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32 Pleasant Street Boston — Photo 1 of 42

32 Pleasant Street Boston — Photo 1 of 42

$2,699,000

Investment Analysis — 32 Pleasant Street

Boston, MA 02129 — Charlestown

Based on HUD Small Area Fair Market Rent for Boston-Cambridge-Quincy, MA-NH HUD Metro FMR Area, a 3-bedroom in 02129 carries an estimated $4,820/mo in gross rent — about a 0.78% cap rate and $21,030/yr in estimated NOI at the $2,699,000 list price. Adjust every assumption in the calculator below.

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Beds

3

Baths

3.5

SqFt

3,002

Style

Single Family

Built

1840

Set in Charlestown’s coveted Gaslight District on Pleasant Street, this stately single-family home offers approximately 3,002 square feet across four beautifully finished levels. A classic façade with three distinctive gabled dormers gives way to an impressive interior blending historic character with refined modern finishes. The main level is designed for both everyday living and entertaining, featuring a spacious living and dining area, exposed brick, custom built-ins and a stunning chef’s kitchen with marble countertops and backsplash, Sub-Zero refrigeration, Thermador range and hood, and an oversized island. Just beyond, a private patio creates a seamless extension of the living space outdoors. Three generously sized bedrooms each feature their own en-suite bathroom, while the expansive top-floor primary suite offers exceptional privacy with a large walk-in closet, beautifully appointed marble bath and additional private balcony. A dedicated office with custom built-ins and a finished lower provide additional flexibility. An exceptional Charlestown home offering remarkable space, quality and location just moments from the Monument, Main Street, waterfront and Downtown Boston.

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 3,002 sq ft principal dwelling). Lot size: 1,205 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.

Open Houses

Property Details

Financials

Original Price$2,699,000
Annual Taxes$22,928

Parking

Garage0
Off-Street0

Interior Specifications

Total Rooms9
FireplacesNone
FlooringHardwood
BasementFull, Finished

Climate & Utilities

HeatingForced Air
CoolingCentral Air
WaterPublic
SewerPublic Sewer

Building & Exterior

ConstructionFrame
RoofShingle
FoundationBrick/Mortar
ZoningRes

Property & Lot

Acres0.03
SqFt Lot1,205
Lot FeaturesOther

Amenities & Appliances

Range • Dishwasher • Disposal • Microwave • Refrigerator • Freezer • Washer • Dryer

Neighborhood

Public Transportation • Shopping • Park • Walk/Jog Trails • Highway Access • Marina

Geography

Property History

Listed
$2,699,000

Sep 23, 2026

MLS® 73581324

Sold
$650,000

Oct 31, 2025

MLS® 73441322

Listed
$649,900

Oct 8, 2025

MLS® 73441322

Expired
$679,900

Nov 30, 2024

MLS® 73226639

Listed
$679,900

Apr 21, 2024

MLS® 73226639

Listing Provided By

Listing Agent: Tracy Shea

Listing Office: Coldwell Banker Realty - Boston

MLS® Number: 73581324