Charlestown Real Estate

Overlooking John Harvard Mall in Charlestown’s historic gaslight district, this handsome, 5+BR/4.5BA, bow front brick townhome, offers 4,000sf of living space and two covered parking spaces. Built circa 1875, the home was rebuilt from the brick façade inward in 2009/10, with all-new framing and major systems, then thoughtfully reimagined in 2024/25 for modern family living. The main level is open and filled with light, with living, dining, and kitchen spaces flowing together beneath crown molding and custom millwork. A gas fireplace with porcelain surround anchors the living area, and a multi-zone sound system carries music throughout. The chef’s kitchen centers on a large marble-topped island and is equipped with a new Thermador six-burner range with grill and double ovens, plus a Sub-Zero refrigerator. Oversized windows and skylights brighten the space, and a French door opens to a private side porch for outdoor dining and grilling. A powder room services this level. The entire second floor is reserved for the primary suite, w/dual walk-in closets and a spa-style bath featuring a freestanding soaking tub, double vanity, and oversized walk-in shower. The third-floor features two generous bedrooms w/dual custom closets; a dedicated home office, full bath, and laundry center. The fourth-floor adds a custom built-in library or study and guest suite. Above it all, the roof deck offers 360-degree views of Boston Harbor and the city skyline. The lower provides versatile living space: a media room w/wet bar and EuroCave wine refrigerator, a gym or au pair suite, an oversized mudroom w/heated floor, abundant storage, and second washer/dryer. A 2-car covered driveway is just off the mudroom. Historic character, modern systems, and a coveted location make this a turnkey Charlestown home.

42 Harvard Street, Boston

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

$1,799,000

4 Beds ⋅ 3 Baths ⋅ 73589976 MLS

Discover the perfect blend of historic Charlestown charm and modern sophistication at 40 Sullivan Street. This beautifully updated four-bedroom, three-bathroom residence offers four levels of thoughtfully designed living space, rich architectural character, and a private brick patio ideal for outdoor entertaining. The inviting living room showcases an ornate fireplace, custom built-in shelving, hardwood floors, and elegant period details. The beautifully appointed eat-in kitchen features white cabinetry, quartz countertops, stainless steel appliances, a farmhouse sink, and distinctive brass pendant lighting. Generous windows fill the space with natural light, while a charming window seat adds warmth and character. Upstairs, four bedrooms offer comfortable accommodations and flexibility for a home office or guest space. Original wide-plank wood floors, decorative fireplaces, and classic millwork preserve the home's historic appeal, while three full bathrooms feature stylish updates, including a freestanding soaking tub and a double vanity with marble countertops. The finished lower level provides an inviting family or media room with a fireplace, built-in shelving, and French doors opening directly to the private, fenced brick patio—a wonderful extension of the living space for dining, entertaining, or relaxing outdoors. Ideally situated in the heart of Charlestown, this distinctive home offers a rare combination of timeless New England character, modern comfort, and versatile living spaces, all within easy reach of neighborhood shops, restaurants, parks, and downtown Boston.

40 Sullivan St, Boston

Listing courtesy of Listing Agent: Jesse MacDonald from Listing Office: Gibson Sotheby's International Realty.

$1,499,000

5 Beds ⋅ 3 Baths ⋅ 73589871 MLS

Rarely available multifamily opportunity in the heart of Charlestown! This 3 unit building is perfect for investors, developers, or end users looking to create something truly special. Unit 1 features 1 bed/1 bath, central A/C, and renovations completed in 2020. Units 2 and 3 each offer 2 beds/1 bath, presenting excellent potential for cosmetic updates and customization. Additional highlights include an enclosed patio, an updated roof deck, separately metered utilities for each unit and updated systems. Just minutes to all that Charlestown has to offer, a flexible layout and tremendous potential, this is a unique opportunity to reimagine or hold a MF property in one of Boston’s most sought-after neighborhoods.

25 Allston St, Boston

Listing courtesy of Listing Agent: The Goodrich Team from Listing Office: Compass.

$1,199,000

2 Beds ⋅ 3 Baths ⋅ 73588861 MLS

Bring your vision to this two-bedroom brick townhouse in Charlestown. The main level offers a kitchen, dining room, living room, half bath and sunroom with access to a rear patio. Upstairs are two bedrooms, a full bath and an enclosed porch off the rear bedroom. A partially finished basement provides additional flexible space and a second full bathroom. With a practical layout and the opportunity to update and personalize, 429 Main Street is ready for its next chapter.

429 Main St, Boston

Listing courtesy of Listing Agent: Yukiko Oyama-Morris from Listing Office: Oyama Investments, Ltd..

$749,000

2 Beds ⋅ 2 Baths ⋅ 73588558 MLS

Lovely duplex condominium in a charming and stylish Greek Revival building, originally built as a single family home in 1845. The main floor of Unit 2 features a spacious living room with bamboo flooring, a large tiled eat-in-kitchen, and an adjacent study. There is a half bath on this level. The second floor is comprised of two carpeted bedrooms and a full bath. This conveniently located home is close to numerous restaurants, shopping, public transportation, and all that Charlestown has to offer! Of Note: The Boston Landmarks Survey of this building indicates that there were later Victorian modifications made to the facade, such as the oriel windows on the second and third floors. It is believed that as a single family home, it was used as the rectory for the Trinity Methodist Episcopal Church, which was on High Street and was modified to house the current Boys and Girls Club. Unit 1 is a law office entered at street level and unit 3 is a residential condominium. FIRST SHOWINGS WILL BE SUNDAY, OCTOBER 11th FROM 1-2 PM.

254-6 Main Street Unit 2, Boston

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

$574,000

1 Beds ⋅ 1 Baths ⋅ 73587892 MLS

Welcome to Parris Landing in the historic Charlestown Navy Yard. This one-bedroom residence pairs sweeping views of the Boston skyline, Zakim Bridge and Navy Yard Park with one of the building’s most desirable conveniences: a self-park garage space. The open kitchen features white cabinetry, granite countertops, stainless steel appliances, gas cooking, a custom pantry and peninsula with bar seating, flowing seamlessly into the living and dining area with bamboo floors and an oversized window framing the city beyond. The sun-filled bedroom offers a spacious walk-in closet with a custom California Closet system, while the full bath features a tiled tub/shower and granite-topped vanity. Parris Landing offers full-service living with 24-hour concierge, professional on-site management, heated outdoor pool, fitness center, clubroom and beautifully maintained common spaces. All of this in an exceptional waterfront location moments from the Harborwalk, Charlestown Ferry, neighborhood dining and the best of the Navy Yard.

42 8th Street Unit 1519, Boston

Listing courtesy of Listing Agent: Paul Whaley/Charlie Ring Team from Listing Office: Coldwell Banker Realty - Boston.

$640,000

2 Beds ⋅ 1 Baths ⋅ 73587696 MLS

Stunning top-floor condo with breathtaking city views! This gorgeous 2-bedroom, 1-bath home combines classic charm with modern convenience, offering spectacular views of the Bunker Hill Monument and the Boston Skyline. The eat-in kitchen features granite countertops and stainless steel appliances. The kitchen opens directly to the sun-drenched living room with a fireplace and decorative windows that flood the home with incredible natural light. The two spacious bedrooms offer ample closet space. High ceilings thru-out. Most windows have been replaced, adding to the comfort and appeal of this inviting home. A true standout is the expansive rooftop deck, where unobstructed city views create an incredible backdrop for morning coffee, entertaining, or watching the city lights at the end of the day. Ideally located just minutes from the USS Constitution, Boston National Historical Park, Harbor Shuttle service, and all that the Charlestown Navy Yard has to offer. Quick access to the Orange Line and the 92 and 93 bus routes, making commuting to downtown Boston a breeze. With its combination of historic charm, wonderful views, outdoor space, and unbeatable location, this is a fantastic opportunity to enjoy the best of Charlestown and Boston living.

73 Sullivan St Unit 4, Boston

Listing courtesy of Listing Agent: The Chi Team from Listing Office: William Raveis R.E. & Home Services.

$1,775,000

3 Beds ⋅ 3 Baths ⋅ 73587337 MLS ⋅ ['40 Mount Vernon Street Condominium'] BLDG.

Located on a sought after gas-lit street, just off Monument Square, this spacious, 3+BR/3BA, 2,192sf, brick home is the result of a spectacular 2024 renovation with exceptional custom finishes throughout. The open main living area centers around a beautiful gas fireplace, framed by custom built-ins, flowing naturally into a gourmet kitchen equipped with white shaker cabinetry, farmer's sink, quartz countertops and JennAir stainless appliances. A private deck is just off the kitchen/living area and features streaming afternoon sun and a built-in gas line for grilling - perfect for entertaining. The main level also offers two bedrooms, including an elegant primary with a custom walk-in closet and ensuite bath w/double vanity and custom tiled shower. A well-appointed second bedroom sits towards the front of the unit, adjacent to a full bath with shower and tub. On the lower level, a spacious family room features a built-in bar with wine fridge, and a conveniently located full bathroom with tiled, glass enclosed shower. This floor also hosts an expansive king size third bedroom w/ample closet space. A private storage unit is located in the common area of the basement. The Navy Yard, Training Field Park, town center restaurants and shops, North End dining, and TD Garden are all just moments away. Rental garage parking at The Nautica Garage.

40 Mount Vernon Street Unit 1, Boston

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

$779,000

2 Beds ⋅ 2 Baths ⋅ 73585013 MLS ⋅ ['Parris Landing Condominiums'] BLDG.

Welcome to Parris Landing #1104, a spacious and well appointed 2-bedroom, 2-bath residence offering 937 square feet of comfortable living in one of Charlestown’s premier full-service buildings. The open layout is highlighted by floor-to-ceiling windows that fill the home with natural light and create a bright, airy feel throughout, and look onto quiet green sections of the park. Both full bathrooms were beautifully updated in 2026, the entire residence has been freshly painted, and there are thoughtful renovation touches throughout like new light fixtures and smart home thermostat, making this home truly move-in ready. The unit also includes one self-parking space in attached garage. Parris Landing offers an exceptional amenity package including a fully equipped fitness center, heated outdoor pool, 24/7 concierge, maintenance services, and professional on-site management. This unit is in building one, the most centrally located placement for all the building has to offer. Enjoy convenient, low-maintenance living in the historic Charlestown Navy Yard with easy access to the waterfront, North End, downtown Boston and major transportation routes including the MBTA ferry stop and bus pick-ups steps from the building.

42 8th St Unit 1104, Boston

Listing courtesy of Listing Agent: Myles Couyoumjian from Listing Office: Coldwell Banker Realty - Boston.

$765,000

1 Beds ⋅ 1 Baths ⋅ 73584482 MLS

Sun-swept 1+ bedroom penthouse loft in the heart of Charlestown! A dramatic open floor plan showcases soaring vaulted ceilings, exposed brick and beams, and a wood-burning fireplace, while skylights flood this top-floor space with beautiful natural light. Original wide-plank pine floors, recently custom matte finished, are a standout feature in this historic home. The kitchen captures a picture-perfect view of the Monument and features ample cabinetry, stainless steel appliances, and a breakfast bar overlooking the main living area. The open living and dining creates an inviting space for everyday living and entertaining, while a unique open loft offers flexibility for a second bedroom, guest space, or home office. Generous closet space, in-unit laundry, air conditioning, low condo fee, exclusive roof rights and dedicated basement storage complete this one-of-a-kind penthouse. Ideally located with neighborhood restaurants, cafes, and shops at your doorstep, and minutes to downtown, TD Garden, public transportation, and Logan Airport.

3 Dexter Row Unit 3, Boston

Listing courtesy of Listing Agent: Shannon McNamara from Listing Office: William Raveis R.E. & Home Services.

$1,195,000

2 Beds ⋅ 2 Baths ⋅ 73584388 MLS

Tucked away just behind the energy and convenience of Main Street, this charming single-family home beautifully blends antique character with thoughtful modern updates and amenities. Ideally located near Rt. 93, Assembly Row, the Orange Line, Whole Foods, Hood Park/Cambridge Crossing and popular neighborhood restaurants and shops like Monument, Junebug, Monroe Home and La Saison Bakery, this home offers both a peaceful setting and easy access to everything you need. The gut-renovated kitchen is the heart of the home, featuring Brazilian White Pearl quartzite countertops, custom hickory cabinetry, Bosch stainless steel appliances and a sun-filled bump-out with floor-to-ceiling windows. French doors in the living area open to a private patio/courtyard that wraps around the side of the home creating a wonderful extension of the living space for outdoor entertaining. The second-floor offers expansive, flexible space with a separate nook ideal for a home office along with an additional living area, full bathroom and laundry. The top floor features a primary bedroom with skylight and a second bedroom being used as a nursery with a beautifully renovated Jack-and-Jill bathroom. Additional features include 3 ductless mini-split systems for air conditioning, a new Burnham gas-fired boiler and ample basement storage. A wonderful opportunity to enjoy the character of a classic single-family home with the comfort, flexibility and upgrades of modern living.

281 1/2 Main Street Unit 281, Boston

Listing courtesy of Listing Agent: Neda Vander Stoep from Listing Office: Coldwell Banker Realty - Boston.

$1,195,000

2 Beds ⋅ 2 Baths ⋅ 73584384 MLS

Tucked away just behind the energy and convenience of Main Street, this charming single-family home beautifully blends antique character with thoughtful modern updates and amenities. Ideally located near Rt. 93, Assembly Row, the Orange Line, Whole Foods, Hood Park/Cambridge Crossing and popular neighborhood restaurants and shops like Monument, Junebug, Monroe Home and La Saison Bakery, this home offers both a peaceful setting and easy access to everything you need. The gut-renovated kitchen is the heart of the home, featuring Brazilian White Pearl quartzite countertops, custom hickory cabinetry, Bosch stainless steel appliances and a sun-filled bump-out with floor-to-ceiling windows. French doors in the living area open to a private patio/courtyard that wraps around the side of the home creating a wonderful extension of the living space for outdoor entertaining. The second-floor offers expansive, flexible space with a separate nook ideal for a home office along with an additional living area, full bathroom and laundry. The top floor features a primary bedroom with skylight and a second bedroom being used as a nursery with a beautifully renovated Jack-and-Jill bathroom. Additional features include 3 ductless mini-split systems for air conditioning, a new Burnham gas-fired boiler and ample basement storage. A wonderful opportunity to enjoy the character of a classic single-family home with the comfort, flexibility and upgrades of modern living.

281 1/2 Main Street, Boston

Listing courtesy of Listing Agent: Neda Vander Stoep from Listing Office: Coldwell Banker Realty - Boston.

Charlestown Real Estate

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