Google street view image for 149 Chestnut St, Brookline, MA 02445

Off market may 1996 for $200K

$1,862,321

Est. refi paymentEst. refi $921/mo

•

2.5 ba

•

2,386

sq ft

149 Chestnut St, Brookline, MA 02445

About this home

149 Chestnut St is a 2,386 square foot multi-family home on a 7,405 square foot lot with 6 bedrooms and 2.5 bathrooms. - it last sold on May 31, 1996 for $200,000. Based on Redfin's Brookline data, we estimate the home's value is $1,862,321.

Multi-familyProperty Type

1953Year Built

7,405 sq ftLot Size

$781Est. Price/Sq.Ft.

Source:Public Records

Redfin Estimate

$1,862,321

$1.7M since sold in May 1996$287K since September

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 16.1% higher than the average sale price ($1.60M) of 5 comparable homes.

SOLD JUN 22, 2026
$1,550,000
A
4 beds2.5 baths2,004 sq ft
101 Forbes St, Jamaica Plain, MA 02130
SOLD SEP 15, 2026
$1,150,000
B
6 beds2.5 baths2,736 sq ft
53 Prince St, Jamaica Plain, MA 02130
SOLD AUG 14, 2026
$1,459,450
C
3 beds2.5 baths2,576 sq ft
63 Mossdale Rd, Jamaica Plain, MA 02130
SOLD MAY 15, 2026
$2,150,000
D
5 beds3.5 baths2,616 sq ft
25A Eliot St, Jamaica Plain, MA 02130
SOLD JUL 22, 2026
$1,710,000
E
3 beds2.5 baths2,188 sq ft
299 Pond St, Jamaica Plain, MA 02130

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Earn from this home

Sell

$1,769,024

Est. take-home

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Est. cash available

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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

OPEN TODAY, 12PM TO 1:30PM
$4,250,000
5 beds3.5 baths6,313 sq ft
120 Rawson Rd, Brookline, MA 02445
EARLY ACCESS
$1,595,000
3 beds2 baths1,105 sq ft
69 Walnut St #7, Brookline, MA 02445
$495,000
1 bed1 bath655 sq ft
44 Washington St #303, 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
OPEN SAT, 12PM TO 1PM
$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
See all

Provided by Redfin

Sale history for 149 Chestnut St

Year

Property tax

Land + Additions

Assessment*

2023

$14,521 (+2.7%)

$652,700 + $803,800

$1,456,500

2022

$14,135 (+8.1%)

$621,600 + $765,500

$1,387,100

2021

$13,071 (+5.8%)

$597,700 + $736,100

$1,333,800

2020

$12,356 (+5.9%)

$543,400 + $764,100

$1,307,500

2019

$11,668 (+8.3%)

$517,500 + $727,700

$1,245,200

2018

$10,770 (+3.4%)

$453,600 + $684,900

$1,138,500

2017

$10,416 (+4.3%)

$428,100 + $626,200

$1,054,300

2016

$9,987 (+7.3%)

$400,100 + $558,300

$958,400

2015

$9,305 (+2.6%)

$373,900 + $497,400

$871,300

2014

$9,070 (+2.7%)

$339,900 + $456,400

$796,300

2013

$8,835 (+2.2%)

$330,000 + $428,400

$758,400

2012

$8,646 (+0.3%)

$330,000 + $428,400

$758,400

2011

$8,623 (+3.0%)

$332,700 + $430,400

$763,100

2010

$8,371 (+3.2%)

$332,700 + $430,400

$763,100

2009

$8,115

$333,000 + $426,100

$759,100

Tax history for 149 Chestnut St

Year

Property tax

Land + Additions

Assessment*

2023

$14,521 (+2.7%)

$652,700 + $803,800

$1,456,500

2022

$14,135 (+8.1%)

$621,600 + $765,500

$1,387,100

2021

$13,071 (+5.8%)

$597,700 + $736,100

$1,333,800

2020

$12,356 (+5.9%)

$543,400 + $764,100

$1,307,500

2019

$11,668 (+8.3%)

$517,500 + $727,700

$1,245,200

2018

$10,770 (+3.4%)

$453,600 + $684,900

$1,138,500

2017

$10,416 (+4.3%)

$428,100 + $626,200

$1,054,300

2016

$9,987 (+7.3%)

$400,100 + $558,300

$958,400

2015

$9,305 (+2.6%)

$373,900 + $497,400

$871,300

2014

$9,070 (+2.7%)

$339,900 + $456,400

$796,300

2013

$8,835 (+2.2%)

$330,000 + $428,400

$758,400

2012

$8,646 (+0.3%)

$330,000 + $428,400

$758,400

2011

$8,623 (+3.0%)

$332,700 + $430,400

$763,100

2010

$8,371 (+3.2%)

$332,700 + $430,400

$763,100

2009

$8,115

$333,000 + $426,100

$759,100

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

Property details

Interior

Basement Information
Basement Sq. Ft: 1,056
Basement Type: Full

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

Heating & Cooling
Heating Type: Forced Hot Water

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

Room Information
# of Rooms: 11

Exterior

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

Property Information
Subdivision Name: BROOKLINE
Living Sq. Ft: 2,386
Gross Sq. Ft: 4,098
# of Units: 2
# of Stories: 2

Lot Information
# of Buildings: 1
Land Sq. Ft: 7,405
Municipality Name: BROOKLINE
Acres: 0.17
Zoning Code: T-6
State Use Description: 2-FAMILY RESIDENCE

Financial

Assessor Information
Assessment Year: 2023

Public facts

Beds: 6
Baths: 2.5
Sq. Ft.: 2,386
Stories: 2.0
Lot Size: 7,405 square feet
Style: Multi-Family (2-4 Unit)
Year Built: 1953
Year Renovated: 1982
County: Norfolk County
APN: 41232

Home facts updated by county records on Jul 20, 2023

Around this home

Schools

William H Lincoln School

Public K-8 • Assigned • 0.4mi

9/10

Brookline High School

Public 9-12 • Assigned • 0.7mi

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
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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

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

$1.77M – $2.14M

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New listings for sale in 02445

OPEN TODAY, 12PM TO 1:30PM

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120 Rawson Rd, Brookline, MA 02445

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EARLY ACCESSCOLDWELL BANKER REALTY COMING SOON

$1,700,000

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$2,350,000

6 beds3 baths5,030 sq ft

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$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

OPEN SAT, 12PM TO 1PM

$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

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Home values near 149 Chestnut St

Data from public records.

Address	Redfin Estimate
166 Chestnut St Apt 2, Brookline, MA 2 Beds \| 1 Baths \| 945 Sq. Ft.	$647,841
156 Chestnut St Apt 1, Brookline, MA 2 Beds \| 2 Baths \| 1118 Sq. Ft.	$816,502

Address	Redfin Estimate
162 Chestnut St, Brookline, MA 8 Beds \| 3 Baths \| 3588 Sq. Ft.	$1,940,498
156 Chestnut St Apt 2, Brookline, MA 3 Beds \| 2 Baths \| 1142 Sq. Ft.	$848,261

Address	Redfin Estimate
160 Chestnut St, Brookline, MA 6 Beds \| 3 Baths \| 4212 Sq. Ft.	—
156 Chestnut St Apt 3, Brookline, MA 3 Beds \| 1 Baths \| 1142 Sq. Ft.	$768,332

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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 149 Chestnut St

Tax history for 149 Chestnut St

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 149 Chestnut St

More real estate resources