Google street view image for 27 High St, Brookline, MA 02445

Off market dec 1999 for $430K

$1,745,491

Est. refi paymentEst. refi $2,791/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 $1,745,491.

Multi-familyProperty Type

1926Year Built

5,227 sq ftLot Size

$769Est. Price/Sq.Ft.

Source:Public Records

Redfin Estimate

$1,745,491

$1.3M since sold in December 1999$120K since October

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 27.9% 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

$1,599,984

Est. take-home

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Est. cash available

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Market trends in 02445, MA

Last updated October 2026

Buyer's Market

Seller's Market

Balanced 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

$1,600,000
4 beds2 baths2,254 sq ft
146-A University Rd #146, Brookline, MA 02445
$399,999
1 bed1 bath490 sq ft
15-17 University Rd Unit 22A, Brookline, MA 02445
$7,900,000
6 beds10.5 baths9,600 sq ft
125 Rockwood St, Brookline, MA 02445
$649,000
2 beds1 bath907 sq ft
9 High Street Pl #3, Brookline, MA 02445
3D WALKTHROUGH
$685,000
2 beds1 bath970 sq ft
8 Homer #4, Brookline, MA 02445
VIDEO TOUR
$599,000
1 bed1 bath869 sq ft
1742 Beacon St #2, Brookline, MA 02445
$1,379,000
3 beds2 baths1,340 sq ft
622 Chestnut Hill Ave, Brookline, MA 02445
$798,800
2 beds2 baths1,099 sq ft
22 Chestnut Pl #114, Brookline, MA 02445
$1,199,000
2 beds2 baths1,220 sq ft
89 Glen Rd #5, Brookline, MA 02445
$2,195,000
3 beds3.5 baths3,525 sq ft
301 Goddard Ave #301, 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

K - 12
Preschool & daycare

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

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
155 deals
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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

$1.66M – $2.01M

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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.	$1,877,093
21 High Street, Brookline, MA 3 Beds \| 3 Baths \| 2516 Sq. Ft.	$1,513,958
82 Walnut Street #2, Brookline, MA 2 Beds \| 1 Baths \| 970 Sq. Ft.	$738,303
72 Walnut Street #3, Brookline, MA 3 Beds \| 1.5 Baths \| 1700 Sq. Ft.	$1,085,379
82 Walnut Street #3,82, Brookline, MA 2 Beds \| 1 Baths \| 970 Sq. Ft.	$732,043

Address	Redfin Estimate
21 High Street #1, Brookline, MA 2 Beds \| 2 Baths \| 1357 Sq. Ft.	$920,521
31 High Street #1, Brookline, MA 3 Beds \| 3.5 Baths \| 2500 Sq. Ft.	$2,674,789
82 Walnut Street #3, Brookline, MA 2 Beds \| 1 Baths \| 970 Sq. Ft.	$744,796
7 Acron Road, Brookline, MA 7 Beds \| 4.5 Baths \| 2697 Sq. Ft.	$2,683,166
82 Walnut Street #2,82, Brookline, MA 2 Beds \| 1 Baths \| 970 Sq. Ft.	$724,479

Address	Redfin Estimate
21 High Street #2, Brookline, MA 3 Beds \| 2 Baths \| 1499 Sq. Ft.	$1,083,142
82 Walnut Street #1, Brookline, MA 2 Beds \| 1 Baths \| 970 Sq. Ft.	$714,779
72 Walnut Street #1, Brookline, MA 3 Beds \| 2.5 Baths \| 1600 Sq. Ft.	$1,346,053
9 Acron Road, Brookline, MA 4 Beds \| 2 Baths \| 2016 Sq. Ft.	$1,585,663

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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

Local insights from Redfin agents

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