Google street view image for 39 Oakland Rd, Brookline, MA 02445

Off Market Sep 1992 for $250K

$1,603,824

Est. refi paymentEst. refi $1,641/mo

•

2 ba

•

3,016

sq ft

39 Oakland Rd, Brookline, MA 02445

About this home

39 Oakland Rd is a 3,016 square foot multi-family home on a 3,049 square foot lot with 6 bedrooms and 2 bathrooms. - it last sold on September 30, 1992 for $250,000. Based on Redfin's Brookline data, we estimate the home's value is $1,603,824.

Multi-familyProperty Type

1915Year Built

3,049 sq ftLot Size

$532Est. Price/Sq.Ft.

Source:Public Records

Redfin Estimate

$1,603,824

$1.4M since sold in September 1992$84K since August

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 11.2% higher than the average sale price ($1.44M) of 6 comparable homes.

SOLD JUL 13, 2026
$1,460,000
A
5 beds2 baths2,894 sq ft
34 Roseway St, Jamaica Plain, MA 02130
SOLD MAY 15, 2026
$1,541,000
B
4 beds2.5 baths2,465 sq ft
9 Kingsboro Park, Jamaica Plain, MA 02130
SOLD JUN 23, 2026
$1,385,000
C
8 beds3 baths3,109 sq ft
57 Mozart St, Jamaica Plain, MA 02130
SOLD FEB 25, 2026
$1,275,000
D
6 beds3 baths3,399 sq ft
23 Burr St, Jamaica Plain, MA 02130
SOLD JAN 8, 2026
$1,440,000
E
7 beds3 baths3,089 sq ft
32 Forbes St, Jamaica Plain, MA 02130
SOLD JUN 22, 2026
$1,550,000
F
4 beds2.5 baths2,004 sq ft
101 Forbes St, Jamaica Plain, MA 02130

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Earn from this home

Sell

$1,523,338

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 SAT, 11:30AM TO 12:30PM
$1,199,000
4 beds2 baths1,825 sq ft
17 High St #2, Brookline, MA 02445
OPEN TODAY, 5PM TO 6:30PM
$1,250,000
3 beds2 baths1,288 sq ft
11 Claflin Rd #2, Brookline, MA 02445
OPEN SAT, 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 SAT, 12PM TO 1PM
$755,000
2 beds1 bath1,003 sq ft
222 Washington St #3, Brookline, MA 02445
OPEN TODAY, 4PM TO 5:30PM
$2,200,000
4 beds2.5 baths2,794 sq ft
17 Davis Ave #1, Brookline, MA 02445
OPEN SAT, 2PM TO 3:30PM
$2,650,000
5 beds4 baths2,986 sq ft
249 Clinton Rd, Brookline, MA 02445
OPEN SAT, 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
OPEN SAT, 11:30AM TO 1PM
$799,000
2 beds1.5 baths913 sq ft
1856 Beacon St Unit PHD, Brookline, MA 02445
$1,950,000
4 beds2 baths2,616 sq ft
36 Milton Rd, Brookline, MA 02445
See all

Provided by Redfin

Sale history for 39 Oakland Rd

Year

Property tax

Land + Additions

Assessment*

2023

$15,096 (+2.7%)

$678,900 + $835,200

$1,514,100

2022

$14,694 (+8.1%)

$646,600 + $795,400

$1,442,000

2021

$13,588 (+6.7%)

$621,700 + $764,800

$1,386,500

2020

$12,735 (+5.9%)

$555,100 + $792,500

$1,347,600

2019

$12,026 (+9.9%)

$528,700 + $754,800

$1,283,500

2018

$10,941 (+3.4%)

$444,900 + $711,700

$1,156,600

2017

$10,582 (+4.3%)

$419,800 + $651,300

$1,071,100

2016

$10,146 (+7.3%)

$392,400 + $581,300

$973,700

2015

$9,454 (+3.3%)

$366,700 + $518,500

$885,200

2014

$9,154 (+2.7%)

$339,400 + $464,300

$803,700

2013

$8,917 (+2.2%)

$329,500 + $435,900

$765,400

2012

$8,726 (+4.3%)

$329,500 + $435,900

$765,400

2011

$8,369 (+3.0%)

$326,200 + $414,400

$740,600

2010

$8,124 (+2.6%)

$326,200 + $414,400

$740,600

2009

$7,920

$326,500 + $414,400

$740,900

Tax history for 39 Oakland Rd

Year

Property tax

Land + Additions

Assessment*

2023

$15,096 (+2.7%)

$678,900 + $835,200

$1,514,100

2022

$14,694 (+8.1%)

$646,600 + $795,400

$1,442,000

2021

$13,588 (+6.7%)

$621,700 + $764,800

$1,386,500

2020

$12,735 (+5.9%)

$555,100 + $792,500

$1,347,600

2019

$12,026 (+9.9%)

$528,700 + $754,800

$1,283,500

2018

$10,941 (+3.4%)

$444,900 + $711,700

$1,156,600

2017

$10,582 (+4.3%)

$419,800 + $651,300

$1,071,100

2016

$10,146 (+7.3%)

$392,400 + $581,300

$973,700

2015

$9,454 (+3.3%)

$366,700 + $518,500

$885,200

2014

$9,154 (+2.7%)

$339,400 + $464,300

$803,700

2013

$8,917 (+2.2%)

$329,500 + $435,900

$765,400

2012

$8,726 (+4.3%)

$329,500 + $435,900

$765,400

2011

$8,369 (+3.0%)

$326,200 + $414,400

$740,600

2010

$8,124 (+2.6%)

$326,200 + $414,400

$740,600

2009

$7,920

$326,500 + $414,400

$740,900

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

Permits

Mar 30, 2010 • Active

Residential building

Remove and replace windows on the building.

Remodel

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: 1,508
Basement Type: Full

Bathroom Information
# of Full Baths: 2

Heating & Cooling
Heating Type: Forced Hot Water

Room Information
# of Rooms: 12

Exterior

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

Property Information
Living Sq. Ft: 3,016
Gross Sq. Ft: 6,422
# of Units: 2
# of Stories: 3

Lot Information
# of Buildings: 1
Land Sq. Ft: 3,049
Municipality Name: BROOKLINE
Acres: 0.07
Zoning Code: T-5
State Use Description: 2-FAMILY RESIDENCE

Financial

Assessor Information
Assessment Year: 2023

Public facts

Beds: 6
Baths: 2.0
Sq. Ft.: 3,016
Stories: 3.0
Lot Size: 3,049 square feet
Style: Multi-Family (2-4 Unit)
Year Built: 1915
Year Renovated: 1959
County: Norfolk County
APN: 40818

Home facts updated by county records on Jul 20, 2023

Around this home

Schools

William H Lincoln School

Public K-8 • Assigned • 0.3mi

9/10

Brookline High School

Public 9-12 • Assigned • 0.4mi

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

$1.52M – $1.85M

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New listings for sale in 02445

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

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17 High St #2, Brookline, MA 02445

OPEN TODAY, 5PM TO 6:30PMHOT HOME

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OPEN SAT, 11AM TO 12:30PM

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OPEN TODAY, 4PM TO 5:30PM

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17 Davis Ave #1, Brookline, MA 02445

OPEN SAT, 2PM TO 3:30PM

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

$749,000

2 beds1 bath903 sq ft

1731 Beacon St #713, Brookline, MA 02445

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OPEN SAT, 11:30AM TO 1PM

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1856 Beacon St Unit PHD, Brookline, MA 02445

Home values near 39 Oakland Rd

Data from public records.

Address	Redfin Estimate
33 Oakland Road, Brookline, MA 8 Beds \| 4 Baths \| 3816 Sq. Ft.	$1,649,162
51 Oakland Road, Brookline, MA 6 Beds \| 2.5 Baths \| 4043 Sq. Ft.	$2,253,683

Address	Redfin Estimate
35 Oakland Road, Brookline, MA 7 Beds \| 3 Baths \| 3571 Sq. Ft.	$1,945,093
36 Oakland Road, Brookline, MA 5 Beds \| 4 Baths \| 3029 Sq. Ft.	$2,351,126

Address	Redfin Estimate
43 Oakland Road, Brookline, MA 7 Beds \| 3 Baths \| 3055 Sq. Ft.	$1,780,330
32 Oakland Road, Brookline, MA 3 Beds \| 1 Baths \| 2094 Sq. Ft.	$1,678,347

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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 39 Oakland Rd

Tax history for 39 Oakland Rd

Permits

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 39 Oakland Rd

More real estate resources