$2,500,000
51 Chestnut Street
Boston, MA, 02129
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.
Property Details
Price:
$2,500,000
MLS #:
73573036
Status:
Active
Beds:
4
Baths:
3.5
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
Charlestown
Neighborhood:
charlestown
Listed Date:
Sep 8, 2026
Finished Sq Ft:
3,593
Total Sq Ft:
3,593
Lot Size:
2,136 sqft / 0.05 acres (approx)
Year Built:
1865
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
Marie Andrews is an award-winning, licensed real estate broker with licenses in Massachusetts and Florida. She has been selling real estate in the greater Boston area for over 20 years. Over the past two decades, Marie has worked for Century 21 Advanced Realty, building a reputation as a multi-million dollar producer. She has developed an extensive network of investors, lenders, and attorneys. Marie has a wide knowledge base on property management, Massachusetts real estate law, and building…
More About MarieMortgage Calculator
Map
Current real estate data for Single Family in Boston as of Sep 11, 2026
333
Single Family Listed
130
Avg DOM
658
Avg $ / SqFt
$1,824,258
Avg List Price
Community
- Address51 Chestnut Street Boston MA
- SubdivisionCharlestown
- CityBoston
- CountySuffolk
- Zip Code02129
Subdivisions in Boston
- Adams Village
- Allston
- Ashmont Hill / Carruth Area
- Bellevue Hill
- Bellevue Hill/ Roxbury Latin
- Boston
- Brighton
- Brighton-Oak Square
- Carruth’s Hill
- Charlestown
- Dorchester
- Fairmount Hill
- Farlow Hill
- Fort Hill Highland Park
- Harbor View-Orient Heights
- Harborview
- Hyde Park
- Jamaica Plain Moss Hill
- Lower Mills
- Lowermills
- Mattapan
- Melville Park
- Mission Hill – Longwood Medical
- Moss Hill
- Moss Hill, across from Emerald Necklace & Jamaica Pond
- Moss Hill, Jamaica Plain
- Orient Heights
- Peak Hill Neighborhood
- Pondside/Monument Square Historic District
- Readville
- Roslindale Village
- ROXBURY
- South End
- St Botolph
- Stonybrook Village
- Thomas Park / Dorchester Heights
- Thompson Square
- Tommy’s Rock
- Well Respected Hyde Park Neighborhood Area of Boston.
- West Roxbury
- West Roxbury’s Bellevue Hill
- West Side
- Woodbourne Historic District
- Woodbourne in JP/Roslindale
Similar Listings Nearby
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 $2,500,000 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 $696. The average price per square foot for Single Family listings in Boston is $658. The average listing price for Single Family in Boston is $1,824,258. To schedule a showing of MLS#73573036 at 51 Chestnut Street in Boston, MA, contact your Pegasus Realty LLC agent at 781-858-3505.
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