Google street view image for 108 Chestnut St, Brookline, MA 02445

Off market

$1,788,787

•

3 ba

•

3,646

sq ft

108 Chestnut St, Brookline, MA 02445

About this home

108 Chestnut St is a 3,646 square foot multi-family home on a 2,178 square foot lot with 9 bedrooms and 3 bathrooms. Based on Redfin's Brookline data, we estimate the home's value is $1,788,787.

Multi-familyProperty Type

1895Year Built

2,178 sq ftLot Size

$491Est. Price/Sq.Ft.

Source:Public Records

Redfin Estimate

$1,788,787

$0 since September

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 18.8% higher than the average sale price ($1.51M) of 6 comparable homes.

SOLD JUL 22, 2026
$1,825,000
A
11 beds3 baths4,236 sq ft
884 Huntington Ave, Boston, MA 02115
SOLD APR 30, 2026
$999,999
B
8 beds3 baths3,898 sq ft
9 E Milton Rd, Brookline, MA 02445
SOLD AUG 21, 2026
$1,930,000
C
9 beds3 baths3,750 sq ft
68 Hillside St, Roxbury, MA 02120
SOLD MAY 18, 2026
$1,495,000
D
8 beds3 baths3,903 sq ft
28 Boylston St, Jamaica Plain, MA 02130
SOLD MAY 20, 2026
$1,400,000
E
9 beds3 baths3,000 sq ft
22 Chestnut Ave, Jamaica Plain, MA 02130
SOLD JUN 23, 2026
$1,385,000
F
8 beds3 baths3,109 sq ft
57 Mozart St, Jamaica Plain, MA 02130

Claim this home to receive a free report every month with insights on the changing estimate.

Earn from this home

Sell

$1,699,135

Est. take-home

List your home with Redfin and save $8,944

Market trends in 02445, MA

Last updated September 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-List Price

97.3%

1.5% MoM

Median sale price

$1.0M

$142K MoM

Avg. days on market

56d

14 days MoM

Recently sold homes

16 MoM

New listings for sale

$495,000
1 bed1 bath655 sq ft
44 Washington St #303, Brookline, MA 02445
EARLY ACCESS
$4,250,000
5 beds4 baths6,313 sq ft
120 Rawson Rd, Brookline, MA 02445
EARLY ACCESS
$1,700,000
4 beds2 baths2,254 sq ft
146 University Rd #2, Brookline, MA 02445
$2,350,000
6 beds3 baths5,030 sq ft
309 Buckminster Rd, Brookline, MA 02445
$4,375,000
5 beds5.5 baths3,539 sq ft
291 Tappan St #291, Brookline, MA 02445
$2,399,900
6 beds4 baths3,454 sq ft
101-103 University Rd, Brookline, MA 02445
$1,195,000
3 beds2 baths1,269 sq ft
114 Franklin St #2, Brookline, MA 02445
$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 TODAY, 1PM TO 2PM
$3,500,000
6 beds5.5 baths4,891 sq ft
115 Dean Rd, Brookline, MA 02445
See all

Provided by Redfin

Sale history for 108 Chestnut St

As the MLS and public records start to fill up, we'll list the details here.

Year

Property tax

Land + Additions

Assessment*

2023

$17,152 (+2.7%)

$547,300 + $1,173,100

$1,720,400

2022

$16,694 (+8.1%)

$521,100 + $1,117,200

$1,638,300

2021

$15,439 (+5.0%)

$501,100 + $1,074,300

$1,575,400

2020

$14,699 (+5.9%)

$455,600 + $1,099,900

$1,555,500

2019

$13,881 (+5.5%)

$433,900 + $1,047,500

$1,481,400

2018

$13,157 (+7.6%)

$372,900 + $1,017,900

$1,390,800

2017

$12,231 (+4.3%)

$351,800 + $886,200

$1,238,000

2016

$11,727 (+7.3%)

$328,800 + $796,600

$1,125,400

2015

$10,927 (−3.1%)

$307,300 + $715,800

$1,023,100

2014

$11,275 (+2.6%)

$279,300 + $710,600

$989,900

2013

$10,984 (+2.2%)

$271,200 + $671,600

$942,800

2012

$10,748 (+1.0%)

$271,200 + $671,600

$942,800

2011

$10,646 (+3.0%)

$268,100 + $674,000

$942,100

2010

$10,335 (+2.6%)

$268,100 + $674,000

$942,100

2009

$10,073

$268,300 + $674,000

$942,300

Tax history for 108 Chestnut St

Year

Property tax

Land + Additions

Assessment*

2023

$17,152 (+2.7%)

$547,300 + $1,173,100

$1,720,400

2022

$16,694 (+8.1%)

$521,100 + $1,117,200

$1,638,300

2021

$15,439 (+5.0%)

$501,100 + $1,074,300

$1,575,400

2020

$14,699 (+5.9%)

$455,600 + $1,099,900

$1,555,500

2019

$13,881 (+5.5%)

$433,900 + $1,047,500

$1,481,400

2018

$13,157 (+7.6%)

$372,900 + $1,017,900

$1,390,800

2017

$12,231 (+4.3%)

$351,800 + $886,200

$1,238,000

2016

$11,727 (+7.3%)

$328,800 + $796,600

$1,125,400

2015

$10,927 (−3.1%)

$307,300 + $715,800

$1,023,100

2014

$11,275 (+2.6%)

$279,300 + $710,600

$989,900

2013

$10,984 (+2.2%)

$271,200 + $671,600

$942,800

2012

$10,748 (+1.0%)

$271,200 + $671,600

$942,800

2011

$10,646 (+3.0%)

$268,100 + $674,000

$942,100

2010

$10,335 (+2.6%)

$268,100 + $674,000

$942,100

2009

$10,073

$268,300 + $674,000

$942,300

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

Permits

Jan 23, 2026 • Final

Residential electrical

Upgrade the electrical service and relocate the meter location to the exterior. Install a new house 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: 1,240
Basement Type: Full

Bathroom Information
# of Full Baths: 3

Heating & Cooling
Heating Type: Forced Hot Water

Room Information
# of Rooms: 18

Exterior

Exterior Information
Physical Condition: Average
Construction Type: Frame
Exterior Wall: Shingle
Roof Shape Type: Gable

Property Information
Living Sq. Ft: 3,646
Gross Sq. Ft: 6,482
# of Units: 3
# of Stories: 3

Lot Information
# of Buildings: 1
Land Sq. Ft: 2,178
Municipality Name: BROOKLINE
Acres: 0.05
Zoning Code: M10
State Use Description: 3-FAMILY RESIDENCE

Financial

Assessor Information
Assessment Year: 2023

Public facts

Beds: 9
Baths: 3.0
Sq. Ft.: 3,646
Stories: 3.0
Lot Size: 2,178 square feet
Style: Multi-Family (2-4 Unit)
Year Built: 1895
Year Renovated: 1979
County: Norfolk County
APN: 40917

Home facts updated by county records on Jul 20, 2023

Around this home

Schools

William H Lincoln School

Public K-8 • Assigned • 0.3mi

9/10

Brookline High School

Public 9-12 • Assigned • 0.6mi

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...
3 weeks ago • Brookline
Benjamin Ginsburg
Redfin Premier agent
155 deals
Was this helpful?

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

6/10 Heat Factor

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

6/10 Wind Factor

62% 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

$1.70M – $2.06M

Reach more buyers when you sell with Redfin. Save up to $17,888 in fees. 3 minutes to get started.

Get a free, detailed breakdown of how we calculated your estimate.

Nearby similar homes

3D WALKTHROUGH

$2,500,000

7 beds3 baths3,948 sq ft

103-105 Colbourne Cres, Brookline, MA 02445

$2,675,000

14 beds8 baths4,608 sq ft

44 Mozart St, Boston, MA 02130

3D WALKTHROUGH

$2,625,000

17 beds7.5 baths7,365 sq ft

34 Circuit St, Roxbury, MA 02119

$1,099,000

6 beds3 baths4,310 sq ft

106 Harrishof St, Dorchester, MA 02121

$1,000,000

6 beds2 baths3,075 sq ft

9-11 Nazing St, Dorchester, MA 02121

$1,150,000

8 beds3 baths2,568 sq ft

1903 Columbus Ave, Roxbury, MA 02119

New listings for sale in 02445

$495,000

1 bed1 bath655 sq ft

44 Washington St #303, Brookline, MA 02445

EARLY ACCESSCOMPASS COMING SOON

$4,250,000

5 beds4 baths6,313 sq ft

120 Rawson Rd, Brookline, MA 02445

EARLY ACCESSCOLDWELL BANKER REALTY COMING SOON

$1,700,000

4 beds2 baths2,254 sq ft

146 University Rd #2, Brookline, MA 02445

$2,350,000

6 beds3 baths5,030 sq ft

309 Buckminster Rd, Brookline, MA 02445

$4,375,000

5 beds5.5 baths3,539 sq ft

291 Tappan St #291, Brookline, MA 02445

$2,399,900

6 beds4 baths3,454 sq ft

101-103 University Rd, Brookline, MA 02445

$1,195,000

3 beds2 baths1,269 sq ft

114 Franklin St #2, Brookline, MA 02445

$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

Home values near 108 Chestnut St

Data from public records.

Address	Redfin Estimate
110 Chestnut St, Brookline, MA 5 Beds \| 2.5 Baths \| 2450 Sq. Ft.	$1,805,406
96 Chestnut St Apt 2, Brookline, MA 2 Beds \| 1 Baths \| 818 Sq. Ft.	$577,620

Address	Redfin Estimate
100 Chestnut St, Brookline, MA 5 Beds \| 1.5 Baths \| 1584 Sq. Ft.	$1,244,983
96 Chestnut St Apt 3, Brookline, MA 2 Beds \| 1 Baths \| 920 Sq. Ft.	$641,265

Address	Redfin Estimate
96 Chestnut St Apt 1, Brookline, MA 2 Beds \| 1 Baths \| 758 Sq. Ft.	$574,361
99 Chestnut St Apt 2, Brookline, MA 1 Beds \| 1 Baths \| 599 Sq. Ft.	$457,574

Download the Redfin App on the Apple App Store

Download the Redfin App from the Google Play Store

Join us

Become an Agent

Get referrals

Careers

Find homes faster

About us

Find us

Subsidiaries

Affiliated Business

Countries

United States

Canada

Updated September 2025: By searching, you agree to the Terms of Use, and Privacy Policy.

Do not sell or share my personal information.

REDFIN and all REDFIN variants, WALK SCORE, and the R logos, are trademarks of Redfin Corporation, registered or pending in the USPTO.

California DRE #01521930

Redfin is licensed to do business in New York as Redfin Real Estate. NY Standard Operating Procedures

New Mexico Real Estate Licenses

TREC: Info About Brokerage Services, Consumer Protection Notice

All mortgage lending products and information are provided by Rocket Mortgage, LLC | NMLS #3030; www.NMLSConsumerAccess.org. Licensed in 50 states. This site is not authorized by the New York State Department of Financial Services for mortgage solicitation or loan applications activities related to properties located in the State of New York.

Redfin Corporation is an affiliated business of Rocket Limited Partnership. Each company, and their subsidiaries, are separate legal entities operated and managed through its own management and governance structures.

If you are using a screen reader, or having trouble reading this website, please call Redfin Customer Support for help at 1-844-759-7732.

REDFIN IS COMMITTED TO AND ABIDES BY THE FAIR HOUSING ACT AND EQUAL OPPORTUNITY ACT. READ REDFIN'S FAIR HOUSING POLICY AND THE NEW YORK STATE FAIR HOUSING NOTICE.

GreatSchools Ratings provided by GreatSchools.org.

02130 homes for sale
02131 homes for sale
02446 homes for sale
02132 homes for sale
02135 homes for sale

Houses for rent in Brookline	Agents near me	Quincy, MA homes for sale	Brookline Housing Market
Houses for sale near me	Boston, MA homes for sale	Brookline, MA homes for sale
Land for sale near me	Newton, MA homes for sale	Arlington, MA homes for sale
Open Houses near me	Cambridge, MA homes for sale	Brookline Property Records
Condos for sale near me	Lexington, MA homes for sale	MA New Listings

The Greater Point homes for sale
Brookline Village homes for sale

Cambridge homes for sale
Boston homes for sale
Newton homes for sale

About this home

Redfin Estimate

Earn from this home

Market trends in 02445, MA

Sale history for 108 Chestnut St

Tax history for 108 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 108 Chestnut St

More real estate resources