Google street view image for 20 Chestnut St, Brookline, MA 02445

Off market nov 1992 for $457K

$2,725,960

Est. refi paymentEst. refi $3,090/mo

•

2.5 ba

•

3,012

sq ft

20 Chestnut St, Brookline, MA 02445

About this home

20 Chestnut St is a 3,012 square foot house on a 0.28 acre lot with 5 bedrooms and 2.5 bathrooms. - it last sold on November 30, 1992 for $457,500. Based on Redfin's Brookline data, we estimate the home's value is $2,725,960.

Single-familyProperty Type

1900Year Built

0.28 acresLot Size

$905Est. Price/Sq.Ft.

Source:Public Records

Redfin Estimate

$2,725,960

$2.3M since sold in November 1992$53K since September

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 18.7% higher than the average sale price ($2.30M) of 5 comparable homes.

SOLD AUG 21, 2026
$1,850,000
A
5 beds2.5 baths3,592 sq ft
117 Sheridan St, Jamaica Plain, MA 02130
SOLD AUG 10, 2026
$1,435,000
B
5 beds2.5 baths3,500 sq ft
58 Arborway, Jamaica Plain, MA 02130
SOLD MAY 14, 2026
$3,285,000
C
5 beds4.5 baths3,658 sq ft
43 Druce St, Brookline, MA 02445
SOLD JUL 2, 2026
$2,425,000
D
5 beds3 baths3,563 sq ft
30 Billings Ln, Jamaica Plain, MA 02130
SOLD DEC 11, 2025
$2,487,000
E
5 beds3.5 baths3,100 sq ft
333 Clark Rd, Brookline, MA 02445

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Earn from this home

Sell

$2,589,861

Est. take-home

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Est. cash available

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Rent

$7,153/mo

Redfin rental estimate

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Market trends in 02445, MA

Last updated September 2026

Buyer's Market

Seller's Market

Balanced market

Sale-to-List Price

98.9%

0.9% MoM

Median sale price

$911K

$254K MoM

Avg. days on market

41d

6 days MoM

Recently sold homes

2 MoM

New listings for sale

NEW 7 HRS AGO
$2,399,900
6 beds4 baths3,454 sq ft
101-103 University Rd, Brookline, MA 02445
OPEN SUN, 11AM TO 12:30PM
$1,195,000
3 beds2 baths1,269 sq ft
114 Franklin St #2, Brookline, MA 02445
OPEN SUN, 11AM TO 1PM
$1,399,000
3 beds3 baths1,946 sq ft
16 Addington #21, Brookline, MA 02445
$775,000
2 beds1 bath947 sq ft
1731 Beacon St #311, Brookline, MA 02445
OPEN SUN, 12PM TO 1:30PM
$3,500,000
6 beds5.5 baths4,891 sq ft
115 Dean Rd, Brookline, MA 02445
OPEN SUN, 2PM TO 3:30PM
$1,500,000
3 beds2.5 baths1,741 sq ft
31 Loveland Rd, Brookline, MA 02445
EARLY ACCESS
$2,350,000
6 beds3 baths3,568 sq ft
309 Buckminster Rd, Brookline, MA 02445
OPEN SUN, 12PM TO 1:30PM
$799,000
3 beds1.5 baths1,265 sq ft
120 Franklin St #3, Brookline, MA 02445
$675,000
2 beds2 baths1,025 sq ft
44 Washington #502, Brookline, MA 02445
EARLY ACCESS
Unknown
7 beds8 baths8,540 sq ft
Brookline, MA 02445
See all

Provided by Redfin

Sale history for 20 Chestnut St

Year

Property tax

Land + Additions

Assessment*

2023

$21,989 (+2.7%)

$1,173,200 + $1,032,300

$2,205,500

2022

$21,403 (+8.1%)

$1,117,300 + $983,100

$2,100,400

2021

$19,792 (+9.7%)

$1,074,300 + $945,300

$2,019,600

2020

$18,036 (+5.9%)

$976,700 + $931,900

$1,908,600

2019

$17,032 (+7.4%)

$930,200 + $887,500

$1,817,700

2018

$15,863 (+1.5%)

$800,200 + $876,600

$1,676,800

2017

$15,629 (−8.6%)

$754,900 + $827,000

$1,581,900

2016

$17,101 (+4.4%)

$705,600 + $935,600

$1,641,200

2015

$16,381 (−3.7%)

$659,400 + $874,400

$1,533,800

2014

$17,006 (+0.7%)

$598,800 + $894,300

$1,493,100

2013

$16,888 (+2.2%)

$581,400 + $868,200

$1,449,600

2012

$16,525 (+0.6%)

$581,400 + $868,200

$1,449,600

2011

$16,426 (+3.0%)

$590,800 + $862,800

$1,453,600

2010

$15,946 (+2.6%)

$590,800 + $862,800

$1,453,600

2009

$15,544

$591,300 + $862,800

$1,454,100

Tax history for 20 Chestnut St

Year

Property tax

Land + Additions

Assessment*

2023

$21,989 (+2.7%)

$1,173,200 + $1,032,300

$2,205,500

2022

$21,403 (+8.1%)

$1,117,300 + $983,100

$2,100,400

2021

$19,792 (+9.7%)

$1,074,300 + $945,300

$2,019,600

2020

$18,036 (+5.9%)

$976,700 + $931,900

$1,908,600

2019

$17,032 (+7.4%)

$930,200 + $887,500

$1,817,700

2018

$15,863 (+1.5%)

$800,200 + $876,600

$1,676,800

2017

$15,629 (−8.6%)

$754,900 + $827,000

$1,581,900

2016

$17,101 (+4.4%)

$705,600 + $935,600

$1,641,200

2015

$16,381 (−3.7%)

$659,400 + $874,400

$1,533,800

2014

$17,006 (+0.7%)

$598,800 + $894,300

$1,493,100

2013

$16,888 (+2.2%)

$581,400 + $868,200

$1,449,600

2012

$16,525 (+0.6%)

$581,400 + $868,200

$1,449,600

2011

$16,426 (+3.0%)

$590,800 + $862,800

$1,453,600

2010

$15,946 (+2.6%)

$590,800 + $862,800

$1,453,600

2009

$15,544

$591,300 + $862,800

$1,454,100

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

Permits

Dec 2, 2025 • Final

Residential electrical

Perform electrical service work on the interior and exterior of the building and replace electrical outlets.

Electrical

May 15, 2025 • Active

Residential electrical

Replace the existing service entrance cable with a new service entrance cable from the meter to the main electrical panel.

Electrical

Permit history is from public records and may be incomplete or inaccurate. Redfin and its agents make no representations about the property condition or permit status. Buyers should independently verify all information.

Property details

Interior

Basement Information
Basement Sq. Ft: 1,020
Basement Type: Full

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

Heating & Cooling
Heating Type: Forced Air

Fireplace Information
# of Fireplaces: 2
Fireplace Type: Wood Stove
Has Fireplace

Room Information
# of Rooms: 9

Exterior

Exterior Information
Physical Condition: Average
Building Style Type: Old
Construction Type: Frame
Exterior Wall: Wood Siding/Shingle
Roof Shape Type: Hip

Property Information
Living Sq. Ft: 3,012
Gross Sq. Ft: 5,178
# of Units: 1
# of Stories: 2

Lot Information
# of Buildings: 1
Land Sq. Ft: 12,197
Municipality Name: BROOKLINE
Acres: 0.28
Zoning Code: S-7
State Use Description: 1-FAMILY RESIDENCE

Financial

Assessor Information
Assessment Year: 2023

Public facts

Beds: 5
Baths: 2.5
Sq. Ft.: 3,012
Stories: 2.0
Lot Size: 0.28 acres
Style: Single Family Residential
Year Built: 1900
Year Renovated: 1979
County: Norfolk County
APN: 40971

Home facts updated by county records on Jul 20, 2023

Around this home

Schools

William H Lincoln School

Public K-8 • Assigned • 0.2mi

9/10

Brookline High School

Public 9-12 • Assigned • 0.4mi

8/10

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

Local insights from Redfin agents

Brookline will continue to be a Seller's market for the foreseeable future, driven by restrictive zoning laws that have limited increases in housing production and a stable population with relatively low turnover. This has resulted in a massive...
1 week ago • Brookline
Benjamin Ginsburg
Redfin Premier agent
155 deals
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Climate risks

1/10 Flood Factor

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

3/10 Fire Factor

0.15% chance of being in a wildfire in next 30 years

5/10 Heat Factor

7 days above 96° expected this year, 15 days in 30 years

6/10 Wind Factor

59% 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

Brookline, MA • 02445

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 hours in June and 4.4 hours in December, placing it below the U.S. average for solar exposure.

9 hrs

4.4 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$2.59M – $3.14M

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New listings for sale in 02445

NEW 7 HRS AGO

$2,399,900

6 beds4 baths3,454 sq ft

101-103 University Rd, Brookline, MA 02445

OPEN SUN, 11AM TO 12:30PM

$1,195,000

3 beds2 baths1,269 sq ft

114 Franklin St #2, Brookline, MA 02445

OPEN SUN, 11AM TO 1PM

$1,399,000

3 beds3 baths1,946 sq ft

16 Addington #21, Brookline, MA 02445

$775,000

2 beds1 bath947 sq ft

1731 Beacon St #311, Brookline, MA 02445

OPEN SUN, 12PM TO 1:30PM

$3,500,000

6 beds5.5 baths4,891 sq ft

115 Dean Rd, Brookline, MA 02445

OPEN SUN, 2PM TO 3:30PM

$1,500,000

3 beds2.5 baths1,741 sq ft

31 Loveland Rd, Brookline, MA 02445

EARLY ACCESSCOLDWELL BANKER REALTY COMING SOON

$2,350,000

6 beds3 baths3,568 sq ft

309 Buckminster Rd, Brookline, MA 02445

OPEN SUN, 12PM TO 1:30PM

$799,000

3 beds1.5 baths1,265 sq ft

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Home values near 20 Chestnut St

Data from public records.

Address	Redfin Estimate
40 Chestnut Street, Brookline, MA 3 Beds \| 1.5 Baths \| 1272 Sq. Ft.	$1,417,578
14 Chestnut Street, Brookline, MA 4 Beds \| 2 Baths \| 2100 Sq. Ft.	$2,286,203

Address	Redfin Estimate
36 Chestnut Street, Brookline, MA 3 Beds \| 1.5 Baths \| 1272 Sq. Ft.	$1,438,960
10 Chestnut Street, Brookline, MA 4 Beds \| 2.5 Baths \| 2290 Sq. Ft.	$2,077,639

Address	Redfin Estimate
26 Chestnut Street, Brookline, MA 7 Beds \| 3.5 Baths \| 5130 Sq. Ft.	$3,176,382
27 Chestnut Street, Brookline, MA 6 Beds \| 3 Baths \| 3972 Sq. Ft.	$2,937,901

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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 02445, MA

Sale history for 20 Chestnut St

Tax history for 20 Chestnut St

Permits

Property details

Around this home

Schools

Lifestyle

Local insights from Redfin agents

Climate risks

Historical weather

Sun exposure

Nearby similar homes

New listings for sale in 02445

Home values near 20 Chestnut St

More real estate resources