Off Market Mar 2020 for $1.2M

$2,165,876

Est. refi paymentEst. refi $2,414/mo

•

2,000

sq ft

27 Upland Rd, Brookline, MA 02445

About this home

Lovely Cape style home in prestigious sought after Brookline neighborhood on a corner lot. Spacious interior featuring an open floor plan and built-in shelves. Perfect for families or those seeking main floor living without stairs. Living space expansion potential in roomy unfinished basement. Ideal quiet location, walking distance to MBTA Green Line, elementary school, and Brookline Village shops. This is your opportunity to make this your perfect home in a special neighborhood where homes don't come on the market very often!

Single-familyProperty Type

1930Year Built

7,535 sq ftLot Size

$1,083Est. Price/Sq.Ft.

1 garage spacesParking

Listed by Mark Richardson • William Raveis R.E. & Home Services

Bought with Mark Richardson • William Raveis R.E. & Home Services

Redfin checked: a few seconds ago

•Source:MLS PIN #72601655

Redfin Estimate

$2,165,876

$886K since sold in March 2020$119K since July

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 3.4% higher than the average sale price ($2.10M) of 6 comparable homes.

SOLD MAR 4, 2026
$910,000
A
5 beds2.5 baths1,943 sq ft
11 Round Hill St, Jamaica Plain, MA 02130
SOLD JUN 23, 2026
$1,750,000
B
3 beds1.5 baths1,380 sq ft
14A Linden Pl, Brookline, MA 02445
SOLD APR 15, 2026
$2,525,000
C
5 beds1.5 baths2,484 sq ft
61 Toxteth St, Brookline, MA 02445
SOLD APR 16, 2026
$2,150,000
D
4 beds3.5 baths2,332 sq ft
209 High St, Brookline, MA 02445
SOLD APR 8, 2026
$2,850,000
E
4 beds2.5 baths3,377 sq ft
24 Blake Rd, Brookline, MA 02445
SOLD DEC 17, 2025
$2,385,000
F
4 beds3 baths2,286 sq ft
21 Hancock Rd, Brookline, MA 02445

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Earn from this home

Sell

$1,165,535

Est. take-home

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Refinance

Est. cash available

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Rent

$5,310/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 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
$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 27 Upland Rd

Year

Property tax

Land + Additions

Assessment*

2023

$13,016 (+2.7%)

$891,000 + $414,500

$1,305,500

2022

$12,669 (+8.1%)

$848,500 + $394,800

$1,243,300

2021

$11,716 (+11.1%)

$815,900 + $379,600

$1,195,500

2020

$10,541 (+5.9%)

$741,700 + $373,800

$1,115,500

2019

$9,955 (+9.2%)

$706,400 + $356,000

$1,062,400

2018

$9,118 (−7.8%)

$620,000 + $343,800

$963,800

2017

$9,889 (+1.5%)

$584,800 + $416,100

$1,000,900

2016

$9,747 (+4.4%)

$546,600 + $388,800

$935,400

2015

$9,336

$510,800 + $363,400

$874,200

2014

$9,339 (+0.7%)

$464,400 + $355,500

$819,900

2013

$9,273 (+2.2%)

$450,900 + $345,100

$796,000

2012

$9,074 (+0.2%)

$450,900 + $345,100

$796,000

2011

$9,057 (+3.0%)

$455,000 + $346,500

$801,500

2010

$8,792 (+2.6%)

$455,000 + $346,500

$801,500

2009

$8,572

$455,400 + $346,500

$801,900

Tax history for 27 Upland Rd

Year

Property tax

Land + Additions

Assessment*

2023

$13,016 (+2.7%)

$891,000 + $414,500

$1,305,500

2022

$12,669 (+8.1%)

$848,500 + $394,800

$1,243,300

2021

$11,716 (+11.1%)

$815,900 + $379,600

$1,195,500

2020

$10,541 (+5.9%)

$741,700 + $373,800

$1,115,500

2019

$9,955 (+9.2%)

$706,400 + $356,000

$1,062,400

2018

$9,118 (−7.8%)

$620,000 + $343,800

$963,800

2017

$9,889 (+1.5%)

$584,800 + $416,100

$1,000,900

2016

$9,747 (+4.4%)

$546,600 + $388,800

$935,400

2015

$9,336

$510,800 + $363,400

$874,200

2014

$9,339 (+0.7%)

$464,400 + $355,500

$819,900

2013

$9,273 (+2.2%)

$450,900 + $345,100

$796,000

2012

$9,074 (+0.2%)

$450,900 + $345,100

$796,000

2011

$9,057 (+3.0%)

$455,000 + $346,500

$801,500

2010

$8,792 (+2.6%)

$455,000 + $346,500

$801,500

2009

$8,572

$455,400 + $346,500

$801,900

*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

Stories

Lot width

—

Lot depth

—

Lot size

7,535

Year renovated

2021

Sq. Ft.

2,000

Year built

1930

Style

Single Family Residential

County

Norfolk County

APN

40851

Parking Spaces

Basement

Yes

Accessible

Yes

HOA Dues

—

Garage

Yes

Features

Views, Green

Last updated by owner on Sep 21, 2021.

Aug 10, 2006 • Active

Residential plumbing

Replace the water heater in the basement.

Plumbing

Water heater

Aug 10, 2006 • Active

Residential gas

Replace a water heater in the basement.

Gas

Plumbing

Water heater

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

Parking

Parking Information
Has Garage
# of Garage Spaces: 1
# of Covered Spaces: 1
Parking Spaces: 2
AttachedGarageYN: Yes
Parking Features: Attached, Off Street

Interior

Bedroom Information
Main Level Bedrooms: 1

Master Bedroom Information
Area: 154
Length: 11
Width: 14
Level: Main,First
Features: Window(s) - Bay/Bow/Box

Bedroom #2 Information
Area: 110
Length: 10
Width: 11
Level: First
Features: Window(s) - Bay/Bow/Box

Bedroom #3 Information
Area: 165
Length: 11
Width: 15
Level: Second

Bedroom #4 Information
Area: 99
Length: 9
Width: 11
Level: Second

Bedroom #5 Information
Area: 81
Length: 9
Width: 9
Level: Second

Bathroom Information
# of Bathrooms (Full): 2

Living Room Information
Area: 198
Length: 11
Width: 18
Level: First
Features: Flooring - Hardwood

Dining Room Information
Area: 110
Length: 10
Width: 11
Level: First
Features: Exterior Access

Kitchen Information
Area: 120
Length: 10
Width: 12
Level: First

Basement Information
Basement: Full, Bulkhead, Sump Pump, Concrete, Unfinished

Laundry Information
Laundry Features: Gas Dryer Hookup, Washer Hookup

Fireplace Information
Has Fireplace
# of Fireplaces (Total): 1

Interior Features
# of Rooms (Total): 8
Window Features: Storm Window(s)
Flooring: Wood, Hardwood
Interior Features: Internet Available - Broadband

Exterior

Building Information
Building Area (Total): 1,656
Foundation Details: Block
Construction Materials: Frame
Year Built Source: Public Records
Year Built Details: Approximate
Color: Yellow

Exterior Features
Fencing: Fenced
Roof: Slate
Patio And Porch Features: Porch, Patio
Exterior Features: Porch, Patio, Storage, Fenced Yard

Property Information
Accessibility Features: No
PropertySubType: Single Family Residence

Lot Information
Lot Size (Acres): 0.17
Lot Features: Corner Lot
Road Frontage Type: Public

Financial

Tax Information
Tax Annual Amount: $9,955
Tax Year: 2019

Utilities

Utility Information
Utilities: for Gas Range, for Gas Oven, for Gas Dryer, Washer Hookup
Sewer: Public Sewer
Water Source: Public
Electric: 110 Volts, Circuit Breakers

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

Location

Location Information
Directions: Route 9 to High St right on Acron Rd to Upland Rd
UnparsedAddress: 27 Upland Rd, Brookline MA 02445

Community Information
Senior CommunityYN: No
Community Features: Public Transportation, Shopping, Park, Walk/Jog Trails, House of Worship, Public School, T-Station

Public facts

Beds: 5
Baths: 2.0
Sq. Ft.: 2,000
Stories: 2.0
Parking Spaces: 3
Basement: Yes
Accessible: Yes
Lot Size: 7,535 square feet
Style: Single Family Residential
Year Built: 1930
Year Renovated: 2021
County: Norfolk County
APN: 40851
HOA Dues: —
Garage: Yes
Features: Views, Green

Home facts updated by owner on Sep 21, 2021

Other

Miscellaneous Information
Heat Zones: 1

Listing Information
Exclusions: Refrigerator And Washer And Dryer Not Included But Negotiable
StandardStatus: Closed

Around this home

Schools

Pierce School

Public K-8 • Assigned • 0.4mi

10/10

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

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

$2.18M – $2.64M

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Nearby similar homes

OPEN SUN, 11AM TO 12PM

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5 beds5.5 baths4,324 sq ft

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6 beds7 baths9,065 sq ft

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VIDEO TOUR

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185 Warren St, Brookline, MA 02445

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5 beds4.5 baths5,234 sq ft

68 Dudley St, Brookline, MA 02445

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4 beds3.5 baths2,924 sq ft

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New listings for sale in 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

$1,495,000

3 beds2 baths1,759 sq ft

12 Kilsyth Rd #3, Brookline, MA 02445

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3D WALKTHROUGH

$6,495,000

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OPEN SAT, 11:30AM TO 12:30PM

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Home values near 27 Upland Rd

Data from public records.

Address	Redfin Estimate
9 Upland Rd, Brookline, MA 6 Beds \| 3 Baths \| 3800 Sq. Ft.	$3,350,330
10 Upland Rd, Brookline, MA 4 Beds \| 2.5 Baths \| 2813 Sq. Ft.	$1,610,105

Address	Redfin Estimate
18 Upland Rd, Brookline, MA 6 Beds \| 2 Baths \| 2390 Sq. Ft.	$1,493,920
30 Upland Rd, Brookline, MA 6 Beds \| 2.5 Baths \| 3619 Sq. Ft.	$2,855,282

Address	Redfin Estimate
14 Upland Rd, Brookline, MA 6 Beds \| 2 Baths \| 2604 Sq. Ft.	$1,636,427
28 Upland Rd, Brookline, MA 3 Beds \| 2.5 Baths \| 1772 Sq. Ft.	$1,822,423

Property information provided by MLS PIN when last listed in 2019. This data may not show owner updates. 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 27 Upland Rd

Tax history for 27 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 27 Upland Rd

More real estate resources