Welcome to Charlestown

Boston’s oldest neighborhood is a charming New England small town with an intriguing historical legacy


Adjoining the Mystic River and Boston Harbor waterways is Charlestown, a charming, waterfront New England city known for its deep Irish-American heritage, historical roots, and small-town sensibility. Charlestown was laid out by one of its earliest settlers, Thomas Graves, in 1629 and later became the first Massachusetts Bay Colony capital.


Today Charlestown is known for its quaint attributes, including a classic Main Street and town square. The town boasts several historically significant sites, such as Boston's Freedom Trail. The famous Bunker Hill Monument is situated at the end of the trail and serves as a memorial to the famed American Revolutionary war battle fought on the very premises.


Families and young professionals have flocked to the area over the years as it evolves into a modern-day urban city with lasting historical significance. From clapboard triple-decker homes to elegant brick townhouses and luxury condominiums, Charlestown has something for everyone.


What to Love

  • Waterfront 
  • Historical significance
  • Classic Main Street
  • Small-town charms
  • Boston’s Freedom Trail
  • Affordable housing options

People & Lifestyle

If you've ever wanted to live in a small town where neighbors stop for a chat when they see you outside or invite you to the latest town square function, Charlestown might be the perfect place for you. Locals frequent the neighborhood watering hole, Warren Tavern, for frothy mugs of beer and steaming bowls of chowder while making good conversation. Charlestown proudly sustains the lasting vestiges of the colonial era from whence it came.


Predominantly composed of families and young professionals, Charlestown offers many family-oriented activities. Stroll down Main Street and peruse the locally-owned shops or spend a sunny afternoon picnicking at Breed's Hill or Paul Revere Park. Charlestown is a town bursting with simple pleasures and a quiet way of life that feels stolen from a bygone era. At the same time, it's only a short drive from the North End's culinary haven and Fenway's numerous attractions.


Dining, Entertainment & Shopping

Charlestown is home to several fantastic, unique pizza places, gastropubs, and rustic taverns that pay homage to their colonial roots. Paul Revere frequented The Warren Tavern, which is the oldest pub in Massachusetts and one of America's most historic watering holes. Stop by to refuel at his legendary pub after spending the day hiking to the Bunker Hill Monument.


Speaking of the monument, the neighboring Monument Restaurant and Tavern is a wonderful weekend brunch spot known for fluffy lemon and poppyseed buttermilk pancakes and signature crab toast.


For mouthwatering wood-fired pizza, visit Brewer's Fork or Figs by Todd English. Brewer's Fork offers patrons a varied selection of draft beers, ciders, and cocktails to complement their burgers, pizzas, and sandwiches. This hair-of-the-dog eatery has received unanimous acclaim from established outlets like Thrillist, Boston Magazine, Draft Magazine, Boston Globe, and more. Sample their transcendent charcuterie and cheese boards while relaxing on their cozy patio with a beer garden vibe.


Figs by Todd English sets itself apart from every other pizza joint because of its crispy, thin-crust pizza molded freeform. You read that right, they don't make traditional round pizzas at Figs, but oblong pies topped with delicious, creative toppings like mustard aioli and their aromatic fig and balsamic vinegar jam.


Things to Do

Relive the colonial era by exploring Boston's Freedom Trail, a 2.5-mile redline meandering through 16 historic sites and over 250 years of history. Witness the story of the American Revolutionary War and beyond as you visit museums, burying grounds, parks, ships, and historical markers, finishing at the Bunker Hill Monument, a 221-foot granite obelisk of national significance.


Along the north end of the Freedom Trail, you'll find the Boston Navy Yard, home of the moored U.S.S. Constitution. The Constitution is one of six original heavy frigates and the oldest warship still commissioned by the U.S. Navy.


The town's largest public gathering is held annually on Halloween in Monument Square. Ghosts, ghouls, and trick-or-treaters run freely in the square seeking their share of candy and frights. The town shuts down the streets to keep things safe and to accommodate the Charlestown Halloween Parade.


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.