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27 Saint James St Boston — Photo 1 of 16

27 Saint James St Boston — Photo 1 of 16

Recent Drop: $10,000

$1,295,000
$1,285,000

$1,285,000

Investment Analysis — 27 Saint James St

Boston, MA 02119 — Tommy's Rock

Based on HUD Small Area Fair Market Rent for Boston-Cambridge-Quincy, MA-NH HUD Metro FMR Area, a 6-bedroom in 02119 carries an estimated $3,390/mo in gross rent — about a 1.45% cap rate and $18,591/yr in estimated NOI at the $1,285,000 list price. Adjust every assumption in the calculator below.

View Standard Listing

Beds

6

Baths

5

SqFt

3,201

Style

Single Family

Built

1842

Set atop a hill in Boston's historic Tommy's Rock, this meticulously maintained Greek Revival dates to the mid-1800s and pairs architectural pedigree with modern comfort. Ten-foot ceilings, generous room proportions, and oversized windows fill the six-bedroom, five-bath home with light. Original pumpkin pine floors, curved staircases, inlaid shutters, and marble fireplaces sit alongside recent updates, including all-new bathrooms and a rebuilt rear deck. An attached in-law suite with its own private entrance adds flexibility for guests, extended family, or income potential. Outside, a multi-tiered, professionally landscaped yard and several decks open onto sweeping Boston skyline views. A two-car driveway and easy access to transit, universities, and a thriving restaurant scene round out the package — historic character, modern living, in one of the city's most sought-after up-and-coming neighborhoods.

ADU Potential

Massachusetts allows one accessory dwelling unit by right in single-family zoning districts statewide (M.G.L. c. 40A §3; 760 CMR 71.00, effective Feb 2025). Estimated maximum ADU size for this property: 900 sq ft (the lesser of 900 sq ft or half the 3,201 sq ft principal dwelling). Lot size: 5,570 sq ft.

Based on listing data, which indicates the property type — not the zoning district. Local dimensional, septic (Title 5), and historic-district requirements still apply. Not legal advice — verify with the municipality.

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$1,295,000
Annual Taxes$12,326

Parking

Garage0
Off-Street2

Interior Specifications

Total Rooms12
Fireplaces2
Flooring--
BasementFull, Walk-Out Access

Climate & Utilities

HeatingBaseboard
CoolingWindow Unit(s)
WaterPublic
SewerPublic Sewer

Building & Exterior

Construction--
RoofShingle
FoundationStone
ZoningR1

Property & Lot

Acres0.13
SqFt Lot5,570
Lot Features--

Neighborhood

Public Transportation • Public School • T-Station • University

Geography

Property History

Price Drop
$1,285,000

Was $1,295,000

Sep 8, 2026

MLS® 73557775

Listed
$1,295,000

Aug 1, 2026

MLS® 73557775

Expired
$1,295,000

Jul 31, 2026

MLS® 73490790

Listed
$1,295,000

Mar 24, 2026

MLS® 73490790

Listing Provided By

Listing Agent: Miller & Co.

Listing Office: Compass

MLS® Number: 73557775