Google street view image for 27 Winslow Rd, Brookline, MA 02446

Off Market Feb 1979 for $44K

$2,446,916

Est. refi paymentEst. refi $280/mo

•

3.5 ba

•

3,632

sq ft

27 Winslow Rd, Brookline, MA 02446

About this home

27 Winslow Rd is a 3,632 square foot house on a 7,405 square foot lot with 7 bedrooms and 3.5 bathrooms. - it last sold on February 01, 1979 for $44,000. Based on Redfin's Brookline data, we estimate the home's value is $2,446,916.

Single-familyProperty Type

1905Year Built

7,405 sq ftLot Size

$674Est. Price/Sq.Ft.

Source:Public Records

Redfin Estimate

$2,446,916

$2.4M since sold in February 1979$52K since August

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 16.2% lower than the average sale price ($2.92M) of 6 comparable homes.

SOLD JUL 31, 2026
$2,375,000
A
5 beds3.5 baths3,195 sq ft
121 Thorndike St, Brookline, MA 02446
SOLD JUL 2, 2026
$2,525,000
B
6 beds3 baths4,605 sq ft
62 Fuller St, 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 DEC 29, 2025
$2,621,500
D
8 beds4.5 baths4,720 sq ft
11 Abbottsford Rd, Brookline, MA 02446
SOLD JUN 26, 2026
$2,952,000
E
6 beds3.5 baths3,052 sq ft
302 Brookline St, Cambridge, MA 02139
SOLD DEC 9, 2025
$3,000,000
F
5 beds4.5 baths2,997 sq ft
6 Elba St, Brookline, MA 02446

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Earn from this home

Sell

$2,324,647

Est. take-home

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Est. cash available

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Rent

$7,779/mo

Redfin rental estimate

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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 27 Winslow Rd

Year

Property tax

Land + Additions

Assessment*

2023

$20,836 (+2.7%)

$1,185,800 + $904,100

$2,089,900

2022

$20,280 (+8.1%)

$1,129,200 + $861,000

$1,990,200

2021

$18,754 (+10.1%)

$1,085,800 + $827,900

$1,913,700

2020

$17,033 (+5.9%)

$987,100 + $815,300

$1,802,400

2019

$16,085 (+10.0%)

$940,100 + $776,500

$1,716,600

2018

$14,624 (+2.1%)

$783,500 + $762,400

$1,545,900

2017

$14,319 (+1.5%)

$739,100 + $710,200

$1,449,300

2016

$14,114 (+4.4%)

$690,800 + $663,700

$1,354,500

2015

$13,520 (+5.7%)

$645,600 + $620,300

$1,265,900

2014

$12,792 (+0.7%)

$538,000 + $585,100

$1,123,100

2013

$12,703 (+2.2%)

$522,300 + $568,100

$1,090,400

2012

$12,431 (+2.1%)

$522,300 + $568,100

$1,090,400

2011

$12,172 (+3.0%)

$517,800 + $559,400

$1,077,200

2010

$11,817 (+2.6%)

$517,800 + $559,400

$1,077,200

2009

$11,516

$517,800 + $559,500

$1,077,300

Tax history for 27 Winslow Rd

Year

Property tax

Land + Additions

Assessment*

2023

$20,836 (+2.7%)

$1,185,800 + $904,100

$2,089,900

2022

$20,280 (+8.1%)

$1,129,200 + $861,000

$1,990,200

2021

$18,754 (+10.1%)

$1,085,800 + $827,900

$1,913,700

2020

$17,033 (+5.9%)

$987,100 + $815,300

$1,802,400

2019

$16,085 (+10.0%)

$940,100 + $776,500

$1,716,600

2018

$14,624 (+2.1%)

$783,500 + $762,400

$1,545,900

2017

$14,319 (+1.5%)

$739,100 + $710,200

$1,449,300

2016

$14,114 (+4.4%)

$690,800 + $663,700

$1,354,500

2015

$13,520 (+5.7%)

$645,600 + $620,300

$1,265,900

2014

$12,792 (+0.7%)

$538,000 + $585,100

$1,123,100

2013

$12,703 (+2.2%)

$522,300 + $568,100

$1,090,400

2012

$12,431 (+2.1%)

$522,300 + $568,100

$1,090,400

2011

$12,172 (+3.0%)

$517,800 + $559,400

$1,077,200

2010

$11,817 (+2.6%)

$517,800 + $559,400

$1,077,200

2009

$11,516

$517,800 + $559,500

$1,077,300

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

Permits

Jun 22, 2015 • Active

Residential gas

Work on gas piping.

Gas

Sep 21, 2011 • Active

Residential gas

Replace the gas water heater.

Gas

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: 1,392
Basement Type: Full

Bathroom Information
# of Full Baths: 3
# of 1/2 Baths: 1

Heating & Cooling
Heating Type: Forced Air

Fireplace Information
# of Fireplaces: 2
Fireplace Type: Wood Stove
Has Fireplace

Room Information
# of Rooms: 12

Exterior

Exterior Information
Physical Condition: Average
Building Style Type: Colonial
Construction Type: Frame
Exterior Wall: Wood Siding/Shingle
Roof Shape Type: Hip

Property Information
Living Sq. Ft: 3,632
Gross Sq. Ft: 5,904
# of Units: 1
# of Stories: 3

Lot Information
# of Buildings: 1
Land Sq. Ft: 7,405
Municipality Name: BROOKLINE
Acres: 0.17
Zoning Code: T-5
State Use Description: 1-FAMILY RESIDENCE

Financial

Assessor Information
Assessment Year: 2023

Public facts

Beds: 7
Baths: 3.5
Sq. Ft.: 3,632
Stories: 3.0
Lot Size: 7,405 square feet
Style: Single Family Residential
Year Built: 1905
Year Renovated: 1970
County: Norfolk County
APN: 30360

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 • 1.3mi

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
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

62% 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

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

$2.33M – $2.81M

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Home values near 27 Winslow Rd

Data from public records.

Address	Redfin Estimate
23 Winslow Rd, Brookline, MA 6 Beds \| 6 Baths \| 3568 Sq. Ft.	$2,920,805
31 Winslow Rd Apartment 4, Brookline, MA 2 Beds \| 1 Baths \| 785 Sq. Ft.	$629,347

Address	Redfin Estimate
31 Winslow Rd Apartment 2, Brookline, MA 2 Beds \| 1 Baths \| 785 Sq. Ft.	$692,166
31 Winslow Rd Apartment 5, Brookline, MA 2 Beds \| 1 Baths \| 670 Sq. Ft.	$695,276

Address	Redfin Estimate
31 Winslow Rd Apartment 3, Brookline, MA 2 Beds \| 1 Baths \| 670 Sq. Ft.	$615,220
31 Winslow Rd Apartment 6, Brookline, MA 2 Beds \| 1 Baths \| 785 Sq. Ft.	$692,272

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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 27 Winslow Rd

Tax history for 27 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 27 Winslow Rd

More real estate resources