Charlestown Real Estate

Coveted 3BR, 2.5BA townhouse at The Nautica offering 3 levels of living, 2 private outdoor spaces & 2 deeded garage parking spaces. Recently renovated & beautifully refreshed, this sun-filled 1804 sq. ft. home features hardwood floors, a spacious fireplace living room and an open kitchen with large island, breakfast bar & direct access to a private brick patio. The 2nd floor offers 2 generous bedrooms, full bath, laundry & flexible home office space. The entire top floor is a private primary suite with vaulted ceilings, sitting area, oversized walk-in closet, en-suite bath & private deck with Boston skyline views. An exceptional combination of space, outdoor living & parking in Charlestown's desirable waterfront neighborhood, moments to the Marina, North End, restaurants, shops & downtown Boston.

64 Constitution Rd Unit 64, Boston

Listing courtesy of Listing Agent: Jane Reitz from Listing Office: Reitz Realty Group.

$1,110,000

3 Beds ⋅ 2 Baths ⋅ 73574831 MLS ⋅ ['South Crescent Condominium'] BLDG.

Gleaming hardwood floors and and a fireplaced livingroom highlight this 3 br , 2ba first floor duplex unit ideally located in Charlestown’s historic Gas Light District. In a solid 1987 brick building designed to blend in seamlessly with its 18th century neighbors, 17 Main St boasts its own private entrance, new stainless steel appliances, ample closet space, and modern conveniences like in-unit laundry and central air conditioning. Imagine a quiet Saturday morning coffee on your own deck. Across the street is John Harvard Mall; around the corner is City Square, and just steps away are TD Garden, the historic North End, and Whole Foods. Or explore stalwart hotspots like Warren Tavern and Prima Boston, both under a minute from your front door. A rare opportunity in a top notch location.

17 Main St Unit 17, Boston

Listing courtesy of Listing Agent: Charles Ball from Listing Office: Berkshire Hathaway HomeServices Commonwealth Real Estate.

$2,399,000

3 Beds ⋅ 4 Baths ⋅ 73574728 MLS

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.

$2,399,000

3 Beds ⋅ 4 Baths ⋅ 73574730 MLS

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.

$1,445,000

2 Beds ⋅ 3 Baths ⋅ 73574591 MLS

Rarely available penthouse duplex with 2 car garage parking! Located within Charlestown's most desirable building and premier location, this fully renovated and picturesque 2 bed/2.5 bath provides an idyllic floorplan with great natural light and designer finishes throughout. Large and dimensional living room features a framed wood fireplace & hand-crafted shelving. Modern kitchen with custom cabinetry, oversized center-island, professional grade appliances, and adjacent formal dining. Primary bed offers space for a king-size, walk-in closet, and spa-like bath with quartz vanity & river-stone frameless glass shower. Spacious guest bed with double closets and dedicated full bath. Enjoy all seasons on the newly renovated courtyard! Additional common areas: well-appointed gym, clubroom, elevator, and sitting cupola with most breathtaking views of Boston. Central AC. Laundry in-unit. A truly special opportunity just steps to the North End, TD Garden, and all restaurants/shops Charlestown has to offer!

47 Harvard St Unit B403, Boston

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

$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.

$1,600,000

4 Beds ⋅ 2 Baths ⋅ 73574480 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.

$1,895,000

3 Beds ⋅ 2 Baths ⋅ 73574175 MLS ⋅ ['295 Bunker Hill Street Condomium'] BLDG.

Perched high above historic Charlestown, this exceptional 1874 residence blends period craftsmanship with modern comfort. Restored in 2000 as part of This Old House TV show’s landmark Charlestown renovation, the home features 12’ ceilings, oversized windows with three exposures, crown moldings and restored hardwood floors. The elegant dining room offers wainscoting and original built-ins, while the renovated kitchen features cherry cabinetry, granite counters, stainless appliances and breakfast bar. A dramatic family room showcases a bay window, white marble mantel and wood-burning fireplace. Two bedrooms plus adjacent office provide a flexible second-floor layout. Exceptional outdoor spaces include a kitchen balcony, private garden patio and spectacular roof deck with 360° city and harbor views, sunsets and Boston fireworks—a rare combination of historic character, natural light and outdoor living.

295 Bunker Hill St Unit 2, Boston

Listing courtesy of Listing Agent: Richard K. Hollander from Listing Office: Coldwell Banker Realty - Hingham.

$649,900

2 Beds ⋅ 1 Baths ⋅ 73574130 MLS

Perched on the top floor, this sun-filled penthouse offers a bright and inviting layout in the heart of Charlestown. The two-bedroom home features soaring ceilings, hardwood floors, recessed lighting, two classic bay windows, an eat-in kitchen, and freshly painted interiors. The second bedroom is smaller in scale and ideally suited for a child’s room, nursery, home office, or other flexible use.Recent updates include a newer boiler and hot water heater, both installed in 2019, along with most windows replaced in 2020. The association is also completing a brand-new roof and roof deck, offering impressive views across historic Charlestown and the Boston skyline. An updated bathroom, basement storage, and free laundry in the building shared between just three units add to the convenience of this well-maintained home, all complemented by a low HOA fee.

118 High Unit 9, Boston

Listing courtesy of Listing Agent: Leah Tringale from Listing Office: Longwood Residential, LLC.

$679,000

1 Beds ⋅ 2 Baths ⋅ 73574079 MLS

Sophisticated and beautifully renovated, this oversized 1 bed, 1.5 bath Charlestown condo blends historic character with modern comfort on a picturesque tree-lined street just .4 mile from Bunker Hill Monument. The warm, inviting living room features pumpkin pine floors, high ceilings with crown molding, custom built-ins and a working wood stove that adds charm and character. The well-appointed kitchen offers granite countertops, new stainless steel appliances and gas cooking, with a designated dining area ideal for entertaining. Step outside to your private deck for morning coffee or al fresco dining. The spacious primary bedroom includes an en suite bath, while a convenient half bath for guests and private basement storage add to the home’s functionality. Ideally situated near Charlestown’s shops, restaurants, neighborhood favorites and public transportation, this inviting home offers a wonderful combination of space, character and city convenience.

35 Mystic St Unit 1, Boston

Listing courtesy of Listing Agent: Georgia Balafas from Listing Office: Corcoran Property Advisors.

$699,000

2 Beds ⋅ 2 Baths ⋅ 73573507 MLS

Beautifully situated in the heart of Charlestown, this inviting two-bedroom home offers a thoughtfully designed layout with all main living space conveniently located on one level. The first-floor condo features comfortable living areas and easy access to an expansive heated lower level, offering approximately 300 square feet of exclusive-use bonus space plus a third bathroom. Not included in the listed square footage, this versatile space is ideal for a playroom, home office, gym, guest area, or additional living space. Ideally located just moments from Waverly Square and all that Charlestown has to offer, including shops, restaurants, parks, and neighborhood amenities.

209 Bunker Hill St Unit 1, Boston

Listing courtesy of Listing Agent: Reig & Losordo from Listing Office: Coldwell Banker Realty - Boston.

$970,000

2 Beds ⋅ 2 Baths ⋅ 73573274 MLS ⋅ ['33 Winthrop Street Condominium'] BLDG.

This beautiful, 2BR/2BA, home is well located in a stately brick townhome a few buildings down from historic Training Field Park, in the heart of Charlestown’s gas light district. The layout, functionality and entertaining flow of this home are highlights. An elegant entry hall flows into a well-appointed kitchen with stainless appliances, granite countertops and maple cabinetry; and overlooks the spacious and open living/dining area. The ample sized guest bedroom offers two windows facing the patio and is serviced by a full bath just across the hall. A sunny private patio area offers both front and rear exterior egress; convenient for bikes or gardening supplies. The serene primary bedroom is tucked at the rear of the home offering privacy, ample closet space, and en-suite bathroom w/shower. Additional features include central air, private enclosed storage room, and wonderful access to local shops, restaurants, parks, transportation and downtown Boston. The Samuel Wilson House c.a. 1868.

33 Winthrop Street Unit 1, Boston

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

Charlestown Real Estate

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