OFF MARKET

$3,470,266

•

5 ba

•

3,770

sq ft

53 Winslow Rd, Brookline, MA 02446

About this home

53 Winslow Rd is a 3,770 square foot multi-family home on a 6,098 square foot lot with 6 bedrooms and 5 bathrooms. Based on Redfin's Brookline data, we estimate the home's value is $3,470,266.

Multi-familyProperty Type

2004Year Built

6,098 sq ftLot Size

$920Est. Price/Sq.Ft.

4 spacesParking

Source:Public Records

Redfin Estimate

$3,470,266

$442K since August

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 1.3% higher than the average sale price ($3.42M) of 6 comparable homes.

SOLD MAY 4, 2026
$3,595,000
A
5 beds4.5 baths4,882 sq ft
105 Babcock St, Brookline, MA 02446
SOLD AUG 17, 2026
$5,000,000
B
5 beds6 baths5,198 sq ft
18 Naples Rd, Brookline, MA 02446
SOLD AUG 13, 2026
$4,050,000
C
5 beds4.5 baths3,738 sq ft
95 Babcock St, Brookline, MA 02446
SOLD JUL 2, 2026
$2,525,000
D
6 beds3 baths4,605 sq ft
62 Fuller St, Brookline, MA 02446
SOLD JUL 31, 2026
$2,375,000
E
5 beds3.5 baths3,195 sq ft
121 Thorndike St, Brookline, MA 02446
SOLD DEC 9, 2025
$3,000,000
F
5 beds4.5 baths2,997 sq ft
6 Elba St, Brookline, MA 02446

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

Earn from this home

Sell

$3,297,280

Est. take-home

List your home with Redfin and save $17,351

Market trends in 02215, MA

Last updated August 2026

Buyer's Market

Seller's Market

Balanced market

Sale-to-List Price

97.0%

0.4% MoM

Median sale price

$750K

$129K MoM

Avg. days on market

43d

10 days MoM

Recently sold homes

11 MoM

New listings for sale

OPEN SUN, 11:30AM TO 12:30PM
$2,175,000
5 beds3.5 baths3,213 sq ft
77 Jordan Rd, Brookline, MA 02446
EARLY ACCESS
Unknown
2 beds1 bath1,007 sq ft
55 Harvard Ave #6, Brookline, MA 02446
NEW 32 HRS AGO
$865,000
2 beds2 baths687 sq ft
58 Pleasant St #2, Brookline, MA 02246
EARLY ACCESS
Unknown
2 beds2 baths1,162 sq ft
Brookline, MA 02446
OPEN SAT, 1PM TO 3PM
$729,900
1 bed1 bath855 sq ft
115 Freeman St #1, Brookline, MA 02446
OPEN SAT, 12PM TO 1:30PM
$789,000
2 beds1 bath1,101 sq ft
648 Washington St #5, Brookline, MA 02446
3D WALKTHROUGH
$629,900
1 bed1.5 baths953 sq ft
50 Longwood Ave #517, Brookline, MA 02446
$815,000
2 beds1.5 baths803 sq ft
55 Sewall Ave Unit PHB, Brookline, MA 02446
EARLY ACCESS
$1,250,000
2 beds2 baths1,187 sq ft
50 Longwood Ave #316, Brookline, MA 02446
OPEN SUN, 12PM TO 2PM
$565,000
1 bed1 bath575 sq ft
1584 Beacon St Unit A, Brookline, MA 02446
See all

Provided by Redfin

Sale history for 53 Winslow Rd

Year

Property tax

Land + Additions

Assessment*

2023

$36,241 (+2.7%)

$1,142,400 + $2,492,600

$3,635,000

2022

$35,276 (+8.1%)

$1,087,900 + $2,373,900

$3,461,800

2021

$32,621 (+4.2%)

$1,046,100 + $2,282,600

$3,328,700

2020

$31,292 (+5.9%)

$951,000 + $2,360,300

$3,311,300

2019

$29,549 (+12.3%)

$905,700 + $2,247,900

$3,153,600

2018

$26,304 (+3.4%)

$754,700 + $2,025,800

$2,780,500

2017

$25,436 (+4.3%)

$712,000 + $1,862,500

$2,574,500

2016

$24,388 (+7.3%)

$665,400 + $1,675,100

$2,340,500

2015

$22,724 (+2.1%)

$621,900 + $1,505,800

$2,127,700

2014

$22,248 (+2.7%)

$518,300 + $1,435,000

$1,953,300

2013

$21,672 (+2.2%)

$503,200 + $1,357,100

$1,860,300

2012

$21,207 (+7.5%)

$503,200 + $1,357,100

$1,860,300

2011

$19,730 (+3.0%)

$500,700 + $1,245,300

$1,746,000

2010

$19,154 (+2.6%)

$500,700 + $1,245,300

$1,746,000

2009

$18,665

$500,700 + $1,245,300

$1,746,000

Tax history for 53 Winslow Rd

Year

Property tax

Land + Additions

Assessment*

2023

$36,241 (+2.7%)

$1,142,400 + $2,492,600

$3,635,000

2022

$35,276 (+8.1%)

$1,087,900 + $2,373,900

$3,461,800

2021

$32,621 (+4.2%)

$1,046,100 + $2,282,600

$3,328,700

2020

$31,292 (+5.9%)

$951,000 + $2,360,300

$3,311,300

2019

$29,549 (+12.3%)

$905,700 + $2,247,900

$3,153,600

2018

$26,304 (+3.4%)

$754,700 + $2,025,800

$2,780,500

2017

$25,436 (+4.3%)

$712,000 + $1,862,500

$2,574,500

2016

$24,388 (+7.3%)

$665,400 + $1,675,100

$2,340,500

2015

$22,724 (+2.1%)

$621,900 + $1,505,800

$2,127,700

2014

$22,248 (+2.7%)

$518,300 + $1,435,000

$1,953,300

2013

$21,672 (+2.2%)

$503,200 + $1,357,100

$1,860,300

2012

$21,207 (+7.5%)

$503,200 + $1,357,100

$1,860,300

2011

$19,730 (+3.0%)

$500,700 + $1,245,300

$1,746,000

2010

$19,154 (+2.6%)

$500,700 + $1,245,300

$1,746,000

2009

$18,665

$500,700 + $1,245,300

$1,746,000

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

Permits

Dec 8, 2014 • Active

Residential electrical

Install a wireless security system.

Electrical

Jul 31, 2006 • Active

Residential electrical

Install a new security system.

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: 1,190

Bathroom Information
# of Full Baths: 4
# of 1/2 Baths: 2

Heating & Cooling
Heating Type: Forced Air

Room Information
# of Rooms: 12

Exterior

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

Property Information
Living Sq. Ft: 3,770
Gross Sq. Ft: 5,080
# of Units: 2
# of Stories: 3

Lot Information
# of Buildings: 1
Land Sq. Ft: 6,098
Municipality Name: BROOKLINE
Acres: 0.14
Zoning Code: T-5
State Use Description: 2-FAMILY RESIDENCE

Financial

Assessor Information
Assessment Year: 2023

Public facts

Beds: 6
Baths: 5.0
Sq. Ft.: 3,770
Stories: 3.0
Lot Size: 6,098 square feet
Style: Multi-Family (2-4 Unit)
Year Built: 2004
Year Renovated: 2004
County: Norfolk County
APN: 4592264

Home facts updated by county records on Jul 20, 2023

Around this home

Schools

Florida Ruffin Ridley School

Public PreK-8 • Assigned • 0.4mi

9/10

Brookline High School

Public 9-12 • Assigned • 1.2mi

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
153 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

64% 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 • 02446

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

39/ 100

Low sunlight

Sunscore

There appears to be significant shading by surrounding buildings, terrain, and vegetation.

4.4 hrs

2.6 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$3.30M – $3.99M

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Home values near 53 Winslow Rd

Data from public records.

Address	Redfin Estimate
45 Winslow Rd, Brookline, MA 7 Beds \| 4 Baths \| 999999 Sq. Ft.	$2,616,705
210 Babcock St, Brookline, MA 7 Beds \| 3.5 Baths \| 4137 Sq. Ft.	$2,978,433

Address	Redfin Estimate
51 Winslow Rd, Brookline, MA 6 Beds \| 5 Baths \| 3770 Sq. Ft.	$3,316,243
204 Babcock St, Brookline, MA 5 Beds \| 2.5 Baths \| 3470 Sq. Ft.	$3,249,679

Address	Redfin Estimate
36 Osborne Rd, Brookline, MA 9 Beds \| 3 Baths \| 4084 Sq. Ft.	$4,260,619
36 Osborne Rd Apartment 1, Brookline, MA 4 Beds \| 4 Baths \| 4069 Sq. Ft.	$2,862,227

Property information provided by undefined .

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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 02215, MA

Sale history for 53 Winslow Rd

Tax history for 53 Winslow Rd

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 02446

Home values near 53 Winslow Rd

More real estate resources