Overview
North of Boston, Charlestown is a waterfront neighborhood steeped in history — Revolutionary War history, to be more specific. The Freedom Trail passes streets lined with brick townhouses and triple-decker homes to the site of a key Revolutionary War battle at Bunker Hill Monument. However, growing beyond it’s historical roots, the neighborhood has turned into a busy, modern-day community.
Explore the Neighborhood:
Kerry D’Ambroise is a resident of Charlestown and loves walking the Navy Yard with her dog Ellie.
Hear more about Kerry’s experience living in Charelstown and why she loves to call this neighborhood home!
Featured Property: The Ropewalk
Nestled within the Charlestown Navy Yard, at 58 13th street, lies the iconic Ropewalk building. Now 97 rental units in the heart of the Navy Yard, this building is rooted in American Naval history. Step inside the Ropewalk, and you’re transported back to an era of industrial innovation. This original structure was built in 1838 as a rope-making facility, the last of its kind in the United States. Crafted by renowned architect Alexander Parris and innovative machinist Daniel Treadwell, the Ropewalk stands as a testament to 19th-century engineering prowess.
Whether you’re drawn to its architectural splendor and historic significance, or its modern renovation and location, if the Ropewalk sounds like the perfect place to call home, then give us a call. Currently we have 4 units available. However, inventory is always changing, so reach out to see if we have the perfect fit.
$2M+ Luxury Market Data
A few short years ago we didn’t track the $2M+ statistics in Charlestown because the market was incredibly thin at this level. However, Charlestown has been on an epic rise over the past decade and, while 2024 was not as strong in many neighborhoods, this area steamed ahead with continued momentum upward. There were 22 sales over $2M in Charlestown in 2024 up from 17 sales in 2023 and $57,528,000 in sales volume up from $44,925,000 in 2023. The average price per square foot jumped a whopping 13% to $942.38 from $867/SF! One thing to know is if you are looking to buy in this neighborhood, you will probably want to work with a real expert, as almost 30% of the inventory traded off-market in 2024!
Landmark Sales for Boston’s Historic Homes:
The most notable sale was an off market transaction at 119 Main Street. Possibly Boston’s most historic home, this meticulously restored 3,200 square foot home is surrounded by professionally landscaped gardens. Selling for $4,400,000 and getting $1,375/SF, this really was one for the books, but it wasn’t the only sale over $4M in the neighborhood! 60 Monument Ave also achieved a sale in this bracket, clocking $4,243,000.
Location
Charlestown is truly a “best of both worlds” neighborhood located on a peninsula north of downtown Boston.
In the Navy Yard area luxurious waterfront homes with beautiful views sit atop the Boston Harbor. As you venture toward the middle of “The Town,” historic brick and wood-frame rowhouses along gas-lit streets frame a cultural identity for the neighborhood.
With so much history to absorb, leisurely strolls around town feel like a requirement for Charlestown residents. The Bunker Hill Monument, Charlestown Navy Yard, and the U.S.S. Constitution are all within minutes of each other while an expanding food and drink scene caters to the gentrifying population.

Recently Sold in Charlestown

30 Monument Square, #202
2 Bed | 1 Bath | 1,274 SF
This elegant 2 bed, 1 bath home boasts soaring ceilings, abundant natural light fr. corner exposure, central air & parking!
Price: $1,200,000

98 High Street, Unit B
3 Bed | 2 Bath | 1,320 SF
Exquisitely located in the heart of Charlestown, close to restaurants, shops, and the “T,” this spectacular three-bedroom home offers exceptional living space over two floors
Price: $1,155,000

380 Bunker Hill Street, #104
2 Bed | 2 Bath | 988 SF
Unit 104 at the boutique building The Armory in Charlestown offers a perfect blend of historic charm and modern living across its two-bedroom, two-full bathroom floor plan.
Price: $970,000

95 Pearl Street, #3
2 Bed | 2 Bath | 842 SF
Embrace Charlestown city living in this sun-drenched, Penthouse 1+ BR, 1 BA condo in a prime location close to vibrant neighborhood amenities & public transit.
Price: $675,000

19 Main Street, Unit B
1 Bed | 1 Bath | 679 SF
Step inside this freshly renovated 1 bedroom 1 bathroom with a bonus office room!
Price: $681,000

464 Main Street, #1
1 Bed | 1 Bath | 747 SF
Experience the allure of Charlestown, one of Boston’s oldest neighborhoods, in this stunning one-bedroom duplex situated on historic Main Street.
Price: $590,000

356-358 Main Street, #12
2 Bed | 1 Bath | 933 SF
This spacious condo offers two levels of living with high ceilings in a professionally managed building.
Price: $599,000

10.5 Hancock Street
2 Bed | 2 Bath | 883 SF
Crisp, move-in ready 2 Bedroom/2 Bath condo on quaint & quiet side street in historic Charlestown.
Price: $760,000

20 Allston Street, #1
2 Bed | 2 Bath | 978 SF
Beautiful 2 bedroom/2 full bathroom duplex features smart open floor plan and the modern amenities you’re looking for
Price: $850,000

50 Baldwin Street
4 Bed | 3.5 Bath | 3,506 SF
Classic 5+ bedroom single family home renovated with care and attention to detail.
Price: $2,050,000

28 Harvard Street, #5
2 Bed | 2 Bath | 1,353 SF
Price: $1,175,000

13 Monument Square, #2
1 Bed | 1 Bath | 873 SF
Positioned directly on Monument Square, this newly-renovated 2 bedroom/2 bath home offers an unparalleled standard of living in Charlestowns most coveted location.
Price: $1,005,000
Contact Kerry
Top Restaurant Picks In Charlestown
- Blackmoor: Casual, modern neighborhood venue offering a menu of casual bites & 34 rotating craft beers.
- Brewers Fork: Craft draft beers, cider, cocktails & wood-fired chow is served at this rustic, atmospheric hangout.
- Dovetail: Casual, industrial-style venue with a raw bar for seafood, plus a brunch menu, pasta & steaks.
- Pier 6: This casual seafood spot on the waterfront boasts a roof deck & a post-dinner singles scene.
- Figs: Stalwart featuring thin-crust pizza with gourmet toppings plus Italian entrees in intimate quarters.
- Monument: Wood-fired pizzas & more gastropub grub in a comfortable setting of brick & weathered woods.
- The Warren Tavern: Claiming to be the oldest bar in Massachusetts, this legendary circa-1780 tavern draws locals & tourists for beer, varied pub food & Colonial charm.

We believe when real estate consumers are presented with a complete and robust spread of data, in conjunction with their personal preferences, decisions can be reached with the most confidence.
To learn more about changing market dynamics moving into 2025 check out our Perspective on the Boston Luxury Housing Market>