Off market feb 1998 for $616K

$2,948,662

Est. refi paymentEst. refi $4,113/mo

•

—

sq ft

21 Winthrop Rd, Brookline, MA

About this home

Single-familyProperty Type

1940Year Built

8,550 sq ftLot Size

1 car garageParking

Listed by Vicky Whitney • Coldwell Banker Residential Brokerage - Brookline

Bought with • Coldwell Banker Residential Brokerage - Brookline

Redfin checked: 7 minutes ago

•Source:MLS PIN #50384232

Redfin Estimate

$2,948,662

$2.3M since sold in February 1998$11K since September

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 5% higher than the average sale price ($2.81M) of 6 comparable homes.

SOLD JUN 29, 2026
$3,215,000
A
4 beds3.5 baths3,002 sq ft
236 Mason Ter, Brookline, MA 02446
SOLD DEC 17, 2025
$2,385,000
B
4 beds3 baths2,286 sq ft
21 Hancock Rd, 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 SEP 25, 2026
$2,810,000
D
5 beds6 baths3,050 sq ft
16 York Ter, Brookline, MA 02446
SOLD SEP 9, 2026
$2,945,000
E
4 beds4.5 baths3,819 sq ft
84 Westbourne Ter #84, Brookline, MA 02446
SOLD JAN 7, 2026
$2,650,000
F
4 beds2 baths2,600 sq ft
29 Mason Ter, Brookline, MA 02446

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

Earn from this home

Sell

$2,763,526

Est. take-home

List your home with Redfin and save $14,743

Refinance

Est. cash available

Get cash now or lower your monthly rate

Rent

$7,481/mo

Redfin rental estimate

List your home for rent

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

$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
OPEN TODAY, 1PM TO 2PM
$3,500,000
6 beds5.5 baths4,891 sq ft
115 Dean Rd, Brookline, MA 02445

Provided by Redfin

Sale history for 21 Winthrop Rd

Year

Property tax

Land + Additions

Assessment*

2023

$22,214 (+2.7%)

$1,236,900 + $991,200

$2,228,100

2022

$21,623 (+8.1%)

$1,178,000 + $944,000

$2,122,000

2021

$19,996 (+9.9%)

$1,132,700 + $907,700

$2,040,400

2020

$18,190 (+5.9%)

$1,029,700 + $895,200

$1,924,900

2019

$17,178 (+9.4%)

$980,700 + $852,600

$1,833,300

2018

$15,700 (+1.5%)

$817,200 + $842,400

$1,659,600

2017

$15,469 (+1.5%)

$771,000 + $794,700

$1,565,700

2016

$15,247 (+4.4%)

$720,500 + $742,700

$1,463,200

2015

$14,605 (+3.7%)

$673,400 + $694,100

$1,367,500

2014

$14,084 (+0.7%)

$561,100 + $675,400

$1,236,500

2013

$13,986 (+2.2%)

$544,800 + $655,700

$1,200,500

2012

$13,686 (+3.8%)

$544,800 + $655,700

$1,200,500

2011

$13,183 (+3.0%)

$538,000 + $628,600

$1,166,600

2010

$12,798 (+2.6%)

$538,000 + $628,600

$1,166,600

2009

$12,471

$538,000 + $628,600

$1,166,600

Tax history for 21 Winthrop Rd

Year

Property tax

Land + Additions

Assessment*

2023

$22,214 (+2.7%)

$1,236,900 + $991,200

$2,228,100

2022

$21,623 (+8.1%)

$1,178,000 + $944,000

$2,122,000

2021

$19,996 (+9.9%)

$1,132,700 + $907,700

$2,040,400

2020

$18,190 (+5.9%)

$1,029,700 + $895,200

$1,924,900

2019

$17,178 (+9.4%)

$980,700 + $852,600

$1,833,300

2018

$15,700 (+1.5%)

$817,200 + $842,400

$1,659,600

2017

$15,469 (+1.5%)

$771,000 + $794,700

$1,565,700

2016

$15,247 (+4.4%)

$720,500 + $742,700

$1,463,200

2015

$14,605 (+3.7%)

$673,400 + $694,100

$1,367,500

2014

$14,084 (+0.7%)

$561,100 + $675,400

$1,236,500

2013

$13,986 (+2.2%)

$544,800 + $655,700

$1,200,500

2012

$13,686 (+3.8%)

$544,800 + $655,700

$1,200,500

2011

$13,183 (+3.0%)

$538,000 + $628,600

$1,166,600

2010

$12,798 (+2.6%)

$538,000 + $628,600

$1,166,600

2009

$12,471

$538,000 + $628,600

$1,166,600

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

Public record

Public record
Permits

Beds

Baths

Stories

Lot width

—

Lot depth

—

Lot size

8,712 Sq. Ft.

Year renovated

1972

Sq. Ft.

2,820

Year built

1940

Style

Single Family Residential

County

Norfolk County

APN

36648

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jul 21, 2023.

Property details

Parking

Parking Information
Has Garage
Has Open Parking
# of Garage Spaces: 1
# of Covered Spaces: 1
Parking Features: Paved Drive, Off Street

Interior

Master Bedroom Information
Level: Second

Bedroom #2 Information
Level: Second

Bedroom #3 Information
Level: Second

Bathroom Information
# of Bathrooms (Full): 3
Master Bathroom Features: Yes

Bathroom #1 Information
Level: First

Bathroom #2 Information
Level: Second

Living Room Information
Level: First

Family Room Information
Level: First

Dining Room Information
Level: First

Kitchen Information
Level: First

Basement Information
Basement: Full, Walk-Out Access

Fireplace Information
Has Fireplace
# of Fireplaces (Total): 1

Interior Features
# of Rooms (Total): 9

Exterior

Building Information
Foundation Details: Concrete Perimeter

Exterior Features
Fencing: Fenced
Roof: Shingle
Patio And Porch Features: Deck
Exterior Features: Deck, Professional Landscaping, Fenced Yard

Property Information
Security Features: Security System

Lot Information
Lot Size (Acres): 0.19

Financial

Tax Information
Tax Annual Amount: $6,540

Utilities

Utility Information
Sewer: Public Sewer, City/Town Sewer
Water Source: Public, City/Town Water

Heating & Cooling
Has Heating
Heating: Steam, Oil

Location

Location Information
Directions: GARDNER ROAD
UnparsedAddress: 21 Winthrop Road, Brookline MA

Community Information
Senior CommunityYN: No

Public facts

Beds: 4
Baths: 4.0
Sq. Ft.: 2,820
Stories: 2.0
Lot Size: 8,712 square feet
Style: Single Family Residential
Year Built: 1940
Year Renovated: 1972
County: Norfolk County
APN: 36648

Home facts updated by county records on Jul 20, 2023

Other

Miscellaneous Information
Heat Zones: 1

Listing Information
Exclusions: Basement Refrigeratr
StandardStatus: Closed

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...
3 weeks ago • Brookline
Benjamin Ginsburg
Redfin Premier agent
155 deals
Was this helpful?

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 • undefined

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

$2.80M – $3.39M

Reach more buyers when you sell with Redfin. Save up to $29,487 in fees. 3 minutes to get started.

Need the cash from your home fast? Sell to .

Nearby similar homes

FOR SALE BY OWNER

$479,800

2 beds1 bath814 sq ft

14 Melvin Ave, Boston, MA 02135

OPEN SAT, 12PM TO 1:30PM3D WALKTHROUGH

$4,250,000

3 beds3.5 baths3,467 sq ft

322 Tappan St #2, Brookline, MA 02445

$2,950,000

4 beds2.5 baths2,000 sq ft

7 Stetson St, Brookline, MA 02446

$1,700,000

5 beds3.5 baths2,460 sq ft

184 Rawson Rd, Brookline, MA 02445

$2,799,999

4 beds4 baths2,763 sq ft

21 Kent Sq #2, Brookline, MA 02446

$1,295,000

3 beds2 baths1,748 sq ft

428 Boylston St, Brookline, MA 02445

New listings for sale in 02445

$495,000

1 bed1 bath655 sq ft

44 Washington St #303, Brookline, MA 02445

EARLY ACCESSCOMPASS COMING SOON

$4,250,000

5 beds4 baths6,313 sq ft

120 Rawson Rd, Brookline, MA 02445

EARLY ACCESSCOLDWELL BANKER REALTY COMING SOON

$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

Home values near 21 Winthrop Rd

Data from public records.

Address	Redfin Estimate
20 Winthrop Rd, Brookline, MA 4 Beds \| 2.5 Baths \| 2489 Sq. Ft.	$2,470,374
15 Winthrop Rd, Brookline, MA 4 Beds \| 4 Baths \| 3233 Sq. Ft.	$3,176,350

Address	Redfin Estimate
16 Winthrop Rd, Brookline, MA 3 Beds \| 2.5 Baths \| 2141 Sq. Ft.	$2,304,093
31 Winthrop Rd, Brookline, MA 4 Beds \| 3 Baths \| 3085 Sq. Ft.	$2,165,808

Address	Redfin Estimate
25 Winthrop Rd, Brookline, MA 8 Beds \| 7.5 Baths \| 6162 Sq. Ft.	—
29 Winthrop Rd, Brookline, MA 2 Beds \| 2.5 Baths \| 2145 Sq. Ft.	$2,042,931

Property information provided by MLS PIN when last listed in 1997. This data may not match . Learn more.

Download the Redfin App on the Apple App Store

Download the Redfin App from the Google Play Store

Join us

Become an Agent

Get referrals

Careers

Find homes faster

About us

Find us

Subsidiaries

Affiliated Business

Countries

United States

Canada

Updated September 2025: By searching, you agree to the Terms of Use, and Privacy Policy.

Do not sell or share my personal information.

REDFIN and all REDFIN variants, WALK SCORE, and the R logos, are trademarks of Redfin Corporation, registered or pending in the USPTO.

California DRE #01521930

Redfin is licensed to do business in New York as Redfin Real Estate. NY Standard Operating Procedures

New Mexico Real Estate Licenses

TREC: Info About Brokerage Services, Consumer Protection Notice

All mortgage lending products and information are provided by Rocket Mortgage, LLC | NMLS #3030; www.NMLSConsumerAccess.org. Licensed in 50 states. This site is not authorized by the New York State Department of Financial Services for mortgage solicitation or loan applications activities related to properties located in the State of New York.

Redfin Corporation is an affiliated business of Rocket Limited Partnership. Each company, and their subsidiaries, are separate legal entities operated and managed through its own management and governance structures.

If you are using a screen reader, or having trouble reading this website, please call Redfin Customer Support for help at 1-844-759-7732.

REDFIN IS COMMITTED TO AND ABIDES BY THE FAIR HOUSING ACT AND EQUAL OPPORTUNITY ACT. READ REDFIN'S FAIR HOUSING POLICY AND THE NEW YORK STATE FAIR HOUSING NOTICE.

GreatSchools Ratings provided by GreatSchools.org.

02130 homes for sale
02131 homes for sale
02446 homes for sale
02132 homes for sale
02135 homes for sale

Houses for rent in Brookline	Agents near me	Quincy, MA homes for sale	Brookline Housing Market
Houses for sale near me	Boston, MA homes for sale	Brookline, MA homes for sale
Land for sale near me	Newton, MA homes for sale	Arlington, MA homes for sale
Open Houses near me	Cambridge, MA homes for sale	Brookline Property Records
Condos for sale near me	Lexington, MA homes for sale	MA New Listings

Aspinwall Hill homes for sale
Washington Square homes for sale

Cambridge homes for sale
Boston homes for sale
Newton homes for sale

About this home

Redfin Estimate

Earn from this home

Market trends in 02445, MA

Sale history for 21 Winthrop Rd

Tax history for 21 Winthrop Rd

Public record

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 21 Winthrop Rd

More real estate resources