Active
1 Days on market
51 Chestnut Street Boston — Photo 1 of 40

51 Chestnut Street Boston — Photo 1 of 40

$2,500,000

51 Chestnut Street, Boston, MA 02129

Boston, MA 02129 — Charlestown

Beds

4

Baths

3.5

SqFt

3,593

Style

Single Family

Built

1865

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.

Market Value Analysis

This Property
Size (SqFt) →Price →
This Property$696/sqft
Local Avg (Boston)$555/sqft
25% AboveMarket Average

* Analysis is based on 23 actively listed and recently sold comparable properties strictly within Boston, MA.

Property Details

Financials

Original Price$2,500,000
Annual Taxes$30,727.7

Parking

Garage1
Off-Street1

Interior Specifications

Total Rooms10
Fireplaces4
FlooringWood, Tile, Carpet, Marble, Hardwood, Flooring - Stone/Ceramic Tile, Flooring - Wood, Flooring - Hardwood
BasementFull, Interior Entry, Unfinished

Climate & Utilities

HeatingForced Air, Baseboard, Natural Gas
CoolingCentral Air
WaterPublic
SewerPublic Sewer

Building & Exterior

ConstructionConventional (2x4-2x6)
RoofRubber
FoundationGranite
ZoningMulti-Fam

Property & Lot

Acres0.05
SqFt Lot2,136
Lot FeaturesOther

Amenities & 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

Neighborhood

Public Transportation • Shopping • Pool • Tennis Court(s) • Park • Walk/Jog Trails

Geography

Floorplan Breakdown

Structural Layout

Third
Master BedroomBedroom 4Bathroom 3
Second
Living RoomDining RoomKitchenFamily RoomBathroom 2
First
Bathroom 1
Main,First
Bedroom 2Bedroom 3
Living Room
Lvl Second

24.5 x 17.416666666

Flooring - Wood, Recessed Lighting, Lighting - Overhead, Archway

Dining Room
Lvl Second

14.25 x 16.416666666

Flooring - Wood, Chair Rail, Recessed Lighting, Lighting - Pendant, Pocket Door, Tray Ceiling(s)

Kitchen
Lvl Second

15.083333333 x 12

Flooring - Wood, Countertops - Stone/Granite/Solid, Kitchen Island, Recessed Lighting, Stainless Steel Appliances, Peninsula, Lighting - Pendant

Family Room
Lvl Second

15.083333333 x 19.083333333

Ceiling Fan(s), Closet, Closet/Cabinets - Custom Built, Flooring - Wood, Recessed Lighting, Lighting - Overhead

Master Bedroom
Lvl Third

13.083333333 x 19.666666666

Bathroom - Full, Walk-In Closet(s), Closet/Cabinets - Custom Built, Flooring - Wood, Recessed Lighting, Tray Ceiling(s)

Bedroom 2
Lvl Main,First

13.75 x 16.583333333

Bedroom 3
Lvl Main,First

13.666666666 x 15.916666666

Flooring - Wall to Wall Carpet, Lighting - Pendant, Decorative Molding

Bedroom 4
Lvl Third

9.833333333 x 14.25

Ceiling Fan(s), Closet, Flooring - Wood, Lighting - Overhead

Bathroom 1
Lvl First

5.25 x 8.166666666

Bathroom - Full, Bathroom - Tiled With Tub & Shower, Flooring - Stone/Ceramic Tile, Countertops - Stone/Granite/Solid, Lighting - Sconce, Lighting - Pendant

Bathroom 2
Lvl Second

Bathroom - Half, Flooring - Stone/Ceramic Tile, Lighting - Sconce, Lighting - Overhead, Pedestal Sink

Bathroom 3
Lvl Third

15.416666666 x 16.25

Bathroom - 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

Property History

Listed
$2,500,000

Sep 8, 2026

MLS® 73573036

Listed
$2,500,000

Sep 8, 2026

MLS® 73573042

Terminated
$2,700,000

Jul 1, 2026

MLS® 73533495

Terminated
$2,700,000

Jul 1, 2026

MLS® 73532468

Listed
$2,700,000

Jun 10, 2026

MLS® 73533495

Listed
$2,700,000

Jun 9, 2026

MLS® 73532468

Sold
$3,100

Aug 15, 2025

MLS® 73413001

Listed
$3,100

Aug 3, 2025

MLS® 73413001

Population

20,032

U.S. Census Bureau, ACS 2024 5-Year Estimates (B01003)

Median Household Income

$157K

U.S. Census Bureau, ACS 2024 5-Year Estimates (B19013)

Renter-Occupied Homes

49.5%

U.S. Census Bureau, ACS 2024 5-Year Estimates (B25003)

New Construction Permits — Suffolk County

2,527 housing units permitted in the last 12 months (+37% vs the prior 12 months) — 2,269 in 5+ unit buildings

U.S. Census Bureau, Building Permits Survey (through Jun '26)

ADU Potential

Massachusetts allows one accessory dwelling unit by right in single-family zoning districts statewide (M.G.L. c. 40A §3; 760 CMR 71.00, effective Feb 2025). Estimated maximum ADU size for this property: 900 sq ft (the lesser of 900 sq ft or half the 3,593 sq ft principal dwelling). Lot size: 2,136 sq ft.

Based on listing data, which indicates the property type — not the zoning district. Local dimensional, septic (Title 5), and historic-district requirements still apply. Not legal advice — verify with the municipality.

Full Boston, MA market report ZIP 02129 market data
Listing Provided By

Listing Agent: Nancy Roth

Listing Office: Gibson Sotheby's International Realty

MLS® Number: 73573036

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