Google street view image for 33 Chestnut St, Brookline, MA 02445

Off market

$2,815,195

•

3.5 ba

•

2,109

sq ft

33 Chestnut St, Brookline, MA 02445

About this home

33 Chestnut St is a 2,109 square foot house on a 0.75 acre lot with 4 bedrooms and 3.5 bathrooms. Based on Redfin's Brookline data, we estimate the home's value is $2,815,195.

Single-familyProperty Type

1865Year Built

0.75 acresLot Size

$1,335Est. Price/Sq.Ft.

Source:Public Records

Redfin Estimate

$2,815,195

$62K since September

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 25.7% higher than the average sale price ($2.24M) of 4 comparable homes.

SOLD JUL 29, 2026
$2,605,000
A
4 beds3.5 baths3,381 sq ft
12 Goodwin Pl Unit 12-1, Brookline, MA 02445
SOLD AUG 13, 2026
$1,817,000
B
4 beds4 baths1,784 sq ft
35 Prince St, Jamaica Plain, MA 02130
SOLD APR 16, 2026
$2,150,000
C
4 beds3.5 baths2,332 sq ft
209 High St, Brookline, MA 02445
SOLD DEC 17, 2025
$2,385,000
D
4 beds3 baths2,286 sq ft
21 Hancock Rd, Brookline, MA 02445

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Earn from this home

Sell

$2,674,674

Est. take-home

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Rent

$6,675/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 14 HRS AGO
$1,190,000
3 beds2 baths1,422 sq ft
23 Strathmore Rd Unit 1A, Brookline, MA 02445
OPEN FRI, 12PM TO 1:30PM
$1,399,000
3 beds3 baths1,946 sq ft
16 Addington #21, Brookline, MA 02445
OPEN SAT, 1:30PM TO 3PM
$1,799,000
3 beds2 baths1,942 sq ft
29 Elm St #3, Brookline, MA 02445
$775,000
2 beds1 bath947 sq ft
1731 Beacon St #311, Brookline, MA 02445
OPEN SAT, 12PM TO 1:30PM
$3,500,000
6 beds5.5 baths4,891 sq ft
115 Dean Rd, Brookline, MA 02445
OPEN SAT, 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 SAT, 12PM TO 1:30PM
$799,000
3 beds1.5 baths1,265 sq ft
120 Franklin St #3, Brookline, MA 02445
OPEN FRI, 5PM TO 6:30PM
$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 33 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

$22,064 (+2.7%)

$1,677,400 + $535,600

$2,213,000

2022

$21,475 (+8.1%)

$1,597,400 + $510,100

$2,107,500

2021

$19,860 (+11.8%)

$1,536,000 + $490,500

$2,026,500

2020

$17,761 (+5.9%)

$1,396,400 + $483,100

$1,879,500

2019

$16,772 (−3.5%)

$1,329,900 + $460,100

$1,790,000

2018

$17,383 (+2.8%)

$1,385,600 + $451,900

$1,837,500

2017

$16,914 (+1.5%)

$1,307,100 + $404,800

$1,711,900

2016

$16,671 (+4.4%)

$1,221,600 + $378,300

$1,599,900

2015

$15,969 (+2.0%)

$1,141,700 + $353,500

$1,495,200

2014

$15,649 (+0.7%)

$1,037,700 + $336,200

$1,373,900

2013

$15,540 (+2.2%)

$1,007,500 + $326,400

$1,333,900

2012

$15,206 (+5.5%)

$1,007,500 + $326,400

$1,333,900

2011

$14,412 (+3.0%)

$947,500 + $327,900

$1,275,400

2010

$13,991 (+2.8%)

$947,500 + $327,900

$1,275,400

2009

$13,611

$945,300 + $327,900

$1,273,200

Tax history for 33 Chestnut St

Year

Property tax

Land + Additions

Assessment*

2023

$22,064 (+2.7%)

$1,677,400 + $535,600

$2,213,000

2022

$21,475 (+8.1%)

$1,597,400 + $510,100

$2,107,500

2021

$19,860 (+11.8%)

$1,536,000 + $490,500

$2,026,500

2020

$17,761 (+5.9%)

$1,396,400 + $483,100

$1,879,500

2019

$16,772 (−3.5%)

$1,329,900 + $460,100

$1,790,000

2018

$17,383 (+2.8%)

$1,385,600 + $451,900

$1,837,500

2017

$16,914 (+1.5%)

$1,307,100 + $404,800

$1,711,900

2016

$16,671 (+4.4%)

$1,221,600 + $378,300

$1,599,900

2015

$15,969 (+2.0%)

$1,141,700 + $353,500

$1,495,200

2014

$15,649 (+0.7%)

$1,037,700 + $336,200

$1,373,900

2013

$15,540 (+2.2%)

$1,007,500 + $326,400

$1,333,900

2012

$15,206 (+5.5%)

$1,007,500 + $326,400

$1,333,900

2011

$14,412 (+3.0%)

$947,500 + $327,900

$1,275,400

2010

$13,991 (+2.8%)

$947,500 + $327,900

$1,275,400

2009

$13,611

$945,300 + $327,900

$1,273,200

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

Permits

Nov 21, 2025 • Active

Residential building

Remove and replace a patio door with a new door of the same size. No structural changes are included.

Remodel

May 17, 2016 • Active

Residential building

Strip the existing roof and install new roofing shingles.

Roofing

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: 589
Basement Type: Partial

Bathroom Information
# of Full Baths: 3
# of 1/2 Baths: 1

Heating & Cooling
Heating Type: Forced Hot Water

Fireplace Information
# of Fireplaces: 1
Fireplace Type: Wood Stove
Has Fireplace

Room Information
# of Rooms: 9

Exterior

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

Property Information
Living Sq. Ft: 2,109
Gross Sq. Ft: 4,088
# of Units: 1
# of Stories: 2

Parking & Garage Information
Parking Type: Attached Garage
Garage / Carport Type: Attached

Lot Information
# of Buildings: 1
Land Sq. Ft: 32,670
Municipality Name: BROOKLINE
Acres: 0.75
Zoning Code: S25
State Use Description: 1-FAMILY RESIDENCE

Financial

Assessor Information
Assessment Year: 2023

Public facts

Beds: 4
Baths: 3.5
Sq. Ft.: 2,109
Stories: 2.0
Lot Size: 0.75 acres
Style: Single Family Residential
Year Built: 1865
Year Renovated: 1966
County: Norfolk County
APN: 41224

Home facts updated by county records on Jul 20, 2023

Around this home

Schools

William H Lincoln School

Public K-8 • Assigned • 0.1mi

9/10

Brookline High School

Public 9-12 • Assigned • 0.5mi

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

2/10 Fire Factor

0.00% 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

63% 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

$2.68M – $3.24M

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Nearby similar homes

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New listings for sale in 02445

NEW 14 HRS AGO

$1,190,000

3 beds2 baths1,422 sq ft

23 Strathmore Rd Unit 1A, Brookline, MA 02445

OPEN FRI, 12PM TO 1:30PM

$1,399,000

3 beds3 baths1,946 sq ft

16 Addington #21, Brookline, MA 02445

OPEN SAT, 1:30PM TO 3PM

$1,799,000

3 beds2 baths1,942 sq ft

29 Elm St #3, Brookline, MA 02445

$775,000

2 beds1 bath947 sq ft

1731 Beacon St #311, Brookline, MA 02445

OPEN SAT, 12PM TO 1:30PM

$3,500,000

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115 Dean Rd, Brookline, MA 02445

OPEN SAT, 2PM TO 3:30PM

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3 beds2.5 baths1,741 sq ft

31 Loveland Rd, Brookline, MA 02445

EARLY ACCESSCOLDWELL BANKER REALTY COMING SOON

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309 Buckminster Rd, Brookline, MA 02445

OPEN SAT, 12PM TO 1:30PM

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OPEN FRI, 5PM TO 6:30PM

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Home values near 33 Chestnut St

Data from public records.

Address	Redfin Estimate
46 Chestnut St, Brookline, MA 5 Beds \| 2 Baths \| 3142 Sq. Ft.	$1,332,365
26 Chestnut St, Brookline, MA 7 Beds \| 3.5 Baths \| 5130 Sq. Ft.	$3,176,382

Address	Redfin Estimate
40 Chestnut St, Brookline, MA 3 Beds \| 1.5 Baths \| 1272 Sq. Ft.	$1,417,578
20 Chestnut St, Brookline, MA 5 Beds \| 2.5 Baths \| 3012 Sq. Ft.	$2,725,960

Address	Redfin Estimate
36 Chestnut St, Brookline, MA 3 Beds \| 1.5 Baths \| 1272 Sq. Ft.	$1,438,960
14 Chestnut St, Brookline, MA 4 Beds \| 2 Baths \| 2100 Sq. Ft.	$2,286,203

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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 33 Chestnut St

Tax history for 33 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 33 Chestnut St

More real estate resources