Charlestown MA Single Family Homes For Sale

Rich in historic character and offering an impressive approx. 3,360 square feet across four levels, this classic 1880 Charlestown brownstone delivers exceptional scale and versatility. The main and upper levels function as an expansive single-family home, with elegant living and dining rooms, an updated kitchen, soaring ceilings, intricate millwork, hardwood floors, oversized windows and four fireplaces. The expansive primary suite is a standout, complete with custom built ins, a fireplace and spacious en-suite bath with dual vanities, soaking tub and glass-enclosed shower. The top floor also offers the potential to be reconfigured into two bedrooms, adding an additional bedroom to the home. A private deck and patio extend the living space outdoors. Separate from the main residence, the garden level features a one-bedroom apartment with its own private entrance, offering excellent rental income potential or a guest suite. Located near the residence there is a deeded heated garage space available separately for purchase, and there are two additional parking spaces available to rent. Convenient to Main Street and all Charlestown has to offer, with easy access to Downtown Boston, the waterfront and major highways.

12 Auburn Street, Boston

Listing courtesy of Listing Agent: Tracy Shea from Listing Office: Coldwell Banker Realty - Boston.

$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.

$785,000

1 Beds ⋅ 2 Baths ⋅ 73556614 MLS

Unique in every way, this row house with a private patio perfectly embodies the historic charm of Charlestown. Ideally located a short distance from the Orange Line T, public amenities like the community garden & theater, and Ctown's best shops & restaurants, this meticulously updated property provides comfort and privacy against the backdrop of vibrant city life. The practical layout features an entryway mudroom, a spacious exposed-beam kitchen & dining area, a 1st floor bath, a generously sized living room with a murphy bed, a top floor bedroom suite with walk-in closet & second full bath, basement storage, and in-unit laundry. Recent updates include A/C (2022), Anderson windows throughout (2024), custom window treatments, a new oven (2025), a new hot water heater (2026), fresh paint, and bedroom carpeting. Located down a charming brick path, this turn-key property is filled with sunlight and views of mature trees in its idyllic setting. Residential exemption available to reduce taxes. All of this with no HOA!

4 Short Street Place, Boston

Listing courtesy of Listing Agent: Coleman Group from Listing Office: William Raveis R.E. & Home Services.

$1,495,000

4 Beds ⋅ 3 Baths ⋅ 73541556 MLS

Nestled in the vibrant heart of Charlestown, this single-family home features 4+BD/2.5BA, hardwood flooring throughout. The bright and airy main floor hosts a fully equipped kitchen with maple cabinets that flows into a dining room, alongside an expansive living area that opens onto an outdoor deck. Upstairs, the primary bedroom boasts its own attached sunroom and ample storage, situated near a full bath and a second walk-in closet bedroom that leads up to a sun-drenched bonus loft. The lower level serves as an ideal in-law suite, complete with a full kitchen, laundry setup, a full bath, and access to a private, fenced-in patio. Supplemented by central heating and air, abundant storage space, and a driveway that accommodates more than one vehicle, this exceptional residence sits just moments from Main St’s premier shops, waterfront dining, and public transit. With its flexible layout and independent lower level, this property also represents an outstanding opportunity for investors.

22 Austin St, Boston

Listing courtesy of Listing Agent: Elynn Chen from Listing Office: Redfin Corp..

$3,995,000

4 Beds ⋅ 6 Baths ⋅ 73541133 MLS

8 Lawrence Street offers the rare opportunity to enjoy the space and lifestyle of a suburban home right in the heart of Charlestown. With over 4,000 sq. ft. of custom-designed living space, this newly constructed home redefines luxury city living. Enter directly from the attached garage into an expansive open-concept main floor, where a sun-filled living room is framed by detailed crown molding and millwork. The gourmet chef’s kitchen flows seamlessly into a dedicated dining room that opens to a private patio and backyard, a true rarity in the city. The 2nd floor is home to a luxurious primary suite with 2 spacious walk-in closets and a spa-like en-suite bathroom, plus a secondary bedroom with its own en-suite and a laundry room. On the 3rd floor, you'll find 2 additional bedrooms with en-suite baths, along with a home office overlooking the surrounding greenery. A full roof deck offers sweeping views of Charlestown and the city skyline.

8 Lawrence St, Boston

Listing courtesy of Listing Agent: The Sarkis Team from Listing Office: Douglas Elliman Real Estate - The Sarkis Team.

$850,000

3 Beds ⋅ 2 Baths ⋅ 73537311 MLS

Single family good location with roof deck. Come and create your own single family. Total rehab needed.

15 Russell St, Boston

Listing courtesy of Listing Agent: Joseph McGonagle from Listing Office: Century 21 Elite Realty.

$2,625,000

5 Beds ⋅ 5 Baths ⋅ 73519421 MLS

There are levels to real estate construction... and this is the top! Welcome home to a no-expense-spared ground-up single family with an idyllic floorplan and designer finishes throughout. Open & inviting living with framed gas fireplace, 9' ceilings, and incredible natural light. Designer kitchen features oversized quartzite island, professional grade appliances, custom cabinetry, built-in bar, and direct access to formal dining. Oversized primary suite, with private balcony, is out of magazine! Featuring space for a kingsize, gigantic walk-in closet, and designer bath with frameless glass shower+double vanity+soaking tub. Generous guest beds with dedicated custom baths. Finished lower-level creates the perfect space for an au pair suite, media room/gym/home office. Enjoy the seasons on your fully enclosed stone patio and breathtaking roofdeck with panoramic views from Boston Harbor, across the Skyline, and over the Monument! A special home that truly "has it all". Free rental parking on Prospect Street!

14 Prospect St, Boston

Listing courtesy of Listing Agent: Adam Geragosian from Listing Office: William Raveis R.E. & Home Services.

$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.

$2,499,000

4 Beds ⋅ 3 Baths ⋅ 73508764 MLS

This highly finished, 4+BR/3BA, 2,600sf, historic brick town home exudes a “Europe in Charlestown” vibe and is ideally located at the top of a charming gas lit cul-de-sac, creating a suburban feel with kids playing on the street. The formal living room parlor, with English marble gas fireplace, solid walnut flooring, surround sound, custom moldings, and pocket doors, opens to a serene dining parlor with wet bar, and dumbwaiter to kitchen. The stunning, state-of-the art kitchen overlooks a lush English garden patio w/fountain, and features European cabinetry, high-end appliances, large island with quartz waterfall, bar seating, and heated floor. A cozy family room w/full bath provides a comfortable sanctuary. A full floor primary suite on the second level features a gorgeous bedroom w/gas FP, custom walk through closet w/laundry, dressing room, and spa bath w/heated floor and separate tub and shower. The upper level offers three bedrooms, and a chic full bath. Historic House Tour 2008.

11 Lawnwood Place, Boston

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

$2,595,000

4 Beds ⋅ 3 Baths ⋅ 73499055 MLS

Situated on a premier gas-lit street in Charlestown’s coveted Monument Area near the Bunker Hill Monument, 33 Cordis Street is a striking 4-column Greek Revival blending historic charm with exceptional potential. Currently used as a single-family but deeded as a two-family, it offers flexible living across four levels with generous bedrooms, expansive living spaces, and views of downtown Boston and the Zakim Bridge. Set on an oversized lot with rare driveway parking for up to four cars. IDEAL FOR AN END USER TO RENOVATE AND CREATE THEIR DREAM HOME or for development. Sold as-is, with potential for a 1,800–2,000 SF rear addition (~6,400 SF total). Potential for 2–3 townhomes (buyer to verify). Pending Landmark status. SEE ATTACHED NATIONAL FLOOR PLANS & INITIAL ARCHITECT ZONING STUDY.

33 Cordis Street, Boston

Listing courtesy of Listing Agent: Ryan Taylor from Listing Office: Fortune RE.

$1,095,000

4 Beds ⋅ 2 Baths ⋅ 73497271 MLS

Tucked away off the street along a private walkway, this updated single-family home offers a rare sense of privacy in the heart of Charlestown. Thoughtfully renovated, this four-bedroom, two full bath home features a bright, sun-filled interior with quartz countertops, brand new stainless steel appliances, fresh paint, and new carpeting throughout. A flexible floor plan includes a first-floor bedroom—ideal for guests, home office, or den—nearby full bath with laundry. Generously sized bedrooms and an airy layout provide comfortable, versatile living. Step outside to a private patio, perfect for relaxing or outdoor dining. Additional highlights include a large, clean basement for storage or workshop use. A unique opportunity to own a single-family home offering both privacy and convenience near Charlestown amenities, transportation, and Boston. This wonderful residence lives and feels much larger than its square footage! Don't miss this truly outstanding opportunity!

18R Polk Street, Boston

Listing courtesy of Listing Agent: Frank Celeste from Listing Office: Gibson Sotheby's International Realty.

$840,000

2 Beds ⋅ 2 Baths ⋅ 73494772 MLS

Distinctive single-family set behind a private gateway along a secluded pathway, featuring a beautifully landscaped courtyard garden with mature perennials and over 1,000 bulbs and a cute garden shed—recognized as a Boston Garden Contest finalist. A compelling alternative to condo living, blending modern updates with old world charm.The kitchen redesigned to maximize space and functionality, offering a central island, exposed wood beams, granite countertops, and stainless steel appliances. A reimagined full bath and laundry area complete this level.Upstairs, the sun-filled living room showcases original wide pumpkin pine floors and a wood-burning fireplace, along with an updated full bathroom. The top floor is devoted to two cathedral-ceiling bedrooms, including a light-filled primary with skylight and additional hallway storage complete this level. A rare blend of timeless charm, excellent walkability to downtown, the waterfront, and local dining.

4 Mead Street Ct, Boston

Listing courtesy of Listing Agent: Lisa Godwin from Listing Office: Gibson Sotheby's International Realty.

$1,399,000

4 Beds ⋅ 2 Baths ⋅ 73405907 MLS

Unlock the potential of a truly special offering in one of Boston’s most treasured neighborhoods—Charlestown’s iconic Gas Light District. Rarely available free-standing single-family house with potential for 3-unit conversion. This once-in-a-generation opportunity invites developers, builders, and investors to reimagine a long-loved home on a large, flat 4,296 sq/ft lot. Zoned 3F per the BBD; possible uses include one-family, two-family (detached or semi-attached), three-family, or rowhouse—buyer to verify all info. The home has been in the same family for 60+ years and offers 9 rooms, 4 beds, and 1.5 baths across 2,467 sq/ft. This is an estate sale and will be sold “as is.” The Seller and Listing Agent make no representations or warranties regarding the property’s condition or future use. Buyer is responsible for all due diligence, plans, and permitting. Bring your vision and be part of Charlestown’s next chapter.

1 Washington Place, Boston

Listing courtesy of Listing Agent: The Pallotta Group from Listing Office: Gibson Sotheby's International Realty.

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Charlestown MA Single Family Homes For Sale

Explore Charlestown, MA single family homes for sale and discover a unique blend of historic charm and modern convenience. As one of Boston’s most sought-after neighborhoods, Charlestown offers beautifully preserved Federal and Greek Revival-style homes, as well as contemporary new construction properties. Whether you're searching for a historic rowhouse or a spacious modern home, Charlestown provides a variety of single-family housing options.

Living in Charlestown means being near the scenic Boston Harbor, the historic Bunker Hill Monument, and the vibrant shops and restaurants at City Square and the Navy Yard. The neighborhood offers an easy commute to downtown Boston via the MBTA Orange Line, commuter rail, and water taxis. With its strong sense of community, waterfront views, and rich history, Charlestown MA single family homes for sale present an incredible opportunity for homebuyers looking for space and character in the heart of the city.

Ready to find your ideal home in Charlestown? Browse our updated listings today to explore available properties. Start your search now and stay connected with the latest updates on Charlestown’s single-family housing market!

At MA New Listings | Coldwell Banker, we take pride in helping clients find the perfect Cambridge, MA homes for sale to fit their lifestyle. Whether you’re searching for a historic property, a modern condo, or a family-friendly home, our expert team is here to guide you through the process. Contact us today to browse our listings and start your journey to your dream home.

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