OFF MARKET

Off Market Dec 1999 for $430K

$1,685,580

Est. refi paymentEst. refi $2,820/mo

•

3 ba

•

2,269

sq ft

27 High St, Brookline, MA 02445

About this home

27 High St is a 2,269 square foot multi-family home on a 5,227 square foot lot with 4 bedrooms and 3 bathrooms. - it last sold on December 23, 1999 for $430,000. Based on Redfin's Brookline data, we estimate the home's value is $1,685,580.

Multi-familyProperty Type

1926Year Built

5,227 sq ftLot Size

$743Est. Price/Sq.Ft.

Source:Public Records

Redfin Estimate

$1,685,580

$1.3M since sold in December 1999$37K since August

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 30.4% lower than the average sale price ($2.42M) of 6 comparable homes.

SOLD APR 16, 2026
$2,150,000
A
4 beds3.5 baths2,332 sq ft
209 High St, Brookline, MA 02445
SOLD JAN 15, 2026
$2,050,500
B
6 beds3.5 baths2,104 sq ft
9 Greenough St, Brookline, MA 02445
SOLD DEC 17, 2025
$2,385,000
C
4 beds3 baths2,286 sq ft
21 Hancock Rd, Brookline, MA 02445
SOLD APR 8, 2026
$2,850,000
D
4 beds2.5 baths3,377 sq ft
24 Blake Rd, Brookline, MA 02445
SOLD JUN 30, 2026
$3,350,000
E
4 beds2.5 baths2,676 sq ft
43 Waverly St, Brookline, MA 02445
SOLD JUN 23, 2026
$1,750,000
F
3 beds1.5 baths1,380 sq ft
14A Linden Pl, Brookline, MA 02445

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Earn from this home

Sell

$1,540,043

Est. take-home

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Refinance

Est. cash available

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Market trends in 02445, MA

Last updated August 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-List Price

98.9%

0.9% MoM

Median sale price

$911K

$254K MoM

Avg. days on market

41d

6 days MoM

Recently sold homes

2 MoM

New listings for sale

OPEN SUN, 12PM TO 1:30PM
$1,175,000
2 beds2 baths1,240 sq ft
18 Chestnut Pl #18, Brookline, MA 02445
OPEN SUN, 12PM TO 1:30PM
$1,175,000
2 beds2 baths1,240 sq ft
18 Chestnut Pl, Brookline, MA 02445
OPEN TODAY, 11:30AM TO 12:30PM
$1,199,000
4 beds2 baths1,825 sq ft
17 High St #2, Brookline, MA 02445
OPEN TODAY, 12PM TO 1:30PM
$1,250,000
3 beds2 baths1,288 sq ft
11 Claflin Rd #2, Brookline, MA 02445
OPEN TODAY, 11AM TO 12:30PM
$1,750,000
5 beds3.5 baths2,460 sq ft
1.8.4 Rawson Rd Unit 1.8.4, Brookline, MA 02445
OPEN TODAY, 12PM TO 1PM
$755,000
2 beds1 bath1,003 sq ft
222 Washington St #3, Brookline, MA 02445
OPEN TODAY, 12:30PM TO 2PM
$2,200,000
4 beds2.5 baths2,794 sq ft
17 Davis Ave #1, Brookline, MA 02445
OPEN TODAY, 2PM TO 3:30PM
$2,650,000
5 beds4 baths2,986 sq ft
249 Clinton Rd, Brookline, MA 02445
OPEN TODAY, 12:30PM TO 1:30PM
$749,000
2 beds1 bath903 sq ft
1731 Beacon St #713, Brookline, MA 02445
$2,250,000
4 beds3 baths4,102 sq ft
205 Gardner Rd, Brookline, MA 02445
See all

Provided by Redfin

Sale history for 27 High St

Year

Property tax

Land + Additions

Assessment*

2023

$16,291 (+2.7%)

$819,600 + $814,400

$1,634,000

2022

$15,857 (+8.1%)

$780,500 + $775,600

$1,556,100

2021

$14,664 (+6.7%)

$750,500 + $745,800

$1,496,300

2020

$13,748 (+5.9%)

$682,300 + $772,500

$1,454,800

2019

$12,982 (+7.7%)

$649,800 + $735,700

$1,385,500

2018

$12,051 (+2.8%)

$565,300 + $708,600

$1,273,900

2017

$11,718 (+4.3%)

$533,300 + $652,700

$1,186,000

2016

$11,235 (+7.3%)

$498,400 + $579,800

$1,078,200

2015

$10,469 (+1.9%)

$465,800 + $514,400

$980,200

2014

$10,272 (+2.7%)

$423,400 + $478,400

$901,800

2013

$10,006 (+2.2%)

$411,100 + $447,800

$858,900

2012

$9,791 (+0.8%)

$411,100 + $447,800

$858,900

2011

$9,710 (+3.0%)

$411,300 + $448,000

$859,300

2010

$9,427 (+2.6%)

$411,300 + $448,000

$859,300

2009

$9,189

$411,600 + $448,000

$859,600

Tax history for 27 High St

Year

Property tax

Land + Additions

Assessment*

2023

$16,291 (+2.7%)

$819,600 + $814,400

$1,634,000

2022

$15,857 (+8.1%)

$780,500 + $775,600

$1,556,100

2021

$14,664 (+6.7%)

$750,500 + $745,800

$1,496,300

2020

$13,748 (+5.9%)

$682,300 + $772,500

$1,454,800

2019

$12,982 (+7.7%)

$649,800 + $735,700

$1,385,500

2018

$12,051 (+2.8%)

$565,300 + $708,600

$1,273,900

2017

$11,718 (+4.3%)

$533,300 + $652,700

$1,186,000

2016

$11,235 (+7.3%)

$498,400 + $579,800

$1,078,200

2015

$10,469 (+1.9%)

$465,800 + $514,400

$980,200

2014

$10,272 (+2.7%)

$423,400 + $478,400

$901,800

2013

$10,006 (+2.2%)

$411,100 + $447,800

$858,900

2012

$9,791 (+0.8%)

$411,100 + $447,800

$858,900

2011

$9,710 (+3.0%)

$411,300 + $448,000

$859,300

2010

$9,427 (+2.6%)

$411,300 + $448,000

$859,300

2009

$9,189

$411,600 + $448,000

$859,600

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

Property details

Interior

Basement Information
Basement Sq. Ft: 1,118
Basement Type: Full

Bathroom Information
# of Full Baths: 3

Heating & Cooling
Heating Type: Forced Hot Water

Room Information
# of Rooms: 11

Exterior

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

Property Information
Subdivision Name: TAUNTON ST
Living Sq. Ft: 2,269
Gross Sq. Ft: 3,732
# of Units: 2
# of Stories: 2

Lot Information
# of Buildings: 1
Land Sq. Ft: 5,227
Municipality Name: BROOKLINE
Acres: 0.12
Zoning Code: T-5
State Use Description: 2-FAMILY RESIDENCE

Financial

Assessor Information
Assessment Year: 2023

Public facts

Beds: 4
Baths: 3.0
Sq. Ft.: 2,269
Stories: 2.0
Lot Size: 5,227 square feet
Style: Multi-Family (2-4 Unit)
Year Built: 1926
Year Renovated: 1980
County: Norfolk County
APN: 40882

Home facts updated by county records on Jul 20, 2023

Around this home

Schools

Pierce School

Public K-8 • Assigned • 0.3mi

10/10

Brookline High School

Public 9-12 • Assigned • 0.6mi

8/10

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

Climate risks

1/10 Flood Factor

Minimal risk of a flood reaching the building in the next 30 years

3/10 Fire Factor

0.15% chance of being 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

60% 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 hours in June and 4.4 hours in December, placing it below the U.S. average for solar exposure.

9 hrs

4.4 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$1.60M – $1.94M

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New listings for sale in 02445

OPEN SUN, 12PM TO 1:30PM

$1,175,000

2 beds2 baths1,240 sq ft

18 Chestnut Pl #18, Brookline, MA 02445

OPEN SUN, 12PM TO 1:30PM

$1,175,000

2 beds2 baths1,240 sq ft

18 Chestnut Pl, Brookline, MA 02445

OPEN TODAY, 11:30AM TO 12:30PM3D WALKTHROUGH

$1,199,000

4 beds2 baths1,825 sq ft

17 High St #2, Brookline, MA 02445

OPEN TODAY, 12PM TO 1:30PMHOT HOME

$1,250,000

3 beds2 baths1,288 sq ft

11 Claflin Rd #2, Brookline, MA 02445

OPEN TODAY, 11AM TO 12:30PM

$1,750,000

5 beds3.5 baths2,460 sq ft

1.8.4 Rawson Rd Unit 1.8.4, Brookline, MA 02445

OPEN TODAY, 12PM TO 1PM

$755,000

2 beds1 bath1,003 sq ft

222 Washington St #3, Brookline, MA 02445

OPEN TODAY, 12:30PM TO 2PM

$2,200,000

4 beds2.5 baths2,794 sq ft

17 Davis Ave #1, Brookline, MA 02445

OPEN TODAY, 2PM TO 3:30PM

$2,650,000

5 beds4 baths2,986 sq ft

249 Clinton Rd, Brookline, MA 02445

OPEN TODAY, 12:30PM TO 1:30PM

$749,000

2 beds1 bath903 sq ft

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Home values near 27 High St

Data from public records.

Address	Redfin Estimate
31 High Street, Brookline, MA 7 Beds \| 3 Baths \| 3297 Sq. Ft.	$1,830,156
21 High Street, Brookline, MA 3 Beds \| 3 Baths \| 2516 Sq. Ft.	$1,399,396

Address	Redfin Estimate
21 High Street #1, Brookline, MA 2 Beds \| 2 Baths \| 1357 Sq. Ft.	$900,191
31 High Street #1, Brookline, MA 3 Beds \| 3.5 Baths \| 2500 Sq. Ft.	$2,386,041

Address	Redfin Estimate
21 High Street #2, Brookline, MA 3 Beds \| 2 Baths \| 1499 Sq. Ft.	$1,082,915
82 Walnut Street #1, Brookline, MA 2 Beds \| 1 Baths \| 970 Sq. Ft.	$708,149

Property information provided by undefined .

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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 27 High St

Tax history for 27 High St

Property details

Around this home

Schools

Lifestyle

Climate risks

Historical weather

Sun exposure

Nearby similar homes

New listings for sale in 02445

Home values near 27 High St

More real estate resources