
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.
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 MLS and other third-party data may be inaccurate or out of date.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
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
Listing Agent: Nancy Roth
Listing Office: Gibson Sotheby's International Realty
MLS® Number: 73573042

