66 Woodcliff Rd, Chestnut Hill, MA 02467

Off Market Feb 2007 for $795K

$1,773,294

Est. refi paymentEst. refi $4,102/mo

•

3,000

sq ft

66 Woodcliff Rd, Chestnut Hill, MA 02467

About this home

Designer's showcase! Stunning renovations throughout this spacious, bright and welcoming home on a lovely Chestnut Hill side street. State-of-the-art kitchen includes stainless steel Subzero refrigerator, Wolfe cooktop, Bosch dishwasher, Wine Cooler plus granite. Open living space leads to gorgeous enormous deck with hot tub overlooking lush grounds. Finished Lower Level for bonus living, work or recreation space. 2 car attached garage. Central Air and more! Home Warranty included.A must see.

Single-familyProperty Type

1950Year Built

8,461 sq ftLot Size

$591Est. Price/Sq.Ft.

2 garage spacesParking

Listed by Bernie Shore • Coldwell Banker Residential Brokerage - Brookline

Bought with Non Member • Non Member Office

Redfin checked: a few seconds ago

•Source:MLS PIN #70505288

Redfin Estimate

$1,773,294

$978K since sold in February 2007$6,000 since August

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 11.3% higher than the average sale price ($1.59M) of 6 comparable homes.

SOLD JUL 1, 2026
$1,735,000
A
5 beds3 baths2,909 sq ft
25 Clearwater Rd, Chestnut Hill, MA 02467
SOLD AUG 3, 2026
$1,355,000
B
3 beds2.5 baths2,590 sq ft
291 Russett Rd, Chestnut Hill, MA 02467
SOLD MAY 29, 2026
$1,690,000
C
4 beds2.5 baths2,511 sq ft
55 Bellingham Rd, Chestnut Hill, MA 02467
SOLD JUN 29, 2026
$1,670,000
D
4 beds2.5 baths2,408 sq ft
87 Payson Rd, Chestnut Hill, MA 02467
SOLD AUG 14, 2026
$1,459,450
E
3 beds2.5 baths2,576 sq ft
63 Mossdale Rd, Jamaica Plain, MA 02130
SOLD JAN 23, 2026
$1,650,000
F
3 beds3.5 baths2,426 sq ft
83 Payson Rd, Chestnut Hill, MA 02467

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Earn from this home

Sell

$1,375,410

Est. take-home

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Refinance

Est. cash available

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Rent

$5,367/mo

Redfin rental estimate

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Market trends in 02467, MA

Last updated August 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-List Price

99.5%

+0.1% MoM

Median sale price

$1.5M

$21K MoM

Avg. days on market

26d

4 days MoM

Recently sold homes

1 MoM

New listings for sale

NEW 22 HRS AGO
$4,980,000
5 beds5.5 baths5,919 sq ft
90 Suffolk Rd, Chestnut Hill, MA 02467
$1,595,000
3 beds2 baths2,100 sq ft
109 Wallis Rd, Chestnut Hill, MA 02467
$2,495,000
4 beds3.5 baths4,614 sq ft
214 Allandale Rd Unit D, Chestnut Hill, MA 02467
LISTED BY REDFIN
$869,000
2 beds2 baths1,310 sq ft
250 Hammond Pond Pkwy Unit 1006N, Chestnut Hill, MA 02467
$549,000
1 bed1.5 baths1,060 sq ft
280 Boylston St #908, Chestnut Hill, MA 02467
$459,000
1 bed1 bath650 sq ft
37 Commonwealth Ave #12, Chestnut Hill, MA 01742
$2,495,000
4 beds4.5 baths4,340 sq ft
79 Woodchester Dr, Chestnut Hill, MA 02467
$2,599,000
9 beds4.5 baths4,464 sq ft
8 White Ave, Chestnut Hill, MA 02467
$1,300,000
2 beds2 baths1,522 sq ft
629 Hammond St Unit E119, Chestnut Hill, MA 02467
$299,999
1 bed1 bath625 sq ft
40 Bryon Rd #4, Chestnut Hill, MA 02467
See all

Provided by Redfin

Sale history for 66 Woodcliff Rd

Date

Event

Price

MLS PIN #70505288

Feb 28, 2007

Sold

$795,600

$265/sq ft

Jan 22, 2007

Listing Removed

—

Jan 4, 2007

Listed

$829,900

$277/sq ft

MLS PIN #30411813

Jul 20, 2000

Sold

$601,500

$201/sq ft

May 21, 2000

Listing Removed

—

May 15, 2000

Listed

$595,000

$198/sq ft

Year

Property tax

Land + Additions

Assessment*

2023

$11,468 (+2.7%)

$554,500 + $595,800

$1,150,300

2022

$11,163 (+8.1%)

$528,100 + $567,400

$1,095,500

2021

$10,323 (+9.5%)

$507,800 + $545,600

$1,053,400

2020

$9,429 (+5.9%)

$461,600 + $536,200

$997,800

2019

$8,904 (−6.3%)

$439,600 + $510,700

$950,300

2018

$9,502 (+1.5%)

$439,700 + $564,700

$1,004,400

2017

$9,361 (+1.5%)

$414,800 + $532,700

$947,500

2016

$9,227 (+4.4%)

$387,700 + $497,800

$885,500

2015

$8,839 (+2.9%)

$362,300 + $465,300

$827,600

2014

$8,590 (+0.7%)

$329,400 + $424,800

$754,200

2013

$8,530 (+2.2%)

$319,800 + $412,400

$732,200

2012

$8,347 (−1.3%)

$319,800 + $412,400

$732,200

2011

$8,455 (+3.0%)

$316,100 + $432,100

$748,200

2010

$8,208 (−11.2%)

$316,100 + $432,100

$748,200

2009

$9,243

$316,100 + $548,500

$864,600

Tax history for 66 Woodcliff Rd

Year

Property tax

Land + Additions

Assessment*

2023

$11,468 (+2.7%)

$554,500 + $595,800

$1,150,300

2022

$11,163 (+8.1%)

$528,100 + $567,400

$1,095,500

2021

$10,323 (+9.5%)

$507,800 + $545,600

$1,053,400

2020

$9,429 (+5.9%)

$461,600 + $536,200

$997,800

2019

$8,904 (−6.3%)

$439,600 + $510,700

$950,300

2018

$9,502 (+1.5%)

$439,700 + $564,700

$1,004,400

2017

$9,361 (+1.5%)

$414,800 + $532,700

$947,500

2016

$9,227 (+4.4%)

$387,700 + $497,800

$885,500

2015

$8,839 (+2.9%)

$362,300 + $465,300

$827,600

2014

$8,590 (+0.7%)

$329,400 + $424,800

$754,200

2013

$8,530 (+2.2%)

$319,800 + $412,400

$732,200

2012

$8,347 (−1.3%)

$319,800 + $412,400

$732,200

2011

$8,455 (+3.0%)

$316,100 + $432,100

$748,200

2010

$8,208 (−11.2%)

$316,100 + $432,100

$748,200

2009

$9,243

$316,100 + $548,500

$864,600

*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

8,461

Year renovated

1969

Sq. Ft.

3,000

Year built

1950

Style

Single Family Residential

County

Norfolk County

APN

42170

Parking Spaces

Basement

Yes

Accessible

HOA Dues

—

Garage

Yes

Features

Pool

Last updated by owner on Oct 12, 2022.

Jul 30, 2025 • Active

Residential building

Repair an existing drain cover and pave over the existing driveway. No changes will be made to the driveway layout. All work must comply with building codes and zoning bylaws.

Grading

Feb 27, 2013 • Active

Residential building

Perform air sealing and insulation work on a residential building.

HVAC

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: 2
# of Covered Spaces: 2
Parking Spaces: 4
AttachedGarageYN: Yes
Parking Features: Under, Garage Door Opener, Paved Drive

Interior

Master Bedroom Information
Area: 234
Length: 18
Width: 13
Level: First
Features: Bathroom - Full,Flooring - Hardwood

Bedroom #2 Information
Area: 156
Length: 13
Width: 12
Level: First
Features: Flooring - Hardwood

Bedroom #3 Information
Area: 182
Length: 14
Width: 13
Level: First
Features: Flooring - Hardwood

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

Bathroom #1 Information
Level: First

Bathroom #2 Information
Level: First

Bathroom #3 Information
Level: Basement

Living Room Information
Area: 330
Length: 22
Width: 15
Level: First
Features: Flooring - Hardwood

Family Room Information
Area: 513
Length: 27
Width: 19
Level: Basement
Features: Flooring - Stone/Ceramic Tile

Dining Room Information
Area: 195
Length: 15
Width: 13
Level: First
Features: Flooring - Hardwood

Kitchen Information
Area: 234
Length: 18
Width: 13
Level: First
Features: Flooring - Hardwood,Countertops - Stone/Granite/Solid

Basement Information
Basement: Finished, Garage Access

Laundry Information
Laundry Features: In Basement, Washer Hookup

Fireplace Information
Has Fireplace
# of Fireplaces (Total): 2
Fireplace Features: Family Room, Living Room

Interior Features
# of Rooms (Total): 8
Window Features: Skylight(s), Insulated Windows
Flooring: Wood, Tile, Marble, Flooring - Stone/Ceramic Tile
Interior Features: Cedar Closet(s), Sun Room, Foyer

Exterior

Building Information
Building Area (Total): 3,000
Foundation Details: Concrete Perimeter
Construction Materials: Frame
Year Built Source: Public Records
Year Built Details: Actual

Exterior Features
Roof: Shingle
Patio And Porch Features: Deck
Exterior Features: Deck, Hot Tub/Spa, Professional Landscaping, Sprinkler System

Pool Information
Has Spa
Spa Features: Private

Property Information
PropertySubType: Single Family Residence

Lot Information
Lot Size (Acres): 0.19
Lot Features: Wooded
Road Surface Type: Paved
Road Frontage Type: Public, Dead End

Financial

Tax Information
Tax Annual Amount: $5,917.48
Tax Year: 2007

Utilities

Utility Information
Utilities: Washer Hookup
Sewer: Public Sewer, City/Town Sewer
Water Source: Public, City/Town Water

Heating & Cooling
Has Heating
Has Cooling
Heating: Hot Water, Oil
Cooling: Central Air

Location

Location Information
Directions: West Roxbury Pky to Intervale to Woodcliff
UnparsedAddress: 66 Woodcliff Rd, Brookline MA 02467

Community Information
Senior CommunityYN: No
Community Features: Public Transportation, Shopping, Pool, Tennis Court(s), Golf

Public facts

Beds: 3
Baths: 3.0
Sq. Ft.: 3,000
Stories: 1.0
Parking Spaces: 4
Basement: Yes
Accessible: No
Lot Size: 8,461 square feet
Style: Single Family Residential
Year Built: 1950
Year Renovated: 1969
County: Norfolk County
APN: 42170
HOA Dues: —
Garage: Yes
Features: Pool

Home facts updated by owner on Oct 12, 2022

Other

Miscellaneous Information
Heat Zones: 3

Listing Information
Exclusions: See Broker-Dining Room Light Fixture
StandardStatus: Closed

Around this home

Schools

Baker School

Public K-8 • Assigned • 0.6mi

9/10

Brookline High School

Public 9-12 • Assigned • 2.5mi

8/10

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

Climate risks

1/10 Flood Factor

Minimal risk of a flood reaching the building in the next 30 years

3/10 Fire Factor

0.31% 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

56% 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

Chestnut Hill, MA • 02467

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

$1.69M – $2.04M

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Nearby similar homes

$1,595,000

3 beds2 baths2,100 sq ft

109 Wallis Rd, Chestnut Hill, MA 02467

$1,790,000

4 beds3 baths2,500 sq ft

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3D WALKTHROUGH

$2,899,900

4 beds3.5 baths4,571 sq ft

28 Kesseler Way, Chestnut Hill, MA 02467

$1,275,000

6 beds4.5 baths4,171 sq ft

16 Bobolink St, West Roxbury, MA 02132

3D WALKTHROUGH

$819,000

4 beds2 baths1,572 sq ft

18 Thurlow St, West Roxbury, MA 02132

$874,900

3 beds1.5 baths2,188 sq ft

79 Redlands Rd, West Roxbury, MA 02132

New listings for sale in 02467

NEW 22 HRS AGO

$4,980,000

5 beds5.5 baths5,919 sq ft

90 Suffolk Rd, Chestnut Hill, MA 02467

$1,595,000

3 beds2 baths2,100 sq ft

109 Wallis Rd, Chestnut Hill, MA 02467

$2,495,000

4 beds3.5 baths4,614 sq ft

214 Allandale Rd Unit D, Chestnut Hill, MA 02467

LISTED BY REDFIN3D WALKTHROUGH

$869,000

2 beds2 baths1,310 sq ft

250 Hammond Pond Pkwy Unit 1006N, Chestnut Hill, MA 02467

$549,000

1 bed1.5 baths1,060 sq ft

280 Boylston St #908, Chestnut Hill, MA 02467

$459,000

1 bed1 bath650 sq ft

37 Commonwealth Ave #12, Chestnut Hill, MA 01742

$2,495,000

4 beds4.5 baths4,340 sq ft

79 Woodchester Dr, Chestnut Hill, MA 02467

$2,599,000

9 beds4.5 baths4,464 sq ft

8 White Ave, Chestnut Hill, MA 02467

$1,300,000

2 beds2 baths1,522 sq ft

629 Hammond St Unit E119, Chestnut Hill, MA 02467

Home values near 66 Woodcliff Rd

Data from public records.

Address	Redfin Estimate
46 Woodcliff Road, Chestnut Hill, MA 3 Beds \| 2.5 Baths \| 1980 Sq. Ft.	$1,357,595
74 Woodcliff Road, Chestnut Hill, MA 3 Beds \| 2.5 Baths \| 2050 Sq. Ft.	$1,388,453

Address	Redfin Estimate
54 Woodcliff Road, Chestnut Hill, MA 5 Beds \| 4 Baths \| 2575 Sq. Ft.	$1,693,487
80 Woodcliff Road, Chestnut Hill, MA 3 Beds \| 2.5 Baths \| 2065 Sq. Ft.	$1,640,077

Address	Redfin Estimate
60 Woodcliff Road, Chestnut Hill, MA 4 Beds \| 3 Baths \| 3582 Sq. Ft.	$2,247,564
86 Woodcliff Road, Chestnut Hill, MA 4 Beds \| 3 Baths \| 4064 Sq. Ft.	$2,327,935

Property information provided by MLS PIN when last listed in 2007. 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 02467, MA

Sale history for 66 Woodcliff Rd

Tax history for 66 Woodcliff Rd

Public record

Property details

Around this home

Schools

Lifestyle

Climate risks

Historical weather

Sun exposure

Nearby similar homes

New listings for sale in 02467

Home values near 66 Woodcliff Rd

More real estate resources