OFF MARKET

Off market

—

•

3 ba

•

3,956

sq ft

66 Chestnut St, Brookline, MA 02445

About this home

66 Chestnut St is a 3,956 square foot multi-family home on a 2,614 square foot lot with 8 bedrooms and 3 bathrooms.

Multi-familyProperty Type

1910Year Built

2,614 sq ftLot Size

Source:Public Records

Redfin Estimate

Unfortunately, we don't have enough data to generate an accurate Estimate at this time.

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

NEW 19 HRS AGO
$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 66 Chestnut St

Date

Event

Price

LISTANZA #4

Apr 26, 2026

Rental Removed

$4,000

$1/sq ft

Apr 2, 2026

Listed for Rent

$4,000

$1/sq ft

LISTANZA #3

May 4, 2026

Rental Removed

$4,000

$1/sq ft

Apr 26, 2026

Listed for Rent

$4,000

$1/sq ft

Apr 2, 2026

Rental Removed

$4,000

$1/sq ft

Mar 1, 2026

Listed for Rent

$4,000

$1/sq ft

LISTANZA #2

May 18, 2025

Rental Removed

$3,675

$1/sq ft

May 1, 2025

Listed for Rent

$3,675

$1/sq ft

LISTANZA #1

Aug 8, 2023

Rental Removed

$3,400

$1/sq ft

Aug 3, 2023

Listed for Rent

$3,400

$1/sq ft

Public Records

Aug 18, 2009

Sold

$700,000

$177/sq ft

Year

Property tax

Land + Additions

Assessment*

2023

$15,284 (+2.7%)

$552,500 + $980,500

$1,533,000

2022

$14,876 (+8.1%)

$526,100 + $933,800

$1,459,900

2021

$13,757 (+5.5%)

$505,900 + $897,900

$1,403,800

2020

$13,037 (+5.9%)

$459,900 + $919,700

$1,379,600

2019

$12,311 (+6.0%)

$438,000 + $875,900

$1,313,900

2018

$11,610 (+3.4%)

$376,900 + $850,400

$1,227,300

2017

$11,228 (+4.3%)

$355,600 + $780,800

$1,136,400

2016

$10,765 (+7.3%)

$332,300 + $700,800

$1,033,100

2015

$10,031 (−0.7%)

$310,600 + $628,600

$939,200

2014

$10,100 (+2.7%)

$282,300 + $604,400

$886,700

2013

$9,838 (+2.2%)

$274,100 + $570,400

$844,500

2012

$9,627 (+0.9%)

$274,100 + $570,400

$844,500

2011

$9,542 (+3.0%)

$271,300 + $573,100

$844,400

2010

$9,263 (+3.6%)

$271,300 + $573,100

$844,400

2009

$8,945

$271,500 + $565,300

$836,800

Tax history for 66 Chestnut St

Year

Property tax

Land + Additions

Assessment*

2023

$15,284 (+2.7%)

$552,500 + $980,500

$1,533,000

2022

$14,876 (+8.1%)

$526,100 + $933,800

$1,459,900

2021

$13,757 (+5.5%)

$505,900 + $897,900

$1,403,800

2020

$13,037 (+5.9%)

$459,900 + $919,700

$1,379,600

2019

$12,311 (+6.0%)

$438,000 + $875,900

$1,313,900

2018

$11,610 (+3.4%)

$376,900 + $850,400

$1,227,300

2017

$11,228 (+4.3%)

$355,600 + $780,800

$1,136,400

2016

$10,765 (+7.3%)

$332,300 + $700,800

$1,033,100

2015

$10,031 (−0.7%)

$310,600 + $628,600

$939,200

2014

$10,100 (+2.7%)

$282,300 + $604,400

$886,700

2013

$9,838 (+2.2%)

$274,100 + $570,400

$844,500

2012

$9,627 (+0.9%)

$274,100 + $570,400

$844,500

2011

$9,542 (+3.0%)

$271,300 + $573,100

$844,400

2010

$9,263 (+3.6%)

$271,300 + $573,100

$844,400

2009

$8,945

$271,500 + $565,300

$836,800

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

Permits

Oct 22, 2021 • Active

Residential electrical

Upgrade the electrical service to add a house meter to a three-family building.

Electrical

Electric meter

Oct 24, 2013 • Active

Residential electrical

Install electrical wiring for a gas fired boiler.

Gas

Plumbing

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: 1,300
Basement Type: Full

Bathroom Information
# of Full Baths: 3

Heating & Cooling
Heating Type: Forced Hot Water

Room Information
# of Rooms: 14

Exterior

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

Property Information
Living Sq. Ft: 3,956
Gross Sq. Ft: 7,008
# of Units: 3
# of Stories: 3

Lot Information
# of Buildings: 1
Land Sq. Ft: 2,614
Municipality Name: BROOKLINE
Acres: 0.06
Zoning Code: M10
State Use Description: 3-FAMILY RESIDENCE

Financial

Assessor Information
Assessment Year: 2023

Public facts

Beds: 8
Baths: 3.0
Sq. Ft.: 3,956
Stories: 3.0
Lot Size: 2,614 square feet
Style: Multi-Family (2-4 Unit)
Year Built: 1910
Year Renovated: 1971
County: Norfolk County
APN: 40940

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 • 0.5mi

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...
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

6/10 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

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OPEN SAT, 12:30PM TO 2:30PM3D WALKTHROUGH

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New listings for sale in 02445

NEW 19 HRS AGO

$4,250,000

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120 Rawson Rd, Brookline, MA 02445

EARLY ACCESSCOLDWELL BANKER REALTY COMING SOON

$1,595,000

3 beds2 baths1,105 sq ft

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$495,000

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EARLY ACCESSCOLDWELL BANKER REALTY COMING SOON

$1,700,000

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$2,350,000

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101-103 University Rd, Brookline, MA 02445

OPEN SAT, 12PM TO 1PM

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Home values near 66 Chestnut St

Data from public records.

Address	Redfin Estimate
70 Chestnut Street #1, Brookline, MA 3 Beds \| 1 Baths \| 1385 Sq. Ft.	$859,151
80 Chestnut Street, Brookline, MA 9 Beds \| 4.5 Baths \| 4326 Sq. Ft.	—

Address	Redfin Estimate
62 Chestnut Street #1, Brookline, MA 2 Beds \| 1 Baths \| 934 Sq. Ft.	$683,338
70 Chestnut Street #2, Brookline, MA 2 Beds \| 1 Baths \| 1220 Sq. Ft.	$806,177

Address	Redfin Estimate
68 Chestnut Street #1, Brookline, MA 2 Beds \| 1 Baths \| 1205 Sq. Ft.	$690,231
70 Chestnut Street #3, Brookline, MA 3 Beds \| 2 Baths \| 1660 Sq. Ft.	$1,241,169

Property information provided by undefined .

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GreatSchools Ratings provided by GreatSchools.org.

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About this home

Redfin Estimate

Market trends in 02445, MA

Sale history for 66 Chestnut St

Tax history for 66 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 66 Chestnut St

More real estate resources