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27 Chestnut Street, Boston MA 02108

Boston, MA 02108 • Beacon Hill
$1,880,000
Est. $11,929/month
3
Beds
2
Baths
1,715
Sq Ft
$1,096
Price/Sq Ft
1880
Year Built
52
Days on Market
Closed Listed Sep 24, 2020 • MLS# 72732235 Copied!

About this home

This lovely, totally renovated three bedroom duplex has the feel of a townhouse. The apartment is situated in the former School of Theology of Boston University on wonderful Chestnut Street. This highly sought after building, with a live-in superintendent, has many amenities, such as a courtyard garden, gym, bike room, storage, elevator and a scenic common roof deck. A focal point of the apartment is a spacious, elegant living room with a soaring south facing window, a new balcony, LED lighting and an architectural fireplace. The recently installed chef’s kitchen has it all, including a pantry and a laundry/storage room. There is a cozy den connected to the kitchen as well as a separate dining area with a newly installed wet bar and wine cooler. The unit includes two beautiful full bathrooms and a private main bedroom suite on the second floor. Located one block away from Boston Common Garage - This is a must see.

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Public Records

Current Owner

Owner CHESTNUT STREET REALTY TRUST
Mailing Address 33 CHESTNUT ST #3 & #4, BOSTON, MA, 02108

Land Use

Use Code 102
Description Condominium
Style Row Middle

Tax Information

Assessed Value $1,481,100
Tax Rate $10.29 per $1,000
Base Tax $15,241
CPA Surcharge 1% ($142)
Estimated Annual Tax $15,383

Assessment History

Year Land Building Total Change
FY2023 $0 $1,339,700 $1,339,700

Municipal Context: BOSTON

Median Home Value $745,000
Avg SF Tax Bill $4,523
Residential Tax Rate $10.29/1000
CPA Surcharge 1%
County Suffolk
Match: geocode_proximity (87.0% confidence) · Data as of Mar 8, 2026

Property Overview

Property Type
Condominium
Listing Type
For Sale
Year Built
1880
Bedrooms
3
Full Bathrooms
2
Living Area
1,715 sq ft
Total Rooms
6
Stories
2
Entry Level
1

Sale Statistics

Sale Overview
Original List Price: $1,880,000
Final Sale Price: $1,880,000
Difference: +$0 (+0.0%)
Performance Metrics
100.0%
List to Sale Ratio
Sold at asking price
52
Days on Market
Average time
Price per Square Foot Analysis
Original $/sq ft: $1,096
Sale $/sq ft: $1,096
This property sold for $1,096 per square foot
Sale Summary

This property sold exactly at the asking price.

The property spent 52 days on market before selling.

Nearby Sales Comparison

Based on 50 similar properties sold within 0.5 miles in the last 90 days

This Property
$1,096/sq ft
Area Average
$413/sq ft
Difference
+165.5%

This property sold for significantly more per square foot than similar nearby properties, suggesting premium features or condition.

Facts & Features

Central AC

Home Facts

Type Residential
Style Condominium
Year Built 1880
Living Area 1,715 sq ft
Bedrooms 3
Full Baths 2
Total Rooms 6

Interior

Heating Natural Gas
Cooling Central Air
Flooring Hardwood
Appliances None
Fireplace None
Fireplaces 1
Basement Y
Laundry Common Area, In Unit
Features Wet Bar

Exterior

Construction None
Architecture None
Roof None
Features Deck - Roof, Patio, City View(s), Garden
Pool None
Spa None
Fencing None
Patio/Porch Deck - Roof, Patio

Parking

Features On Street

Utilities

Electric None
Water Public
Sewer Public Sewer
Gas None
Other None

Financial

Annual Tax $15,707
Assessed Value $1,746,400

Interior Features

Flooring: Hardwood
Appliances:
Interior Features: Wet Bar
Windows:
Basement: Y
Laundry: Common Area, In Unit
Security: Intercom

Construction & Materials

Year Built: 1880
Structure Type: Low-Rise
Exterior Materials:
Roof:
Foundation:
Stories: 2

Heating, Cooling & Utilities

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

Exterior & Lot

Exterior Features: Deck - Roof, Patio, City View(s), Garden
Patio & Porch: Deck - Roof, Patio
Fencing:
Other Structures:
Lot Features:
Road Surface:

Parking & Garage

Parking Features: On Street

Special Features

Fireplaces: 1
Fireplace Type:
View: Yes
View Type: City
Community Amenities: Public Transportation, Shopping, Park, Walk/Jog Trails, Medical Facility, Laundromat, Bike Path, Highway Access, House of Worship, Private School, Public School, T-Station, University

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
Park Street School
0.2 mi
Grades K-07
Advent School
0.2 mi
Grades K-06
The Learning Project
0.5 mi
Grades K-06
Kingsley Montessori School
0.9 mi
Grades PK-06
St. John Elementary School
0.9 mi
Grades PK-08
A
Eliot K-8 Innovation School
1.0 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
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
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
7.8 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
2.1 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
2.4 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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Monthly Payment Breakdown

Principal & Interest $0
Property Tax $1,309
Homeowners Insurance $200
HOA Fee $914/mo
PMI (if <20% down) $0

Loan Summary

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Total principal paid $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

46.3%
Price Range
53
Total Days on Market
1
Previous Sales

Property Timeline

Current Active Listing - MLS #73504892
Full transaction history available when tracking began
🏡
Currently Listed
Apr 21, 2026
$2,699,000
MLS #73504892 - Active
Sold
Jan 15, 2021
$1,880,000
Property sold
Days on Market: 53
🏠
Listed for Sale
Sep 24, 2020
$1,880,000
Original listing
Agent: Sally T. Brewster Office: Brewster & Berkowitz R. E.
Previous Transaction - MLS #72624900
Full transaction history available when tracking began
🏷️
Previously Sold
Apr 24, 2020
$1,450,000
MLS #72624900

Price & Status History

Date Event Price Change
Apr 25, 2026 Sold $2,699,000
Sep 24, 2020 New Listing Added $1,880,000
Apr 24, 2020 Sold $1,450,000

Market Statistics

Days on Market
52 days
Price per Sq Ft
$1,096

Tax History

Year Taxes Assessment
2020 $15,707 $1,746,400

Financial Details

Annual Property Tax
$15,707
Tax Year 2020
HOA Fee
$914
Monthly
Assessed Value
$1,746,400

Listing Information

Listing Agent Sally T. Brewster
Listing Office Brewster & Berkowitz R. E.
Agent MLS ID NB110095
Office MLS ID NB1079
Listing Data Updated Jan 19, 2021 11:02 AM EST
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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Market Analytics for Boston, MA

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