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32 Chestnut Street # 2, Boston MA 02108

Boston, MA 02108 • Beacon Hill
$2,800,000
Est. $16,461/month
4
Beds
2
Baths
2,740
Sq Ft
$1,022
Price/Sq Ft
0.06
Acres
1821
Year Built
Condominium
Type
16
Days on Market
Pending Listed Nov 14, 2025 • MLS# 73454938 Copied!

About this home

Incredible rare opportunity on upper Chestnut Street, this distinguished Beacon Hill residence is on the market for the first time in over 50 years allowing for personalization and restoration at a truly iconic location. Rich in period detail, the unit features 3 living levels, multiple fireplaces, box windows, and abundant natural light. Double etched-glass doors open to the gracious entry foyer and staircase which lead to beautifully proportioned rooms. The first level features living & dining rooms w/ marble fireplaces and Chestnut St views. The upper two floors offer 4+ bedrooms and 2 full baths and spectacular sunlight. The top floor features a full staircase to the roof with sweeping city views (a new slate and rubber roof in 2024 temporarily replaced the deck). Additional common storage in the bldg’s lower level. A timeless Beacon Hill gem ready for its next chapter.

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Property Overview

Property Type
Condominium
Listing Type
For Sale
Year Built
1821
Bedrooms
4
Full Bathrooms
2
Living Area
2,740 sq ft
Total Rooms
8
Stories
3
Entry Level
2

Facts & Features

Central AC

Home Facts

Type Residential
Style Condominium
Year Built 1821
Living Area 2,740 sq ft
Lot Size 0.06 acres
Bedrooms 4
Full Baths 2
Total Rooms 8

Interior

Heating Baseboard
Cooling Central Air
Flooring Hardwood
Appliances None
Fireplace Dining Room, Living Room, Master Bedroom, Bedroom
Fireplaces 4
Basement Y
Laundry In Unit
Features Closet, Entrance Foyer

Exterior

Construction Brick
Architecture None
Roof Slate, Rubber
Features Deck - Roof, Other
Pool None
Spa None
Fencing None
Patio/Porch Deck - Roof

Parking

Features On Street

Utilities

Electric None
Water Public
Sewer Public Sewer
Gas None
Other None

Financial

Annual Tax $25,227
Assessed Value $2,178,500

Interior Features

Flooring: Hardwood
Appliances:
Interior Features: Closet, Entrance Foyer
Windows:
Basement: Y
Laundry: In Unit
Security:

Construction & Materials

Year Built: 1821
Structure Type: Townhouse
Exterior Materials: Brick
Roof: Slate, Rubber
Foundation:
Stories: 3

Heating, Cooling & Utilities

Heating: Baseboard
Heating Zones: 1
Cooling: Central Air
Cooling Zones: 1
Hot Water:
Water Source: Public
Sewer: Public Sewer
Energy Features:

Exterior & Lot

Exterior Features: Deck - Roof, Other
Patio & Porch: Deck - Roof
Fencing:
Other Structures:
Lot Features:
Road Surface:

Parking & Garage

Parking Features: On Street

Special Features

Fireplaces: 4
Fireplace Type: Dining Room, Living Room, Master Bedroom, Bedroom
Community Amenities: Public Transportation, Shopping, Tennis Court(s), Park, Walk/Jog Trails, Medical Facility, Conservation Area, Highway Access, House of Worship, T-Station, University

Location

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Neighborhood

Beacon Hill

32 Chestnut Street # 2, Boston MA 02108

Boston, MA 02108

Walkability

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Nearby Schools

School District
Boston School District local
C-
🎓 Where Graduates Go Class of 2021
52% attend college
38% 4-Year 14% 2-Year 7% Out of State 7% Working
⚠ School Safety 2024-25
3.7% Above Average
3.2% Suspensions 0.3% In-School 0.5% Emergency
↓ 1.8% below state avg
E

Elementary Schools

10 schools
Park Street School
0.2 mi
Grades K-07
Advent School
0.2 mi
Grades K-06
The Learning Project
0.6 mi
Grades K-06
Kingsley Montessori School
0.9 mi
Grades PK-06
St. John Elementary School
0.9 mi
Grades PK-08
A
Eliot K-8 Innovation School
1.0 mi | #48 of 352 | Score: 57.2
Improved 2 spots from last year
-1.1 below state avg
784 students Diverse
Strong Attendance
Grades PK-08
D
Melvin H. King South End Academy
1.0 mi | #24 of 25 | Score: 20.2
Improved 363 spots from last year
-38.1 below state avg
125 students Diverse
Rising School Diverse Student Body
Grades PK-12
F
Blackstone Elementary School
1.1 mi | #809 of 824 | Score: 26.3
Improved 12 spots from last year
-31.9 below state avg
582 students Moderate
Grades PK-06
C
Hurley K-8 School
1.4 mi | #258 of 352 | Score: 35.8
Dropped 23 spots from last year
-22.4 below state avg
335 students Moderate
Grades PK-08
C
Harvard-Kent Elementary School
1.4 mi | #589 of 824 | Score: 41.5
Dropped 181 spots from last year
-16.7 below state avg
334 students Very Diverse
Diverse Student Body
Grades PK-06
M

Middle Schools

10 schools
Middle School Academy
1.9 mi
F
Higginson/Lewis K-8 School
2.7 mi | #349 of 352 | Score: 23.6
Improved 3 spots from last year
-34.6 below state avg
213 students Diverse
Grades 03-08
Nativity Prep School
3.0 mi
Grades 05-08
A
Uncommon Schools - Roxbury Preparatory Dorchester Campus Middle School
3.2 mi | #4 of 16 | Score: 41.9
Improved 187 spots from last year
-16.3 below state avg
1,126 students Diverse
Rising School College Ready Curriculum
Grades 05-08
Dearborn Middle School
3.5 mi
Mother Caroline Academy
3.6 mi
Grades 05-08
Epiphany School
4.5 mi
Grades 05-08
C
Ohrenberger School
7.8 mi | #265 of 352 | Score: 34.9
Improved 20 spots from last year
-23.3 below state avg
477 students Diverse
Rising School Diverse Student Body
Grades 03-08
Edwards Middle
1.5 mi
UP Academy
1.9 mi
H

High Schools

10 schools
C
Quincy Upper School
0.7 mi | #268 of 346 | Score: 44.6
Improved 4 spots from last year
-13.6 below state avg
557 students Very Diverse
12 sports • 208 athletes
High Graduation Rate Diverse Student Body
Grades 06-12
Newman School
0.8 mi
Grades 07-12
Cathedral High School
1.1 mi
9 sports • 430 athletes
Grades 07-12
D
Charlestown High School
1.6 mi | #322 of 346 | Score: 31.0
Improved 49 spots from last year
-27.2 below state avg
754 students Diverse
11 sports • 488 athletes
Early College Program Rising School
Grades 07-12
A-
O'Bryant School of Math & Science
2.1 mi | #90 of 346 | Score: 61.1
Improved 94 spots from last year
+2.9 above state avg
1,509 students Very Diverse
High Graduation Rate Rising School College Ready Curriculum Diverse Student Body
Grades 07-12
A+
Boston Latin School
2.2 mi | #19 of 346 | Score: 73.3
Improved 61 spots from last year
+15.1 above state avg
2,424 students Very Diverse
18 sports • 2,006 athletes
Strong AP Program High Graduation Rate Rising School Strong Athletics
Grades 07-12
B
Dearborn STEM Academy
2.2 mi | #13 of 25 | Score: 31.7
Improved 356 spots from last year
-26.6 below state avg
565 students Diverse
10 sports • 242 athletes
Early College Program Rising School
Grades 07-12
C-
East Boston High School
2.4 mi | #305 of 346 | Score: 37.3
Improved 31 spots from last year
-20.9 below state avg
1,252 students Less Diverse
14 sports • 584 athletes
Early College Program Rising School
Grades 07-12
A+
Boston Latin Academy
3.0 mi | #2 of 25 | Score: 63.9
Improved 214 spots from last year
+5.7 above state avg
1,693 students Very Diverse
17 sports • 1,298 athletes
High Graduation Rate Rising School Strong Athletics Diverse Student Body
Grades 07-12
C
Ruth Batson Academy
3.0 mi | #19 of 25 | Score: 27.6
Improved 346 spots from last year
-30.6 below state avg
604 students Diverse
8 sports • 128 athletes
Early College Program Rising School
Grades 07-12
Learn about these ratings
School data provided by BMN Schools

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Monthly Payment Breakdown

Principal & Interest $0
Property Tax $2,102
Homeowners Insurance $200
PMI (if <20% down) $0

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Payment Over Time

Interest
Principal
Year 1
95% Interest
Year 15
50/50
Year 30
95% Principal
* Estimates only. Actual payments may vary. Consult with a lender for accurate figures.

Property History

Market Insights

Property Timeline

🏠
Listed for Sale
Nov 14, 2025
$2,800,000
Original listing
Agent: Rebecca Davis Tulman and Leslie Singleton Adam Office: Gibson Sotheby's International Realty
🏠
Listed for Sale
Nov 14, 2025
$2,800,000
Original listing
Agent: Rebecca Davis Tulman and Leslie Singleton Adam Office: Gibson Sotheby's International Realty

Price & Status History

Date Event Price Change
Nov 14, 2025 New Listing Added $2,800,000 —
Nov 14, 2025 New Listing Added $2,800,000 —

Market Statistics

Days on Market
16 days
Price per Sq Ft
$1,022

Tax History

Year Taxes Assessment
2025 $25,227 $2,178,500

Financial Details

Annual Property Tax
$25,227
Tax Year 2025
HOA Fee
$0
Per month
Assessed Value
$2,178,500

Listing Information

Listing Agent Rebecca Davis Tulman and Leslie Singleton Adam
Listing Office Gibson Sotheby's International Realty
Agent MLS ID TM348767
Office MLS ID AN7429
Listing information is deemed reliable but not guaranteed. Data provided by MLS Property Information Network, Inc. All information should be independently verified.

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