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

Multi 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)$576/sqft
21% 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

Garage0
Off-Street1

Interior Specifications

Total Rooms10
Fireplaces4
FlooringWood, Tile, Carpet, Marble, Hardwood, Stone/Ceramic Tile
BasementUnfinished

Climate & Utilities

HeatingCentral, Baseboard, Natural Gas, Forced Air
CoolingCentral Air
WaterPublic
SewerPublic Sewer

Building & Exterior

ConstructionFrame
RoofRubber
FoundationGranite
ZoningMulti-Fam

Property & Lot

Acres0.05
SqFt Lot2,136
Lot FeaturesOther

Amenities & Appliances

Range • Dishwasher • Microwave • Refrigerator • Freezer • Washer • Dryer • Range Hood

Neighborhood

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

Geography

Property History

Listed
$2,500,000

Sep 8, 2026

MLS® 73573042

Listed
$2,500,000

Sep 8, 2026

MLS® 73573036

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)

Listing Provided By

Listing Agent: Nancy Roth

Listing Office: Gibson Sotheby's International Realty

MLS® Number: 73573042

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