Google street view image for 105 Winthrop Rd, Brookline, MA 02445

Off Market Jun 2014 for $1.8M

$2,589,247

Est. refi paymentEst. refi $19,442/mo

•

5.5 ba

•

7,962

sq ft

105 Winthrop Rd, Brookline, MA 02445

About this home

105 Winthrop Rd is a 7,962 square foot multi-family home on a 3,760 square foot lot with 9 bedrooms and 5.5 bathrooms. - it last sold on June 04, 2014 for $1,825,000. Based on Redfin's Brookline data, we estimate the home's value is $2,589,247.

Multi-familyProperty Type

1925Year Built

3,760 sq ftLot Size

$325Est. Price/Sq.Ft.

Source:Public Records

Redfin Estimate

$2,589,247

$764K since sold in June 2014$327K since July

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 21.5% lower than the average sale price ($3.30M) of 6 comparable homes.

SOLD APR 27, 2026
$4,100,000
A
6 beds4.5 baths5,058 sq ft
282 Buckminster Rd, Brookline, MA 02445
SOLD AUG 10, 2026
$2,075,000
B
12 beds5.5 baths3,810 sq ft
19 Claymoss Rd, Brighton, MA 02135
SOLD JAN 13, 2026
$1,800,000
C
9 beds4 baths3,102 sq ft
589-591 Washington St, Brookline, MA 02446
SOLD JUL 15, 2026
$2,625,000
D
6 beds5 baths4,860 sq ft
39 Greycliff Rd, Brighton, MA 02135
SOLD AUG 17, 2026
$5,000,000
E
5 beds6 baths5,198 sq ft
18 Naples Rd, Brookline, MA 02446
SOLD JUN 5, 2026
$4,200,000
F
6 beds6.5 baths6,000 sq ft
36 Naples Rd, Brookline, MA 02446

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Earn from this home

Sell

$1,399,924

Est. take-home

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Refinance

Est. cash available

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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 FRI, 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 105 Winthrop Rd

Year

Property tax

Land + Additions

Assessment*

2016

$17,968 (+10.3%)

$495,700 + $1,228,700

$1,724,400

2015

$16,291 (−1.4%)

$421,100 + $1,104,300

$1,525,400

2014

$16,522 (+2.7%)

$382,900 + $1,067,700

$1,450,600

2013

$16,094 (+2.2%)

$371,700 + $1,009,800

$1,381,500

2012

$15,749 (+3.4%)

$371,700 + $1,009,800

$1,381,500

2011

$15,232 (+3.0%)

$371,700 + $976,300

$1,348,000

2010

$14,788 (+2.6%)

$371,700 + $976,300

$1,348,000

2009

$14,410

$371,700 + $976,300

$1,348,000

Tax history for 105 Winthrop Rd

Year

Property tax

Land + Additions

Assessment*

2016

$17,968 (+10.3%)

$495,700 + $1,228,700

$1,724,400

2015

$16,291 (−1.4%)

$421,100 + $1,104,300

$1,525,400

2014

$16,522 (+2.7%)

$382,900 + $1,067,700

$1,450,600

2013

$16,094 (+2.2%)

$371,700 + $1,009,800

$1,381,500

2012

$15,749 (+3.4%)

$371,700 + $1,009,800

$1,381,500

2011

$15,232 (+3.0%)

$371,700 + $976,300

$1,348,000

2010

$14,788 (+2.6%)

$371,700 + $976,300

$1,348,000

2009

$14,410

$371,700 + $976,300

$1,348,000

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

Permits

Aug 10, 2015 • Active

Certificate of occupancy

Renovate an existing three-family home according to plans. Install a roof deck and a sprinkler system, and perform work on an unfinished basement.

Fire sprinkler

Remodel

Aug 4, 2015 • Active

Residential electrical

Install a new fire notification system.

Electrical

Fire sprinkler

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

Parking

Parking / Garage Information
Primary Garage Type: Basement
Parking Type: Garage
Garage Type: Basement

Interior

Unit Information
# of Units: 3

Room Information
# of Rooms: 18

Heating Information
Heating Fuel Type: Gas
Heat Type: Steam

Basement Information
Unfinished Basement Sq. Ft.: 1,878

Bathroom Information
# of Baths (Total): 6
# of Half Baths: 1
# of Full Baths: 5

Bedroom Information
# of Bedrooms: 9

Exterior

Exterior Information
Roof Type: Gravel
Structural Style: Row End or Row Middle
Property Condition: Average
Framework Structure Material: Wood Frame
Exterior Material: Brick

Lot Information
Lot Size (Sq. Ft.): 3,760

Property Information
Property Legal Description: MAPNUM:000000 WARDNUM:00 BLOCKNUM:000217 LOTNUM:000044 UNITNUM:00000
Total number of Stories: 3
Total Sq. Ft. of All Structures: 6,084
Total Sq. Ft. of All Structures Description: Living Area
Total Finished Sq. Ft. of All Buildings on Property: 6,084
Total Assessor Sq. Ft. of Buildings: 7,962
Permitted Remodel Year: 1992
# of Structures on Property: 1

Financial

Assessor Information
Year of Last Land Appraisal: 2016

Public facts

Beds: 9
Baths: 5.5
Sq. Ft.: 7,962
Stories: 3.0
Lot Size: 3,760 square feet
Style: Multi-Family (2-4 Unit)
Year Built: 1925
Year Renovated: 1992
County: Norfolk County
APN: B217L0044S0001

Home facts updated by county records on Oct 17, 2018

Around this home

Schools

Pierce School

Public K-8 • Assigned • 0.6mi

10/10

Brookline High School

Public 9-12 • Assigned • 0.4mi

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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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

$2.46M – $2.98M

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1002 Beacon St, Brookline, MA 02446

New listings for sale in 02445

OPEN SUN, 12PM TO 1:30PM

$998,000

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OPEN SAT, 11AM TO 12:30PM

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124 Chestnut St #1, Brookline, MA 02445

OPEN FRI, 12:30PM TO 2PM

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OPEN SAT, 12PM TO 2PM

$2,200,000

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26 Parkway Rd, Brookline, MA 02445

OPEN SUN, 11AM TO 12PM

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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 105 Winthrop Rd

Data from public records.

Address	Redfin Estimate
111 Winthrop Rd, Brookline, MA 14 Beds \| 12 Baths \| 4608 Sq. Ft.	—
101 Winthrop Rd Apartment 3, Brookline, MA 3 Beds \| 2 Baths \| 1668 Sq. Ft.	$1,493,282

Address	Redfin Estimate
107 Winthrop Rd, Brookline, MA 10 Beds \| 7.5 Baths \| 5998 Sq. Ft.	—
97A Winthrop Rd Apartment 97A, Brookline, MA 3 Beds \| 2 Baths \| 1049 Sq. Ft.	$1,238,928

Address	Redfin Estimate
101 Winthrop Rd Apartment 2, Brookline, MA 3 Beds \| 2 Baths \| 1668 Sq. Ft.	$1,405,885
97 Winthrop Rd, Brookline, MA 6 Beds \| 4 Baths \| 3162 Sq. Ft.	$2,227,890

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About this home

Redfin Estimate

Earn from this home

Market trends in 02445, MA

Sale history for 105 Winthrop Rd

Tax history for 105 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 105 Winthrop Rd

More real estate resources