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, investor/developer, or buyer looking to convert into a spectacular single family home. 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/FP 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. A lush garden patio completes this special offering.
Property Details
Price:
$2,700,000
MLS #:
73532468
Status:
Active
Beds:
4
Baths:
3.5
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
Charlestown
Neighborhood:
charlestown
Listed Date:
Jun 9, 2026
Finished Sq Ft:
3,593
Total Sq Ft:
3,593
Lot Size:
2,136 sqft / 0.05 acres (approx)
Year Built:
1865
See this Listing
Schools
Elementary School:
Bps
Middle School:
Bps
High School:
Bps
Interior
Above Grade Finished Area
3593
Appliances
Gas Water Heater, Water Heater, Tankless Water Heater, Range, Dishwasher, Disposal, Microwave, Refrigerator, Freezer, Washer, Dryer, Range Hood, Stainless Steel Appliance(s), Gas Cooktop
Bathrooms
3 Full Bathrooms, 1 Half Bathroom
Below Grade Finished Area
1230
Cooling
Central Air
Fireplaces Total
4
Flooring
Wood, Tile, Carpet, Marble, Hardwood, Flooring – Stone/Ceramic Tile, Flooring – Wood, Flooring – Hardwood
Heating
Forced Air, Baseboard, Natural Gas
Interior Features
Bathroom – Full, Bathroom – Tiled With Shower Stall, Lighting – Overhead, Dining Area, Beadboard, Lighting – Pendant, Archway, Vestibule, Chair Rail, Bathroom, Kitchen, Foyer, Living/Dining Rm Combo
Laundry Features
Third Floor
Main Level Bedrooms
2
Exterior
Architectural Style
Italianate
Community Features
Public Transportation, Shopping, Pool, Tennis Court(s), Park, Walk/Jog Trails, Medical Facility, Laundromat, Bike Path, Conservation Area, Highway Access, House of Worship, Marina, Private School, Public School, T-Station, University
Construction Materials
Conventional (2×4-2×6)
Covered Spaces
1
Exterior Features
Deck – Roof, Patio, Garden
Garage Spaces
1
Lot Features
Other
Parking Features
Detached, Leased
Parking Spots
1
Parking Total
1
Patio And Porch Features
Deck – Roof, Patio
Roof
Rubber
Financial
Tax Year
2026
Taxes
$30,728
Map
Community
- Address51 Chestnut Street Boston MA
- SubdivisionCharlestown
- CityBoston
- CountySuffolk
- Zip Code02129
Subdivisions in Boston
- Adams Village
- Ashmont Hill
- Ashmont Hill / Carruth Area
- Back Bay
- Bay Village
- Beacon Hill
- Bellevue Hill
- Boston
- Brighton-Oak Square
- Charlestown
- Chestnut Hill
- Chestnut Hill /Brookline line
- Chestnut Hill Park Condominium
- Clam Point Neighborhood
- Eight Streets Neighborhood
- Ellis South End Neighborhood
- Fairmount Hill
- Fields Corner
- Gas Light District
- Golf Course Neighborhood
- Harbor View
- Harborview
- Highland
- Hyde Park
- Jamaica Plain
- Lower Mills
- Melville Park
- Metropolitan Heights Area
- Metropolitan Hill
- Mission Hill – Longwood Medical
- Oak Square
- Parkway neighborhood
- Roslindale
- Roslindale – WC Bates
- roslindale village
- Roxbury’s Moreland Street Historic District
- Savin Hill: Minutes to Carson Beach/UMass Boston T-Stop
- South Boston
- Suffolk County
- Sumner Hill
- Thomas Park
- Woodbourne
Market Summary
Current real estate data for Single Family in Boston as of Jun 10, 2026
439
Single Family Listed
114
Avg DOM
708
Avg $ / SqFt
$1,992,198
Avg List Price
Property Summary
- Located in the Charlestown subdivision, 51 Chestnut Street Boston MA is a Single Family for sale in Boston, MA, 02129. It is listed for $2,700,000 and features 4 beds, 4 baths, and has approximately 3,593 square feet of living space, and was originally constructed in 1865. The current price per square foot is $751. The average price per square foot for Single Family listings in Boston is $708. The average listing price for Single Family in Boston is $1,992,198. To schedule a showing of MLS#73532468 at 51 Chestnut Street in Boston, MA, contact your Cornerstone Real Estate agent at 617-238-7400.
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Courtesy of Gibson Sotheby’s International Realty. The property listing data and information set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information are for the personal, non-commercial use of consumers having a good faith interest in purchasing or leasing listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing or leasing. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information set forth herein.
51 Chestnut Street
Boston, MA