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101 Chestnut Street, Boston MA 02108

Boston, MA 02108 • Beacon Hill
$3,595,000
Est. $21,988/month
3
Beds
3
Baths
2,500
Sq Ft
$1,438
Price/Sq Ft
1918
Year Built
Stock Cooperative
Type
59
Days on Market
Active Price Drop -$155,000 Listed Apr 10, 2026 • MLS# 73499714 Copied!

About this home

One of the most notable buildings in all of Boston, 101 Chestnut Street in Beacon Hill is known for its incredibly gracious architecture, intimate community. and impeccable service. The elegant entry courtyard w/ fountain is the perfect backdrop to this one of a kind residence that's both welcoming and distinguished. Unit E offers 2500 sqft of living space on one floor: 3 bedrooms, 3 bathrooms and a graceful living/dining room w/ front facing Chestnut Street views. The expansive space occupies a desirable corner exposure w/ courtyard views seen from the chef's kitchen & addt'l exposures throughout. The primary bedroom is generously proportioned & boasts South facing sun. A primary bathroom & oversized closet offer incredible storage. A separate bedroom wing w/ 2 add'tl bedrooms & 2 bathrooms is on the West side of the unit & offer privacy. 101 Chestnut features a concierge and a beautifully landscaped common roofdeck. A private storage closet completes this truly exceptional offering.

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Public Records

Current Owner

Owner ONE HUNDRED ONE CHESTNUT
Mailing Address 311 SUMMER ST SUITE #200, BOSTON, MA, 02210

Land Use

Use Code 112
Description Apartments (8+ units)
Style APT 7-30 UNITS

Tax Information

Assessed Value $27,413,400

Assessment History

Year Land Building Total Change
FY2023 $12,213,200 $15,193,500 $27,413,400 —

Building Permit History

Issued Type / Work Status Value
Jun 3, 2025 Short Form Bldg Permit
EXTREN
Renovations - Exterior
Permit #SF1693301 		Open $85,000
Feb 14, 2024 Electrical Fire Alarms
FA
Fire Alarm
Permit #EFA1568164 		Open $2,000
Nov 1, 2023 Plumbing Permit
PLUMBING
Plumbing
Permit #PL1540745 		Open $5,000
Oct 30, 2023 Short Form Bldg Permit
EXTREN
Renovations - Exterior
Permit #SF1535809 		Closed $173,000
Oct 5, 2023 Long Form/Alteration Permit
INTEXT
Interior/Exterior Work
Permit #ALT1420635 		Open $100,000
Aug 22, 2023 Plumbing Permit
PLUMBING
Plumbing
Permit #PL1512447 		Closed $60,000
Oct 5, 2022 Electrical Permit
ELECTRICAL
Electrical
Permit #E1398661 		Closed $3,000
Sep 27, 2022 Long Form/Alteration Permit
INTREN
Renovations - Interior NSC
Permit #ALT1374073 		Closed $96,952
Sep 8, 2022 Short Form Bldg Permit
INTREN
Renovations - Interior NSC
Permit #SF1390280 		Closed $50,000
Jul 18, 2022 Gas Permit
GAS
Gas
Permit #G1353750 		Open $1,000
Jul 12, 2022 Plumbing Permit
PLUMBING
Plumbing
Permit #PL1353744 		Open $1,000
Jun 13, 2022 Short Form Bldg Permit
INTREN
Renovations - Interior NSC
Permit #SF1345911 		Closed $995,000
Nov 8, 2021 Certificate of Occupancy
18 UnitsCertificate for: (1) Unit # RAlt725503 - 9/7/17, SF1057079 - 2/27/20
Permit #COO1262895 		Closed $200,000
Sep 29, 2021 Electrical Fire Alarms
FA
Fire Alarm
Permit #EFA1250809 		Closed $1,500
Jun 10, 2021 Electrical Low Voltage
LVOLT
Low Voltage
Permit #ELV1207034 		Closed $2,000
Data: City of Boston Open Data (Analyze Boston)

Municipal Context: BOSTON

Property Data Comparison

Discrepancies found between MLS and assessor records.

Field Assessor MLS Match
Sqft 49,744 2,500 ✗
Year built 1,918 1,918 ✓
Match: address_exact (90.0% confidence) · Data as of Jun 1, 2026

Property Overview

Property Type
Stock Cooperative
Listing Type
For Sale
Year Built
1918
Bedrooms
3
Full Bathrooms
3
Living Area
2,500 sq ft
Total Rooms
6
Stories
1
Entry Level
2

Facts & Features

Central AC

Home Facts

Type Residential
Style Stock Cooperative
Year Built 1918
Living Area 2,500 sq ft
Bedrooms 3
Full Baths 3
Total Rooms 6

Interior

Heating Central
Cooling Central Air
Flooring Wood
Appliances Range, Dishwasher, Disposal, Refrigerator, Freezer, Washer, Dryer
Fireplace Living Room, Master Bedroom
Fireplaces 3
Basement N
Laundry None
Features None

Exterior

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

Parking

Features None

Utilities

Electric None
Water Public
Sewer Public Sewer
Gas None
Other None

Financial

Annual Tax 0.00
Assessed Value 0.00

Interior Features

Flooring: Wood
Appliances: Range, Dishwasher, Disposal, Refrigerator, Freezer, Washer, Dryer
Interior Features:
Windows:
Basement: N
Laundry:
Security: Concierge

Construction & Materials

Year Built: 1918
Structure Type: Mid-Rise
Exterior Materials: Brick, See Remarks
Roof: Rubber, Other
Foundation:
Stories: 1

Heating, Cooling & Utilities

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

Exterior & Lot

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

Parking & Garage

Parking Features:

Special Features

Fireplaces: 3
Fireplace Type: Living Room, Master Bedroom
Community Amenities: Public Transportation, Shopping, Tennis Court(s), Park, Walk/Jog Trails, Medical Facility, Bike Path, Highway Access, Other

Location

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Neighborhood

Beacon Hill

101 Chestnut Street, 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
< 0.1 mi
Grades K-07
Advent School
0.1 mi
Grades K-06
The Learning Project
0.3 mi
Grades K-06
Kingsley Montessori School
0.7 mi
Grades PK-06
D
Melvin H. King South End Academy
0.9 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
St. John Elementary School
1.1 mi
Grades PK-08
A
Eliot K-8 Innovation School
1.2 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
C
Hurley K-8 School
1.3 mi | #258 of 352 | Score: 35.8
Dropped 23 spots from last year
-22.4 below state avg
335 students Moderate
Grades PK-08
Kids Are People School
1.3 mi
Grades PK-12
M

Middle Schools

10 schools
Middle School Academy
2.0 mi
F
Higginson/Lewis K-8 School
2.6 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
2.9 mi
Grades 05-08
A
Uncommon Schools - Roxbury Preparatory Dorchester Campus Middle School
3.1 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
3.4 mi
Mother Caroline Academy
3.5 mi
Grades 05-08
Epiphany School
4.4 mi
Grades 05-08
C
Ohrenberger School
7.7 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
1.6 mi
UP Academy
2.0 mi
H

High Schools

10 schools
Newman School
0.6 mi
Grades 07-12
C
Quincy Upper School
0.8 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
Cathedral High School
1.1 mi
9 sports • 430 athletes
Grades 07-12
D
Charlestown High School
1.7 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+
Boston Latin School
2.0 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
A-
O'Bryant School of Math & Science
2.0 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
B
Dearborn STEM Academy
2.1 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
2.6 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
2.9 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
3.1 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 $0
Homeowners Insurance $200
HOA Fee $3,610/mo
PMI (if <20% down) $0

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Payment Over Time

Interest
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Year 1
95% Interest
Year 15
50/50
Year 30
95% Principal
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Property History

Market Insights

1
Price Changes
4.1%
Price Range

Property Timeline

↓
Price Reduced
May 9, 2026
$3,595,000 $155,000 (-4.13%)
From $3,750,000 to $3,595,000 (-4.1%)
🏠
Listed for Sale
Apr 10, 2026
$3,750,000
Original listing
Agent: Rebecca Davis Tulman and Leslie Singleton Adam Office: Gibson Sotheby's International Realty

Price & Status History

Date Event Price Change
May 9, 2026 Price Changed $3,595,000 -$155,000
Apr 10, 2026 New Listing Added $3,750,000 —

Market Statistics

Days on Market
59 days
Price per Sq Ft
$1,438
Total Price Drop
-$155,000

Tax History

Year Taxes Assessment
2025 $0 $0

Financial Details

Annual Property Tax
$0
Tax Year 2025
HOA Fee
$3,610
Monthly
Assessed Value
$0

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 Data Updated May 13, 2026 3:05 AM EDT
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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