Google street view image for 39 Winthrop Rd, Brookline, MA 02445

Off market dec 1986 for $330K

$1,958,420

Est. refi paymentEst. refi $2,212/mo

•

3.5 ba

•

2,268

sq ft

39 Winthrop Rd, Brookline, MA 02445

About this home

39 Winthrop Rd is a 2,268 square foot condo with 3 bedrooms and 3.5 bathrooms. - it last sold on December 22, 1986 for $330,000. Based on Redfin's Brookline data, we estimate the home's value is $1,958,420.

CondoProperty Type

1910Year Built

$864Est. Price/Sq.Ft.

Source:Public Records

Redfin Estimate

$1,958,420

$1.6M since sold in December 1986$142K since September

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 10.6% higher than the average sale price ($1.77M) of 6 comparable homes.

SOLD SEP 21, 2026
$1,575,000
A
3 beds2 baths1,877 sq ft
1471 Beacon St Unit 10(PH), Brookline, MA 02446
SOLD AUG 7, 2026
$1,350,000
B
3 beds2 baths2,012 sq ft
63 Winthrop Rd #1, Brookline, MA 02445
SOLD JUL 30, 2026
$1,430,000
C
3 beds2 baths1,696 sq ft
483 Washington St #1, Brookline, MA 02446
SOLD MAY 1, 2026
$2,600,000
D
3 beds3.5 baths1,837 sq ft
1517 Beacon #4, Brookline, MA 02445
SOLD APR 30, 2026
$1,815,000
E
3 beds2 baths1,870 sq ft
95 Mason Ter #6, Brookline, MA 02446
SOLD JAN 30, 2026
$1,850,000
F
3 beds2.5 baths1,850 sq ft
1521 Beacon St #1, Brookline, MA 02446

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Earn from this home

Sell

$1,860,361

Est. take-home

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Refinance

Est. cash available

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Rent

$6,359/mo

Redfin rental estimate

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Market trends in 02445, MA

Last updated September 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-List Price

98.8%

1.0% MoM

Median sale price

$883K

$282K MoM

Avg. days on market

42d

8 days MoM

Recently sold homes

1 MoM

New listings for sale

$495,000
1 bed1 bath655 sq ft
44 Washington St #303, Brookline, MA 02445
EARLY ACCESS
$4,250,000
5 beds4 baths6,313 sq ft
120 Rawson Rd, 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
$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
$775,000
2 beds1 bath947 sq ft
1731 Beacon St #311, Brookline, MA 02445
$3,500,000
6 beds5.5 baths4,891 sq ft
115 Dean Rd, Brookline, MA 02445
See all

Provided by Redfin

Sale history for 39 Winthrop Rd

Year

Property tax

Land + Additions

Assessment*

2023

$15,748 (+0.8%)

$1,579,500

2022

$15,627 (+5.0%)

$1,533,600

2021

$14,880 (+4.7%)

$1,518,400

2020

$14,207 (+5.9%)

$1,503,400

2019

$13,416 (+4.0%)

$1,431,800

2018

$12,900 (+3.4%)

$1,363,600

2017

$12,474 (+4.3%)

$1,262,600

2016

$11,960 (+7.3%)

$1,147,800

2015

$11,145 (−0.1%)

$1,043,500

2014

$11,160 (−32.3%)

$979,800

2013

$16,477 (+3.0%)

$407,900 + $1,006,400

$1,414,300

2012

$15,992 (+2.7%)

$407,900 + $994,900

$1,402,800

2011

$15,565 (+3.0%)

$407,900 + $969,500

$1,377,400

2010

$15,110 (+2.6%)

$407,900 + $969,500

$1,377,400

2009

$14,724

$407,900 + $969,500

$1,377,400

Tax history for 39 Winthrop Rd

Year

Property tax

Land + Additions

Assessment*

2023

$15,748 (+0.8%)

$1,579,500

2022

$15,627 (+5.0%)

$1,533,600

2021

$14,880 (+4.7%)

$1,518,400

2020

$14,207 (+5.9%)

$1,503,400

2019

$13,416 (+4.0%)

$1,431,800

2018

$12,900 (+3.4%)

$1,363,600

2017

$12,474 (+4.3%)

$1,262,600

2016

$11,960 (+7.3%)

$1,147,800

2015

$11,145 (−0.1%)

$1,043,500

2014

$11,160 (−32.3%)

$979,800

2013

$16,477 (+3.0%)

$407,900 + $1,006,400

$1,414,300

2012

$15,992 (+2.7%)

$407,900 + $994,900

$1,402,800

2011

$15,565 (+3.0%)

$407,900 + $969,500

$1,377,400

2010

$15,110 (+2.6%)

$407,900 + $969,500

$1,377,400

2009

$14,724

$407,900 + $969,500

$1,377,400

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

Permits

May 26, 2026 • Active

Residential building

Roofing

Oct 1, 2020 • Active

Residential building

Replace the shingle roof by removing existing roofing material and installing new architectural shingles. Remove all waste and debris from the site.

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: 1,440
Basement Type: Full

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: 7

Exterior

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

Property Information
Living Sq. Ft: 2,268
Gross Sq. Ft: 2,268
# of Units: 1
# of Stories: 2

Lot Information
# of Buildings: 1
Municipality Name: BROOKLINE
Zoning Code: T-6
State Use Description: CONDOMINIUM

Financial

Assessor Information
Assessment Year: 2023

Public facts

Beds: 3
Baths: 3.5
Sq. Ft.: 2,268
Stories: 2.0
Lot Size: —
Style: Condo/Co-op
Year Built: 1910
Year Renovated: —
County: Norfolk County
APN: 36643

Home facts updated by county records on Jul 20, 2023

Around this home

Schools

Pierce School

Public K-8 • Assigned • 0.5mi

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...
3 weeks ago • Brookline
Benjamin Ginsburg
Redfin Premier agent
155 deals
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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

$1.86M – $2.25M

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Home values near 39 Winthrop Rd

Data from public records.

Address	Redfin Estimate
53 Winthrop Road, Brookline, MA 4 Beds \| 4 Baths \| 1955 Sq. Ft.	—
35 Winthrop Road, Brookline, MA 8 Beds \| 3.5 Baths \| 3544 Sq. Ft.	$2,576,446

Address	Redfin Estimate
51 Winthrop Road, Brookline, MA 4 Beds \| 2.5 Baths \| 2237 Sq. Ft.	$1,873,312
47 Winthrop Road Unit 1, Brookline, MA 4 Beds \| 3.5 Baths \| 2062 Sq. Ft.	$1,643,352

Address	Redfin Estimate
47 Winthrop Road Unit 2, Brookline, MA 4 Beds \| 3.5 Baths \| 2530 Sq. Ft.	$1,917,206
34 Winthrop Road, Brookline, MA 4 Beds \| 3.5 Baths \| 2683 Sq. Ft.	$2,848,005

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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 39 Winthrop Rd

Tax history for 39 Winthrop Rd

Permits

Property details

Around this home

Schools

Lifestyle

Local insights from Redfin agents

Historical weather

Sun exposure

Nearby similar homes

New listings for sale in 02445

Home values near 39 Winthrop Rd

More real estate resources