Dimensions9.833333333 x 14.25
FeaturesCeiling Fan(s), Closet, Flooring - Wood, Lighting - Overhead
LevelThird
51 Chestnut Street, Boston MA 02129
Boston, MA 02129 • Charlestown
$2,500,000
Est. $15,402/month
Estimate assumptions
20% down, a 30-year loan at 6.5%, and $200/month estimated insurance.
Includes the supplied property-tax and HOA inputs; missing inputs contribute $0. HOA fees with an unspecified frequency are treated as monthly. PMI and closing costs are excluded.
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About this home
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.
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Recently Sold Nearby
Property History
Property Timeline
Listed for Sale
Sep 8, 2026
$2,500,000
Original listing
Agent: Nancy Roth
Office: Gibson Sotheby's International Realty
| Date | Event | Price | Change | $/sqft | Details |
|---|---|---|---|---|---|
| 09/08/2026 | 🏠 Listed for Sale | $2,500,000 | - | - | Original listing |
Tax History
| Year | Taxes | Assessment |
|---|---|---|
| 2026 | $30,728 | $2,454,500 |
Financial Details
Annual Property Tax
$30,728
Tax Year 2026
Assessed Value
$2,454,500
Facts & Features
1 Car Garage
Central AC
Home Facts
Type
Residential
Style
Single Family Residence
Year Built
1865
Living Area
3,593 sq ft
Lot Size
0.05 acres
Bedrooms
4
Full Baths
3
Half Baths
1
Total Rooms
10
Interior
Heating
Forced Air, Baseboard, Natural Gas
Cooling
Central Air
Flooring
Wood, Tile, Carpet, Marble, Hardwood, Flooring - Stone/ceramic Tile, Flooring - Wood, Flooring - Hardwood
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
Fireplace
Family Room, Living Room, Master Bedroom
Fireplaces
4
Basement
Full, Interior Entry, Unfinished
Laundry
Third Floor
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
Exterior
Construction
Conventional (2x4-2x6)
Architecture
Italianate
Roof
Rubber
Features
Deck - Roof, Patio, Garden
Pool
None
Spa
None
Fencing
None
Patio/Porch
Deck - Roof, Patio
Parking
Garage Spaces
1
Has Garage
Yes
Features
Detached, Leased
Total Spaces
1
Utilities
Electric
None
Water
Public
Sewer
Public Sewer
Gas
None
Other
For Gas Range
Financial
Annual Tax
$30,728
Assessed Value
$2,454,500
HOA & Community
Fee Includes
None
Amenities
None
Optional Fee Includes
None
MA Disclosures
Lead Paint
Unknown
Seller Disclosures
4 Fireplaces: 1 Electric Fireplace In Entry Parlor; 1 Gas Fireplace In Den Off Kitchen, And The Two Wood Burning Fireplaces Are In 2nd Floor Living Room And Primary Bedroom. Neither Of These Wood Fp Chimneys Are Lined. Seller Does Not Use As A Result.
Exclusions
2nd Floor Dining Room Brass Uplight.
Additional Details
Possession
None
Accepted Financing
None
Structure Type
[]
House Color
Mauve
Sq Ft Source
Public Record
Sq Ft Disclosures
There is an additional 1,230 sqft of unfinished basement space with egress to the patio via bulkhead
Documents
None
County
Suffolk
Total market time (incl. prior listings)
4 days
Property Overview
Property Type
Single Family Residence
Listing Type
For Sale
Year Built
1865
Bedrooms
4
Full Bathrooms
3
Half Bathrooms
1
Living Area
3,593 sq ft
Total Rooms
10
Main Level Bedrooms
2
Floor Layout
Interactive room guide
Floor Layout
Finished Area
3,593 sq ft above grade
1,230 sq ft below grade
Dimensions15.416666666 x 16.25
FeaturesBathroom - Full, Bathroom - Double Vanity/Sink, Bathroom - Tiled With Tub & Shower, Bathroom - With Shower Stall, Skylight, Walk-In Closet(s), Closet/Cabinets - Custom Built, Flooring - Marble, Countertops - Stone/Granite/Solid, Recessed Lighting, Lighting - Pendant
LevelThird
Dimensions13.083333333 x 19.666666666
FeaturesBathroom - Full, Walk-In Closet(s), Closet/Cabinets - Custom Built, Flooring - Wood, Recessed Lighting, Tray Ceiling(s)
LevelThird
Dimensions15.083333333 x 12
FeaturesFlooring - Wood, Countertops - Stone/Granite/Solid, Kitchen Island, Recessed Lighting, Stainless Steel Appliances, Peninsula, Lighting - Pendant
LevelSecond
FeaturesBathroom - Half, Flooring - Stone/Ceramic Tile, Lighting - Sconce, Lighting - Overhead, Pedestal Sink
LevelSecond
Dimensions14.25 x 16.416666666
FeaturesFlooring - Wood, Chair Rail, Recessed Lighting, Lighting - Pendant, Pocket Door, Tray Ceiling(s)
LevelSecond
Dimensions15.083333333 x 19.083333333
FeaturesCeiling Fan(s), Closet, Closet/Cabinets - Custom Built, Flooring - Wood, Recessed Lighting, Lighting - Overhead
LevelSecond
Dimensions24.5 x 17.416666666
FeaturesFlooring - Wood, Recessed Lighting, Lighting - Overhead, Archway
LevelSecond
Dimensions13.75 x 16.583333333
FeaturesCloset/Cabinets - Custom Built, Flooring - Wood, French Doors, Recessed Lighting, Lighting - Overhead, Decorative Molding
LevelMain,First
Dimensions13.666666666 x 15.916666666
FeaturesFlooring - Wall to Wall Carpet, Lighting - Pendant, Decorative Molding
LevelMain,First
Dimensions5.25 x 8.166666666
FeaturesBathroom - Full, Bathroom - Tiled With Tub & Shower, Flooring - Stone/Ceramic Tile, Countertops - Stone/Granite/Solid, Lighting - Sconce, Lighting - Pendant
LevelFirst
FeaturesYes
Display Options
Outdoor Areas
Patio & porchDeck - Roof, Patio
Room Markers
OOffice (1)
KKitchen (1)
BRBedroom (5)
BABathroom (4)
DDining (1)
LLiving (2)
Conceptual diagram based on MLS room data. It is not to scale and is not a substitute for architectural plans or on-site measurements.
Interior Features
Flooring:
Wood, Tile, Carpet, Marble, Hardwood, Flooring - Stone/Ceramic Tile, Flooring - Wood, Flooring - Hardwood
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
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
Windows:
Basement:
Full, Interior Entry, Unfinished
Laundry:
Third Floor
Security:
Construction & Materials
Style:
Italianate
Year Built:
1865
Structure Type:
Exterior Materials:
Conventional (2x4-2x6)
Roof:
Rubber
Foundation:
Granite
Heating, Cooling & Utilities
Heating:
Forced Air, Baseboard, Natural Gas
Heating Zones:
4
Cooling:
Central Air
Cooling Zones:
2
Hot Water:
Water Source:
Public
Sewer:
Public Sewer
Energy Features:
Exterior & Lot
Exterior Features:
Deck - Roof, Patio, Garden
Patio & Porch:
Deck - Roof, Patio
Fencing:
Other Structures:
Lot Features:
Other
Road Surface:
Parking & Garage
Garage Spaces:
1
Total Parking Spaces:
1
Parking Features:
Detached, Leased
Special Features
Fireplaces:
4
Fireplace Type:
Family Room, Living Room, Master Bedroom
Community Amenities:
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
Nearby Schools
School District
Boston School District local
C-
Where Graduates Go
Class of 2021
52%
attend college
38%
4-Year
14%
2-Year
7%
Out of State
7%
Working
School Safety
2024-25
3.7%
Above Average
3.2%
Suspensions
0.3%
In-School
0.5%
Emergency
1.8% below state avg
Elementary Schools
10 schools
C
Harvard-Kent Elementary School
0.1 mi
|
#594 of 825
|
Score: 41.1
Dropped 186 spots from last year
-17.1 below state avg
315 students
Very Diverse
Diverse Student Body
Grades PK-06
A-
Warren-Prescott K-8 School
0.3 mi
|
#86 of 352
|
Score: 50.9
Improved 3 spots from last year
-7.3 below state avg
544 students
Diverse
Strong Attendance
Grades PK-08
D
Horace Mann School for the Deaf Hard of Hearing
0.5 mi
|
#374 of 346
|
Score: 33.9
Same rank as last year
78 students
Diverse
Diverse Student Body
Grades PK-12
A
Eliot K-8 Innovation School
0.7 mi
|
#47 of 352
|
Score: 57.5
Improved 3 spots from last year
-0.7 below state avg
779 students
Diverse
Strong Attendance
Grades PK-08
St. John Elementary School
0.9 mi
Grades PK-08
C+
Mario Umana Academy
0.9 mi
|
#11 of 16
|
Score: 26.5
Improved 333 spots from last year
-31.7 below state avg
585 students
Less Diverse
Rising School
Grades PK-08
East Boston Central Catholic School
1.0 mi
Grades PK-08
D
O'Donnell Elementary School
1.1 mi
|
#784 of 825
|
Score: 29.9
Dropped 59 spots from last year
-28.3 below state avg
248 students
Less Diverse
Grades PK-06
B+
Alighieri Dante Montessori School
1.1 mi
|
#5 of 12
|
Score: 45.2
Improved 124 spots from last year
-13 below state avg
100 students
Diverse
Rising School
Strong Attendance
Grades PK-06
C-
Kennedy Patrick J Elementary School
1.2 mi
|
#669 of 825
|
Score: 37.4
Improved 48 spots from last year
-20.8 below state avg
285 students
Less Diverse
Rising School
Grades PK-06
Middle Schools
10 schools
Middle School Academy
2.9 mi
F
Higginson/Lewis K-8 School
4.0 mi
|
#349 of 352
|
Score: 23.2
Improved 3 spots from last year
-35 below state avg
246 students
Diverse
Grades 03-08
Nativity Prep School
4.3 mi
Grades 05-08
A
Uncommon Schools - Roxbury Preparatory Dorchester Campus Middle School
4.5 mi
|
#4 of 16
|
Score: 42.5
Improved 187 spots from last year
-15.7 below state avg
1,225 students
Diverse
Rising School
College Ready Curriculum
Grades 05-08
Dearborn Middle School
4.8 mi
Mother Caroline Academy
4.9 mi
Grades 05-08
Epiphany School
5.7 mi
Grades 05-08
C
Ohrenberger School
9.1 mi
|
#266 of 352
|
Score: 35.0
Improved 19 spots from last year
-23.2 below state avg
458 students
Diverse
Diverse Student Body
Grades 03-08
Edwards Middle
0.5 mi
UP Academy
2.9 mi
High Schools
10 schools
D
Charlestown High School
0.3 mi
|
#319 of 346
|
Score: 32.9
Improved 52 spots from last year
-25.4 below state avg
646 students
Diverse
11 sports
• 488 athletes
Early College Program
Rising School
Grades 07-12
C-
East Boston High School
1.3 mi
|
#300 of 346
|
Score: 38.2
Improved 36 spots from last year
-20 below state avg
1,181 students
Moderate
14 sports
• 584 athletes
Early College Program
Rising School
Grades 07-12
C
Quincy Upper School
2.0 mi
|
#279 of 346
|
Score: 44.4
Dropped 7 spots from last year
-13.8 below state avg
575 students
Very Diverse
12 sports
• 208 athletes
Diverse Student Body
Grades 06-12
Newman School
2.0 mi
Grades 07-12
Cathedral High School
2.4 mi
9 sports
• 430 athletes
Grades 07-12
A+
Boston Latin School
3.4 mi
|
#20 of 346
|
Score: 73.7
Improved 60 spots from last year
+15.5 above state avg
2,382 students
Very Diverse
18 sports
• 2,006 athletes
Strong AP Program
High Graduation Rate
Rising School
Strong Athletics
Grades 07-12
A-
O'Bryant School of Math & Science
3.5 mi
|
#90 of 346
|
Score: 61.6
Improved 94 spots from last year
+3.4 above state avg
1,518 students
Very Diverse
High Graduation Rate
Rising School
College Ready Curriculum
Diverse Student Body
Grades 07-12
B
Dearborn STEM Academy
3.6 mi
|
#13 of 25
|
Score: 33.4
Improved 356 spots from last year
-24.8 below state avg
565 students
Moderate
10 sports
• 242 athletes
Early College Program
Rising School
Grades 07-12
C
Ruth Batson Academy
4.1 mi
|
#20 of 25
|
Score: 29.1
Improved 345 spots from last year
-29.1 below state avg
584 students
Diverse
8 sports
• 128 athletes
Early College Program
Rising School
Grades 07-12
A+
Boston Latin Academy
4.3 mi
|
#2 of 25
|
Score: 64.9
Improved 214 spots from last year
+6.7 above state avg
1,669 students
Very Diverse
17 sports
• 1,298 athletes
Strong AP Program
High Graduation Rate
Rising School
Strong Athletics
Grades 07-12
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Year 15
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Location
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Neighborhood
Charlestown
51 Chestnut Street, Boston MA 02129
Boston, MA 02129
Listing Information
Listing Agent
Nancy Roth
Listing Office
Gibson Sotheby's International Realty
Office Phone
617-242-4222
Agent MLS ID
H8000088
Office MLS ID
BB9059
Listing Data Updated
Sep 12, 2026 3:05 AM EDT
Listing information is deemed reliable but not guaranteed. Data provided by MLS Property Information Network, Inc. All information should be independently verified.
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