Off Market Jul 2004 for $2.5M

$5,123,826

Est. refi paymentEst. refi $15,659/mo

•

4.5 ba

•

6,359

sq ft

108 Upland Rd, Brookline, MA 02445

About this home

Single-familyProperty Type

1880Year Built

0.25 acresLot Size

$806Est. Price/Sq.Ft.

2 garage spacesParking

Listed by Susan Rothstein • Hammond Residential R. E.

Bought with Sally Wilde • Hammond Residential R. E.

Source:MLS PIN #30384740

Redfin Estimate

$5,123,826

$2.6M since sold in July 2004$50K since July

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 56.6% higher than the average sale price ($3.27M) of 6 comparable homes.

SOLD AUG 14, 2026
$2,000,000
A
8 beds5 baths5,076 sq ft
16 Kennard Rd, Brookline, MA 02445
SOLD JUL 24, 2026
$2,325,000
B
7 beds4 baths4,544 sq ft
54 Clark Rd, Brookline, MA 02445
SOLD APR 27, 2026
$4,100,000
C
6 beds4.5 baths5,058 sq ft
282 Buckminster 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 AUG 13, 2026
$4,050,000
E
5 beds4.5 baths3,738 sq ft
95 Babcock St, Brookline, MA 02446
SOLD JUL 13, 2026
$3,875,000
F
5 beds4.5 baths6,205 sq ft
66 Mason Ter, Brookline, MA 02446

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Earn from this home

Sell

$4,100,889

Est. take-home

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Refinance

Est. cash available

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Rent

$8,386/mo

Redfin rental estimate

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Market trends in 02445, MA

Last updated July 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-List Price

100.2%

0.1% MoM

Median sale price

$1.2M

$85K MoM

Avg. days on market

30d

9 days MoM

Recently sold homes

7 MoM

New listings for sale

OPEN SUN, 12PM TO 1:30PM
$998,000
2 beds2 baths1,218 sq ft
1731 Beacon St #402, Brookline, MA 02445
OPEN SAT, 11AM TO 12:30PM
$859,000
3 beds1.5 baths1,233 sq ft
124 Chestnut St #1, Brookline, MA 02445
OPEN FRI, 12:30PM TO 2PM
$2,895,000
7 beds3.5 baths4,805 sq ft
71 Addington Rd, Brookline, MA 02445
OPEN SAT, 12PM TO 2PM
$2,200,000
9 beds3 baths4,364 sq ft
26 Parkway Rd, Brookline, MA 02445
OPEN SUN, 11AM TO 12PM
$4,800,000
5 beds5.5 baths4,324 sq ft
221 Gardner Rd, Brookline, MA 02445
EARLY ACCESS
Unknown
5 beds6 baths3,539 sq ft
291 Tappan St, Brookline, MA 02445
OPEN SUN, 11AM TO 12:30PM
$1,495,000
3 beds2 baths1,759 sq ft
12 Kilsyth Rd #3, Brookline, MA 02445
$560,000
1 bed1 bath860 sq ft
77 Pond Ave #509, Brookline, MA 02445
$2,999,000
4 beds3.5 baths3,265 sq ft
52 Clinton Rd, Brookline, MA 02445
3D WALKTHROUGH
$6,495,000
9 beds7.5 baths8,619 sq ft
372 Warren St, Brookline, MA 02445
See all

Provided by Redfin

Sale history for 108 Upland Rd

Date

Event

Price

Public Records

Jul 20, 2004

Sold

$2,500,000

$393/sq ft

MLS PIN #30384740

Jun 1, 2000

Sold

$1,490,625

$234/sq ft

Mar 7, 2000

Listing Removed

—

Feb 10, 2000

Listed

$1,595,000

$251/sq ft

Public Records

Jun 20, 1991

Sold

$625,000

$98/sq ft

Year

Property tax

Land + Additions

Assessment*

2023

$35,413 (+2.7%)

$1,178,900 + $2,373,100

$3,552,000

2022

$34,471 (+8.1%)

$1,122,700 + $2,260,100

$3,382,800

2021

$31,876 (+7.9%)

$1,079,500 + $2,173,200

$3,252,700

2020

$29,544 (+5.9%)

$981,400 + $2,145,000

$3,126,400

2019

$27,900 (−3.0%)

$934,700 + $2,042,900

$2,977,600

2018

$28,757 (+1.5%)

$845,300 + $2,194,500

$3,039,800

2017

$28,333 (+1.5%)

$797,400 + $2,070,300

$2,867,700

2016

$27,927 (+4.4%)

$745,300 + $1,934,800

$2,680,100

2015

$26,751 (+1.9%)

$696,500 + $1,808,300

$2,504,800

2014

$26,261 (−7.2%)

$633,100 + $1,672,500

$2,305,600

2013

$28,313 (+2.2%)

$614,700 + $1,815,600

$2,430,300

2012

$27,705 (+3.5%)

$614,700 + $1,815,600

$2,430,300

2011

$26,778 (+3.0%)

$616,100 + $1,753,600

$2,369,700

2010

$25,996 (+2.6%)

$616,100 + $1,753,600

$2,369,700

2009

$25,332

$616,100 + $1,753,600

$2,369,700

Tax history for 108 Upland Rd

Year

Property tax

Land + Additions

Assessment*

2023

$35,413 (+2.7%)

$1,178,900 + $2,373,100

$3,552,000

2022

$34,471 (+8.1%)

$1,122,700 + $2,260,100

$3,382,800

2021

$31,876 (+7.9%)

$1,079,500 + $2,173,200

$3,252,700

2020

$29,544 (+5.9%)

$981,400 + $2,145,000

$3,126,400

2019

$27,900 (−3.0%)

$934,700 + $2,042,900

$2,977,600

2018

$28,757 (+1.5%)

$845,300 + $2,194,500

$3,039,800

2017

$28,333 (+1.5%)

$797,400 + $2,070,300

$2,867,700

2016

$27,927 (+4.4%)

$745,300 + $1,934,800

$2,680,100

2015

$26,751 (+1.9%)

$696,500 + $1,808,300

$2,504,800

2014

$26,261 (−7.2%)

$633,100 + $1,672,500

$2,305,600

2013

$28,313 (+2.2%)

$614,700 + $1,815,600

$2,430,300

2012

$27,705 (+3.5%)

$614,700 + $1,815,600

$2,430,300

2011

$26,778 (+3.0%)

$616,100 + $1,753,600

$2,369,700

2010

$25,996 (+2.6%)

$616,100 + $1,753,600

$2,369,700

2009

$25,332

$616,100 + $1,753,600

$2,369,700

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

Permits

Aug 1, 2023 • Active

Residential building

Waterproof the chimney and fill any cracks with mortar.

Roofing

Jul 14, 2016 • Active

Residential building

Install an iron handrail at the front porch and front walkway steps. Extend a wood picket fence along the property line.

ADU

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: 2,630
Basement Type: Full

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

Heating & Cooling
Heating Type: Forced Hot Water

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: Victorian
Construction Type: Frame
Exterior Wall: Wood Siding/Shingle
Roof Shape Type: Gable

Property Information
Living Sq. Ft: 6,359
Gross Sq. Ft: 10,791
# of Units: 1
# of Stories: 3

Lot Information
# of Buildings: 1
Land Sq. Ft: 10,890
Municipality Name: BROOKLINE
Acres: 0.25
Zoning Code: S10
State Use Description: 1-FAMILY RESIDENCE

Financial

Assessor Information
Assessment Year: 2023

Public facts

Beds: 7
Baths: 4.5
Sq. Ft.: 6,359
Stories: 3.0
Lot Size: 0.25 acres
Style: Single Family Residential
Year Built: 1880
Year Renovated: 1970
County: Norfolk County
APN: 40765

Home facts updated by county records on Jul 20, 2023

Around this home

Schools

William H Lincoln School

Public K-8 • Assigned • 0.4mi

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
151 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

58% 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

$4.87M – $5.89M

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Nearby similar homes

OPEN SUN, 11AM TO 12PM

$4,800,000

5 beds5.5 baths4,324 sq ft

221 Gardner Rd, Brookline, MA 02445

OPEN SAT, 12PM TO 1:30PM3D WALKTHROUGH

$4,250,000

3 beds3.5 baths3,467 sq ft

322 Tappan St #2, Brookline, MA 02445

$3,995,000

5 beds4.5 baths5,234 sq ft

68 Dudley St, Brookline, MA 02445

$1,888,000

3 beds3 baths2,160 sq ft

50 Franklin St, Brookline, MA 02445

$11,750,000

6 beds5 baths7,502 sq ft

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OPEN FRI, 3:30PM TO 4:30PM

$2,799,999

4 beds4 baths2,763 sq ft

21 Kent Sq #2, Brookline, MA 02446

New listings for sale in 02445

OPEN SUN, 12PM TO 1:30PM

$998,000

2 beds2 baths1,218 sq ft

1731 Beacon St #402, Brookline, MA 02445

OPEN SAT, 11AM TO 12:30PM

$859,000

3 beds1.5 baths1,233 sq ft

124 Chestnut St #1, Brookline, MA 02445

OPEN FRI, 12:30PM TO 2PM

$2,895,000

7 beds3.5 baths4,805 sq ft

71 Addington Rd, Brookline, MA 02445

OPEN SAT, 12PM TO 2PM

$2,200,000

9 beds3 baths4,364 sq ft

26 Parkway Rd, Brookline, MA 02445

OPEN SUN, 11AM TO 12PM

$4,800,000

5 beds5.5 baths4,324 sq ft

221 Gardner Rd, Brookline, MA 02445

EARLY ACCESSCOMPASS COMING SOON

Unknown

5 beds6 baths3,539 sq ft

291 Tappan St, Brookline, MA 02445

OPEN SUN, 11AM TO 12:30PM

$1,495,000

3 beds2 baths1,759 sq ft

12 Kilsyth Rd #3, Brookline, MA 02445

$560,000

1 bed1 bath860 sq ft

77 Pond Ave #509, Brookline, MA 02445

$2,999,000

4 beds3.5 baths3,265 sq ft

52 Clinton Rd, Brookline, MA 02445

Home values near 108 Upland Rd

Data from public records.

Address	Redfin Estimate
100 Upland Road, Brookline, MA 6 Beds \| 3.5 Baths \| 5940 Sq. Ft.	$4,914,417
78 Upland Road, Brookline, MA 9 Beds \| 5.5 Baths \| 6767 Sq. Ft.	$5,415,884

Address	Redfin Estimate
94 Upland Road, Brookline, MA 8 Beds \| 3.5 Baths \| 4719 Sq. Ft.	$3,305,033
70 Upland Road, Brookline, MA 5 Beds \| 5.5 Baths \| 5312 Sq. Ft.	$3,987,086

Address	Redfin Estimate
84 Upland Road, Brookline, MA 5 Beds \| 3.5 Baths \| 4374 Sq. Ft.	$3,973,867
62 Upland Road, Brookline, MA 6 Beds \| 3.5 Baths \| 3572 Sq. Ft.	$3,174,030

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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 108 Upland Rd

Tax history for 108 Upland 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 108 Upland Rd

More real estate resources