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27 Chestnut Street, Boston MA 02108

Boston, MA 02108 • Beacon Hill
$2,699,000
Est. $16,407/month
3
Beds
2
Baths
2,180
Sq Ft
$1,238
Price/Sq Ft
1913
Year Built
Condominium
Type
12 hours 2 minutes
Time on Market
Active Listed Apr 21, 2026 • MLS# 73504892 Copied!

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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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

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

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

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

Parking & Garage

Parking Features: On Street

Location

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Neighborhood

Beacon Hill

27 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
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
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
7.9 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
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
2.2 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
Learn about these ratings
School data provided by BMN Schools

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Monthly Payment Breakdown

Principal & Interest $0
Property Tax $1,327
Homeowners Insurance $200
HOA Fee $1,233/mo
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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

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

Price & Status History

Date Event Price Change
Apr 21, 2026 New Listing Added $2,699,000 —

Market Statistics

Time on Market
12 hours 2 minutes
Price per Sq Ft
$1,238

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

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 Apr 21, 2026 4:20 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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BMN Boston Real Estate

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