Charlestown Homes for Sale

Charlestown Homes for Sale

Welcome to Charlestown, one of Boston's most historic and vibrant neighborhoods! Nestled along the banks of the Mystic River, this charming enclave is known for its rich maritime heritage and stunning views of the iconic Boston skyline. With its cobblestone streets, beautifully preserved 19th-century architecture, and a tight-knit community feel, Charlestown offers a unique blend of old-world charm and modern convenience.

As a resident of Charlestown, you’ll enjoy easy access to a plethora of amenities, including trendy shops, eclectic dining options, and lush parks. The neighborhood is home to the renowned Bunker Hill Monument, the USS Constitution, and the picturesque Charlestown Navy Yard, making it a haven for history buffs and outdoor enthusiasts alike. With its proximity to downtown Boston and excellent public transportation options, commuting is a breeze, allowing you to experience all that the city has to offer while retreating to the serene atmosphere of Charlestown.

For those looking to make Charlestown their home, there are a variety of homes for sale that cater to diverse tastes and lifestyles. From charming brownstones and modern condos to spacious single-family homes, you’ll find properties that reflect the neighborhood’s character and appeal. Whether you're a first-time buyer or seeking a family home, Charlestown’s real estate market is thriving, offering opportunities for everyone.

Explore the charm of Charlestown today and discover why so many are drawn to call this remarkable neighborhood home. With its rich history, vibrant community, and stunning homes for sale, Charlestown is the perfect place to start your next chapter!

Newest Charlestown Homes for Sale

$1,499,000
3 Beds ⋅ 4 Baths ⋅ 73582257 MLS
A fully renovated, single family home in Charlestown! This house offers 4 levels of thoughtfully designed living space. The main floor features an open floor plan anchored by a large kitchen island, perfect for every-day living. Find a half bath on this level for added convenience. On the 2nd level there are two generous sized bedrooms, a bathroom with a tub and a laundry closet. Upstairs is the primary suite, large enough to include a work from home space or secondary hang out area. The finished lower level provides a flexible bonus space to be used as a media/man cave, kids playroom, additional home office or gym and inclusive of another half bath. Step outside to your private deck and patio, perfect for outdoor dining, entertainment or relaxing. Additional features include; an abundance of storage space, tons of natural light and central ac. Live just minutes from Hood Park, many restaurants/coffee shops and all that Charlestown has to offer!

39 Essex St, Boston

Listing courtesy of Listing Agent: The Goodrich Team from Listing Office: Compass.
$1,975,000
3 Beds ⋅ 3 Baths ⋅ 73582095 MLS
Rarely available and checking all the boxes, this renovated single-family home offers an expansive 1965sf of living space across three thoughtfully designed levels, 3 bedrooms, 3 full bathrooms, garage parking and two private outdoor spaces. Enter through the front door or directly from the garage to a versatile den, ideal for a home office, gym or additional living space, with a full bathroom and sliding glass doors opening to a back yard with private patio. Upstairs, the recently renovated kitchen features an oversized island, custom cabinetry, a striking tile backsplash and high-end appliances, along with a sun-drenched bay window framing the dining area. The kitchen overlooks a spacious front-facing living room with custom built-ins and a gas fireplace, while windows at both ends fill the entire level with natural light. The upper floor features a primary suite with another beautiful bay window and ensuite bathroom, two additional bedrooms and a conveniently located full bathroom. Crowning the home is a private roof deck with panoramic views. An additional unfinished basement provides excellent additional storage. A truly complete Charlestown offering combining space, style, parking and exceptional outdoor living.

11 Woods Place, Boston

Listing courtesy of Listing Agent: Tracy Shea from Listing Office: Coldwell Banker Realty - Boston.
$2,699,000
3 Beds ⋅ 4 Baths ⋅ 73581324 MLS
Set in Charlestown’s coveted Gaslight District on Pleasant Street, this stately single-family home offers approximately 3,002 square feet across four beautifully finished levels. A classic façade with three distinctive gabled dormers gives way to an impressive interior blending historic character with refined modern finishes. The main level is designed for both everyday living and entertaining, featuring a spacious living and dining area, exposed brick, custom built-ins and a stunning chef’s kitchen with marble countertops and backsplash, Sub-Zero refrigeration, Thermador range and hood, and an oversized island. Just beyond, a private patio creates a seamless extension of the living space outdoors. Three generously sized bedrooms each feature their own en-suite bathroom, while the expansive top-floor primary suite offers exceptional privacy with a large walk-in closet, beautifully appointed marble bath and additional private balcony. A dedicated office with custom built-ins and a finished lower provide additional flexibility. An exceptional Charlestown home offering remarkable space, quality and location just moments from the Monument, Main Street, waterfront and Downtown Boston.

32 Pleasant Street, Boston

Listing courtesy of Listing Agent: Tracy Shea from Listing Office: Coldwell Banker Realty - Boston.
$770,000
1 Beds ⋅ 2 Baths ⋅ 73579400 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), all new Anderson windows (2024), custom window treatments, a new oven (2025), a new hot water heater (2026), fresh paint throughout, 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.
$3,800,000
5 Beds ⋅ 4 Baths ⋅ 73578963 MLS
Extraordinary Location directly on the Training Field! Step into a piece of living history with this magnificent, single family masterpiece located in the heart of historic Charlestown. One garage parking space included! Originally constructed in 1800 as the legendary Old Salem Turnpike Hotel, this rare property seamlessly blends centuries of architectural heritage with the outstanding updates for sophisticated modern living. Boasting an impressive 3,578 square feet of meticulously maintained space, this grand 12-room estate offers an unparalleled lifestyle just across from the Training Field and minutes to downtown Boston. Boasting 4-5 Bedrooms and 4 full baths, plus a library, family room, and sunroom, it spreads comfortably across multiple stories. Expansive formal first floor living room, dining room, and gourmet kitchen! Enormous sun-filled yard is a gardener's paradise! Flexible floor plan for any lifestyle! This home retains its grand presence, timeless wood-siding exterior, and striking architectural character. Amazing intact wide-plank pine flooring throughout, plus multiple period fireplaces, one in almost every room! Perfect for New England winters. Situated on a generous 3,485 sq. ft. parcel, this home offers a rare blend of historic neighborhood charm and private outdoor space. Multi-zone heating and central air, plus premium updates throughout, ensure effortless comfort without sacrificing historic integrity. Located in one of Boston’s most coveted and historic enclaves, it offers top-tier convenience. Close to vibrant local dining, boutique shopping, and the historic Charlestown Navy Yard. Enjoy seamless access to the visual charm of gas-lit streets and quick transit to downtown Boston. This is a true once-in-a-generation legacy property. By appointment only.

16 Common Street, Boston

Listing courtesy of Listing Agent: Frank Celeste from Listing Office: Gibson Sotheby's International Realty.
$1,800,000
3 Beds ⋅ 3 Baths ⋅ 73578918 MLS
Tucked off Monument Square on a gas-lit private way, this beautiful, 3+BR/2.5BA, single family home features 1,925+/- sf, an ideal open layout, sunny corner exposure and 1 car parking. The main level features an open concept “great” room with elegant living room with gas fireplace, with handsome white mantel, crown molding, and freshly sanded hardwood floors; an updated chef’s kitchen with white shaker cabinetry, quartz countertops, brand new stainless appliances, including gas range; and dining space with glass slider to a large private deck. Two generous bedrooms, each with corner exposure, and a well-appointed full bath with tub/shower make up the second level. A spacious and loft-like primary bedroom is located on the top level and features two sets of double closets and an updated full bath with glass enclosed shower with stone surround and white quartz-topped vanity. It also provides the perfect nook for a home office. The finished lower level offers a playroom/media room space, a half bath, storage, laundry center and direct egress to parking. This home is located close to everything Charlestown has to offer, including wonderful parks, shopping, restaurants and transportation, and the tucked away location gives it a suburban feel.

4 Concord Avenue, Boston

Listing courtesy of Listing Agent: Nancy Roth from Listing Office: Gibson Sotheby's International Realty.
$1,999,995
3 Beds ⋅ 3 Baths ⋅ 73578652 MLS
Beloved Historic Training Field/ Winthrop Square Location - Sunny and spacious three bedroom, two and half bath home offers a roofdeck with city views, a deck off the kitchen, and a juliet balcony. Enter from Park Street or Common Street to an open, combination floorplan of living room with wood floors and a gas fireplace, which connects to the dining room with a bay window overlooking the Training Field, plus a wall of three French doors for added light. The kitchen with gas cooking has direct access to an enclosed deck for outside enjoyment and entertainment. The first floor powder room and coat closet add to ease of living. The second floor bedroom/office has a French Door to a juliet balcony overlooking the park, and ample closet space. A hall Library off of the second corner bedroom, and a full bath, complete the second floor. The top floor showcases a Main Bedroom Suite with 7 windows with views overlooking the Training Field and city, a glimpse of the USS Constitution masts, with light from three sides, plus a walk-in closet/dressing room and a full bathroom. The hallway spiral staircase leads to a roofdeck with expansive sky, city and park views. The lower level offers an unfinished basement plus a laundry room, and ample storage. Garage parking available for rent nearby. Close proximity to the bus and walking to Boston and Charlestown restaurants and shops.

56 Park Street, Boston

Listing courtesy of Listing Agent: Diane Valle from Listing Office: Boston Portfolio Properties, LLC.
$2,899,000
5 Beds ⋅ 4 Baths ⋅ 73578129 MLS
Situated across from Monument Square, this beautifully designed 5 bedroom, 3.5 bathroom single-family home offers expansive living space with sophisticated finishes throughout. A grand marble foyer sets the tone, leading to an elegant living room with high ceilings, custom built-ins, detailed millwork and hardwood floors. The stunning kitchen features a large island, Wolf range, Viking refrigerator, floor-to-ceiling cabinetry and custom lighting, opening to a sun-filled dining area with corner exposure and direct access to a large fenced patio. Upstairs, the generous primary suite offers a separate office, walk-in closet and beautifully appointed bathroom with double vanity and glass-enclosed shower. Four additional bedrooms and two full guest bathrooms provide exceptional flexibility. A partially finished basement offers additional space for a family room, gym or playroom. An exceptional Charlestown home combining scale, thoughtful design and a premier location.

4 Concord Street, Boston

Listing courtesy of Listing Agent: Tracy Shea from Listing Office: Coldwell Banker Realty - Boston.
$2,100,000
6 Beds ⋅ 3 Baths ⋅ 73577599 MLS
Exceptional 4-story Charlestown residence offering 6 bedrooms, substantial living space, private outdoor space, and elevated Boston-area views. Set nearly 15 feet above Cambridge Street, this south-facing red-brick home offers an uncommon combination of privacy, natural light, and scale in one of Boston's most desirable neighborhoods. The remodeled kitchen and dining area feature rich mahogany cabinetry, premium marble surfaces, and elegant gold accents, while the spacious living room provides an inviting setting for everyday living and entertaining. The remodeled primary bath includes a Jacuzzi tub and smart bidet. Outside, a fenced yard and expansive newly paved patio create a private retreat for dining and entertaining. The remodeled second-floor balcony captures views of the illuminated Encore Boston Harbor and Boston skyline. Conveniently located near Sullivan Square and Assembly, with easy access to downtown Boston, dining, shopping, and transportation. A truly special Charlestown home offering exceptional flexibility, character, and city living. First showings Friday, Sep 18 5:00-6:30.

21 Parker St, Boston

Listing courtesy of Listing Agent: The Optimium Team from Listing Office: eXp Realty LLC - Corporate Office.
$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.
$1,600,000
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.
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