Active
2 Days on market
101 Chestnut Street #E Boston — Photo 1 of 23

101 Chestnut Street #E Boston — Photo 1 of 23

$3,499,950

101 Chestnut Street #E, Boston, MA 02108

Boston, MA 02108 — Beacon Hill

Beds

2

Baths

3

SqFt

2,500

Style

Stock Cooperative

Built

1918

Set within one of Beacon Hill’s most distinguished buildings, 101 Chestnut Street is celebrated for its gracious architecture, elegant courtyard and exceptional service. Unit E offers approximately 2,500 sq. ft. of expansive single-floor living with 2 bedrooms plus a library/office/guest room and 3 full baths. At the heart of the residence is an impressive 22' × 22' living and dining room, offering exceptional scale for both entertaining and everyday living. Desirable corner exposure brings natural light throughout, while the south-facing primary suite features generous proportions, an en suite bath and exceptional closet space. A separate guest wing provides wonderful privacy with a second bedroom, full bath and flexible library/office/guest room with an additional bath. Courtyard views, a well-appointed kitchen, concierge service, beautifully landscaped common roof deck and private storage complete this gracious Beacon Hill residence.

Market Value Analysis

This Property
Size (SqFt) →Price →
This Property$1400/sqft
Local Avg (Boston)$949/sqft
48% AboveMarket Average

* Analysis is based on 24 actively listed and recently sold comparable properties strictly within Boston, MA.

Property Details

Financials

Original Price$3,499,950
Annual Taxes--
HOA Fee$3610

Parking

Garage0
Off-Street0

Interior Specifications

Total Rooms6
Fireplaces3
FlooringWood
BasementN

Climate & Utilities

HeatingCentral
CoolingCentral Air
WaterPublic
SewerPublic Sewer

Building & Exterior

ConstructionBrick, See Remarks
RoofRubber, Other
Foundation--
ZoningRes

Property & Lot

Acres--
SqFt Lot--
Lot Features--

Amenities & Appliances

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

Neighborhood

Public Transportation • Shopping • Tennis Court(s) • Park • Walk/Jog Trails • Medical Facility

Geography

Floorplan Breakdown

Structural Layout

Second
Living RoomDining RoomKitchenPrimary BedroomBedroom 2
Living Room
Lvl Second

22 x 22

Dining Room
Lvl Second

22 x 22

Kitchen
Lvl Second

16 x 14

Primary Bedroom
Lvl Second

18 x 22

Bedroom 2
Lvl Second

15 x 14

Property History

Price Increase
$3,499,950

Was $3,499,000

Sep 14, 2026

MLS® 73576624

Listed
$3,499,950

Sep 14, 2026

MLS® 73576624

Terminated
$3,595,000

Jun 26, 2026

MLS® 73499714

Listed
$3,595,000

Apr 10, 2026

MLS® 73499714

Expired
$3,999,999

Nov 30, 2025

MLS® 73363206

Listed
$3,999,999

Apr 23, 2025

MLS® 73363206

Population

3,794

U.S. Census Bureau, ACS 2024 5-Year Estimates (B01003)

Median Household Income

$213K

U.S. Census Bureau, ACS 2024 5-Year Estimates (B19013)

Renter-Occupied Homes

49.4%

U.S. Census Bureau, ACS 2024 5-Year Estimates (B25003)

New Construction Permits — Suffolk County

2,337 housing units permitted in the last 12 months (+13% vs the prior 12 months) — 2,062 in 5+ unit buildings

U.S. Census Bureau, Building Permits Survey (through Jul '26)

Listing Provided By

Listing Agent: Rebecca Davis Tulman And Leslie Singleton Adam

Listing Office: Gibson Sotheby's International Realty

MLS® Number: 73576624

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