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

Off market may 1991 for $630K

$2,937,901

Est. refi paymentEst. refi $4,250/mo

•

3 ba

•

3,972

sq ft

27 Chestnut St, Brookline, MA 02445

About this home

27 Chestnut St is a 3,972 square foot house on a 0.57 acre lot with 6 bedrooms and 3 bathrooms. - it last sold on May 16, 1991 for $630,000. Based on Redfin's Brookline data, we estimate the home's value is $2,937,901.

Single-familyProperty Type

1845Year Built

0.57 acresLot Size

$740Est. Price/Sq.Ft.

Source:Public Records

Redfin Estimate

$2,937,901

$2.3M since sold in May 1991$130K since September

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 26.6% higher than the average sale price ($2.32M) of 6 comparable homes.

SOLD JUL 24, 2026
$2,325,000
A
7 beds4 baths4,544 sq ft
54 Clark Rd, Brookline, MA 02445
SOLD SEP 24, 2026
$2,500,000
B
6 beds3.5 baths5,748 sq ft
2 Mason Ter, Brookline, MA 02446
SOLD AUG 21, 2026
$1,850,000
C
5 beds2.5 baths3,592 sq ft
117 Sheridan St, Jamaica Plain, MA 02130
SOLD JUL 2, 2026
$2,425,000
D
5 beds3 baths3,563 sq ft
30 Billings Ln, Jamaica Plain, MA 02130
SOLD OCT 15, 2025
$2,300,000
E
5 beds3.5 baths3,873 sq ft
14 Irving St, Brookline, MA 02445
SOLD JUL 2, 2026
$2,525,000
F
6 beds3 baths4,605 sq ft
62 Fuller St, Brookline, MA 02446

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Earn from this home

Sell

$2,791,299

Est. take-home

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Refinance

Est. cash available

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Rent

$7,635/mo

Redfin rental estimate

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Market trends in 02445, MA

Last updated September 2026

Buyer's Market

Seller's Market

Balanced 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

NEW 24 HRS AGO
$2,399,900
6 beds4 baths3,454 sq ft
101-103 University Rd, Brookline, MA 02445
OPEN TODAY, 11AM TO 12:30PM
$1,195,000
3 beds2 baths1,269 sq ft
114 Franklin St #2, Brookline, MA 02445
OPEN TODAY, 11AM TO 1PM
$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, 12PM TO 1:30PM
$3,500,000
6 beds5.5 baths4,891 sq ft
115 Dean Rd, Brookline, MA 02445
OPEN TODAY, 2PM TO 3:30PM
$1,500,000
3 beds2.5 baths1,741 sq ft
31 Loveland Rd, Brookline, MA 02445
EARLY ACCESS
$2,350,000
6 beds3 baths3,568 sq ft
309 Buckminster Rd, Brookline, MA 02445
OPEN TODAY, 12PM TO 1:30PM
$799,000
3 beds1.5 baths1,265 sq ft
120 Franklin St #3, Brookline, MA 02445
$675,000
2 beds2 baths1,025 sq ft
44 Washington #502, Brookline, MA 02445
EARLY ACCESS
Unknown
7 beds8 baths8,540 sq ft
Brookline, MA 02445
See all

Provided by Redfin

Sale history for 27 Chestnut St

Year

Property tax

Land + Additions

Assessment*

2023

$25,699 (+2.7%)

$1,181,300 + $1,396,300

$2,577,600

2022

$25,015 (+8.1%)

$1,125,100 + $1,329,800

$2,454,900

2021

$23,133 (+9.1%)

$1,081,800 + $1,278,700

$2,360,500

2020

$21,211 (+5.9%)

$983,400 + $1,261,200

$2,244,600

2019

$20,030 (−1.2%)

$936,600 + $1,201,100

$2,137,700

2018

$20,271 (+1.5%)

$956,200 + $1,186,600

$2,142,800

2017

$19,972 (+1.4%)

$902,100 + $1,119,400

$2,021,500

2016

$19,687 (+4.4%)

$843,100 + $1,046,200

$1,889,300

2015

$18,858 (−1.0%)

$787,900 + $977,800

$1,765,700

2014

$19,042 (+0.7%)

$716,200 + $955,600

$1,671,800

2013

$18,909 (+2.2%)

$695,300 + $927,800

$1,623,100

2012

$18,503 (+4.5%)

$695,300 + $927,800

$1,623,100

2011

$17,699 (+3.0%)

$662,600 + $903,700

$1,566,300

2010

$17,182 (+2.8%)

$662,600 + $903,700

$1,566,300

2009

$16,708

$659,300 + $903,700

$1,563,000

Tax history for 27 Chestnut St

Year

Property tax

Land + Additions

Assessment*

2023

$25,699 (+2.7%)

$1,181,300 + $1,396,300

$2,577,600

2022

$25,015 (+8.1%)

$1,125,100 + $1,329,800

$2,454,900

2021

$23,133 (+9.1%)

$1,081,800 + $1,278,700

$2,360,500

2020

$21,211 (+5.9%)

$983,400 + $1,261,200

$2,244,600

2019

$20,030 (−1.2%)

$936,600 + $1,201,100

$2,137,700

2018

$20,271 (+1.5%)

$956,200 + $1,186,600

$2,142,800

2017

$19,972 (+1.4%)

$902,100 + $1,119,400

$2,021,500

2016

$19,687 (+4.4%)

$843,100 + $1,046,200

$1,889,300

2015

$18,858 (−1.0%)

$787,900 + $977,800

$1,765,700

2014

$19,042 (+0.7%)

$716,200 + $955,600

$1,671,800

2013

$18,909 (+2.2%)

$695,300 + $927,800

$1,623,100

2012

$18,503 (+4.5%)

$695,300 + $927,800

$1,623,100

2011

$17,699 (+3.0%)

$662,600 + $903,700

$1,566,300

2010

$17,182 (+2.8%)

$662,600 + $903,700

$1,566,300

2009

$16,708

$659,300 + $903,700

$1,563,000

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

Permits

May 17, 2018 • Active

Residential building

Remove and replace an existing fence.

Remodel

Sep 23, 2016 • Active

Residential mechanical - sheet metal

Replace two gas furnaces in the basement of a residential building.

Gas

HVAC

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: 1,556
Basement Type: Full

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

Heating & Cooling
Heating Type: Forced Air

Fireplace Information
# of Fireplaces: 4
Fireplace Type: Wood Stove
Has Fireplace

Room Information
# of Rooms: 12

Exterior

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

Property Information
Living Sq. Ft: 3,972
Gross Sq. Ft: 6,838
# of Units: 1
# of Stories: 3

Lot Information
# of Buildings: 1
Land Sq. Ft: 24,829
Municipality Name: BROOKLINE
Acres: 0.57
Zoning Code: S25
State Use Description: 1-FAMILY RESIDENCE

Financial

Assessor Information
Assessment Year: 2023

Public facts

Beds: 6
Baths: 3.0
Sq. Ft.: 3,972
Stories: 3.0
Lot Size: 0.57 acres
Style: Single Family Residential
Year Built: 1845
Year Renovated: 1974
County: Norfolk County
APN: 41223

Home facts updated by county records on Jul 20, 2023

Around this home

Schools

William H Lincoln School

Public K-8 • Assigned • 0.2mi

9/10

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 weeks 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

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 • 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

$2.79M – $3.38M

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EARLY ACCESSCOLDWELL BANKER REALTY COMING SOON

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Home values near 27 Chestnut St

Data from public records.

Address	Redfin Estimate
46 Chestnut Street, Brookline, MA 5 Beds \| 2 Baths \| 3142 Sq. Ft.	$1,332,365
26 Chestnut Street, Brookline, MA 7 Beds \| 3.5 Baths \| 5130 Sq. Ft.	$3,176,382

Address	Redfin Estimate
40 Chestnut Street, Brookline, MA 3 Beds \| 1.5 Baths \| 1272 Sq. Ft.	$1,417,578
20 Chestnut Street, Brookline, MA 5 Beds \| 2.5 Baths \| 3012 Sq. Ft.	$2,725,960

Address	Redfin Estimate
36 Chestnut Street, Brookline, MA 3 Beds \| 1.5 Baths \| 1272 Sq. Ft.	$1,438,960
14 Chestnut Street, Brookline, MA 4 Beds \| 2 Baths \| 2100 Sq. Ft.	$2,286,203

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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 Chestnut St

Tax history for 27 Chestnut St

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 02445

Home values near 27 Chestnut St

More real estate resources