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!
3 New Things Coming to Charlestown
Currently for sale in Charlestown
15 Harvard St, #2
Located in Charlestown’s City Square, this 2 bed, 2 bath floor-through condo at 15 Harvard St #2 offers soaring 10’ ceilings, built-ins, and a gas fireplace. The chef’s kitchen features quartz countertops, stainless appliances, and a Bertazzoni gas range, while the spacious dining area is perfect for entertaining. The oversized primary suite boasts a marble mantel, walk-in closet, and a luxurious bath with a jacuzzi tub and marble mosaic floors. With central A/C, in-unit laundry, private storage, and a location just steps from John Harvard Mall and vibrant Main Street, this 1,002 sqft home has it all.
Learn more$2M+ Luxury Market Data
In 2025, Charlestown recorded 22 sales at or above $2M, matching 2024’s elevated activity and well ahead of the 17 sales logged in 2023. Total dollar volume climbed again, reaching approximately $58.2M! Pricing told a nuanced but optimistic story. The average price per square foot landed at $956.00, building on the sharp gains seen in 2024 ($942.38/SF) and far surpassing 2023 levels ($867/SF). Trophy properties push the ceiling even higher: multiple sales exceeded $1,100/SF, and one off-market Mount Vernon Street transaction captured an eye-catching $1,647.43/SF. The Best Homes Trade Quietly
$58,174,500
TOTAL SALES VOLUME
$912.32
AVG. PRICE PER SQ. FOOT
22
NUMBER OF $2M+ PROPERTIES SOLDData sourced from LINK & MLS Pin on single family and condo properties sold in 2025 over $2 million.
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.
The Best Homes Trade Quietly
One of the most consistent throughlines remains off-market activity. Roughly one-third of all $2M+ sales in 2025 never hit the MLS, closely mirroring 2024. These transactions were concentrated among best-in-class single-family homes and discreet condo offerings, underscoring that access continues to be a decisive advantage for buyers and sellers operating at this level.
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 2026 check out our Perspective on the Boston Luxury Housing Market>
