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42 Harvard Street, Boston
$4,750,000
5 Beds ⋅ 5 Baths ⋅ UNDER AGREEMENT Status ⋅ 73590132 MLS ⋅ 4,000 SqFt.
Overlooking John Harvard Mall in Charlestown’s historic gaslight district, this handsome, 5+BR/4.5BA, bow front brick townhome, offers 4,000sf of living space and two covered parking spaces. Built circa 1875, the home was rebuilt from the brick façade inward in 2009/10, with all-new framing and major systems, then thoughtfully reimagined in 2024/25 for modern family living. The main level is open and filled with light, with living, dining, and kitchen spaces flowing together beneath crown molding and custom millwork. A gas fireplace with porcelain surround anchors the living area, and a multi-zone sound system carries music throughout. The chef’s kitchen centers on a large marble-topped island and is equipped with a new Thermador six-burner range with grill and double ovens, plus a Sub-Zero refrigerator. Oversized windows and skylights brighten the space, and a French door opens to a private side porch for outdoor dining and grilling. A powder room services this level. The entire second floor is reserved for the primary suite, w/dual walk-in closets and a spa-style bath featuring a freestanding soaking tub, double vanity, and oversized walk-in shower. The third-floor features two generous bedrooms w/dual custom closets; a dedicated home office, full bath, and laundry center. The fourth-floor adds a custom built-in library or study and guest suite. Above it all, the roof deck offers 360-degree views of Boston Harbor and the city skyline. The lower provides versatile living space: a media room w/wet bar and EuroCave wine refrigerator, a gym or au pair suite, an oversized mudroom w/heated floor, abundant storage, and second washer/dryer. A 2-car covered driveway is just off the mudroom. Historic character, modern systems, and a coveted location make this a turnkey Charlestown home.

42 Harvard Street, Boston
51 Chestnut Street, Boston
$2,500,000
4 Beds ⋅ 4 Baths ⋅ UNDER AGREEMENT Status ⋅ 73573036 MLS ⋅ 3,593 SqFt.
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
103 West Springfield Street, Boston
$3,495,000
4 Beds ⋅ 4 Baths ⋅ UNDER AGREEMENT Status ⋅ 73532800 MLS ⋅ 3,132 SqFt.
There is room for the whole family in this remarkably renovated home, a beautiful blend of modernism and original detail that is timeless. Built in 1856 for clipper ship sea captain Jeremiah White, there are 4 bedrooms, 3 and a half baths, original fireplaces, moldings and hardwood floors throughout. The eat-in kitchen with vented gas cooking is open to the dining/sitting area with direct access to the large patio for easy entertaining and grilling. The floor above has a sunny and spacious living room with a bay window and adjacent library with a built-in bar. The full-floor primary suite has a walk-in closet and gorgeous bath with twin vanities, WC, heated floors and large shower with a bench. The top floor has 2 bedrooms sharing a Jack & Jill bath with a tub and a laundry room. The garden level has a guest suite with a private entrance, a utility room and additional laundry room. There is a central heat pump HVAC system with 5 zones and 2 rental garage spaces just around the corner!

103 West Springfield Street, Boston
16 Chestnut Street, Boston
$2,850,000
4 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 73512592 MLS ⋅ 3,446 SqFt.
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
195 Chestnut Avenue, Boston
$1,680,000
4 Beds ⋅ 3 Baths ⋅ SOLD Status ⋅ 73389712 MLS ⋅ 2,249 SqFt.
Designed by renowned architect Luther Briggs, the character and allure of this 1858 Italianate Victorian are beyond words. Loved and pampered by its current owners for 37 years, every inch of 195 Chestnut has a story to tell. From its slate roof with owned solar panels to the 5-zone Buderus heating system, no expense has been spared and no detail overlooked to keep this home in its clearly impeccable condition. *DON'T MISS THE ATTACHED LIST OF ADDITIONS AND IMPROVEMENTS.* Open first floor with chef's kitchen, crowd-friendly dining room, brilliant cabinetry & storage solutions everywhere; energy-efficient wood stove w granite hearth. Hidden hatch to the basement. Upstairs, 3 generous bedrooms, exquisite full bath, custom wood shutters & a sweeping skylit staircase to the private top floor’s 4th bedroom, fitness room & sleek new bathroom. All windows restored & have Harvey storms; major house-wide renovations, including 3rd floor dormer, in 2008. And the front yard is a gardener's Eden!

195 Chestnut Avenue, Boston
30 Green Street, Boston
$2,385,000
4 Beds ⋅ 3 Baths ⋅ SOLD Status ⋅ 73382544 MLS ⋅ 2,550 SqFt.
This spacious, 4++BR/2.5BA, free-standing, single family home is well located near town center and Monument Square Park, and includes a separate 2,070sf lot with Cross Street access, creating a park-like backyard with lush gardens and expansive lawn. An elegant dining room w/wood burning fireplace, and corner exposure, flows into a chef’s kitchen w/fireplace, wrap around white cabinetry, granite countertops, and stainless appliances. A modern addition features a mudroom w/shiplap walls and a “great room” w/exposed beams and double French doors opening to a brick patio. The second level features a beautiful parlor room/BR w/wood burning FP, white marble mantel, soaring ceilings, and bay window. The Zen-like primary suite features a dressing room/office, en-suite full BA, custom walk-in closet, and spacious bedroom overlooking the garden, w/exposed beams, double closet, and private deck. Two generous bedrooms, a nursery/office, and a full bath with clawfoot tub complete the upper level.

30 Green Street, Boston
31 Monument Sq, Boston
$5,300,000
6 Beds ⋅ 6 Baths ⋅ SOLD Status ⋅ 73345406 MLS ⋅ 4,656 SqFt.
Perched atop Bunker Hill on the prestigious Monument Square, this exquisite trophy brownstone seamlessly unites historic elegance with contemporary comfort. A masterfully renovated single-family home, it showcases rich architectural details, intricate wainscoting, elegant woodwork, resplendent pocket doors, and marble fireplaces—all bathed in abundant natural light, courtesy of its unique corner lot location. Meticulously restored period details preserve the home’s timeless grandeur while blending seamlessly with modern upgrades.At the heart of the home, a chef’s kitchen boasts top-of-the-line appliances, while expansive living and dining areas provide an exceptional setting for entertaining. Generously sized bedrooms and thoughtfully curated amenities enhance everyday living, with the luxurious primary suite offering a spacious walk-through closet and a serene en-suite bath. A "Grand Dame" that also boasts modern infrastructure; this extraordinary property is truly one of a kind.

31 Monument Sq, Boston
36 Winthrop Street, Boston
$3,075,000
6 Beds ⋅ 7 Baths ⋅ SOLD Status ⋅ 73294864 MLS ⋅ 3,834 SqFt.
Discover this exceptional brick single-family home located on historic and sought-after Winthrop Square in Charlestown.This stunning residence, featuring 6 beds and 7 baths, underwent a complete renovation in 2020. Step into a bright living kitchen area adorned with expansive quartz countertops and island seating, flowing seamlessly into a dining room highlighted by a full wall of windows, plus an inviting bar area.The second floor boasts a luxurious primary suite with two walk-in closets and a spacious en suite bath, along with an additional bedroom featuring its own bath. On the third floor, find three more bedrooms, two full baths, and a rooftop deck with breathtaking monument views. A private staircase from first floor leads to additional bed with deck and bath, ideal for guests. The finished basement includes a large media room, gym, and ample storage.This home showcases meticulous attention to detail, with accent lighting, elegant moldings,skylights+designer wallpaper throughout.

36 Winthrop Street, Boston
39 Union Park, Boston
$10,200,000
5 Beds ⋅ 8 Baths ⋅ SOLD Status ⋅ 73273806 MLS ⋅ 6,830 SqFt.
Impeccably renovated and restored, 39 Union Park is a sophisticated townhome that masterfully combines classical detailing with contemporary elegance. Spanning over 6,800 sqft across 6 levels, the home offers 5 beds, 6 full + 2 half baths, alongside multiple expansive living and dining spaces perfect for entertaining or family life. A grand parlor level offers formal spaces and a butler’s pantry, while the upper family level features a custom kitchen with SubZero/Gaggenau appliances and a family room with rear deck. A full-floor primary suite provides unparalleled luxury and the top floor boasts two bedroom suites and laundry room. Lower levels offer a stunning guest suite, study/5th bed, and a garden-level entertainment area with full kitchen that seamlessly transitions to a tiered, landscaped garden. Designed with integrity and set in Boston's most vibrant neighborhood, 39 Union Park boasts generous proportions and views of the private park and fountains. Includes 1 garage pkg space.

39 Union Park, Boston
1 Harvard Place, Boston
$2,750,000
4 Beds ⋅ 4 Baths ⋅ SOLD Status ⋅ 73228964 MLS ⋅ 3,010 SqFt.
This spectacular Italianate brick, 4+BR/3.5BA, home features 3,000+sf with a gorgeous blend of period detail and high-end renovation. A beautiful living/dining area with marble mantel with gas FP opens to a chef’s kitchen with shaker cabinetry, quartz countertops, stainless appliances, including a Thermador gas range, island, and pantry. The second level offers a stunning corner exposure parlor room w/four oversized windows, gas fireplace w/Carrara marble mantel, and intricate crown molding. French doors lead to an exceptional media room w/custom built-ins. A luxurious primary suite encompasses the third level and features a spacious bedroom w/gas FP, custom built, walk through closet, and spa-like bathroom w/double vanity, glass enclosed shower, soaking tub, and radiant heated floor. Two generous bedrooms and a full BA make up the top level. A sleek garden level studio apartment, C/Air, brick patio w/mahogany fence, 3 car parking, incl. garage and electric charger complete this home.

1 Harvard Place, Boston
37 High St, Boston
$2,750,000
5 Beds ⋅ 5 Baths ⋅ SOLD Status ⋅ 73221104 MLS ⋅ 4,676 SqFt.
Presenting 37 High St, an exquisite Mansard Style townhome nestled in the prestigious Monument Square area. This distinguished residence exudes timeless elegance with its meticulously preserved period details. Boasting five generous bedrooms and four and a half bathrooms, along with a game room and guest bedroom. Upon entering the first floor, you're greeted by a grand staircase which leads to spacious dining room, a Butlers kitchen, and an inviting open living area. Ascend to the second floor to discover a captivating piano room adorned with original crown moldings and classic mirror frames, generous sized bedroom, complete with a en-suite bath, Continuing upwards, the third floor mirrors the layout of the second, offering two additional bedrooms, and a bath. The fourth floor presents a versatile game room and two more bedrooms. Descend to the lower level, where you'll find a open lay-out kitchen/dining area, a cozy den, and a wine closet, which leads out to a charming patio.

37 High St, Boston
56 Baldwin St, Boston
$1,900,000
4 Beds ⋅ 3 Baths ⋅ SOLD Status ⋅ 73211921 MLS ⋅ 2,390 SqFt.
Beautiful classic brick townhome featuring 4+BR/2.5BA across 2,390sf of living space. Elegant marble entry leads to open living/dining area with gas fireplace, crown molding, and hardwood floors. The first floor offers a powder room off the hallway and a recently updated kitchen with stainless appliances, a Bosch 5-burner gas cooktop, quartz countertops, and bar seating. The kitchen opens to a spacious patio. The second level features the Primary bedroom with custom closets, soaring ceilings, marble mantel and a second bedroom with a newly renovated bath. The third floor offers two additional bedrooms, a secluded office, and renovated bathroom. The basement offers ample storage.

56 Baldwin St, Boston
20 Monument Square, Boston
$3,950,000
5 Beds ⋅ 7 Baths ⋅ SOLD Status ⋅ 73155831 MLS ⋅ 5,500 SqFt.
Magnificent home with premier City location on Monument Square. Renovated for today's modern living. The first floor offers an open floor plan ideal for entertaining including a living room, a dining room and a large kitchen with Calacatta quartz countertops. Amazing outdoor deck and courtyard off of the kitchen. Original 1800's architectural details throughout. Second floor includes primary bedroom suite, spa bathroom, steam shower and a family room with custom built-ins and an office. The third floor has two great-sized bedrooms and two bathrooms. The top floor has two bedrooms and a family room with staircase to a large roof deck with 360-degree views of the City. Owners' unit is 4700 square feet plus garden apartment for au pair or income and storage. Two parking spaces! Convenient neighborhood, this beautiful home offers City living at its finest.

20 Monument Square, Boston

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