101 Chestnut Street # R, Boston MA 02108
Boston, MA 02108 • Beacon Hill
$4,400,000
Track this home for price, status, and open-house alerts.
Sale Statistics
Sale Overview
Original List Price:
$5,100,000
Final Sale Price:
$4,400,000
Difference:
$700,000 (-13.7%)
Performance Metrics
86.3%
List to Sale Ratio
Sold below asking price
122
Days on Market
Extended listing
Price per Square Foot Analysis
Original $/sq ft:
$1,700
Sale $/sq ft:
$1,467
This property sold for $1,467 per square foot
Sale Summary
This property sold for 13.7% below the original asking price.
At 122 days on market, this property took longer than average to sell.
About this home
One of Beacon Hill's most prized doorman buildings,101 Chestnut Street is an Italian-Renaissance style building with a distinctive bricked courtyard with fountain surrounded by an open colonnade. Stunning penthouse duplex...elegant foyer leads to gracious formal living room, featuring fireplace, high ceilings, deep crown moldings and Juliet balcony. An exquisite formal dining room with fireplace, wainscoting, built-in china cabinets affords spectacular views of Chestnut Street to the golden dome of the State House. Cozy library features custom built-ins, fireplace and powder room. The unique kitchen has casual dining area, pantry, ample storage and Beacon Hill vistas. Spacious master suite includes fireplace, dressing room, his and hers baths. A large guest suite with full bath and versatile third bedroom/office with full bath complete this distinctive offering. Amenities include roof deck, Brimmer garage rental, storage room....One of the most beautifully appointed homes on the Hill.
View in the App
Save this property, schedule tours instantly, and get alerts when the price drops
Scan with phone
Public Records & Permits
Log in to view assessor & tax records, ownership history, and recent building permits for this property.
BMN Estimate
Get the number an algorithm can't give you
A free agent CMA factors in condition, upgrades, and the street — the things comps alone can't see.
Recently Sold Nearby
Property History
Market Insights
44.3%
Price Range
34
Total Days on Market
2
Previous Sales
Property Timeline
Previous Transaction - MLS #73357969
Full transaction history available when tracking began
Previously Sold
Jul 22, 2025
$7,900,000
MLS #73357969
Previous Transaction - MLS #72893873
Full transaction history available when tracking began
Previously Sold
Dec 8, 2021
$6,825,000
MLS #72893873
Sold
Oct 23, 2018
$4,400,000
Property sold
Days on Market: 34
Listed for Sale
May 10, 2018
$4,500,000
Original listing
Agent: William J. Milbury
Office: Milbury and Company
| Date | Event | Price | Change | $/sqft | Details |
|---|---|---|---|---|---|
| 07/22/2025 | 🏷️ Previously Sold | $7,900,000 | - | - | MLS #73357969 |
| 12/08/2021 | 🏷️ Previously Sold | $6,825,000 | - | - | MLS #72893873 |
| 10/23/2018 | ✓ Sold | $4,400,000 | - | - | Property sold |
| 05/10/2018 | 🏠 Listed for Sale | $4,500,000 | - | - | Original listing |
Tax History
| Year | Taxes | Assessment |
|---|---|---|
| 2018 | $0 | $0 |
Financial Details
Annual Property Tax
$0
Tax Year 2018
HOA Fee
$4,200
Monthly
Assessed Value
$0
Facts & Features
1 Car Garage
Central AC
Home Facts
Type
Residential
Style
Stock Cooperative
Year Built
1925
Living Area
3,000 sq ft
Bedrooms
3
Full Baths
4
Half Baths
1
Total Rooms
7
Interior
Heating
Central
Cooling
Central Air
Flooring
Hardwood
Appliances
None
Fireplace
Dining Room, Family Room, Living Room, Master Bedroom, Bedroom
Fireplaces
5
Basement
N
Laundry
Fourth Floor, In Unit
Features
Entrance Foyer, Wired For Sound
Exterior
Construction
Stone
Architecture
Other (see Remarks)
Roof
None
Features
Deck - Access Rights
Pool
None
Spa
None
Fencing
None
Patio/Porch
Deck - Access Rights
Parking
Garage Spaces
1
Has Garage
Yes
Features
Detached, Rented
Total Spaces
1
Utilities
Electric
None
Water
Public
Sewer
Public Sewer
Gas
None
Other
For Gas Range
Financial
Annual Tax
0.00
Assessed Value
0.00
HOA & Community
HOA Fee
$4,200 Monthly
Fee Includes
Heat, Insurance, Snow Removal
Amenities
Fitness Center, Storage, Garden Area
Optional Fee Includes
None
Pets
Yes w/ Restrictions
MA Disclosures
Seller Disclosures
Cooperative Association Approval Process...common Area Work In Process (seller To Assume Current Assessment) Taxes Are Included In The Listed Monthly Coop. Fee...
Exclusions
All Window Treatment And Light Fixtures Are Excluded...
Additional Details
Possession
None
Accepted Financing
Contract
Structure Type
["Duplex"]
Unit/Building
R
Sq Ft Source
Owner
Sq Ft Disclosures
Approximate...
Documents
None
County
Suffolk
Total market time (incl. prior listings)
34 days
Property Overview
Property Type
Stock Cooperative
Listing Type
Sold
Year Built
1925
Bedrooms
3
Full Bathrooms
4
Half Bathrooms
1
Living Area
3,000 sq ft
Total Rooms
7
Stories
2
Entry Level
5
Floor Layout
Interactive room guide
Floor Layout
FeaturesBathroom - Full, Flooring - Hardwood
FeaturesFlooring - Hardwood, Window(s) - Picture, Wainscoting
FeaturesFlooring - Hardwood, Dining Area, Pantry, Countertops - Stone/Granite/Solid
FeaturesBathroom - Full, Flooring - Hardwood
FeaturesFlooring - Hardwood, Balcony - Exterior, French Doors
FeaturesBathroom - Full, Walk-In Closet(s), Flooring - Hardwood, Dressing Room
FeaturesBathroom - Half, Flooring - Hardwood
FeaturesYes
Display Options
Outdoor Areas
Patio & porchDeck - Access Rights
Room Markers
BABathroom (4)
BRBedroom (5)
DDining (1)
KKitchen (1)
LLiving (2)
OOffice (1)
Conceptual diagram based on MLS room data. It is not to scale and is not a substitute for architectural plans or on-site measurements.
Interior Features
Flooring:
Hardwood
Appliances:
Interior Features:
Entrance Foyer, Wired for Sound
Windows:
Basement:
N
Laundry:
Fourth Floor, In Unit
Security:
Intercom, Doorman, Security System
Construction & Materials
Style:
Other (See Remarks)
Year Built:
1925
Structure Type:
Duplex
Exterior Materials:
Stone
Roof:
Foundation:
Stories:
2
Heating, Cooling & Utilities
Heating:
Central
Cooling:
Central Air
Hot Water:
Water Source:
Public
Sewer:
Public Sewer
Energy Features:
Exterior & Lot
Exterior Features:
Deck - Access Rights
Patio & Porch:
Deck - Access Rights
Fencing:
Other Structures:
Lot Features:
Road Surface:
Parking & Garage
Garage Spaces:
1
Total Parking Spaces:
1
Parking Features:
Detached, Rented
Special Features
Fireplaces:
5
Fireplace Type:
Dining Room, Family Room, Living Room, Master Bedroom, Bedroom
Community Amenities:
Public Transportation, Shopping, Medical Facility, University
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
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
1.4 mi
Grades PK-12
Middle Schools
10 schools
Middle School Academy
1.9 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
1.9 mi
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
Location
Loading map...
Neighborhood
Beacon Hill
101 Chestnut Street # R, Boston MA 02108
Boston, MA 02108
Listing Information
Listing Agent
William J. Milbury
Listing Office
Milbury and Company
Office Phone
508-997-7400
Agent MLS ID
A9500738
Office MLS ID
A95340
Listing Data Updated
Oct 24, 2018 5:22 PM EDT
Listing information is deemed reliable but not guaranteed. Data provided by MLS Property Information Network, Inc. All information should be independently verified.
Contact Us
Ask about this property — free, no obligation.
Similar Homes for Sale
Comparable Properties
Customize Comparable Search
Finding comparable properties...
Loading market insights for Boston.