INNOVATE
Real Estate
No photos available for this listing

$2,700,000

51 Chestnut Street, Boston MA 02129
Boston, MA 02129
Listed by Nancy Roth
Bedrooms
4
Bathrooms
3.1
Living area
3,593 sqft
Year built
1865

About this home

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.

Highlights

Fireplace

Property details

MLS #
73532468
Property type
Single Family Residence
Subdivision
Charlestown
Status
Active
Days on market
N/A
On market date
N/A
Stories
N/A
Garage spaces
1
Lot size
0.05 acres

Location

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Nearby schools

Within 10 miles · public school directory data (NCES)

Elementary
Harvard-Kent
0.11 mi away · Grades -1-6
Nearest school -- attendance-zone data not available here
5.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
347
Student:teacher ratio
8.9:1
District
Boston
Middle
Next Wave Junior High
1.67 mi away · Grades 7-8
Nearest school -- attendance-zone data not available here
5.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
18
Student:teacher ratio
9.0:1
District
Somerville
High
Charlestown High
0.33 mi away · Grades 7-12
Nearest school -- attendance-zone data not available here
5.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
821
Student:teacher ratio
9.8:1
District
Boston

Mortgage calculator

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Est. monthly payment
$16,410/mo
$540,000 down
$2,160,000 loan
Principal & interest$14,010
Property tax (est.)$2,250
Home insurance (est.)$150

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Data source: Listing information provided by MLS Property Information Network via Trestle/CoreLogic. Last updated June 23, 2026.

Information herein deemed reliable but not guaranteed; all measurements, school assignments, HOA fees, taxes, and feature lists are approximate and should be independently verified. Equal Housing Opportunity.