27 Chestnut Street, Boston MA 02108
Boston, MA 02108 • Beacon Hill
$2,699,000
Est. $16,407/month
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About this home
This spectacular 3+ bedroom, 2 bath duplex w/ 18ft ceilings combines Beacon Hill elegance w/ contemporary style! With a unique double height living room, the spaces are extraordinary, creating an architectural masterpiece all within one of the most notable South Slope buildings. Oversized windows add to the appeal of this incredible condo. Polished concrete flooring along w/ industrial elements including a metal staircase & steel beam accents, create a space that is both visually appealing, as well as open, inviting & dramatic. A private entry is located off the building's enclosed courtyard-a hidden oasis. An inviting sitting room, bdrm & bath are located on the upper floor that overlooks the expansive lower floor where the living room & den have access to a charming enclosed patio. Two addt'l bdrms & a bath are located on one side of the unit, and the opposite side offers a large dining room & fantastic oversized kitchen. Common courtyard, common deck w/sweeping views, live-in super.
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Recently Sold Nearby
Property History
Property Timeline
Listed for Sale
Apr 21, 2026
$2,699,000
Original listing
Agent: Rebecca Davis Tulman and Leslie Singleton Adam
Office: Gibson Sotheby's International Realty
| Date | Event | Price | Change | $/sqft | Details |
|---|---|---|---|---|---|
| 04/21/2026 | 🏠 Listed for Sale | $2,699,000 | - | - | Original listing |
Tax History
| Year | Taxes | Assessment |
|---|---|---|
| 2026 | $15,918 | $1,623,100 |
Financial Details
Annual Property Tax
$15,918
Tax Year 2026
HOA Fee
$1,233
Monthly
Assessed Value
$1,623,100
Facts & Features
Central AC
Home Facts
Type
Residential
Style
Condominium
Year Built
1913
Living Area
2,180 sq ft
Bedrooms
3
Full Baths
2
Total Rooms
7
Interior
Heating
Forced Air, Natural Gas
Cooling
Central Air
Flooring
Concrete, Other
Appliances
Range, Dishwasher, Refrigerator, Freezer, Washer, Dryer
Fireplace
None
Basement
N
Laundry
In Unit, Electric Dryer Hookup
Features
None
Exterior
Construction
See Remarks
Architecture
Other (see Remarks)
Roof
Other
Features
Deck - Roof, Patio, Patio - Enclosed
Pool
None
Spa
None
Fencing
None
Patio/Porch
Deck - Roof, Patio, Patio - Enclosed
Parking
Features
On Street
Utilities
Electric
None
Water
Public
Sewer
Public Sewer
Gas
None
Other
For Electric Range, For Electric Oven, For Electric Dryer
Financial
Annual Tax
$15,918
Assessed Value
$1,623,100
HOA & Community
HOA Fee
$1,233 Monthly
Fee Includes
Heat, Water, Sewer, Insurance, Maintenance Structure, Maintenance Grounds, Snow Removal, Trash, Air Conditioning, Reserve Funds
Amenities
Hot Water, Elevator(s), Fitness Center, Storage, Garden Area
Optional Fee Includes
None
Owner-Occupied Units
29
Pets
Yes
MA Disclosures
Seller Disclosures
Phenomenal Common Roofdeck, One Of The Highest In The City, With Incredible River And City Views. Fee Also Includes Live-in Superintendent.
Additional Details
Possession
None
Accepted Financing
None
Structure Type
["High-Rise"]
Unit/Building
GA
Sq Ft Source
Master Deed
Documents
None
County
Suffolk
Total market time (incl. prior listings)
90 days
Property Overview
Property Type
Condominium
Listing Type
For Sale
Year Built
1913
Bedrooms
3
Full Bathrooms
2
Living Area
2,180 sq ft
Total Rooms
7
Stories
2
Entry Level
1
Floor Layout
Interactive room guide
Floor Layout
Finished Area
2,180 sq ft above grade
Dimensions11 x 14
Dimensions9 x 18
Dimensions10 x 22
Dimensions12 x 13
Dimensions11 x 33
Dimensions12 x 14
Display Options
Outdoor Areas
Patio & porchDeck - Roof, Patio, Patio - Enclosed
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:
Concrete, Other
Appliances:
Range, Dishwasher, Refrigerator, Freezer, Washer, Dryer
Interior Features:
Windows:
Basement:
N
Laundry:
In Unit, Electric Dryer Hookup
Security:
Intercom, Other
Construction & Materials
Style:
Other (See Remarks)
Year Built:
1913
Structure Type:
High-Rise
Exterior Materials:
See Remarks
Roof:
Other
Foundation:
Stories:
2
Heating, Cooling & Utilities
Heating:
Forced Air, Natural Gas
Heating Zones:
2
Cooling:
Central Air
Cooling Zones:
2
Hot Water:
Water Source:
Public
Sewer:
Public Sewer
Energy Features:
Exterior & Lot
Exterior Features:
Deck - Roof, Patio, Patio - Enclosed
Patio & Porch:
Deck - Roof, Patio, Patio - Enclosed
Fencing:
Other Structures:
Lot Features:
Road Surface:
Parking & Garage
Parking Features:
On Street
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
Advent School
0.2 mi
Grades K-06
Park Street School
0.2 mi
Grades K-07
The Learning Project
0.6 mi
Grades K-06
St. John Elementary School
0.9 mi
Grades PK-08
Kingsley Montessori School
0.9 mi
Grades PK-06
A
Eliot K-8 Innovation School
0.9 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
1.2 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
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
A-
Warren-Prescott K-8 School
1.4 mi
|
#85 of 352
|
Score: 51.3
Improved 4 spots from last year
-7 below state avg
507 students
Diverse
Grades PK-08
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
3.1 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
3.6 mi
Mother Caroline Academy
3.6 mi
Grades 05-08
Epiphany School
4.5 mi
Grades 05-08
C
Ohrenberger School
7.9 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
High Schools
10 schools
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
Newman School
0.8 mi
Grades 07-12
Cathedral High School
1.2 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
2.2 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
2.3 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
2.3 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
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Property Tax
$1,327
Homeowners Insurance
$200
HOA Fee
$1,233/mo
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95% Interest
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Location
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Neighborhood
Beacon Hill
27 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
Jul 20, 2026 2:13 PM 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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