Google street view image for 16 Winthrop Rd, Brookline, MA 02445

OFF MARKET

$2,337,213

•

2.5 ba

•

2,141

sq ft

16 Winthrop Rd, Brookline, MA 02445

About this home

16 Winthrop Rd is a 2,141 square foot house on a 4,792 square foot lot with 3 bedrooms and 2.5 bathrooms. Based on Redfin's Brookline data, we estimate the home's value is $2,337,213.

Single-familyProperty Type

1935Year Built

4,792 sq ftLot Size

$1,092Est. Price/Sq.Ft.

Source:Public Records

Redfin Estimate

$2,337,213

$37K since July

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 12.2% higher than the average sale price ($2.08M) of 6 comparable homes.

SOLD APR 13, 2026
$2,210,000
A
3 beds2.5 baths1,740 sq ft
30 York Ter, Brookline, MA 02446
SOLD JUN 23, 2026
$1,750,000
B
3 beds1.5 baths1,380 sq ft
14A Linden Pl, Brookline, MA 02445
SOLD APR 8, 2026
$2,850,000
C
4 beds2.5 baths3,377 sq ft
24 Blake Rd, Brookline, MA 02445
SOLD DEC 17, 2025
$2,385,000
D
4 beds3 baths2,286 sq ft
21 Hancock Rd, Brookline, MA 02445
SOLD APR 16, 2026
$2,150,000
E
4 beds3.5 baths2,332 sq ft
209 High St, Brookline, MA 02445
SOLD AUG 14, 2026
$1,156,000
F
3 beds2 baths1,986 sq ft
11 Country Rd, Chestnut Hill, MA 02467

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Earn from this home

Sell

$2,220,381

Est. take-home

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Rent

$5,759/mo

Redfin rental estimate

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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 SAT, 11AM TO 12:30PM
$859,000
3 beds1.5 baths1,233 sq ft
124 Chestnut St #1, Brookline, MA 02445
OPEN TODAY, 12:30PM TO 2PM
$2,895,000
7 beds3.5 baths4,805 sq ft
71 Addington Rd, Brookline, MA 02445
OPEN SAT, 12PM TO 2PM
$2,200,000
9 beds3 baths4,364 sq ft
26 Parkway Rd, Brookline, MA 02445
OPEN SUN, 11AM TO 12PM
$4,800,000
5 beds5.5 baths4,324 sq ft
221 Gardner 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 16 Winthrop Rd

As the MLS and public records start to fill up, we'll list the details here.

Year

Property tax

Land + Additions

Assessment*

2023

$18,028 (+2.7%)

$1,087,300 + $720,900

$1,808,200

2022

$17,547 (+8.1%)

$1,035,500 + $686,500

$1,722,000

2021

$16,227 (+10.4%)

$995,700 + $660,100

$1,655,800

2020

$14,703 (+5.9%)

$905,200 + $650,700

$1,555,900

2019

$13,884 (+10.3%)

$862,100 + $619,700

$1,481,800

2018

$12,583 (+1.5%)

$718,300 + $611,800

$1,330,100

2017

$12,398 (+1.4%)

$677,800 + $577,100

$1,254,900

2016

$12,221 (+4.4%)

$633,400 + $539,400

$1,172,800

2015

$11,706 (+4.0%)

$592,000 + $504,100

$1,096,100

2014

$11,257 (+1.9%)

$493,300 + $495,000

$988,300

2013

$11,042 (+2.2%)

$478,900 + $468,900

$947,800

2012

$10,805 (+3.0%)

$478,900 + $468,900

$947,800

2011

$10,495 (+3.0%)

$479,000 + $449,800

$928,800

2010

$10,189 (+2.6%)

$479,000 + $449,800

$928,800

2009

$9,930

$479,000 + $449,900

$928,900

Tax history for 16 Winthrop Rd

Year

Property tax

Land + Additions

Assessment*

2023

$18,028 (+2.7%)

$1,087,300 + $720,900

$1,808,200

2022

$17,547 (+8.1%)

$1,035,500 + $686,500

$1,722,000

2021

$16,227 (+10.4%)

$995,700 + $660,100

$1,655,800

2020

$14,703 (+5.9%)

$905,200 + $650,700

$1,555,900

2019

$13,884 (+10.3%)

$862,100 + $619,700

$1,481,800

2018

$12,583 (+1.5%)

$718,300 + $611,800

$1,330,100

2017

$12,398 (+1.4%)

$677,800 + $577,100

$1,254,900

2016

$12,221 (+4.4%)

$633,400 + $539,400

$1,172,800

2015

$11,706 (+4.0%)

$592,000 + $504,100

$1,096,100

2014

$11,257 (+1.9%)

$493,300 + $495,000

$988,300

2013

$11,042 (+2.2%)

$478,900 + $468,900

$947,800

2012

$10,805 (+3.0%)

$478,900 + $468,900

$947,800

2011

$10,495 (+3.0%)

$479,000 + $449,800

$928,800

2010

$10,189 (+2.6%)

$479,000 + $449,800

$928,800

2009

$9,930

$479,000 + $449,900

$928,900

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

Permits

Oct 25, 2012 • Active

Residential gas

Replace a gas boiler and perform necessary testing.

Gas

Oct 25, 2012 • Active

Residential plumbing

Install a new water heater for a boiler system.

Plumbing

Water heater

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: 891
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: 1
Fireplace Type: Wood Stove
Has Fireplace

Room Information
# of Rooms: 8

Exterior

Exterior Information
Physical Condition: Average
Building Style Type: Colonial
Construction Type: Frame
Exterior Wall: Brick
Roof Shape Type: Gable

Property Information
Living Sq. Ft: 2,141
Gross Sq. Ft: 3,985
# of Units: 1
# of Stories: 2

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

Lot Information
# of Buildings: 1
Land Sq. Ft: 4,792
Municipality Name: BROOKLINE
Acres: 0.11
Zoning Code: T-6
State Use Description: 1-FAMILY RESIDENCE

Financial

Assessor Information
Assessment Year: 2023

Public facts

Beds: 3
Baths: 2.5
Sq. Ft.: 2,141
Stories: 2.0
Lot Size: 4,792 square feet
Style: Single Family Residential
Year Built: 1935
Year Renovated: 1969
County: Norfolk County
APN: 36614

Home facts updated by county records on Jul 20, 2023

Around this home

Schools

Pierce School

Public K-8 • Assigned • 0.4mi

10/10

Brookline High School

Public 9-12 • Assigned • 0.3mi

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
151 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

5/10 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 9.2 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

Estimated sale price

$2.22M – $2.69M

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Nearby similar homes

OPEN SUN, 11AM TO 12PM

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New listings for sale in 02445

OPEN SUN, 12PM TO 1:30PM

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1731 Beacon St #402, Brookline, MA 02445

OPEN SAT, 11AM TO 12:30PM

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124 Chestnut St #1, Brookline, MA 02445

OPEN TODAY, 12:30PM TO 2PM

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OPEN SAT, 12PM TO 2PM

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OPEN SUN, 11AM TO 12PM

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5 beds5.5 baths4,324 sq ft

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EARLY ACCESSCOMPASS COMING SOON

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

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Home values near 16 Winthrop Rd

Data from public records.

Address	Redfin Estimate
20 Winthrop Rd, Brookline, MA 4 Beds \| 2.5 Baths \| 2489 Sq. Ft.	$2,557,619
21 Winthrop Rd, Brookline, MA 4 Beds \| 3 Baths \| - Sq. Ft.	$3,065,909

Address	Redfin Estimate
10 Winthrop Rd, Brookline, MA 3 Beds \| 1.5 Baths \| 2042 Sq. Ft.	$2,002,725
15 Winthrop Rd, Brookline, MA 4 Beds \| 4 Baths \| 3233 Sq. Ft.	$3,169,475

Address	Redfin Estimate
25 Winthrop Rd, Brookline, MA 8 Beds \| 7.5 Baths \| 6162 Sq. Ft.	$3,172,996
31 Winthrop Rd, Brookline, MA 4 Beds \| 3 Baths \| 3085 Sq. Ft.	$2,080,657

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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 16 Winthrop Rd

Tax history for 16 Winthrop 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 02445

Home values near 16 Winthrop Rd

More real estate resources