Charlestown Homes

$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.
$1,799,000
3 Beds ⋅ 4 Baths ⋅ 73582226 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.
$1,975,000
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.
$825,000
2 Beds ⋅ 1 Baths ⋅ 73581413 MLS
Just two blocks from Monument Square, this charming 2 bedroom, 1 bathroom home offers 941 square feet of living space filled with classic Charlestown character and original architectural details. A bright, front-facing living room with corner exposure features original wide-plank pumpkin pine floors and a marble-surround wood-burning fireplace. Oversized classic pocket doors open to the dining room, highlighted by an additional marble mantel, custom built-in cabinetry, and direct access to the private outdoor space. The outdoor area includes a deck, patio and additional extended garden space. The kitchen is tucked toward the rear of the home with exposed brick accents, while high ceilings, crown moldings, original wood floors and period details carry throughout. The primary bedroom enjoys corner exposure and abundant natural light, with a second bedroom providing valuable flexibility for guests, a home office or additional living space. A quintessential Charlestown home in an ideal location just moments from Monument Square.

34 Bartlett Street Unit 1, 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 ⋅ 73580012 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 Charlestown'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, 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.
$1,050,000
2 Beds ⋅ 2 Baths ⋅ 73579458 MLS
Rare, Spectacular Residence in a Beautiful Historic Building — gut-rehabbed and masterfully rebuilt in 2016!This gorgeous 2nd floor, 2-bedroom, 2-bath floor-through unit is a true showstopper, offering a sophisticated blend of classic architectural details and open-concept living. Entertain in style in the fireplaced living room, featuring custom built-ins, surround sound speakers, raised panel wainscoting, cornice moldings, and oversized windows that flood the space with natural light.The gourmet kitchen is a chef's dream, boasting high-end stainless steel appliances, gleaming granite counters, an x-large breakfast bar, a wine fridge, and abundant cabinetry. The formal dining area with banquette seating is perfect for intimate dinners or lively gatherings.Retreat to the primary suite, complete with generous closet space and a spa-like bath finished in luxurious Carrara marble, with basketweave floors and matching shower tiles. The oversized second bedroom is served by a beautifully appointed guest bath finished in honed travertine.Step outside to your own entertainment-sized private deck — sun-drenched all day and outfitted with built-in gas and water lines, ideal for al fresco dining, morning coffee, or evenings under the stars.This move-in-ready home is complete with every modern amenity: central air, in-unit laundry, a Nest thermostat, a 2025 water heater, and extra deeded storage. Common roof replaced on 9/10/2026, offering true peace of mind for years to come.Perfectly situated on a pretty, quiet, gas-lit street, this residence puts you moments from public transportation, Whole Foods, boutique shopping, top-rated dining, entertainment, and the historic Bunker Hill Monument.Don't miss this rare opportunity to own a sophisticated, turnkey home in the heart of historic Charlestown!

21 Salem St Unit 2, Boston

Listing courtesy of Listing Agent: Elena Kac from Listing Office: William Raveis R.E. & Home Services.
$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.
$1,725,000
2 Beds ⋅ 3 Baths ⋅ 73578966 MLS
Sun-filled Penthouse with Private Roof Deck Plus Parking on Highly Desirable Mt. Vernon Street in Charlestown! Stunning 1595 SF Upper Duplex in a beautifully maintained brownstone! Entertainer's dream layout with enormous front-facing living room, dining area and updated chef's kitchen. Viking appliances, high end cabinetry, breakfast island and long runs of stone counters make this a truly impressive and functional space! California King Sized Primary bedroom with bay windows, oversized closet and en-suite bathroom in the rear of the first level. Additional half bathroom off the kitchen. Second level is the perfect home sanctuary and the layout lends to so many options! Kitchenette area next to your massive private roof deck with arguably the best views in Charlestown will be a hit with all! Ideal for a work-from-home space or additional den area plus a second bedroom and an additional full bathroom! Central air, in-unit laundry, towering ceilings, and sparkling hardwood floors throughout, plus the building has a new roof! Wonderful value!

30 Mt. Vernon Street Unit 3, Boston

Listing courtesy of Listing Agent: Frank Celeste from Listing Office: Gibson Sotheby's International Realty.
$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.
$860,000
2 Beds ⋅ 1 Baths ⋅ 73578274 MLS ⋅ ['2 Monument Square Condominium'] BLDG.
Located in a stately brick townhouse on the front corner of Monument Square, close to Training Field Park, this garden level, 2BR/1BA, condo offers 946sf of well-appointed living space. The spacious and open living/dining room features views to the front garden, custom built-in bookshelves, crown molding, and an exposed brick wall with inset arch. The roomy chef’s kitchen overlooks the patio, with wrap-around cherry cabinetry, wine rack, stainless appliances, including a gas range, and a walk-in pantry/laundry room with great storage. The primary bedroom w/double wide closet and large window overlooks the patio and is tucked at the rear for privacy. A full bathroom w/tiled shower with bench seat and white vanity is just outside the door. A generous second bedroom features crown molding, a doublewide closet, and two windows. This condo offers direct egress to a beautiful, enclosed common patio w/grill and dining space – perfect for entertaining and al-fresco dining. Amenities include: central air conditioning, in-unit W/D, gleaming hardwood floors, and large private storage closet just outside the unit door.

2 Monument Square Unit 1, Boston

Listing courtesy of Listing Agent: Nancy Roth from Listing Office: Gibson Sotheby's International Realty.
$775,000
1 Beds ⋅ 1 Baths ⋅ 73578230 MLS ⋅ ['Warren Court Condominium Trust'] BLDG.
This spacious and freshly updated, 1BR/1BA, second floor condominium is located in the heart of Charlestown’s gas light district, featuring a sunny, southwest, corner exposure and a deeded parking space. The elegant living/dining room features a wood burning fireplace with a handsome white mantle, flanked by custom built-in shelving and cabinetry, and a double wide custom coat and storage closet. A bay window provides the perfect dining nook with drum shade lighting. Just off the living area is a well-appointed kitchen with white shaker cabinetry, quartz countertops and brand new stainless steel appliances, including a 5-burner gas range with griddle. The newly renovated full bathroom features a marble tile floor, white vanity w/marble top, glass fronted medicine cabinet and white subway tiled shower w/marble tile floor and glass doors. The oversized bedroom is tucked at the rear for privacy and offers a double wide custom closet, plenty of space for a home office, and additional closet w/brand new washer/dryer. Newly finished hardwood floors throughout give the space a fresh feel. Amenities: private deck with Monument views, in-unit W/D, central air conditioning, deeded parking space and professional management.

1 Pleasant Street Unit 3, Boston

Listing courtesy of Listing Agent: Nancy Roth from Listing Office: Gibson Sotheby's International Realty.
$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.
$799,000
2 Beds ⋅ 2 Baths ⋅ 73577307 MLS
This beautifully maintained 2 bedroom, 1.5 bathroom duplex home offers a private entrance, two private outdoor spaces and a thoughtfully designed layout across two floors. The bright and open living level features hardwood floors, abundant natural light and a seamless flow between living and dining areas. The spacious kitchen is appointed with white cabinetry, stainless steel appliances, generous counter space and a marble-topped island, which is included in the sale. Off the kitchen there is a conveniently located powder room and sliding glass doors that open directly to a private deck with a grill connected to a plumbed gas line that is also included. The bedroom level features two well-proportioned bedrooms, a full bathroom, in-unit laundry and excellent closet space, with the primary bedroom offering direct access to a second private outdoor space. Additional highlights include central air and ample storage throughout. Ideally situated in Charlestown with easy access to neighborhood shops, restaurants, parks, public transportation and Downtown Boston.

126 Elm Street Unit 2, Boston

Listing courtesy of Listing Agent: Tracy Shea from Listing Office: Coldwell Banker Realty - Boston.
$1,799,000
3 Beds ⋅ 3 Baths ⋅ 73575423 MLS
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 ⋅ 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.
$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.
$999,000
2 Beds ⋅ 2 Baths ⋅ 73573211 MLS
Located in the heart of Charlestown’s coveted Gas Light District, this stunning recently renovated 2-bedroom plus office, 2-bath residence offers exceptional space, thoughtful design, and high-end finishes throughout. The main level features soaring ceilings and two oversized bedrooms, including a spacious primary suite with a generous walk-in closet, en-suite bath, and in-unit laundry. Downstairs, the home opens to a bright, expansive living, dining and kitchen area, creating a comfortable setting for both everyday living and entertaining. The kitchen is outfitted with top-of-the-line appliances and beautifully selected finishes, while a second full bath, dedicated office nook, and defined entry space add functionality. A private entrance, deeded parking, extra spacious additional basement storage, and low monthly HOA provide added convenience. Ideally positioned on an extremely private dead end street with very little traffic, near Charlestown’s restaurants, cafes, shops, and waterfront, this is a truly special opportunity in one of Boston’s most sought-after neighborhoods.

74 Washington St Unit 1, Boston

Listing courtesy of Listing Agent: The Goodrich Team from Listing Office: Compass.
$1,499,000
3 Beds ⋅ 2 Baths ⋅ 73573139 MLS
3 BEDROOMS + OFFICE w/ PARKING + OUTDOOR SPACE Bright, spacious, and beautifully renovated, this 1,430 SF 3+ bedroom, 2 bath condo offers an exceptionally wide and livable layout in the heart of Charlestown. Featuring three exposures and an abundance of windows, natural light pours into every room throughout the day. Gut renovated in 2022, the home combines modern finishes with thoughtful design. The open-concept living, dining, and kitchen area is ideal for both everyday living and entertaining. Three generous bedrooms plus a dedicated office provide exceptional flexibility for today's lifestyle. Enjoy seamless indoor-outdoor living with a private deck complete with a direct gas line for grilling. Additional highlights include a full parking space with direct access, private storage, and a basement gym. A rare opportunity to own a turnkey home with space, light, and amenities.

322 Bunker Hill St Unit 2, Boston

Listing courtesy of Listing Agent: Reig & Losordo from Listing Office: Coldwell Banker Realty - Boston.
$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.
$1,995,000
3 Beds ⋅ 2 Baths ⋅ 73572980 MLS ⋅ ['The School House On Monument'] BLDG.
Designed by Graham Gund Architect, experience unparalleled luxury at The Schoolhouse, ideally situated on Monument Square overlooking the "Bunker Hill Monument". This home is the second largest in the building. Thoughtfully renovated 2 years ago, this exceptional corner 3-bedroom, 2-full-bath residence seamlessly blends architectural grandeur with modern sophistication. Soaring 13-foot ceilings, expansive windows, gleaming hardwood floors, and abundant natural light create a remarkable sense of space and scale throughout. The bright and gracious corner living and dining area offers an elegant setting for both everyday living and entertaining. The open eat-in chef’s kitchen is beautifully appointed with custom cabinetry, updated countertops, a striking custom tile backsplash, premium Wolf oven with induction cooktop, and Sub-Zero refrigerator. The spacious front-facing primary suite features a picturesque window seat, two generous closets, and a beautifully appointed en-suite bath with glass-enclosed walk-in shower. Two additional sunny bedrooms share a well-designed full bath with tub. Central air and in-unit laundry add to the comfort and convenience of this impeccable home. A professionally managed elevator building with package room, dedicated garage parking space, private storage, and an unbeatable location just moments from Charlestown’s historic charm, shops, restaurants, and neighborhood amenities complete this truly exceptional offering.

30 Monument Square Unit 207, Boston

Listing courtesy of Listing Agent: Beth Dickerson from Listing Office: Gibson Sotheby's International Realty.
$817,000
2 Beds ⋅ 2 Baths ⋅ 73570370 MLS ⋅ ['Nautica'] BLDG.
Bright and spacious 2-bed/2-bath residence with garage parking at Nautica in historic Charlestown. This is a City of Boston - BPDA unit with specific income requirements. Inquire with listing agent for more details. This well-appointed home features an open-concept living and dining area with hardwood floors, gas fireplace, custom built-ins, and oversized windows offering abundant natural light and Navy Yard views. The kitchen includes stainless steel appliances, ample cabinetry, and a functional layout ideal for everyday living and entertaining. Generous primary suite with excellent closet space and sun-filled exposure. Spacious second bedroom perfect for guests, home office, or nursery. Additional features include central air, in-unit laundry, elevator access, and garage parking. Professionally managed elevator building with beautifully landscaped grounds. Buyer's income and assets subject to verification and approval by BPDA.

73 Chelsea St Unit 305, Boston

Listing courtesy of Listing Agent: Jesse MacDonald from Listing Office: Gibson Sotheby's International Realty.
$775,000
2 Beds ⋅ 2 Baths ⋅ 73570071 MLS
Welcome to this stunning 2 bed, 2 bath condo with a spacious layout and high-end finishes. The chef’s kitchen boasts quartzite counters, stainless steel appliances, a wine fridge, and an oversized island perfect for entertaining. Hardwood floors and high ceilings flow into a bright living room, while a custom breakfast nook framed by bay windows offers the ideal spot for morning coffee. The lower level features a king-sized primary suite, second bedroom, full bath, laundry, and generous storage. Enjoy private outdoor living with both a deck and patio, plus an additional storage area. Ideally located near Assembly Row, Sullivan Square T stop, and major highways—this home is a must-see!

25 Brighton St Unit 1, Boston

Listing courtesy of Listing Agent: Sarah Fillmann from Listing Office: Coldwell Banker Realty - Boston.
$2,299,000
4 Beds ⋅ 4 Baths ⋅ 73566537 MLS ⋅ ['56 Belmont Street Condo Association'] BLDG.
Discover unparalleled luxury in Charlestown, a stunning condominium residence with direct elevator entry that exemplifies amazing design and top-tier materials. This luxurious house is in great condition, ready for you to move in and enjoy. The heart of this home is undoubtedly the open floor plan kitchen, a culinary masterpiece boasting shaker cabinets crowned with elegant molding, and stone countertops that provide both beauty and durability. Cooking enthusiasts will appreciate the high-end range oven and stovetop, complemented by a wall chimney range hood and a built-in refrigerator. A large kitchen island offers ample space for preparation and casual dining, while a kitchen bar and wine cooler invite effortless entertaining. The backsplash adds a touch of artistry to this already impressive space. The living room offers a warm and inviting atmosphere, enhanced by a fireplace that serves as a focal point and intricate crown molding that adds a touch of sophistication. Garage arking

56 Belmont St Unit 2, Boston

Listing courtesy of Listing Agent: Herion Karbunara from Listing Office: Herion Karbunara.
$1,200,000
2 Beds ⋅ 2 Baths ⋅ 73562449 MLS ⋅ ['Chestnut Street Condominiums'] BLDG.
Absolutely Premier Location! Tree-lined and Gaslit Chestnut Street between the historic Training Field and Monument Square! A remarkable Home with a Garage Parking Space! Boutique style elevator building! Professionally managed. 2 Bedroom, 2 Bathroom residence with an impressive open Living room and dining room with a wood-burning Fireplace! Chef's kitchen with a large shelved pantry! Laundry in-unit! All systems and finishes are original and require updating or replacement. Come and renovate on your own and make this your perfect dream home. Exceptional floor plan for easy City living. The primary bedroom is enormous, with an en suite bathroom. Minutes from Everything in Charlestown & Boston! Bring your creative ideas to this ultimate blank canvas! A truly rare opportunity is that this residence can also be delivered totally renovated. Please contact the agent for more detailed information. Don't miss these outstanding options to be in the best location in town!

33 Chestnut Street Unit 104, Boston

Listing courtesy of Listing Agent: Frank Celeste from Listing Office: Gibson Sotheby's International Realty.
$774,000
2 Beds ⋅ 2 Baths ⋅ 73541180 MLS
Welcome to 273 Bunker Hill Street, a freshly updated Charlestown residence offering over 1,200 square feet of thoughtfully designed living space. This spacious 2 Bed +Den, 1.5 Bath home features a brand-new full bathroom, generous living and dining areas, abundant natural light, a flexible layout ideal for entertaining, working from home, or simply enjoying city living, and the added benefit of private outdoor space. Perfectly positioned in one of Boston's most historic and sought-after neighborhoods, you'll be moments from Pier 6, The Monument, Tatte, Dovetail, Prima, Warren Tavern, the Bunker Hill Monument, Harborwalk, neighborhood parks, and local boutiques. Commuters will appreciate convenient access to Downtown Boston, North Station, Cambridge, major highways, and public transportation. Combining size, updates, location, outdoor space, and lifestyle, 273 Bunker Hill Street presents an exceptional opportunity to enjoy the very best of Charlestown living.

273 Bunker Hill St Unit 1, Boston

Listing courtesy of Listing Agent: Waypoint Realty Group from Listing Office: Coldwell Banker Realty - Boston.
$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.
$1,175,000
3 Beds ⋅ 4 Baths ⋅ 73540015 MLS ⋅ ["D'apice Condominiums"] BLDG.
Built in 2013, this townhouse-style residence offers modern, low-maintenance living in one of Charlestown's most convenient locations. The sun-filled open-concept living, dining, and kitchen area is designed for everyday living and effortless entertaining, anchored by a kitchen featuring granite countertops, stainless steel appliances, and abundant cabinetry. Upstairs offers spacious bedrooms and well-appointed baths, while the finished lower level provides flexible space for a guest suite, home office, gym, media room, or extended living. A private rooftop deck, two deeded off-street parking spaces, and a 3-minute walk to Sullivan Square Station complete the package. Enjoy direct Orange Line access to North Station, Haymarket, Downtown Crossing, and Back Bay, nearby Green Line connections to Cambridge and Somerville, immediate access to both northbound and southbound I-93, and minutes to Assembly Row, Bow Market, Cambridge Crossing, Kendall Square, Logan Airport, and downtown Boston.

8 Brighton St Unit 1, Boston

Listing courtesy of Listing Agent: Jack Yang from Listing Office: Coldwell Banker Realty - Cambridge.
$795,000
1 Beds ⋅ 1 Baths ⋅ 73538234 MLS
Welcome home to this beautifully renovated, sun-drenched 1-bedroom, 1-bathroom residence offering the ultimate blend of historic Charlestown charm and sleek, modern luxury. Situated in the absolute best location in the neighborhood, this home defines turn-key living. The current owner has already meticulously completed every update you could possibly want, leaving nothing left for you to do but move in, unpack, and enjoy.

100 Main Street Unit 2, Boston

Listing courtesy of Listing Agent: Daniel Wang from Listing Office: Engel & Volkers Boston.
$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 ⋅ 73495408 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.
$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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