free. During its heyday, the Navy Yards maintained and resupplied warships, as well as building increasingly advanced vessels as technology moved ever forward. After 174 years of service, the Navy Yard now enjoys a second career as a historic site, and the home of both the legendary USS Constitution as well as the 20th century destroyer-class warship, the USS Cassin Young. The contrast between the two ships illustrates the transition from timber and sail to steam and steel.

Figs by Todd English

Not every Charlestown hot spot is a historic site; some of them just have fantastic pizza. Created by one of Boston’s most recognizable celebrity chefs, Figs by Todd English serves up what just might be the best Neapolitan-style pizza in Boston, if not all of New England. The wafer-thin crusts and free-form shape of these pizzas are all part of the experience and the experience is always worth having.

USS Constitution & Museum

None other than George Washington named this proud fixture of the War of 1812. Undefeated in battle, the USS Constitution is a beloved symbol of American resilience, as well as a tangible link to the nation’s past. Work on the ship began in the latter part of 1794, which enabled it to launch in 1797. It undertook its maiden voyage on July 22, 1798.

Retiring from active service in 1881, “Old Ironsides” found a new calling as a museum ship in 1907. The Constitution has required plenty of restoration over the years – most notably in 1925, 1970, and 1995. Despite its many repairs, workers have kept the ship sound while staying true to the original construction. A fixture in Charlestown, the USS Constitution is open to the public year-round, providing a tangible link to Boston’s past for visitors and residents alike.

Warren Tavern

While there is some debate on the matter, the historic Warren Tavern stakes its claim to the tile of “oldest bar in Massachusetts” with gusto. Founded in 1780 – a full 15 years before the Bell in Hand Tavern in Government Center poured its first draft – the Warren Tavern has some serious history under its belt. Named for Dr. Joseph Warren, the revolutionary figure who sent Paul Revere on his famous ride, the original tavern counted Revere, George Washington, Benjamin Franklin, and other legendary figures of the time among its patrons.

Though it has periodically closed its doors or served other functions, the historic building at the corner of Main and Pleasant Street has proudly hosted the modern incarnation of Warren Tavern for more than four decades. You can enjoy a cold one and some of New England’s best clam chowder in the same haunt that our nation’s first president once did.

History of Charlestown, MA

The Massachusett First Nations tribe knew the peninsula as Mishawum before it became Charlestown. In 1624, they welcomed two settlers, Thomas and Jane Walford, into the region. Not long after, the first governor of the Massachusetts Bay Colony, John Endicott, sent Ralph, Richard, and William Sprage over to Mishawum with instructions to found a settlement proper. Thomas Walford acted as an interpreter for Sachem (paramount chief) Wonohaquaham (also known as Sagamore John) and the would-be settlers. Business concluded swiftly and efficiently, and settlers founded the town of Charlestown. They incorporated in 1628.

While not every interaction between the First Nation and European settlers was amicable, every account of these meetings paints the picture of a friendly, collaborative relationship. While the Walfords eventually had a falling out with their fellow colonists, Wonohaquaham and the residents of Charlestown enjoyed a friendly relationship. During his final days, Wonohaquaham entrusted the care and upbringing of his two sons to the Reverend John Wilson.

Separations, New Towns, and Opportunity

The original territory that made up Charlestown was, in a word, large. As more residents flocked to the area, chunks of the territory broke off, with Woburn in 1642, Malden in 1649 (including the land that comprises modern-day Melrose and Everett), and Stoneham in 1725. Holdings south of the Mystic River became part Medford in 1754. In time, Medford would transfer some of its territory to Charlestown. That transfer had to wait due to the volatile political climate.

The Battle of Bunker Hill

The day is June 17, 1775, during the Siege of Boston. One of the first major conflicts between the British Redcoats and the nascent American Revolutionaries kicks into full gear. With British soldiers occupying Boston, colonial forces learn of plans to fortify the hills surrounding the city. If that happened, the British would control Boston Harbor. Outnumbered and outgunned, 1,200 revolutionaries led by William Prescott undertake a mission to occupy Bunker Hill and nearby Breed’s Hill. Moving under the cover of darkness, they take up position and wait for the British to realize their predicament. They do not have to wait long.

As the sun rises, the British realize the danger and move to attack. The Revolutionaries know that they are short on ammunition and do not shoot until they see “the whites of their eyes”. Though the British have a larger force, the Revolutionaries successfully repel them. Frustrated, the British regroup and attack a second time, and are again rebuffed by the scrappy colonists. Mustering resources for a third and final attack, the Redcoats eventually succeed at driving the revolutionaries out of their hastily constructed redoubt fortresses. The colonists have finally run out of ammunition.

The British Reconsider

The British declare it a victory, but it is Pyrrhic one. The British army assumed that the untrained colonist militia would melt before English military discipline. The opposite was true and the British sustained massive causalities, especially among their officer corps. The revolutionaries got away with minimal losses. Sobered by this realization, the British army adopts a cautious, methodical approach for the rest of the war. Ironically, it is this approach that allows the revolutionary army to fight to victory, despite being outnumbered and outgunned.

A legal holiday and numerous monuments commemorate the battle and with good reason. Without the ingenuity and bravery shown at Bunker Hill, American Independence might never have happened.


The Battle of Bunker Hill was a decisive blow for the revolutionary forces, but the town of Charlestown had suffered serious damage. Wharves, dockyards, and the rest of Charlestown’s infrastructure lay in ruins at the hands of the frustrated British army. Once the war was over, however, rebuilding could commence in earnest. In 1786, residents constructed the first bridge to span the Charles River, connecting Charlestown to the city of Boston and ushering a new era of urbanization.

In 1800, Charlestown unveiled a new, 87-acre Navy Yard. This enterprise eventually proved integral to Charlestown’s identity and its larger role in preserving the young nation’s hard-won independence. Businesses like Schrafft’s candy company and Bunker Hill Breweries emerged as major players in the growing nation. Sadly, this nation was about to undergo some serious growing pains. As civil war broke out across the nation, Charlestown stepped up to do its part.

More than 26,000 souls joined up with the Union Army and Navy in Charlestown’s Navy Yard, which proceeded to turn out some of the most well-known and distinguished ships of the day. The USS Hartford served as Admiral David G. Farragut’s flagship during the conflict, and it was from this deck that he allegedly uttered his famous orders, “damn the torpedoes: full speed ahead!” during the Battle of Mobile Bay.

Additionally, the twin-turreted, steam powered, ironclad monitor ship the USS Monadnock launched from the Charlestown Navy Yard in 1863. It played a vital role in the conflict and proved essential in the final naval battles of the war.

From Middlesex to Suffolk: Joining up with Boston

After the Civil War, Charlestown cultivated a fresh water supply from the Mystic Lakes, which led to an even greater increase in population and prosperity. Its nearby neighbor was likewise enjoying explosive growth, and the idea of joining forces began to gain steam. Debate, discussion, and discourse culminated in a vote held on October 7th, 1873. The residents of Charlestown opted to merge with Boston, where citizens strongly approved the measure. Over the course of the following year, Charlestown finally dissolved its town government, joining the city of Boston.

Charlestown, Boston Population

Charlestown, MA has certainly grown since the days of Jane and Thomas Walford, or the 1800 census, which proudly noted a population of 2,751 residents. Today, an estimated 17,208 of Boston’s 694,583 residents call Charlestown home. That gives it a population density of 11,972 people per square mile, which is 1,869 less than Boston’s overall average of 13,841 people per square mile.

Real Estate Data on Homes for Sale in Charlestown, MA

Since joining the city of Boston, Charlestown has consistently been among its most desirable neighborhoods. It packs an entire city’s worth of community and history into a single neighborhood, creating an easily accessible, tight-knit community. Gorgeous homes for sale in Charlestown, MA continue to attract prospective homeowners with their unique charms.

Given these factors, it makes sense that Charlestown is one of the hottest markets in Boston. The median price of homes for sale in Charlestown, MA is approximately $822,590, which is a fair step above Boston’s median value of $599,400. However, that figure does not tell the whole story. Specifically, with a price per square foot of $718, Charlestown not only offers more bang for your buck than comparable neighborhoods such as Back Bay’s rate of $1,254 per square foot, or Beacon Hill’s $1,234 per square foot, it is actually slightly less than the city of Boston’s mark of $732 per square foot.

Simply put, Charlestown residents get a lot more home for their dollar, especially when compared with the going rate for similarly historic neighborhoods.

Transportation near Homes for Sale in Charlestown, MA

Bordered by the Northern Expressway viaduct of I-93, connected to Chelsea by Route 1, and plugged into downtown via the Orange Line as well as the harbor, Charlestown has a wide array of transportation options available to residents.

Public Transportation near Homes for Sale in Charlestown, MA

As the rest of Boston, the MBTA serves Charlestown. The Orange Line provides access to Downtown Boston and from there, the rest of the greater Boston metropolitan area. The Community College station, located near Bunker Hill Community College, serves the neighborhood center. The Sullivan Square T stop provides access to The Neck, up by East Somerville. The 92 and 93 bus routes also run through Charlestown, both providing access to Downtown Boston throughout the day.

In addition, while the Charlestown Navy Yard might not be the busy shipyard it was in its heyday, it still acts as a port for the Boston to Charlestown Ferry, administered by Boston Harbor Cruises. For less than the price of a decent latte, you can skip the rush hour traffic while enjoying your commute in style.

Driving near Homes for Sale in Charlestown, MA

In the eyes of many, Boston is a public transportation town, first, foremost, and everything in-between. While public transit is a solid option in the neighborhood, approximately 53.7% of Charlestown residents still drive to work. While some residents opt to forgo driving altogether, or at least for their daily commute, more than half still rely on personal vehicles to get around.

While it remains a far cry from the wide-open spaces and uncongested roadways of a remote, rural suburb, Charlestown is far from the worst places to drive in Boston. As anywhere else in the city, expect traffic, and expect it to be worse during rush hour. Overall, driving in Charlestown is roughly on par with most Boston neighborhoods, though at times a little lighter.

Parking near Homes for Sale in Charlestown, MA

Parking in Boston always presents something of a challenge, and Charlestown is no exception. That said, parking in Charlestown compares quite favorably with much of The Hub, especially considering its proximity to Downtown Boston. With no event parking to speak of, the influx of traffic that comes with concerts and sporting events is blissfully not a concern in Charlestown; parking availability is far more consistent than in other Boston neighborhoods.

Other Forms of Transit near Homes for Sale in Charlestown, MA

Of course, not everyone needs to rely on outside transportation for his or her daily commute. If the numbers are any indication, residents of Charlestown find it far easier than most to do so. In Charlestown, roughly 5% of commuters use a bike to get to and from their destinations. This is larger number of cyclists than 97.5% of American neighborhoods.

Even with such a large number of cyclists, whopping 12.3% of the neighborhood’s residents elect to forgo outside transportation of any sort for their daily commute. With such close proximity to Downtown Boston, many residents simply choose to make their way on their own terms.

Education near Homes for Sale in Charlestown, MA

As the birthplace of American education, it comes as no surprise that Greater Boston is home to some of the most highly regarded schools in the nation, if not the world. From top universities to excellent primary education, Boston’s reputation as an education destination is decidedly well earned.

Public Schools near Homes for Sale in Charlestown, MA

In every neighborhood in Boston, Charlestown provides primary education based on regional districts. The town provides a selection of schools within a radius of one mile of the students’ home addresses. That option gives parents and students more choices.

Once it is time to enroll in secondary education, each of Boston’s public high schools are open to any residents, regardless of their address. According to neighborhood ranking website, Boston’s Public Schools rank in the 99th percentile for diversity, and the 90th percentile for the best places to teach in the United States. Unsurprisingly, Niche also recognizes Boston as one of the districts with the best teachers in Massachusetts.

Within the neighborhood’s borders, the K-8 Warren-Prescott School, K1-5 Harvard/Kent Elementary School, and 6-8 Clarence R. Edwards Middle School provide local primary education Charlestown High School is a favorite with residents due to its competitive boys’ basketball program, routinely ranked as one of the top teams nationwide.

Colleges and Universities near Homes for Sale in Charlestown, MA

Boston is widely regarded as a premier destination for higher education, and Charlestown is no exception. With three highly regarded schools within its borders, Charlestown, MA is an excellent place to pursue a degree.

Founded in 1977, the MGH Institute of Health Professions is young by the standards of Boston universities. Founded by Massachusetts General Hospital and situated in the Charlestown Navy Yard, this graduate school boasts some of the best programs in the nation. The benchmark ranking media company U.S. News & World Report had many good things to say about the school. In its most recent rankings, it ranked MGH’s Master of Science in Speech-Language Pathology program 7th nationwide, while the university’s Doctor of Physical Therapy track ranked 8th in the United States. Both rankings set MGH as the best such program in Massachusetts.

Recently, Cambridge College, a post-secondary school focused on providing education to working adults, consolidated its four schools into a single, new campus situated in Hood Office Park in Charlestown. The thriving neighborhood was a major reason for the move. In addition, since many of its students work full-time, the convenient free parking was a major draw.

Perhaps the most well known of Charlestown, MA’s colleges and universities, Bunker Hill Community College is the largest community college in Massachusetts. It has more than 13,000 students taking classes at its 42-acre campus in Charlestown. In addition to having a T station named after it, the school also featured prominently in the film Good Will Hunting, as Robin Williams’ character Dr. Sean Maguire was a teacher at BHCC.

Daily Life in Charlestown, MA

Nestled between the Charles and Mystic Rivers, Charlestown brings the best elements of quaint New England living, and combines them with the rich history and urban sophistication that only living in Boston can truly provide. With all the culture, dining, businesses, shopping, and historic sites of Downtown Boston just across the bridge, residents enjoy the best of all worlds while living in a tranquil, scenic peninsula.

Many residents enjoy the fact that there is no raucous nightlife in Charlestown. Even late-night club-hoppers see this as an advantage, not a drawback. All the excitement of Downtown is barely a stone’s throw away. When the night’s excitement is at an end, Charlestown provides a welcome respite from the hustle and bustle of Downtown Boston; it is a refuge on the shore of the waterfront.

None of this is to say, of course, that Charlestown lacks its own attractions. The Boston Harborwalk and Freedom Trail both pass through Charlestown and its dining and bar scene are the best. Residents see a lack of national attention as a plus; it reduces the wait time at their favorite spots.

Charlestown has many fun stores for shopping or for just browsing. Stores such as Place and Gather for home accents, Boston Organics for organic fruits and vegetables, The Active Gaming Company for games, Armory for sporting goods, Emack & Bolio’s for ice cream, Ardyss Body Magic for natural food supplements, and many more will keep you entertained and supplied with all your needs.

Charlestown is a Great Place to Live

So, what is it like to live in Charlestown, MA? I hope that this article answers that question for you. In summary, residents describe living in Charlestown as combining all of their favorite aspects of living in Boston, but without the high cost of Beacon Hill or the Back Bay, and avoiding the constant commotion of Downtown. Charlestown is a pleasant, charming neighborhood that never quite goes full suburb. It fully embraces its heritage as one of New England’s great historic port towns.

Awarded a coveted “A” grade from neighborhood ranking site, Charlestown is widely regarded as one of the best places to live, not just in Boston, but also in all of New England. If that sounds like home to you, then you have good news; you are already at the premier portal for finding homes for sale in Charlestown, MA. If you have any questions, feel free to reach out. We are here to help! When you find that perfect place in Charlestown, there is only one thing left to say – Welcome Home.

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