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$1,895,000
4 Beds ⋅ 4 Baths ⋅ 73582480 MLS
The one you have been waiting for! Here is your chance to own a picture-perfect 4 bed/3.5 bath single family with TWO car garage parking. Ground-up construction by one of Charlestown’s premier builders, this flawless property provides everything you could ask for, and then some. Step into luxury-level living with incredible natural light, three sides of exposure, an idyllic floor plan, and designer finishes throughout. Magazine-quality kitchen features floor-to-ceiling cabinetry, professional-grade appliances, built-in breakfast bar, and direct access to formal dining. Oversized living room (suitable for a suburban sectional!) is the ideal space to relax or entertain. Primary suite is out of a magazine—offering room for a king-size, bow window with reading nook, walk-in closet, and custom bath featuring double vanity & frameless glass shower. Large and dimensional guest beds, with dedicated full baths, are optimal for the growing family. Ample space for home office and/or gym. Enjoy the seasons on your private balcony and expansive, fully enclosed stone patio—perfect for alfresco dining and entertaining guests. A truly rare opportunity just steps to everything Charlestown has to offer!

44 Sackville St, Boston

Listing courtesy of Listing Agent: Adam Geragosian from Listing Office: William Raveis R.E. & Home Services.
$1,799,000
3 Beds ⋅ 4 Baths ⋅ 73582323 MLS
Located on a charming side street in the heart of Charlestown, this exceptional 3-bedroom, 3.5-bath home with off-street parking offers the space and feel of a single-family residence with the convenience of city living. The main level features an open-concept living, dining, and kitchen area with custom cabinetry, stainless steel appliances, and a commercial-style Thermador range. Sliding doors lead to a private, fenced-in patio—ideal for entertaining. The lower level offers a versatile bonus family room, home office or gym space, full bath, and laundry, providing excellent additional living space and storage. Upstairs, the spacious primary suite is filled with natural light and features a walk-in closet and luxurious en-suite bath with a tub, large frameless step in glass shower, and double vanity. The top floor includes two generously sized bedrooms, one with a built-in Murphy bed and desk, plus a renovated full bath with double vanity. Additional highlights include central A/C, hardwood floors, and abundant storage throughout. Offering a flexible layout, private outdoor space, and off-street parking, this home combines the feel of a single-family residence with the convenience of being close to everything Charlestown has to offer.

6 Franklin St Unit 2, Boston

Listing courtesy of Listing Agent: Martha Toti from Listing Office: Coldwell Banker Realty - Boston.
$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.
$2,100,000
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.
$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.
$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.

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