Charlestown Real Estate

Welcome to Charlestown, a vibrant neighborhood nestled in the heart of Boston, Massachusetts. Known for its rich history and picturesque charm, Charlestown offers a unique blend of old-world charm and modern convenience, making it one of the most desirable places to call home in Suffolk County.

As one of the oldest neighborhoods in Boston, Charlestown is steeped in historical significance. Walk the cobblestone streets lined with beautifully preserved 19th-century brownstones, and you’ll feel the echoes of the past. The iconic Bunker Hill Monument stands tall, commemorating the historic Battle of Bunker Hill, while the Charlestown Navy Yard showcases the area’s maritime heritage.

Residents of Charlestown enjoy a tight-knit community atmosphere, complemented by an array of local shops, cafes, and restaurants that cater to every palate. The neighborhood is also home to the renowned Charlestown Community Center, offering recreational activities and programs for all ages. For those who appreciate the outdoors, the scenic waterfront parks and the nearby Boston Harbor provide ample opportunities for leisurely strolls, picnics, and breathtaking views of the city skyline.

Convenience is key in Charlestown, with easy access to public transportation, including the T, making commuting to downtown Boston a breeze. Whether you’re a first-time homebuyer or looking to invest in a historic property, Charlestown offers a diverse range of real estate options, from charming condos to spacious single-family homes.

Experience the perfect blend of history, community, and urban living in Charlestown—where every street tells a story and every day feels like a new adventure. Come and discover why this neighborhood is truly a hidden gem in Boston!

Newest Listings in Charlestown

$1,600,000

4 Beds ⋅ 2 Baths ⋅ 73574516 MLS

Rarely available, and well loved through generations, this handsome, 4+BR/2BA, brick two-family home on coveted Auburn Street offers nearly 2,600 square feet of living space and an additional 917sf of unfinished basement space, providing an extraordinary opportunity for an investor, contractor, or end-user to build equity or seamlessly convert to a single-family residence. Set on a picturesque, tree-lined street, the building features a grand entry foyer, tall ceiling height throughout, large windows that flood the rooms with natural light, and a blend of rich original oak and pine floors. The oversized first-floor, 1BR/1BA apartment offers a spacious 900+sf layout, featuring formal living and dining room parlors with pine floors, a full bath with tub, and an inviting kitchen that opens onto a private deck, which leads to a large, fenced in yard waiting to be brought back to a lush sanctuary. The “owner’s” unit is an impressive 3+BR/1BA, 1,600sf upper duplex with a spectacular front living room parlor with white marble mantel, ornate ceiling medallion and crown molding. A formal dining room parlor flows to the updated kitchen featuring stainless appliances and quartz countertops. A full bath with tub and a separate laundry room/pantry complete this level. The upper level offers 3 bedrooms, plus study, bathed in light from front and back windows and a skylight. This home is close to all Charlestown has to offer with great parks, local dining, shopping, and transport to downtown Boston.

24 Auburn Street, Boston

Listing courtesy of Listing Agent: Nancy Roth from Listing Office: Gibson Sotheby's International Realty.

$2,500,000

4 Beds ⋅ 4 Baths ⋅ 73573036 MLS

Located on a gas-lit street near Monument Square, this rarely available, 4BR/3.5BA, two-family home offers 3,593+sf and an extraordinary opportunity for an owner occupant to live in the "owner's unit" and keep a tenant in 1st floor unit; or buyers looking to convert into a spectacular single family home; or a developer/investor to convert into two high-end condos. The grand entrance is defined by soaring ceilings, period moldings, and a sweeping staircase that leads to an impressive formal living room. An elegant dining room flows into a chef’s kitchen with luxury finishes and top-tier appliances. A charming family room w/wet bar and gas FP provides an inviting hub for daily living. A spacious primary suite w/fireplace has ample closet space and marble spa bath. An addt’l bedroom and full bath complete this level. The separate entrance, 1BR rental unit in the rear of the first floor is well maintained. The crown jewel is an expansive 480sf private roof deck w/head house, wet bar, and panoramic views of the harbor, Monument, and Boston skyline. An unfinished basement offers future expansion capabilities, and a lush garden patio completes this special offering.

51 Chestnut Street, Boston

Listing courtesy of Listing Agent: Nancy Roth from Listing Office: Gibson Sotheby's International Realty.

$2,850,000

4 Beds ⋅ 4 Baths ⋅ 73512592 MLS

Perfectly positioned between the Training Field and the Charlestown Navy Yard, this newly renovated single-family brownstone offers four levels of luxury living in one of the neighborhood’s most coveted locations. The home features 4 bedrooms plus a large finished lower level with dedicated storage—ideal for a media room, gym, or playroom. A stunning chef’s kitchen with marble surfaces and Thermador appliances opens to a private patio with a gas grill hookup, perfect for indoor-outdoor entertaining.The primary suite is a true retreat, complete with a steam shower, gas stove, and a dedicated sitting area that opens to a private balcony with breathtaking city views. A second-level south-facing roof deck with a gas fire-pit hookup provides exceptional outdoor living. Beautiful exposed brick, refined finishes, and thoughtful craftsmanship are showcased throughout. This home combines new construction, period detail, historic surroundings, and unmatched Charlestown Walkability.

16 Chestnut Street, Boston

Listing courtesy of Listing Agent: Zachary Endicott from Listing Office: RE/MAX Encore.

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