Charlestown Real Estate

Welcome to Charlestown, a vibrant and historic neighborhood nestled in the heart of Boston, Massachusetts. Known for its rich maritime history and stunning waterfront views, Charlestown is a unique blend of old-world charm and modern living. As one of the oldest neighborhoods in Boston, Charlestown boasts a captivating array of brick townhouses, cobblestone streets, and iconic landmarks, including the Bunker Hill Monument and the USS Constitution.

Charlestown’s location offers the best of both worlds: a tight-knit community atmosphere combined with easy access to the bustling city life of Boston. Residents enjoy a plethora of local amenities, from quaint cafes and boutique shops to scenic parks and recreational areas. The Charlestown Navy Yard, a historic site turned cultural hub, provides a perfect backdrop for leisurely strolls along the waterfront, while the nearby Charlestown Common offers green space for picnics and outdoor activities.

For families, Charlestown is an ideal place to settle down, with excellent schools and a strong sense of community spirit. The neighborhood hosts numerous events throughout the year, fostering connections among residents and creating a welcoming environment for newcomers.

With convenient public transportation options, including the T and ferry services, getting to downtown Boston or other surrounding areas is a breeze. Whether you’re looking to explore the rich history, enjoy the vibrant local culture, or simply relax by the waterfront, Charlestown is a neighborhood that truly has it all. Discover why so many are proud to call this charming community home!

Newest Listings in Charlestown

$798,000

1 Beds ⋅ 2 Baths ⋅ 73556988 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. Take advantage of the city's residential exemption to lower your taxes. All of this with no HOA!

4 Short Street Pl Unit 4, Boston

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

$899,900

2 Beds ⋅ 2 Baths ⋅ 73556897 MLS

Experience the charm of a converted historic schoolhouse in one of Charlestown's most sought-after neighborhoods. This sun-filled residence is defined by soaring ceilings, oversized windows, and timeless architectural details that create an impressive sense of scale throughout. The spacious living and dining areas offer exceptional flexibility for everyday living or entertaining, while the granite kitchen and dedicated home office provide both style and function. Enjoy sweeping skyline and harbor views from the common roof deck, along with easy elevator access and private storage. Ideally situated just moments from the Bunker Hill Monument, Navy Yard, Harborwalk, Spaulding Rehabilitation Hospital, North End, TD Garden, downtown Boston, public transportation, and major commuter routes, this home blends historic character with an unbeatable city lifestyle.

68 Baldwin Street Unit 43, Boston

Listing courtesy of Listing Agent: Paul Coleman from Listing Office: Lamacchia Realty, Inc..

$798,000

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.

$715,000

1 Beds ⋅ 1 Baths ⋅ 73555967 MLS

Tucked away in Charlestown’s City Square, this oversized one bedroom, one bathroom condo offers a rare blend of charm and modern updates. The bedroom features soaring ceilings and a charming loft, creating a flexible retreat perfect for additional storage, a reading nook, or a creative workspace. The freshly renovated bathroom is flooded with natural light. Open up the Juliette balcony skylight to enjoy fresh air and views, adding to the home's peaceful, tucked-away feel. Rich in character and thoughtfully updated, this one-of-a-kind residence offers the perfect balance of historic Charlestown charm and modern comfort.

21 Harvard St Unit 4, Boston

Listing courtesy of Listing Agent: Kerry D'Ambroise from Listing Office: Columbus and Over Group, LLC.

$700,000

2 Beds ⋅ 2 Baths ⋅ 73555889 MLS

This spacious, thoughtfully designed condo offers two levels of living in a professionally managed building. Soaring ceilings enhance the open-concept main level, where a well-appointed kitchen features white cabinetry, stainless steel appliances, granite countertops, a subway tile backsplash, and a peninsula with bar seating—perfect for casual dining and entertaining. The inviting living area includes a fireplace with custom built-ins, creating a warm and functional focal point. A convenient half bath is located just off the entry. Upstairs, the generous primary bedroom can fit a queen or king size bed and has excellent natural light. A separate loft-style room with a door and closet provides exceptional versatility—ideal for a guest space, home office, or additional sleeping area. The full bathroom is located next to both bedrooms. Don’t miss the in-unit laundry and central air conditioning!

356-358 Main St Unit 12, Boston

Listing courtesy of Listing Agent: Kerry D'Ambroise from Listing Office: Columbus and Over Group, LLC.

$1,100,000

73554761 MLS

Retail Condo in the heart of Charlestown! This street level space sits on the corner of High & Green Streets boasting 1,550 SF of excellent retail space plus an additional 800 SF of basement storage space available.

54 High St, Boston

Listing courtesy of Listing Agent: Whitney Gallivan from Listing Office: Boston Realty Advisors.

$2,199,000

3 Beds ⋅ 3 Baths ⋅ 73552745 MLS

Looking for more space? This townhouse-style condo offers three levels of thoughtfully designed living, featuring three bedrooms, private home office, and two and a half bathrooms—the perfect blend of comfort, functionality, and modern luxury. The open-concept main living level is ideal for both everyday living and entertaining, anchored by a chef's kitchen appointed with Sub-Zero and Wolf appliances, custom cabinetry, and high-end finishes. Expansive living and dining areas are filled with natural light. The primary suite is complete with a walk-in closet and a luxurious ensuite bath featuring a soaking tub. Two oversized bedrooms and a private home office offers the ideal work-from-home setup to round out the space. Don't miss the private roof deck and wet bar. The coveted garage parking and a private yard, this home offers the ease of townhouse living with the benefits of condominium ownership. Ideally located in historic Charlestown, you'll enjoy easy access to neighborhood restaur

237 Bunker Hill St Unit 237, Boston

Listing courtesy of Listing Agent: Kerry D'Ambroise from Listing Office: Columbus and Over Group, LLC.

$799,000

2 Beds ⋅ 1 Baths ⋅ 73550273 MLS

Historic charm, modern updates, and generous deeded PRIVATE basement storage come together in this beautifully renovated home, ideally located on one of Charlestown’s most coveted Gaslight District streets. The thoughtfully designed open-concept layout features a spacious living room and a stunning chef’s kitchen with a peninsula perfect for casual dining and entertaining. Two well-proportioned bedrooms and a stylish full bath offer comfortable living, while energy-efficient mini-splits provide year-round heating and cooling. Wake up to peaceful views of blooming hydrangeas from the rear bedroom, and enjoy two exceptional shared outdoor spaces: a beautifully landscaped garden and yard, plus a spectacular rooftop deck with sweeping city views. Just moments from everything Charlestown has to offer, including local shops, incredible restaurants, and the iconic Bunker Hill Monument. This is a must-see property!

17 Cordis Street Unit A, Boston

Listing courtesy of Listing Agent: Sarah Fillmann from Listing Office: Coldwell Banker Realty - Boston.

$649,999

1 Beds ⋅ 1 Baths ⋅ 73550028 MLS

Set on a picture-perfect block in Charlestown's Gas Light District, this brownstone residence blends historic character with thoughtful updates. Soaring high ceilings, pocket doors, and intricate crown moulding set an elegant tone throughout, while two marble decorative fireplaces anchor the living and bedroom spaces with old-world charm. The kitchen has been tastefully upgraded with quartz counters for a clean, modern feel that stands in easy contrast to the unit's period details. A flexible layout offers one bedroom plus a bonus room, ideal as a home office or walk-in-closet, and custom-built closets add smart, tailored storage throughout. The building was recently registered as historic, preserving the architectural integrity of the block for years to come. Outside, the unit comes with both roof deck rights and back deck rights. Steps to Monument Square, the neighborhood's best restaurants, and everything that makes this one of Charlestown's most sought-after enclaves.

19 Salem St Unit 2, Boston

Listing courtesy of Listing Agent: The Ali Joyce Team from Listing Office: Real Broker MA, LLC.

$530,000

1 Beds ⋅ 1 Baths ⋅ 73547047 MLS ⋅ ['Essex Towers Condominium'] BLDG.

One-bedroom condominium with bonus room and high ceilings. Exceptionally versatile, this home lives much larger than its square footage. The thoughtfully designed floor plan includes a spacious primary bedroom plus a separate room with a window and closet, currently used as a home office and guest space. The functional layout flows from the kitchen into the living room, creating comfortable everyday living. Additional features include central air conditioning, in-unit washer and dryer, and a pet-friendly association. Located in a professionally managed elevator building with direct elevator access from the lobby to the garden level. Conveniently situated near Charlestown's shops, restaurants, public transportation, and major commuter routes.

356-358 Main Street Unit 1, Boston

Listing courtesy of Listing Agent: Jayne Kramer from Listing Office: Engel & Volkers Boston.

$5,799,900

73545961 MLS

Rare Jewel APPROVED BY THE CITY OF BOSTON AS AN 8 UNIT BROWNSTONE CONDO PROJECT WITH PARKING FOR EVERY UNIT. One of the most sought after neighborhoods in Boston...dripping with the charm that defines Boston...surrounded by other Brownstones and located in this enchanting Monument Sq Neighborhood. Adorned with stunning views of the Boston Skyline. Two years in the making, this amazing project comes with plans and has already been approved. ORIGINAL STRUCTURE HAS 7100 SQ FT WITH 10,900 ADDITIONAL SQ FT IN THE APPROVED ADDITION. This exceptional design is comprised of multi level units with substantial city view roof decks. Appeal period has passed. Buyer will have to do own structurals, mechanicals & file for actual building permit. The vacant building features the original Brownstone along with a new addtion designed by KDI. Gross Sales Proformas are over $16 million. EVERY SINGLE UNIT HAS A NON TANDEM PARKING SPOT. Energy Code Compliance Opinion attached. ARCHITECT PLANS ATTACHED!

46 High St, Boston

Listing courtesy of Listing Agent: The Steve Bremis Team from Listing Office: Steve Bremis Realty Group.

$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..

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