OFF MARKET

Off Market Nov 2011 for $2M

$3,948,843

Est. refi paymentEst. refi $4,736/mo

•

4,170

sq ft

21 Penniman Rd, Brookline, MA 02445

About this home

Wonderful tree-lined st.close to public transportation & playgrounds.Impressive 12RM/4.5BTH Col.beautifully renovated 2008-2009.1st fl has LR w/beamed ceiling & fp and gorgeous Kitch w/ ss appl,honed granite counters & white cab.Kitch & LR have access to tri-level deck w/ hot tub & blue stone patios.2nd fl has 3BRS/2BTH inc MSTR BR w/ dressing area,veranda & BTH w/ Jacuzzi/walk-in shower/double sinks.3rd fl has 2BRS/1BTH.Lower level has sep.entrance to Exercise RM,BR &BTH...ideal for au pair.

Single-familyProperty Type

1921Year Built

0.25 acresLot Size

$947Est. Price/Sq.Ft.

1 garage spacesParking

Listed by Tamar Harrison • Hammond Residential R. E.

Bought with Megan Kopman • Ballast Realty Group, LLC

Redfin checked: 2 minutes ago

•Source:MLS PIN #71249419

Redfin Estimate

$3,948,843

$1.9M since sold in November 2011$148K since July

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 15% higher than the average sale price ($3.43M) of 6 comparable homes.

SOLD JUN 15, 2026
$2,200,000
A
5 beds3.5 baths3,463 sq ft
401 Clinton Rd, Brookline, MA 02445
SOLD MAY 14, 2026
$3,285,000
B
5 beds4.5 baths3,658 sq ft
43 Druce St, Brookline, MA 02445
SOLD JUN 15, 2026
$3,300,000
C
4 beds4.5 baths3,628 sq ft
98 Spooner Rd, Chestnut Hill, MA 02467
SOLD APR 29, 2026
$3,085,000
D
6 beds5.5 baths3,907 sq ft
8 Penniman Rd, Brookline, MA 02445
SOLD MAY 28, 2026
$4,125,000
E
5 beds4.5 baths4,001 sq ft
34 Hyslop Rd, Brookline, MA 02445
SOLD MAY 4, 2026
$4,600,000
F
5 beds6.5 baths4,300 sq ft
3 Cleveland, Brookline, MA 02445

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Sell

$2,681,138

Est. take-home

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Est. cash available

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Rent

$8,299/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

$998,000
2 beds2 baths1,218 sq ft
1731 Beacon St #402, Brookline, MA 02445
$859,000
3 beds1.5 baths1,233 sq ft
124 Chestnut St #1, Brookline, MA 02445
$2,895,000
7 beds3.5 baths4,805 sq ft
71 Addington Rd, Brookline, MA 02445
$2,200,000
9 beds3 baths4,364 sq ft
26 Parkway 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
See all

Provided by Redfin

Sale history for 21 Penniman Rd

Date

Event

Price

MLS PIN #71249419

Nov 15, 2011

Sold

$2,062,500

$495/sq ft

Aug 29, 2011

Contingent

—

Aug 11, 2011

Price Changed

$2,345,000

$562/sq ft

Jun 16, 2011

Listed

$2,495,000

$598/sq ft

MLS PIN #30275662

Jan 29, 1999

Sold

$915,000

$219/sq ft

Dec 14, 1998

Listing Removed

—

Nov 13, 1998

Listed

$959,000

$230/sq ft

MLS PIN #50287937

Dec 22, 1995

Sold

$630,000

$151/sq ft

Aug 28, 1995

Listing Removed

—

May 31, 1995

Listed

$639,500

$153/sq ft

Public Records

Jul 2, 1987

Sold

$639,500

$153/sq ft

Year

Property tax

Land + Additions

Assessment*

2023

$30,885 (+2.7%)

$1,028,600 + $2,069,200

$3,097,800

2022

$30,063 (+8.1%)

$979,600 + $1,970,600

$2,950,200

2021

$27,800 (+7.9%)

$941,900 + $1,894,800

$2,836,700

2020

$25,774 (+5.9%)

$856,300 + $1,871,100

$2,727,400

2019

$24,339 (−0.9%)

$815,500 + $1,782,000

$2,597,500

2018

$24,549 (+1.5%)

$823,400 + $1,771,600

$2,595,000

2017

$24,187 (+1.4%)

$776,800 + $1,671,300

$2,448,100

2016

$23,849 (+4.4%)

$726,000 + $1,562,800

$2,288,800

2015

$22,846 (−4.7%)

$678,500 + $1,460,600

$2,139,100

2014

$23,961 (+0.7%)

$616,900 + $1,486,800

$2,103,700

2013

$23,794 (+2.2%)

$598,900 + $1,443,500

$2,042,400

2012

$23,283 (+7.6%)

$598,900 + $1,443,500

$2,042,400

2011

$21,634 (+3.2%)

$575,200 + $1,339,300

$1,914,500

2010

$20,971 (+14.9%)

$575,200 + $1,336,500

$1,911,700

2009

$18,248

$573,400 + $1,133,600

$1,707,000

Tax history for 21 Penniman Rd

Year

Property tax

Land + Additions

Assessment*

2023

$30,885 (+2.7%)

$1,028,600 + $2,069,200

$3,097,800

2022

$30,063 (+8.1%)

$979,600 + $1,970,600

$2,950,200

2021

$27,800 (+7.9%)

$941,900 + $1,894,800

$2,836,700

2020

$25,774 (+5.9%)

$856,300 + $1,871,100

$2,727,400

2019

$24,339 (−0.9%)

$815,500 + $1,782,000

$2,597,500

2018

$24,549 (+1.5%)

$823,400 + $1,771,600

$2,595,000

2017

$24,187 (+1.4%)

$776,800 + $1,671,300

$2,448,100

2016

$23,849 (+4.4%)

$726,000 + $1,562,800

$2,288,800

2015

$22,846 (−4.7%)

$678,500 + $1,460,600

$2,139,100

2014

$23,961 (+0.7%)

$616,900 + $1,486,800

$2,103,700

2013

$23,794 (+2.2%)

$598,900 + $1,443,500

$2,042,400

2012

$23,283 (+7.6%)

$598,900 + $1,443,500

$2,042,400

2011

$21,634 (+3.2%)

$575,200 + $1,339,300

$1,914,500

2010

$20,971 (+14.9%)

$575,200 + $1,336,500

$1,911,700

2009

$18,248

$573,400 + $1,133,600

$1,707,000

*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

0.25 Acres

Year renovated

1980

Sq. Ft.

3,750

Year built

1921

Style

Single Family Residential

County

Norfolk County

APN

38970

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jul 21, 2023.

Jul 11, 2016 • Active

Residential mechanical - sheet metal

Remove and replace the existing air conditioning system. Replace the indoor fan coil unit and outdoor condenser while keeping all existing ductwork.

HVAC

May 13, 2015 • Active

Residential building

Remove and replace water-damaged sheetrock, insulation, and trim.

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

Parking

Parking Information
Has Garage
Has Open Parking
# of Garage Spaces: 1
# of Covered Spaces: 1
Parking Spaces: 4
AttachedGarageYN: Yes
Parking Features: Attached, Under, Garage Door Opener, Insulated, Paved Drive, Paved

Interior

Master Bedroom Information
Area: 266
Length: 19
Width: 14
Level: Second
Features: Closet/Cabinets - Custom Built,Flooring - Hardwood,Flooring - Wall to Wall Carpet,Balcony / Deck,French Doors

Bedroom #2 Information
Area: 182
Length: 14
Width: 13
Level: Second
Features: Closet,Flooring - Hardwood

Bedroom #3 Information
Area: 196
Length: 14
Width: 14
Level: Second
Features: Closet,Flooring - Hardwood

Bedroom #4 Information
Area: 323
Length: 19
Width: 17
Level: Third
Features: Closet,Flooring - Hardwood

Bedroom #5 Information
Area: 304
Length: 19
Width: 16
Level: Third
Features: Closet,Flooring - Hardwood,Flooring - Wall to Wall Carpet

Bathroom Information
# of Bathrooms (Full): 4
# of Bathrooms (Half): 1
Master Bathroom Features: Yes

Bathroom #1 Information
Level: First
Features: Bathroom - Half,Flooring - Hardwood

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

Bathroom #3 Information
Level: Second
Features: Bathroom - Full,Flooring - Stone/Ceramic Tile,Countertops - Stone/Granite/Solid,Jacuzzi / Whirlpool Soaking Tub

Living Room Information
Area: 378
Length: 27
Width: 14
Level: First
Features: Closet/Cabinets - Custom Built,Flooring - Hardwood,Balcony / Deck,French Doors

Family Room Information
Area: 180
Length: 18
Width: 10
Level: First
Features: Flooring - Wall to Wall Carpet,French Doors

Dining Room Information
Area: 294
Length: 21
Width: 14
Level: First
Features: Flooring - Hardwood

Kitchen Information
Area: 252
Length: 18
Width: 14
Level: First
Features: Flooring - Hardwood,Balcony / Deck,Countertops - Stone/Granite/Solid,French Doors,Kitchen Island

Basement Information
Basement: Full, Finished, Walk-Out Access, Interior Entry, Garage Access, Concrete

Laundry Information
Laundry Features: Flooring - Stone/Ceramic Tile, Second Floor, Washer Hookup

Fireplace Information
Has Fireplace
# of Fireplaces (Total): 1
Fireplace Features: Living Room

Interior Features
# of Rooms (Total): 12
Door Features: French Doors
Window Features: Screens
Flooring: Wood, Tile, Carpet, Stone / Slate, Flooring - Hardwood, Flooring - Wall to Wall Carpet, Flooring - Stone/Ceramic Tile
Interior Features: Closet, Closet/Cabinets - Custom Built, Bathroom - Full, Entrance Foyer, Library, Bathroom, Bedroom, Exercise Room

Exterior

Building Information
Building Area (Total): 4,170
Foundation Details: Block
Year Built Source: Public Records
Year Built Details: Approximate
Color: Red Brick

Exterior Features
Roof: Slate, Rubber
Patio And Porch Features: Porch, Deck, Deck - Wood, Patio
Exterior Features: Porch, Deck, Deck - Wood, Patio, Rain Gutters, Hot Tub/Spa, Professional Landscaping, Sprinkler System, Screens

Pool Information
Has Spa
Spa Features: Private

Property Information
PropertySubType: Single Family Residence
Security Features: Security System

Lot Information
Lot Size (Acres): 0.25

Financial

Tax Information
Tax Annual Amount: $19,796
Tax Year: 2011

Utilities

Utility Information
Utilities: for Gas Range, Washer Hookup, Icemaker Connection
Sewer: Public Sewer, City/Town Sewer
Water Source: Public, City/Town Water

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

Location

Location Information
Directions: Dean Road to Penniman Road
UnparsedAddress: 21 Penniman Road, Brookline MA 02445

Community Information
Senior CommunityYN: No
Community Features: Public Transportation, Shopping, Tennis Court(s), Park, Walk/Jog Trails, Highway Access, House of Worship, Private School, Public School, T-Station, University

Public facts

Beds: 6
Baths: 4.5
Sq. Ft.: 3,750
Stories: 3.0
Lot Size: 0.25 acres
Style: Single Family Residential
Year Built: 1921
Year Renovated: 1980
County: Norfolk County
APN: 38970

Home facts updated by county records on Jul 20, 2023

Other

Miscellaneous Information
Heat Zones: 5

Listing Information
Exclusions: Tv In Master Bedroom Suite
StandardStatus: Closed

Around this home

Schools

Roland Hayes School

Public PreK-8 • Assigned • 0.4mi

9/10

Brookline High School

Public 9-12 • Assigned • 1.1mi

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
152 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

54% 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 9.2 hours in June and 4.4 hours in December, placing it below the U.S. average for solar exposure.

9.2 hrs

4.4 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$3.75M – $4.54M

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Nearby similar homes

$8,200,000

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5 beds4.5 baths5,234 sq ft

68 Dudley St, Brookline, MA 02445

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3 beds3.5 baths3,790 sq ft

331 Heath St, Chestnut Hill, MA 02467

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6 beds7 baths13,200 sq ft

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New listings for sale in 02445

$998,000

2 beds2 baths1,218 sq ft

1731 Beacon St #402, Brookline, MA 02445

$859,000

3 beds1.5 baths1,233 sq ft

124 Chestnut St #1, Brookline, MA 02445

$2,895,000

7 beds3.5 baths4,805 sq ft

71 Addington Rd, Brookline, MA 02445

$2,200,000

9 beds3 baths4,364 sq ft

26 Parkway 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

$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

Home values near 21 Penniman Rd

Data from public records.

Address	Redfin Estimate
44 Penniman Rd, Brookline, MA 5 Beds \| 4.5 Baths \| 5706 Sq. Ft.	$4,292,258
15 Penniman Rd, Brookline, MA 6 Beds \| 4.5 Baths \| 4186 Sq. Ft.	$3,858,505

Address	Redfin Estimate
47 Penniman Rd, Brookline, MA 6 Beds \| 3.5 Baths \| 3141 Sq. Ft.	$3,030,126
8 Penniman Rd, Brookline, MA 6 Beds \| 5.5 Baths \| 3907 Sq. Ft.	$3,781,514

Address	Redfin Estimate
9 Penniman Rd, Brookline, MA 5 Beds \| 4.5 Baths \| 4123 Sq. Ft.	$3,420,344
18 Penniman Rd, Brookline, MA 4 Beds \| 3.5 Baths \| 3031 Sq. Ft.	$3,733,471

Property information provided by MLS PIN when last listed in 2011. 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 21 Penniman Rd

Tax history for 21 Penniman 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 21 Penniman Rd

More real estate resources