
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
* Analysis is based on 24 actively listed and recently sold comparable properties strictly within Boston, MA.
Property Details
Financials
Parking
Interior Specifications
Climate & Utilities
Building & Exterior
Property & Lot
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
$2,500,000
Sep 8, 2026
MLS® 73573042
$2,500,000
Sep 8, 2026
MLS® 73573036
$2,700,000
Jul 1, 2026
MLS® 73533495
$2,700,000
Jul 1, 2026
MLS® 73532468
$2,700,000
Jun 10, 2026
MLS® 73533495
$2,700,000
Jun 9, 2026
MLS® 73532468
$3,100
Aug 15, 2025
MLS® 73413001
$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 Agent: Nancy Roth
Listing Office: Gibson Sotheby's International Realty
MLS® Number: 73573042
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