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4 Beds
4 Baths
3,593 sqft

$2,500,000

51 Chestnut Street, Boston MA, 02129

Price per sqft$695.80
Built in1865
Property size3,593 sqft
Property typeResidential

Overview

Active

Listed Sep 8, 2026

Updated 5 days ago

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.

$16,633/mo

Est. mortgage payment based on a $2,500,000 home price.

All estimates are provided by Luxury Presence for informational purposes only. Actual amounts may vary.

Additional information

MLS® ID
73573036

Interior Features

Bedrooms
4
Bathrooms
4
Fireplace
Yes
Cooling
Yes
Heating
Yes
Basement
Yes

Exterior Features

Lot Size
0.05 Acres

Other Property Details

Taxes
$30,728
Tax Frequency
Annually
Garage
Yes
55+/Senior Community
No

This listing is provided by Nancy Roth with Gibson Sotheby's International Realty

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Data last updated 2:46 AM UTC, 9/13/2026

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