OFF MARKET

Off Market Jul 2014 for $2.4M

$4,162,154

Est. refi paymentEst. refi $7,245/mo

•

3,938

sq ft

56 Upland Rd, Brookline, MA 02445

About this home

Spectacular 1890's Shingle-style home on the Philbrick Green in historic Pill Hill.Beautifully maintained and thoughtfully improved home offers 11 generously proportioned rooms filled with light and distinctive architectural detail perfect for grand entertaining and comfortable family living. A welcoming porch invites you to a gracious entry hall and elegant living room.2011 stunning kitchen and mudroom remodel, banquet-size dining room with French doors to large deck with pergola and lush private gardens.Stunning stair tower leads to second and third floor comprising a luxurious master suite, large playroom,4 family bedrooms and an office.Many recent and substantial upgrades include 2008 exterior shingles and roof improvement including lead coated copper valleys,2006 multi-zone hydro air heating and air conditioning and bathroom additions,perimeter French drain.This wonderful home in Lincoln School district is close to Brookline Village,Longwood Medical area and public transportation.

Single-familyProperty Type

1890Year Built

7,800 sq ftLot Size

$1,057Est. Price/Sq.Ft.

3 spacesParking

Listed by Dolores Boylan • Hammond Residential R. E.

Bought with Vee Brooks • Coldwell Banker Residential Brokerage - Weston

Redfin checked: a few seconds ago

•Source:MLS PIN #71675290

Redfin Estimate

$4,162,154

$1.7M since sold in July 2014$105K since July

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 52.9% higher than the average sale price ($2.72M) of 6 comparable homes.

SOLD OCT 15, 2025
$2,300,000
A
5 beds3.5 baths3,873 sq ft
14 Irving St, Brookline, MA 02445
SOLD AUG 13, 2026
$4,050,000
B
5 beds4.5 baths3,738 sq ft
95 Babcock St, Brookline, MA 02446
SOLD MAY 1, 2026
$2,750,000
C
4 beds3.5 baths3,963 sq ft
236 Walnut St, Brookline, MA 02445
SOLD JUL 2, 2026
$2,525,000
D
6 beds3 baths4,605 sq ft
62 Fuller St, Brookline, MA 02446
SOLD JAN 15, 2026
$2,385,000
E
5 beds3.5 baths3,390 sq ft
11 Robinwood Ave, Jamaica Plain, MA 02130
SOLD JUL 24, 2026
$2,325,000
F
7 beds4 baths4,544 sq ft
54 Clark Rd, Brookline, MA 02445

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Earn from this home

Sell

$2,522,878

Est. take-home

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Refinance

Est. cash available

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Rent

$8,213/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 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
OPEN SAT, 11:30AM TO 12:30PM
$999,000
3 beds2 baths1,240 sq ft
1896 Beacon St Ph 3, Brookline, MA 02445
See all

Provided by Redfin

Sale history for 56 Upland Rd

Date

Event

Price

MLS PIN #71675290

Jul 30, 2014

Sold

$2,450,000

$622/sq ft

May 29, 2014

Price Changed

$2,450,000

$622/sq ft

May 29, 2014

Contingent

—

May 5, 2014

Listed

$2,595,000

$659/sq ft

MLS PIN #70158080

Aug 12, 2005

Sold

$2,100,000

$533/sq ft

Jun 3, 2005

Listing Removed

—

Mar 15, 2005

Listed

$2,195,000

$557/sq ft

Public Records

Jan 10, 1989

Sold

$600,000

$152/sq ft

Year

Property tax

Land + Additions

Assessment*

2023

$28,080 (+2.7%)

$1,076,700 + $1,739,700

$2,816,400

2022

$27,332 (+8.3%)

$1,025,300 + $1,656,900

$2,682,200

2021

$25,228 (+8.4%)

$985,900 + $1,588,400

$2,574,300

2020

$23,281 (+5.9%)

$896,300 + $1,567,300

$2,463,600

2019

$21,985 (+4.9%)

$853,600 + $1,492,700

$2,346,300

2018

$20,961 (+1.5%)

$769,500 + $1,446,300

$2,215,800

2017

$20,653 (+1.5%)

$726,000 + $1,364,400

$2,090,400

2016

$20,357 (+6.4%)

$678,500 + $1,275,100

$1,953,600

2015

$19,129 (−4.3%)

$634,100 + $1,157,000

$1,791,100

2014

$19,979 (+0.7%)

$576,500 + $1,177,600

$1,754,100

2013

$19,840 (+2.2%)

$559,700 + $1,143,300

$1,703,000

2012

$19,414 (+1.8%)

$559,700 + $1,143,300

$1,703,000

2011

$19,076 (+3.0%)

$559,100 + $1,129,000

$1,688,100

2010

$18,518 (+2.6%)

$559,100 + $1,129,000

$1,688,100

2009

$18,045

$559,100 + $1,128,900

$1,688,000

Tax history for 56 Upland Rd

Year

Property tax

Land + Additions

Assessment*

2023

$28,080 (+2.7%)

$1,076,700 + $1,739,700

$2,816,400

2022

$27,332 (+8.3%)

$1,025,300 + $1,656,900

$2,682,200

2021

$25,228 (+8.4%)

$985,900 + $1,588,400

$2,574,300

2020

$23,281 (+5.9%)

$896,300 + $1,567,300

$2,463,600

2019

$21,985 (+4.9%)

$853,600 + $1,492,700

$2,346,300

2018

$20,961 (+1.5%)

$769,500 + $1,446,300

$2,215,800

2017

$20,653 (+1.5%)

$726,000 + $1,364,400

$2,090,400

2016

$20,357 (+6.4%)

$678,500 + $1,275,100

$1,953,600

2015

$19,129 (−4.3%)

$634,100 + $1,157,000

$1,791,100

2014

$19,979 (+0.7%)

$576,500 + $1,177,600

$1,754,100

2013

$19,840 (+2.2%)

$559,700 + $1,143,300

$1,703,000

2012

$19,414 (+1.8%)

$559,700 + $1,143,300

$1,703,000

2011

$19,076 (+3.0%)

$559,100 + $1,129,000

$1,688,100

2010

$18,518 (+2.6%)

$559,100 + $1,129,000

$1,688,100

2009

$18,045

$559,100 + $1,128,900

$1,688,000

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

Public record

Public record
Permits

Beds

Baths

4.5

Stories

Lot width

—

Lot depth

—

Lot size

7,841 Sq. Ft.

Year renovated

1981

Sq. Ft.

3,938

Year built

1890

Style

Single Family Residential

County

Norfolk County

APN

40772

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jul 21, 2023.

Property details

Parking

Parking Information
Has Garage
Has Open Parking
Parking Spaces: 3
Parking Features: Detached, Paved Drive, Off Street

Interior

Master Bedroom Information
Area: 304
Length: 16
Width: 19
Level: Second
Features: Flooring - Hardwood

Bedroom #2 Information
Area: 285
Length: 19
Width: 15
Level: Second
Features: Flooring - Hardwood

Bedroom #3 Information
Area: 180
Length: 15
Width: 12
Level: Second
Features: Flooring - Hardwood

Bedroom #4 Information
Area: 270
Length: 15
Width: 18
Level: Third
Features: Flooring - Hardwood

Bedroom #5 Information
Area: 210
Length: 15
Width: 14
Level: Third
Features: Flooring - Hardwood

Bathroom Information
# of Bathrooms (Full): 2
# of Bathrooms (Half): 3
Master Bathroom Features: Yes

Bathroom #1 Information
Level: First
Features: Bathroom - Half

Bathroom #2 Information
Level: Second
Features: Bathroom - Full,Countertops - Stone/Granite/Solid

Bathroom #3 Information
Level: Third
Features: Bathroom - Full,Countertops - Stone/Granite/Solid

Living Room Information
Area: 308
Length: 22
Width: 14
Level: First
Features: Flooring - Hardwood

Dining Room Information
Area: 304
Length: 16
Width: 19
Level: First
Features: Flooring - Hardwood

Kitchen Information
Area: 285
Length: 19
Width: 15
Level: First
Features: Pantry

Office Room Information
Area: 90
Length: 9
Width: 10
Level: Second
Features: Flooring - Hardwood

Basement Information
Basement: Full

Laundry Information
Laundry Features: In Basement, Electric Dryer Hookup, Washer Hookup

Fireplace Information
Has Fireplace
# of Fireplaces (Total): 4
Fireplace Features: Dining Room, Living Room, Master Bedroom, Bedroom

Interior Features
# of Rooms (Total): 11
Flooring: Wood, Flooring - Hardwood
Interior Features: Bathroom - Half, Office, Bedroom, Bathroom, Foyer, Sauna/Steam/Hot Tub, Walk-Up Attic

Exterior

Building Information
Building Area (Total): 3,938
Foundation Details: Stone
Construction Materials: Frame
Year Built Source: Public Records
Year Built Details: Approximate
Color: Grey/Blue

Exterior Features
Fencing: Fenced
Roof: Shingle
Patio And Porch Features: Porch, Deck
Exterior Features: Porch, Deck, Hot Tub/Spa, Sprinkler System, Fenced Yard

Pool Information
Has Spa
Spa Features: Private

Property Information
PropertySubType: Single Family Residence

Lot Information
Lot Size (Acres): 0.18
Road Frontage Type: Public

Financial

Tax Information
Tax Annual Amount: $19,979
Tax Year: 2014

Utilities

Utility Information
Utilities: for Electric Dryer, Washer Hookup
Sewer: Public Sewer
Water Source: Public

Heating & Cooling
Has Heating
Has Cooling
Heating: Natural Gas, Hydro Air
Cooling: Central Air

Location

Location Information
Directions: High or Walnut to Irving to Upland
UnparsedAddress: 56 Upland Rd, Brookline MA 02445

Community Information
Senior CommunityYN: No
Community Features: Public Transportation, Shopping, Tennis Court(s), Park, Walk/Jog Trails

Public facts

Beds: 5
Baths: 4.5
Sq. Ft.: 3,938
Stories: 3.0
Lot Size: 7,841 square feet
Style: Single Family Residential
Year Built: 1890
Year Renovated: 1981
County: Norfolk County
APN: 40772

Home facts updated by county records on Jul 20, 2023

Other

Miscellaneous Information
Heat Zones: 3

Listing Information
StandardStatus: Closed

Around this home

Schools

William H Lincoln School

Public K-8 • Assigned • 0.5mi

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

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

$3.96M – $4.79M

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Nearby similar homes

OPEN SUN, 11AM TO 12PM

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221 Gardner Rd, Brookline, MA 02445

OPEN SAT, 12PM TO 1:30PM3D WALKTHROUGH

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New listings for sale in 02445

OPEN SAT, 11AM TO 12:30PM

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124 Chestnut St #1, Brookline, MA 02445

OPEN FRI, 12:30PM TO 2PM

$2,895,000

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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

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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

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3D WALKTHROUGH

$6,495,000

9 beds7.5 baths8,619 sq ft

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Home values near 56 Upland Rd

Data from public records.

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

Address	Redfin Estimate
78 Upland Road, Brookline, MA 9 Beds \| 5.5 Baths \| 6767 Sq. Ft.	$5,415,884
52 Upland Road, Brookline, MA 8 Beds \| 3.5 Baths \| 4651 Sq. Ft.	$4,197,705

Address	Redfin Estimate
70 Upland Road, Brookline, MA 5 Beds \| 5.5 Baths \| 5312 Sq. Ft.	$3,987,086
43 Upland Road, Brookline, MA 6 Beds \| 3.5 Baths \| 3890 Sq. Ft.	$3,710,744

Property information provided by MLS PIN when last listed in 2014. This data may not match . Learn more.

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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 56 Upland Rd

Tax history for 56 Upland Rd

Public record

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 56 Upland Rd

More real estate resources