Google satellite image for 29 Chestnut Pl, Brookline, MA 02445

Off market mar 1983 for $290K

$4,286,758

Est. refi paymentEst. refi $1,904/mo

•

5 ba

•

4,295

sq ft

29 Chestnut Pl, Brookline, MA 02445

About this home

29 Chestnut Pl is a 4,295 square foot house on a 0.72 acre lot with 4 bedrooms and 5 bathrooms. - it last sold on March 11, 1983 for $290,000. Based on Redfin's Brookline data, we estimate the home's value is $4,286,758.

Single-familyProperty Type

1907Year Built

0.72 acresLot Size

$998Est. Price/Sq.Ft.

Source:Public Records

Redfin Estimate

$4,286,758

$4.0M since sold in March 1983$550K since October

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 23.7% higher than the average sale price ($3.47M) of 6 comparable homes.

SOLD MAR 6, 2026
$3,400,000
A
4 beds4.5 baths4,182 sq ft
115 Clark Rd, Brookline, MA 02445
SOLD OCT 23, 2026
$3,875,000
B
5 beds4.5 baths6,419 sq ft
540 Chestnut Hill Ave, Brookline, MA 02445
SOLD OCT 23, 2026
$4,625,000
C
5 beds5.5 baths4,324 sq ft
221 Gardner Rd, Brookline, MA 02445
SOLD MAY 14, 2026
$3,285,000
D
5 beds4.5 baths3,658 sq ft
43 Druce St, Brookline, MA 02445
SOLD NOV 3, 2026
$3,615,500
E
7 beds4.5 baths4,726 sq ft
111 Clinton Rd, Brookline, MA 02445
SOLD AUG 14, 2026
$2,000,000
F
8 beds5 baths5,076 sq ft
16 Kennard Rd, Brookline, MA 02445

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Earn from this home

Sell

$4,073,306

Est. take-home

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Refinance

Est. cash available

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Rent

$8,143/mo

Redfin rental estimate

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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

96.3%

1.1% MoM

Median sale price

$1.1M

$119K MoM

Avg. days on market

58d

3 days MoM

Recently sold homes

1 MoM

New listings for sale

NEW 1 DAY AGO
$545,000
1 bed1 bath870 sq ft
99 Pond Ave #326, Brookline, MA 02445
$11,750,000
6 beds5 baths7,502 sq ft
71 Sears Rd, Brookline, MA 02445
OPEN SUN, 12PM TO 1:30PM
$1,500,000
4 beds2 baths2,254 sq ft
146-A University Rd #146, Brookline, MA 02445
OPEN SAT, 12PM TO 1PM
$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
VIDEO TOUR
$599,000
1 bed1 bath869 sq ft
1742 Beacon St #2, Brookline, MA 02445
$798,800
2 beds2 baths1,099 sq ft
22 Chestnut Pl #114, Brookline, MA 02445
See all

Provided by Redfin

Sale history for 29 Chestnut Pl

Year

Property tax

Land + Additions

Assessment*

2023

$35,659 (+2.7%)

$2,068,200 + $1,508,400

$3,576,600

2022

$34,709 (+8.1%)

$1,969,700 + $1,436,500

$3,406,200

2021

$32,097 (+10.1%)

$1,893,900 + $1,381,300

$3,275,200

2020

$29,144 (+5.9%)

$1,721,700 + $1,362,300

$3,084,000

2019

$27,521 (+3.1%)

$1,639,700 + $1,297,400

$2,937,100

2018

$26,702 (+1.5%)

$1,540,800 + $1,281,800

$2,822,600

2017

$26,308 (+1.8%)

$1,453,600 + $1,209,200

$2,662,800

2016

$25,855 (+4.4%)

$1,358,500 + $1,122,800

$2,481,300

2015

$24,767 (−0.2%)

$1,269,600 + $1,049,400

$2,319,000

2014

$24,807 (+0.7%)

$1,154,000 + $1,024,000

$2,178,000

2013

$24,635 (+2.2%)

$1,120,400 + $994,200

$2,114,600

2012

$24,106 (+5.4%)

$1,120,400 + $994,200

$2,114,600

2011

$22,876 (+3.0%)

$1,055,700 + $968,700

$2,024,400

2010

$22,208 (+2.8%)

$1,055,700 + $968,700

$2,024,400

2009

$21,610

$1,052,800 + $968,700

$2,021,500

Tax history for 29 Chestnut Pl

Year

Property tax

Land + Additions

Assessment*

2023

$35,659 (+2.7%)

$2,068,200 + $1,508,400

$3,576,600

2022

$34,709 (+8.1%)

$1,969,700 + $1,436,500

$3,406,200

2021

$32,097 (+10.1%)

$1,893,900 + $1,381,300

$3,275,200

2020

$29,144 (+5.9%)

$1,721,700 + $1,362,300

$3,084,000

2019

$27,521 (+3.1%)

$1,639,700 + $1,297,400

$2,937,100

2018

$26,702 (+1.5%)

$1,540,800 + $1,281,800

$2,822,600

2017

$26,308 (+1.8%)

$1,453,600 + $1,209,200

$2,662,800

2016

$25,855 (+4.4%)

$1,358,500 + $1,122,800

$2,481,300

2015

$24,767 (−0.2%)

$1,269,600 + $1,049,400

$2,319,000

2014

$24,807 (+0.7%)

$1,154,000 + $1,024,000

$2,178,000

2013

$24,635 (+2.2%)

$1,120,400 + $994,200

$2,114,600

2012

$24,106 (+5.4%)

$1,120,400 + $994,200

$2,114,600

2011

$22,876 (+3.0%)

$1,055,700 + $968,700

$2,024,400

2010

$22,208 (+2.8%)

$1,055,700 + $968,700

$2,024,400

2009

$21,610

$1,052,800 + $968,700

$2,021,500

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

Permits

Jun 3, 2026 • Active

Residential building

Roofing

Mar 9, 2020 • Active

Residential building

Remove existing shingles and a rubber membrane from a residential roof. Install an ice and water shield, drip edges, architectural shingles, and a ridge vent. Install a new fully adhered membrane with recovery board and flashing on the flat roof section.

Roofing

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: 2,116
Basement Type: Full

Bathroom Information
# of Full Baths: 4
# of 1/2 Baths: 2

Heating & Cooling
Heating Type: Forced Hot Water

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

Room Information
# of Rooms: 10

Exterior

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

Property Information
Living Sq. Ft: 4,295
Gross Sq. Ft: 6,866
# of Units: 1
# of Stories: 2

Lot Information
# of Buildings: 1
Land Sq. Ft: 31,363
Municipality Name: BROOKLINE
Acres: 0.72
Zoning Code: S25
State Use Description: 1-FAMILY RESIDENCE

Financial

Assessor Information
Assessment Year: 2023

Public facts

Beds: 4
Baths: 5.0
Sq. Ft.: 4,295
Stories: 2.0
Lot Size: 0.72 acres
Style: Single Family Residential
Year Built: 1907
Year Renovated: 1970
County: Norfolk County
APN: 41227

Home facts updated by county records on Jul 20, 2023

Around this home

Schools

K - 12
Preschool & daycare

William H Lincoln School

Public K-8 • Assigned • 0.2mi

9/10

Brookline High School

Public 9-12 • Assigned • 0.5mi

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

5/10 Heat Factor

7 days above 96° expected this year, 14 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)

34°

21°

36°

22°

51°

33°

59°

42°

68°

52°

80°

62°

84°

66°

79°

61°

74°

57°

63°

48°

52°

38°

39°

26°

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

$4.07M – $4.93M

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Renovated kitchen • Breakfast bar • South-facing windows

Home values near 29 Chestnut Pl

Data from public records.

Address	Redfin Estimate
35 Chestnut Pl, Brookline, MA 6 Beds \| 4 Baths \| 4409 Sq. Ft.	$3,952,680
22 Chestnut Pl Apt 110, Brookline, MA 1 Beds \| 1.5 Baths \| 830 Sq. Ft.	$608,360
22 Chestnut Pl Apt 207, Brookline, MA 1 Beds \| 1.5 Baths \| 826 Sq. Ft.	$555,155
22 Chestnut Pl Apt 401, Brookline, MA 2 Beds \| 2 Baths \| 1095 Sq. Ft.	$720,173
22 Chestnut Pl Apt 504, Brookline, MA 2 Beds \| 2 Baths \| 1102 Sq. Ft.	$783,518
22 Chestnut Pl Apt 517, Brookline, MA 2 Beds \| 2 Baths \| 1099 Sq. Ft.	$803,015
22 Chestnut Pl Apt 605, Brookline, MA 2 Beds \| 2 Baths \| 1288 Sq. Ft.	$910,175

Address	Redfin Estimate
22 Chestnut Pl Apt G1, Brookline, MA 1 Beds \| 1 Baths \| 935 Sq. Ft.	$596,185
22 Chestnut Pl Apt 112, Brookline, MA 2 Beds \| 2 Baths \| 1190 Sq. Ft.	$822,948
22 Chestnut Pl Apt 212, Brookline, MA 2 Beds \| 2 Baths \| 1223 Sq. Ft.	$817,469
22 Chestnut Pl Apt 411, Brookline, MA 1 Beds \| 1.5 Baths \| 902 Sq. Ft.	$581,697
22 Chestnut Pl Apt 506, Brookline, MA 1 Beds \| 1.5 Baths \| 827 Sq. Ft.	$581,718
22 Chestnut Pl Apt 601, Brookline, MA 2 Beds \| 2 Baths \| 1095 Sq. Ft.	$748,332
22 Chestnut Pl Apt 607, Brookline, MA 1 Beds \| 1.5 Baths \| 828 Sq. Ft.	$602,668

Address	Redfin Estimate
22 Chestnut Pl Apt 109, Brookline, MA - Beds \| 1 Baths \| 463 Sq. Ft.	$373,360
22 Chestnut Pl Apt 206, Brookline, MA 1 Beds \| 1.5 Baths \| 830 Sq. Ft.	$587,364
22 Chestnut Pl Apt 216, Brookline, MA 2 Beds \| 2 Baths \| 1097 Sq. Ft.	$754,876
22 Chestnut Pl Apt 503, Brookline, MA 1 Beds \| 1.5 Baths \| 826 Sq. Ft.	$599,072
22 Chestnut Pl Apt 514, Brookline, MA 3 Beds \| 3 Baths \| 2267 Sq. Ft.	$1,449,658
22 Chestnut Pl Apt 604, Brookline, MA 2 Beds \| 2 Baths \| 1103 Sq. Ft.	$777,205
22 Chestnut Pl Apt M2, Brookline, MA 1 Beds \| 1 Baths \| 477 Sq. Ft.	$391,893

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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 29 Chestnut Pl

Tax history for 29 Chestnut Pl

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 29 Chestnut Pl

More real estate resources