There are multiple listings for this address:
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:
Pending
Beds:
4
Baths:
3.5
Type:
Single Family
Subtype:
Multi Family
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
See this Listing
Schools
Elementary School:
Bps
Middle School:
Bps
High School:
Bps
Interior
Above Grade Finished Area
3593
Appliances
Range, Dishwasher, Microwave, Refrigerator, Freezer, Washer, Dryer, Range Hood
Bathrooms
3 Full Bathrooms, 1 Half Bathroom
Below Grade Finished Area
1230
Cooling
Central Air
Fireplaces Total
4
Flooring
Wood, Tile, Carpet, Marble, Hardwood, Stone/Ceramic Tile
Heating
Central, Baseboard, Natural Gas, Forced Air
Interior Features
Ceiling Fan(s), Storage, Stone/Granite/Solid Counters, Walk-In Closet(s), Bathroom with Shower Stall, Living Room, Dining Room, Kitchen, Family Room, Laundry Room, Office/Den, Sunroom
Levels
4
Exterior
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
Frame
Exterior Features
Balcony/Deck, Garden
Lot Features
Other
Open Parking Spaces
1
Parking Features
Leased
Parking Spots
1
Parking Total
1
Patio And Porch Features
Deck – Roof, Patio
Roof
Rubber
Spa Features
Bath
Stories
4
Window Features
Skylight(s), Insulated Windows
Financial
Tax Year
2026
Taxes
$30,728
Map
Community
- Address51 Chestnut Street Boston MA
- CityBoston
- CountySuffolk
- Zip Code02129
Subdivisions in Boston
- Adams Village
- Ashmont Hill
- Ashmont Hill / Carruth Area
- Ashmont Hill / Peabody Square
- Beacon Hill
- Bellevue Hill
- Boston
- Central JP
- Charlestown
- Clam Point
- Doctor’s Row
- Dorchester
- East Boston
- Fairmount Hill
- Forest Hills
- Fort Hill Highland Park
- Frederick Douglas Park South End
- George Wright Golf Course Neighborhood
- Harborview
- Highland
- Holy Name Parish neighborhood
- Hyde Park
- Jeffries Point
- Lower Mills
- Lower Mills and East Milton Square
- Melville Park
- Moss Hill
- Mount Hope
- Nubian Square
- Oak Square
- Oak Square Brighton/Newton Liine
- Orient Heights
- Over The Bridge – Savin Hill
- Peak Hill Neighborhood
- Pondside
- Pondside Jamaica Plain
- Readville
- Roslindale
- Roxbury
- Savin Hill OTB
- Savin Hill/JFK
- South Boston
- South Boston’s City Point
- Thompson Square
- Truman Parkway/ Monahan Park
- Ward 20
- Well Respected Hyde Park Neighborhood Area of Boston.
- West Roxbury
- Woodbourne
Market Summary
Current real estate data for Single Family in Boston as of Nov 04, 2026
405
Single Family Listed
123
Avg DOM
665
Avg $ / SqFt
$1,896,348
Avg List Price
Property Summary
- 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 $665. The average listing price for Single Family in Boston is $1,896,348. To schedule a showing of MLS#73573036 at 51 Chestnut Street in Boston, MA, contact your Cornerstone Real Estate agent at 617-238-7400.
Similar Listings Nearby
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
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 #:
73573042
Status:
Pending
Beds:
4
Baths:
3.5
Type:
Multi Family
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
Units:
2
See this Listing
Schools
Elementary School:
Bps
Middle School:
Bps
High School:
Bps
Interior
Above Grade Finished Area
3593
Appliances
Range, Dishwasher, Microwave, Refrigerator, Freezer, Washer, Dryer, Range Hood
Bathrooms
3 Full Bathrooms, 1 Half Bathroom
Below Grade Finished Area
1230
Cooling
Central Air
Fireplaces Total
4
Flooring
Wood, Tile, Carpet, Marble, Hardwood, Stone/Ceramic Tile
Heating
Central, Baseboard, Natural Gas, Forced Air
Interior Features
Ceiling Fan(s), Storage, Stone/Granite/Solid Counters, Walk-In Closet(s), Bathroom with Shower Stall, Living Room, Dining Room, Kitchen, Family Room, Laundry Room, Office/Den, Sunroom
Levels
4
Exterior
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
Frame
Exterior Features
Balcony/Deck, Garden
Lot Features
Other
Open Parking Spaces
1
Parking Features
Leased
Parking Spots
1
Parking Total
1
Patio And Porch Features
Deck – Roof, Patio
Roof
Rubber
Spa Features
Bath
Stories
4
Window Features
Skylight(s), Insulated Windows
Financial
Tax Year
2026
Taxes
$30,728
Map
Community
- Address51 Chestnut Street Boston MA
- CityBoston
- CountySuffolk
- Zip Code02129
Subdivisions in Boston
- Adams Village
- Ashmont Hill
- Ashmont Hill / Carruth Area
- Ashmont Hill / Peabody Square
- Beacon Hill
- Bellevue Hill
- Boston
- Central JP
- Charlestown
- Clam Point
- Doctor’s Row
- Dorchester
- East Boston
- Fairmount Hill
- Forest Hills
- Fort Hill Highland Park
- Frederick Douglas Park South End
- George Wright Golf Course Neighborhood
- Harborview
- Highland
- Holy Name Parish neighborhood
- Hyde Park
- Jeffries Point
- Lower Mills
- Lower Mills and East Milton Square
- Melville Park
- Moss Hill
- Mount Hope
- Nubian Square
- Oak Square
- Oak Square Brighton/Newton Liine
- Orient Heights
- Over The Bridge – Savin Hill
- Peak Hill Neighborhood
- Pondside
- Pondside Jamaica Plain
- Readville
- Roslindale
- Roxbury
- Savin Hill OTB
- Savin Hill/JFK
- South Boston
- South Boston’s City Point
- Thompson Square
- Truman Parkway/ Monahan Park
- Ward 20
- Well Respected Hyde Park Neighborhood Area of Boston.
- West Roxbury
- Woodbourne
Market Summary
Current real estate data for Multi Family in Boston as of Nov 04, 2026
405
Multi Family Listed
123
Avg DOM
665
Avg $ / SqFt
$1,896,348
Avg List Price
Property Summary
- 51 Chestnut Street Boston MA is a Multi Family for sale in Boston, MA, 02129. It is listed for $2,500,000 To schedule a showing of MLS#73573042 at 51 Chestnut Street in Boston, MA, contact your Cornerstone Real Estate agent at 617-238-7400.
