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

Off market sep 1992 for $250K

$1,724,926

Est. refi paymentEst. refi $1,606/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 $1,724,926.

Multi-familyProperty Type

1915Year Built

3,049 sq ftLot Size

$572Est. Price/Sq.Ft.

Source:Public Records

Redfin Estimate

$1,724,926

$1.5M since sold in September 1992$55K since October

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 34.6% higher than the average sale price ($1.28M) 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 SEP 15, 2026
$1,150,000
B
6 beds2.5 baths2,736 sq ft
53 Prince St, Jamaica Plain, MA 02130
SOLD SEP 14, 2026
$879,000
C
8 beds2 baths2,868 sq ft
187 Highland St, Roxbury, MA 02119
SOLD MAY 15, 2026
$1,541,000
D
4 beds2.5 baths2,465 sq ft
9 Kingsboro Park, Jamaica Plain, MA 02130
SOLD JUN 23, 2026
$1,385,000
E
8 beds3 baths3,109 sq ft
57 Mozart St, Jamaica Plain, MA 02130
SOLD FEB 25, 2026
$1,275,000
F
6 beds3 baths3,399 sq ft
23 Burr St, Jamaica Plain, MA 02130

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Earn from this home

Sell

$1,638,439

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

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 21 HRS AGO
$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
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
$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 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

K - 12
Preschool & daycare

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

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

$1.64M – $1.98M

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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.	$1,934,436
51 Oakland Road, Brookline, MA 6 Beds \| 2.5 Baths \| 4043 Sq. Ft.	$2,415,011
28 Oakland Road, Brookline, MA 6 Beds \| 4.5 Baths \| 3016 Sq. Ft.	$3,082,996
40 Oakland Road, Brookline, MA 7 Beds \| 3.5 Baths \| 4095 Sq. Ft.	$2,445,394
20 Rice Street #1, Brookline, MA 3 Beds \| 1 Baths \| 979 Sq. Ft.	$752,035
16 Rice Street #1, Brookline, MA 3 Beds \| 1 Baths \| 978 Sq. Ft.	$711,944
7 Franklin Street #3, Brookline, MA 3 Beds \| 1 Baths \| 981 Sq. Ft.	$715,852

Address	Redfin Estimate
35 Oakland Road, Brookline, MA 7 Beds \| 3 Baths \| 3571 Sq. Ft.	$1,976,167
36 Oakland Road, Brookline, MA 5 Beds \| 4 Baths \| 3029 Sq. Ft.	$2,523,797
40 Oakland Road #2, Brookline, MA 3 Beds \| 3 Baths \| 2199 Sq. Ft.	$1,897,793
1 Vogel Terrace, Brookline, MA 3 Beds \| 1.5 Baths \| 1650 Sq. Ft.	$1,685,235
20 Rice Street #2, Brookline, MA 3 Beds \| 1 Baths \| 978 Sq. Ft.	$798,873
16 Rice Street #2, Brookline, MA 3 Beds \| 1 Baths \| 976 Sq. Ft.	$698,513
7 Franklin Street #2, Brookline, MA 3 Beds \| 1 Baths \| 981 Sq. Ft.	$767,864

Address	Redfin Estimate
43 Oakland Road, Brookline, MA 7 Beds \| 3 Baths \| 3055 Sq. Ft.	—
32 Oakland Road, Brookline, MA 3 Beds \| 1 Baths \| 2094 Sq. Ft.	$1,716,841
40 Oakland Road #1, Brookline, MA 4 Beds \| 3.5 Baths \| 2600 Sq. Ft.	$1,944,107
3 Franklin Street, Brookline, MA 9 Beds \| 3 Baths \| 3698 Sq. Ft.	—
20 Rice Street #3, Brookline, MA 3 Beds \| 1 Baths \| 978 Sq. Ft.	$743,299
16 Rice Street #3, Brookline, MA 3 Beds \| 1 Baths \| 982 Sq. Ft.	$781,494
7 Franklin Street #1, Brookline, MA 3 Beds \| 1 Baths \| 981 Sq. Ft.	$690,727

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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

Local insights from Redfin agents

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