Dimensions16 x 14
LevelSecond
101 Chestnut Street, Boston MA 02108
Boston, MA 02108 • Beacon Hill
$3,499,950
Est. $21,508/month
Estimate assumptions
20% down, a 30-year loan at 6.5%, and $200/month estimated insurance.
Includes the supplied property-tax and HOA inputs; missing inputs contribute $0. HOA fees with an unspecified frequency are treated as monthly. PMI and closing costs are excluded.
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About this home
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.
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Recently Sold Nearby
Property History
Market Insights
1
Price Changes
42.9%
Price Range
1
Previous Sales
Property Timeline
Price Increased
Sep 14, 2026
$3,499,950
+$950
(+0.03%)
From $3,499,000 to $3,499,950 (+0.0%)
Listed for Sale
Sep 14, 2026
$3,499,000
Original listing
Agent: Rebecca Davis Tulman and Leslie Singleton Adam
Office: Gibson Sotheby's International Realty
Previous Transaction - MLS #72717171
Full transaction history available when tracking began
Previously Sold
May 18, 2021
$2,000,000
MLS #72717171
| Date | Event | Price | Change | $/sqft | Details |
|---|---|---|---|---|---|
| 09/14/2026 | ↑ Price Increased | $3,499,950 | +$950 | - | From $3,499,000 to $3,499,950 (+0.0%) |
| 09/14/2026 | 🏠 Listed for Sale | $3,499,000 | - | - | Original listing |
| 05/18/2021 | 🏷️ Previously Sold | $2,000,000 | - | - | MLS #72717171 |
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
Facts & Features
Central AC
Home Facts
Type
Residential
Style
Stock Cooperative
Year Built
1918
Living Area
2,500 sq ft
Stories
1
Bedrooms
2
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
Study
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
HOA & Community
HOA Fee
$3,610 Monthly
Fee Includes
Water, Sewer, Insurance, Maintenance Structure, Maintenance Grounds, Snow Removal, Trash, Reserve Funds
Amenities
Hot Water, Laundry, Elevator(s), Fitness Center, Storage, Garden Area
Optional Fee Includes
None
Owner-Occupied Units
18
Pets
Yes
MA Disclosures
Lead Paint
Unknown
Seller Disclosures
Prospective Buyers Will Need To Submit Necessary Coop Application And Go Through Coop Interview Process.
Exclusions
Fireplace Mantel In Living Room Is Excluded.
Additional Details
Possession
None
Accepted Financing
None
Structure Type
["Mid-Rise"]
Unit/Building
E
Sq Ft Source
Other
Sq Ft Disclosures
Wonderful front exposure over Chestnut Street with all living space on one floor.
Documents
None
County
Suffolk
Property Overview
Property Type
Stock Cooperative
Listing Type
For Sale
Year Built
1918
Bedrooms
2
Full Bathrooms
3
Living Area
2,500 sq ft
Total Rooms
6
Stories
1
Entry Level
2
Floor Layout
Interactive room guide
Floor Layout
Finished Area
2,500 sq ft above grade
Dimensions15 x 14
LevelSecond
Dimensions22 x 22
LevelSecond
Dimensions22 x 22
LevelSecond
Dimensions18 x 22
LevelSecond
FeaturesYes
Display Options
Outdoor Areas
Patio & porchDeck - Roof
Room Markers
OOffice (1)
KKitchen (1)
BRBedroom (5)
BABathroom (4)
DDining (1)
LLiving (2)
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:
Wood
Appliances:
Range, Dishwasher, Disposal, Refrigerator, Freezer, Washer, Dryer
Interior Features:
Study
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
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
0.4 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: 20.4
Improved 363 spots from last year
-37.8 below state avg
80 students
Diverse
Rising School
Grades PK-12
St. John Elementary School
1.1 mi
Grades PK-08
F
Blackstone Elementary School
1.1 mi
|
#808 of 825
|
Score: 26.2
Improved 13 spots from last year
-32 below state avg
572 students
Moderate
Grades PK-06
A
Eliot K-8 Innovation School
1.1 mi
|
#47 of 352
|
Score: 57.5
Improved 3 spots from last year
-0.7 below state avg
779 students
Diverse
Strong Attendance
Grades PK-08
C
Hurley K-8 School
1.3 mi
|
#259 of 352
|
Score: 35.7
Dropped 24 spots from last year
-22.5 below state avg
337 students
Moderate
Grades PK-08
Kids Are People School
1.4 mi
Grades PK-12
Middle Schools
10 schools
Middle School Academy
2.0 mi
F
Higginson/Lewis K-8 School
2.6 mi
|
#349 of 352
|
Score: 23.2
Improved 3 spots from last year
-35 below state avg
246 students
Diverse
Grades 03-08
Nativity Prep School
2.9 mi
Grades 05-08
A
Uncommon Schools - Roxbury Preparatory Dorchester Campus Middle School
3.2 mi
|
#4 of 16
|
Score: 42.5
Improved 187 spots from last year
-15.7 below state avg
1,225 students
Diverse
Rising School
College Ready Curriculum
Grades 05-08
Dearborn Middle School
3.5 mi
Mother Caroline Academy
3.5 mi
Grades 05-08
Epiphany School
4.5 mi
Grades 05-08
C
Ohrenberger School
7.7 mi
|
#266 of 352
|
Score: 35.0
Improved 19 spots from last year
-23.2 below state avg
458 students
Diverse
Diverse Student Body
Grades 03-08
Edwards Middle
1.5 mi
UP Academy
2.0 mi
High Schools
10 schools
Newman School
0.6 mi
Grades 07-12
C
Quincy Upper School
0.8 mi
|
#279 of 346
|
Score: 44.4
Dropped 7 spots from last year
-13.8 below state avg
575 students
Very Diverse
12 sports
• 208 athletes
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
|
#319 of 346
|
Score: 32.9
Improved 52 spots from last year
-25.4 below state avg
646 students
Diverse
11 sports
• 488 athletes
Early College Program
Rising School
Grades 07-12
A+
Boston Latin School
2.0 mi
|
#20 of 346
|
Score: 73.7
Improved 60 spots from last year
+15.5 above state avg
2,382 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: 61.6
Improved 94 spots from last year
+3.4 above state avg
1,518 students
Very Diverse
High Graduation Rate
Rising School
College Ready Curriculum
Diverse Student Body
Grades 07-12
B
Dearborn STEM Academy
2.2 mi
|
#13 of 25
|
Score: 33.4
Improved 356 spots from last year
-24.8 below state avg
565 students
Moderate
10 sports
• 242 athletes
Early College Program
Rising School
Grades 07-12
C-
East Boston High School
2.5 mi
|
#300 of 346
|
Score: 38.2
Improved 36 spots from last year
-20 below state avg
1,181 students
Moderate
14 sports
• 584 athletes
Early College Program
Rising School
Grades 07-12
A+
Boston Latin Academy
2.9 mi
|
#2 of 25
|
Score: 64.9
Improved 214 spots from last year
+6.7 above state avg
1,669 students
Very Diverse
17 sports
• 1,298 athletes
Strong AP Program
High Graduation Rate
Rising School
Strong Athletics
Grades 07-12
C
Ruth Batson Academy
3.1 mi
|
#20 of 25
|
Score: 29.1
Improved 345 spots from last year
-29.1 below state avg
584 students
Diverse
8 sports
• 128 athletes
Early College Program
Rising School
Grades 07-12
Learn about these ratings
Monthly Payment Calculator
Monthly Payment
$0
Principal, interest, taxes & insurance
Loan Amount
$0
After down payment
Total Interest
$0
Over life of loan
Total Cost
$0
Including down payment
%
Down: $0
%
Monthly Payment Breakdown
Principal & Interest
$0
Property Tax
$0
Homeowners Insurance
$200
HOA Fee
$3,610/mo
PMI (if <20% down)
$0
Loan Summary
Total of 360 payments
$0
Total principal paid
$0
Total interest paid
$0
Rate Impact
-0.5% Rate
$0/mo
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Current Rate
$0/mo
+0.5% Rate
$0/mo
Cost $0/mo
Payment Over Time
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.
Location
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Neighborhood
Beacon Hill
101 Chestnut Street, Boston MA 02108
Boston, MA 02108
Listing Information
Listing Agent
Rebecca Davis Tulman and Leslie Singleton Adam
Listing Office
Gibson Sotheby's International Realty
Office Phone
857-310-5632
Agent MLS ID
TM348767
Office MLS ID
AN7429
Listing Data Updated
Sep 14, 2026 11:22 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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