Google street view image for 165 Winthrop Rd, Brookline, MA 02445

Off Market Sep 1977 for $69K

—

Est. refi paymentEst. refi $440/mo

•

8 ba

•

5,136

sq ft

165 Winthrop Rd, Brookline, MA 02445

About this home

165 Winthrop Rd is a 5,136 square foot multi-family home on a 10,454 square foot lot with 10 bedrooms and 8 bathrooms. - it last sold on September 21, 1977 for $69,090.

Multi-familyProperty Type

1891Year Built

10,454 sq ftLot Size

$13Price/Sq.Ft.

Source:Public Records

Redfin Estimate

There isn’t enough information to generate an accurate estimate at this time. Learn More

Market trends in 02445, MA

Last updated July 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-List Price

100.2%

0.1% MoM

Median sale price

$1.2M

$85K MoM

Avg. days on market

30d

9 days MoM

Recently sold homes

7 MoM

New listings for sale

OPEN SUN, 12PM TO 1:30PM
$998,000
2 beds2 baths1,218 sq ft
1731 Beacon St #402, Brookline, MA 02445
OPEN SUN, 11AM TO 12:30PM
$859,000
3 beds1.5 baths1,233 sq ft
124 Chestnut St #1, Brookline, MA 02445
OPEN SUN, 11AM TO 12PM
$2,895,000
7 beds3.5 baths4,805 sq ft
71 Addington Rd, Brookline, MA 02445
$2,200,000
9 beds3 baths4,364 sq ft
26 Parkway Rd, Brookline, MA 02445
EARLY ACCESS
Unknown
5 beds6 baths3,539 sq ft
291 Tappan St, Brookline, MA 02445
OPEN SUN, 11AM TO 12:30PM
$1,495,000
3 beds2 baths1,759 sq ft
12 Kilsyth Rd #3, Brookline, MA 02445
$560,000
1 bed1 bath860 sq ft
77 Pond Ave #509, Brookline, MA 02445
$2,999,000
4 beds3.5 baths3,265 sq ft
52 Clinton Rd, Brookline, MA 02445
3D WALKTHROUGH
$6,495,000
9 beds7.5 baths8,619 sq ft
372 Warren St, Brookline, MA 02445
See all

Provided by Redfin

Sale history for 165 Winthrop Rd

Year

Property tax

Land + Additions

Assessment*

2023

$30,592 (+16.2%)

$1,392,900 + $1,675,500

$3,068,400

2022

$26,337 (+14.0%)

$1,392,900 + $1,191,700

$2,584,600

2021

$23,098 (+27.5%)

$1,041,700 + $1,315,200

$2,356,900

2020

$18,110 (+76.1%)

$1,392,900 + $523,500

$1,916,400

2019

$10,283 (−3.0%)

$892,700 + $204,700

$1,097,400

2018

$10,601 (−38.7%)

$744,800 + $375,800

$1,120,600

2017

$17,281 (+4.3%)

$702,600 + $1,046,500

$1,749,100

2016

$16,569 (+11.7%)

$656,700 + $933,400

$1,590,100

2015

$14,828 (+3.9%)

$557,900 + $830,500

$1,388,400

2014

$14,274 (+2.7%)

$507,100 + $746,100

$1,253,200

2013

$13,904 (+2.2%)

$492,300 + $701,200

$1,193,500

2012

$13,606 (+3.7%)

$492,300 + $701,200

$1,193,500

2011

$13,116 (+3.0%)

$492,300 + $668,400

$1,160,700

2010

$12,733 (+2.6%)

$492,300 + $668,400

$1,160,700

2009

$12,408

$492,300 + $668,400

$1,160,700

Tax history for 165 Winthrop Rd

Year

Property tax

Land + Additions

Assessment*

2023

$30,592 (+16.2%)

$1,392,900 + $1,675,500

$3,068,400

2022

$26,337 (+14.0%)

$1,392,900 + $1,191,700

$2,584,600

2021

$23,098 (+27.5%)

$1,041,700 + $1,315,200

$2,356,900

2020

$18,110 (+76.1%)

$1,392,900 + $523,500

$1,916,400

2019

$10,283 (−3.0%)

$892,700 + $204,700

$1,097,400

2018

$10,601 (−38.7%)

$744,800 + $375,800

$1,120,600

2017

$17,281 (+4.3%)

$702,600 + $1,046,500

$1,749,100

2016

$16,569 (+11.7%)

$656,700 + $933,400

$1,590,100

2015

$14,828 (+3.9%)

$557,900 + $830,500

$1,388,400

2014

$14,274 (+2.7%)

$507,100 + $746,100

$1,253,200

2013

$13,904 (+2.2%)

$492,300 + $701,200

$1,193,500

2012

$13,606 (+3.7%)

$492,300 + $701,200

$1,193,500

2011

$13,116 (+3.0%)

$492,300 + $668,400

$1,160,700

2010

$12,733 (+2.6%)

$492,300 + $668,400

$1,160,700

2009

$12,408

$492,300 + $668,400

$1,160,700

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

Permits

Jul 16, 2018 • Active

Residential building

Remodel all floors of the building and convert the structure into a five-family residence.

Addition

Remodel

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: 1,821
Basement Type: Full

Bathroom Information
# of Full Baths: 8

Heating & Cooling
Heating Type: Forced Hot Water

Fireplace Information
# of Fireplaces: 5
Fireplace Type: Wood Stove
Has Fireplace

Room Information
# of Rooms: 19

Exterior

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

Property Information
Living Sq. Ft: 5,136
Gross Sq. Ft: 5,894
# of Units: 5
# of Stories: 3

Lot Information
# of Buildings: 1
Land Sq. Ft: 10,454
Municipality Name: BROOKLINE
Acres: 0.24
Zoning Code: M10
State Use Description: APARTMENT BLDG - 4-8 UNITS

Financial

Assessor Information
Assessment Year: 2023

Public facts

Beds: 10
Baths: 8.0
Sq. Ft.: 5,136
Stories: 3.0
Lot Size: 10,454 square feet
Style: Multi-Family (5+ Unit)
Year Built: 1891
Year Renovated: 1975
County: Norfolk County
APN: 37220

Home facts updated by county records on Jul 20, 2023

Around this home

Schools

Michael Driscoll 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...
2 months ago • Brookline
Benjamin Ginsburg
Redfin Premier agent
152 deals
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Climate risks

1/10 Flood Factor

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

1/10 Fire Factor

Unlikely to be 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

58% 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 9.2 hours in June and 4.4 hours in December, placing it below the U.S. average for solar exposure.

9.2 hrs

4.4 hrs

JuneDecember

Provided by Shadowmap

Is this your home?

Track this home’s value and nearby sales activity

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New listings for sale in 02445

OPEN SUN, 12PM TO 1:30PM

$998,000

2 beds2 baths1,218 sq ft

1731 Beacon St #402, Brookline, MA 02445

OPEN SUN, 11AM TO 12:30PM

$859,000

3 beds1.5 baths1,233 sq ft

124 Chestnut St #1, Brookline, MA 02445

OPEN SUN, 11AM TO 12PM

$2,895,000

7 beds3.5 baths4,805 sq ft

71 Addington Rd, Brookline, MA 02445

$2,200,000

9 beds3 baths4,364 sq ft

26 Parkway Rd, Brookline, MA 02445

EARLY ACCESS

Unknown

5 beds6 baths3,539 sq ft

291 Tappan St, Brookline, MA 02445

OPEN SUN, 11AM TO 12:30PM

$1,495,000

3 beds2 baths1,759 sq ft

12 Kilsyth Rd #3, Brookline, MA 02445

$560,000

1 bed1 bath860 sq ft

77 Pond Ave #509, Brookline, MA 02445

$2,999,000

4 beds3.5 baths3,265 sq ft

52 Clinton Rd, Brookline, MA 02445

3D WALKTHROUGH

$6,495,000

9 beds7.5 baths8,619 sq ft

372 Warren St, Brookline, MA 02445

Home values near 165 Winthrop Rd

Data from public records.

Address	Redfin Estimate
175 Winthrop Rd Apartment 1, Brookline, MA 2 Beds \| 2 Baths \| 1520 Sq. Ft.	$956,579
157 Winthrop Rd Apartment 1, Brookline, MA 5 Beds \| 3.5 Baths \| 3919 Sq. Ft.	$2,579,309

Address	Redfin Estimate
175 Winthrop Rd Apartment 2, Brookline, MA 3 Beds \| 2 Baths \| 1730 Sq. Ft.	$1,306,748
157 Winthrop Rd Apartment 157, Brookline, MA 5 Beds \| 3.5 Baths \| 3919 Sq. Ft.	$2,408,347

Address	Redfin Estimate
175 Winthrop Rd Apartment 3, Brookline, MA 5 Beds \| 2.5 Baths \| 2650 Sq. Ft.	$1,803,739
35 University Rd Apartment 1, Brookline, MA 4 Beds \| 1 Baths \| 1488 Sq. Ft.	$905,814

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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 165 Winthrop Rd

Tax history for 165 Winthrop Rd

Permits

Property details

Around this home

Schools

Lifestyle

Local insights from Redfin agents

Climate risks

Historical weather

Sun exposure

Is this your home?

Nearby similar homes

New listings for sale in 02445

Home values near 165 Winthrop Rd

More real estate resources