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

51 Chestnut Street Boston — Photo 1 of 40

$2,500,000

Investment Analysis — 51 Chestnut Street

Boston, MA 02129 — Charlestown

Based on rent reported on the MLS listing, a 2-unit multi-family in 02129 carries $3,100/mo in gross rent — about a -0.10% cap rate and $-2,456/yr in estimated NOI at the $2,500,000 list price. Adjust every assumption in the calculator below.

View Standard Listing

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 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.

Estimates — not financial advice

These figures are illustrative estimates for informational purposes only — not an appraisal, valuation, or guarantee of rent, income, or returns, and not financial, tax, or investment advice. Rent is either the figure reported on the MLS listing — in-place rent that may differ from market and is not verified against the actual leases — or, where the listing reports none, an estimate from HUD Small Area Fair Market Rents, a government benchmark that may differ from actual market rent. Each figure is labelled with its source. Cap rate, NOI, and returns depend on the assumptions shown, which you can change. MLS and other third-party data may be inaccurate or out of date. Verify all figures independently and consult your own financial, tax, and legal advisors before making any investment decision.

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

Listing Provided By

Listing Agent: Nancy Roth

Listing Office: Gibson Sotheby's International Realty

MLS® Number: 73573042