Off market nov 2011 for $1.5M

$3,625,684

Est. refi paymentEst. refi $10,279/mo

•

2.5 ba

•

2,436

sq ft

20 Chestnut St #3, Boston, MA 02108

About this home

Beautiful Penthouse Duplex on the Hill. One block from Louisburg Sq & Boston Common. Second Floor Entrance to Private Stairway, Floor-Thru on 3rd and 4th Floors. Elegant Space with 3 Fireplaces, Large Living Room Opens to Spacious Dining Room with Bow Window and Juliet Balcony. New Private Mahogany Deck, Great City Views and Sun, Hardwood Floors and Elegant Moldings Throughout. Bedroom on 3rd Level could be used as parlor or office. 4th Floor Master Suite, 2 Baths, laundry, and child's playroom

CondoProperty Type

1880Year Built

$1,488Est. Price/Sq.Ft.

Listed by David Chen • Benjamin Realty

Bought with Douglas Murphy • MP Realty, A Buy America Company

Source:MLS PIN #70361377

Redfin Estimate

$3,625,684

$2.0M since sold in November 2011$99K since October

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 38.8% higher than the average sale price ($2.61M) of 6 comparable homes.

SOLD JUL 10, 2026
$3,230,000
A
2 beds2.5 baths1,764 sq ft
82 Mount Vernon St #1, Boston, MA 02108
SOLD OCT 21, 2026
$2,830,000
B
4 beds3 baths2,183 sq ft
131 Mount Vernon St #2, Boston, MA 02108
SOLD JUL 22, 2026
$4,000,000
C
2 beds2.5 baths2,317 sq ft
63 Mount Vernon St #4, Boston, MA 02108
SOLD OCT 20, 2026
$2,350,000
D
3 beds2.5 baths1,500 sq ft
93 Revere St #4, Boston, MA 02114
SOLD AUG 20, 2026
$1,915,000
E
3 beds2 baths1,400 sq ft
40 Joy St #9, Boston, MA 02114
SOLD OCT 28, 2026
$1,350,000
F
2 beds1 bath1,052 sq ft
41 Pinckney St #1, Boston, MA 02114

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$2,625,995

Est. take-home

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Est. cash available

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Rent

$3,570/mo

Redfin rental estimate

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Market trends in South Slope, MA

Last updated October 2026

Buyer's Market

Seller's Market

Balanced market

Sale-to-list price

96.5%

+1.7% MoM

Median sale price

$3.3M

$2M MoM

Avg. days on market

29d

33 days MoM

Recently sold homes

3 MoM

New listings for sale

3D WALKTHROUGH
$599,000
1 bed1 bath591 sq ft
21 Beacon St Unit 4T, Boston, MA 02108
$7,800,000
3 beds3.5 baths2,882 sq ft
46 Beacon St #2, Boston, MA 02108
$1,449,000
2 beds2 baths1,378 sq ft
45 Province St #1402, Boston, MA 02108
See all

Provided by Redfin

Sale history for 20 Chestnut St #3

Date

Event

Price

Public Records

Nov 21, 2011

Sold

$1,590,000

$653/sq ft

MLS PIN #70361377

Jul 14, 2006

Sold

$1,270,000

$521/sq ft

May 26, 2006

Listing Removed

—

Apr 5, 2006

Listed

$1,449,000

$595/sq ft

Public Records

Sep 3, 1996

Sold

$675,000

$277/sq ft

Public Records

Sep 2, 1993

Sold

$570,000

$234/sq ft

Public Records

Apr 4, 1990

Sold

$525,000

$216/sq ft

Year

Property tax

Land + Additions

Assessment*

2023

$40,445 (+4.6%)

$3,765,800

2022

$38,668 (+48.8%)

$3,554,000

2021

$25,994 (−1.9%)

$2,436,200

2020

$26,490 (+4.2%)

$2,508,500

2019

$25,417 (+6.6%)

$2,411,500

2018

$23,844 (+1.9%)

$2,275,200

2017

$23,394 (+3.0%)

$2,209,100

2016

$22,711 (−2.6%)

$2,064,600

2015

$23,313 (+3.9%)

$1,925,100

2014

$22,431 (+3.4%)

$1,783,100

2013

$21,694 (+2.5%)

$1,651,000

2012

$21,167 (+1.4%)

$1,623,200

2009

$20,869 (+28.2%)

$1,631,700

2006

$16,275

$1,531,000

Tax history for 20 Chestnut St #3

Year

Property tax

Land + Additions

Assessment*

2023

$40,445 (+4.6%)

$3,765,800

2022

$38,668 (+48.8%)

$3,554,000

2021

$25,994 (−1.9%)

$2,436,200

2020

$26,490 (+4.2%)

$2,508,500

2019

$25,417 (+6.6%)

$2,411,500

2018

$23,844 (+1.9%)

$2,275,200

2017

$23,394 (+3.0%)

$2,209,100

2016

$22,711 (−2.6%)

$2,064,600

2015

$23,313 (+3.9%)

$1,925,100

2014

$22,431 (+3.4%)

$1,783,100

2013

$21,694 (+2.5%)

$1,651,000

2012

$21,167 (+1.4%)

$1,623,200

2009

$20,869 (+28.2%)

$1,631,700

2006

$16,275

$1,531,000

*Taxable value of land and structures on it ("additions") is determined regularly by local assessors and does not affect market price.

Property details

Interior

Bathroom Information
# of Full Baths: 2
# of 1/2 Baths: 1

Heating & Cooling
Heating Type: Forced Hot Water

Fireplace Information
# of Fireplaces: 3
Has Fireplace

Room Information
# of Rooms: 7

Exterior

Exterior Information
Physical Condition: Average
Building Style Type: Row House
Exterior Wall: Brick
Roof Shape Type: Gable

Property Information
Subdivision Name: TWENTY CHESTNUT STREET CONDO
Living Sq. Ft: 2,436
Gross Sq. Ft: 2,436
# of Units: 1
# of Stories: 2

Lot Information
# of Buildings: 1
Municipality Name: BOSTON
Zoning Code: CD
State Use Description: CONDOMINIUM

Financial

Assessor Information
Assessment Year: 2023

Public facts

Beds: 2
Baths: 2.5
Sq. Ft.: 2,436
Stories: 2.0
Lot Size: —
Style: Condo/Co-op
Year Built: 1880
Year Renovated: 2021
County: Suffolk County
APN: 3356419

Home facts updated by county records on Aug 26, 2023

Around this home

Schools

K - 12
Preschool & daycare

Josiah Quincy Elementary School

Public PreK-5 • Assigned • 0.7mi

8/10

Quincy Upper School

Public 6-12 • Assigned • 0.7mi

3/10

Boston Adult Academy

Public 11-12 • Assigned • 0.6mi

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

Climate risks

1/10 Flood Factor

Minimal risk of a flood reaching the building in the next 30 years

1/10 Fire Factor

Unlikely to be in a wildfire in next 30 years

6/10 Heat Factor

7 days above 97° expected this year, 15 days in 30 years

6/10 Wind Factor

64% chance of strong winds in next 30 years

3/10 Air Factor

3 unhealthy days expected this year, 3 days in 30 years

Provided by First Street

Historical weather

Boston, MA • 02108

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

In this area, properties receive around 9.2 hours in June and 4.4 hours in December, placing it below the U.S. average for solar exposure.

9.2 hrs

4.4 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$3.45M – $4.17M

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Nearby similar homes

$700,000

1 bed1 bath675 sq ft

151 Tremont St Unit 16T, Boston, MA 02111

City skyline views • Remodeled kitchen • Remodeled bathroom

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1 bed1 bath664 sq ft

165 Tremont St #705, Boston, MA 02111

Oversized windows • Hardwood floors • Open concept kitchen

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2 beds1 bath1,278 sq ft

105 Beacon St., #10, Boston, MA 02116

Charles river views • Historic character • Private roof deck

$405,000

Studio1 bath637 sq ft

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Oak parquet flooring • Open balcony • Lush gardens

$525,000

1 bed1 bath550 sq ft

41 Revere St #4, Boston, MA 02114

Cozy kitchenette • Granite counters • In-unit laundry

$899,000

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10 Bowdoin St #409, Boston, MA 02114

Elevator building • Private storage unit • $519 HOA

New listings for sale in 02108

3D WALKTHROUGH

$599,000

1 bed1 bath591 sq ft

21 Beacon St Unit 4T, Boston, MA 02108

Common roof deck • Updated open kitchen • Large closets

$7,800,000

3 beds3.5 baths2,882 sq ft

46 Beacon St #2, Boston, MA 02108

Concierge services • Front facing views • Parlor level living

$1,449,000

2 beds2 baths1,378 sq ft

45 Province St #1402, Boston, MA 02108

Private terrace • Designer finishes • Gas cooking

Home values near 20 Chestnut St #3

Data from public records.

Address	Redfin Estimate
19 Chestnut Street #1A, Boston, MA 1 Beds \| 1 Baths \| 541 Sq. Ft.	$717,999
24 Chestnut Street, Boston, MA 4 Beds \| 6.5 Baths \| 6445 Sq. Ft.	$7,332,923
20 Chestnut Street #20A, Boston, MA 2 Beds \| 1 Baths \| 1435 Sq. Ft.	$2,704,940
18 Chestnut Street #2, Boston, MA 1 Beds \| 1 Baths \| 690 Sq. Ft.	$852,859
18 Chestnut Street #5, Boston, MA 2 Beds \| 2 Baths \| 1280 Sq. Ft.	$2,022,635
14 Chestnut Street, Boston, MA 7 Beds \| 5 Baths \| 7000 Sq. Ft.	$9,930,767
18 Chestnut Street Penthouse, Boston, MA 2 Beds \| 2 Baths \| 1350 Sq. Ft.	$1,400,141

Address	Redfin Estimate
19 Chestnut Street #2B, Boston, MA 1 Beds \| 1 Baths \| 537 Sq. Ft.	$725,670
22 Chestnut Street, Boston, MA 7 Beds \| 5.5 Baths \| 8239 Sq. Ft.	$11,632,786
20 Chestnut Street #2, Boston, MA 2 Beds \| 1 Baths \| 1699 Sq. Ft.	$1,679,764
18 Chestnut Street #3, Boston, MA 2 Beds \| 1.5 Baths \| 1660 Sq. Ft.	$3,036,046
18 Chestnut Street #6, Boston, MA 2 Beds \| 1 Baths \| 1350 Sq. Ft.	$1,827,463
20-20A Chestnut Street #1, Boston, MA 4 Beds \| 4.5 Baths \| 3119 Sq. Ft.	$4,958,562
20 Chestnut Street #1&2,20, Boston, MA 3 Beds \| 3 Baths \| 3160 Sq. Ft.	$5,209,607

Address	Redfin Estimate
19 Chestnut Street #5B, Boston, MA 1 Beds \| 1 Baths \| 441 Sq. Ft.	$658,537
20 Chestnut Street #20A, Boston, MA 3 Beds \| 3.5 Baths \| 3640 Sq. Ft.	$6,672,949
18 Chestnut Street #1, Boston, MA 1 Beds \| 1 Baths \| 665 Sq. Ft.	$838,150
18 Chestnut Street #4, Boston, MA 2 Beds \| 2 Baths \| 1180 Sq. Ft.	$2,159,269
16 Chestnut Street, Boston, MA 5 Beds \| 6.5 Baths \| 6100 Sq. Ft.	$6,635,213
20 Chestnut Street Penthouse, Boston, MA 3 Beds \| 3 Baths \| 2131 Sq. Ft.	$3,110,269

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GreatSchools Ratings provided by GreatSchools.org.

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About this home

Redfin Estimate

Earn from this home

Market trends in South Slope, MA

Sale history for 20 Chestnut St #3

Tax history for 20 Chestnut St #3

Property details

Around this home

Schools

Lifestyle

Climate risks

Historical weather

Sun exposure

Nearby similar homes

New listings for sale in 02108

Home values near 20 Chestnut St #3

More real estate resources