66 Woodcliff Rd, Chestnut Hill, MA 02467

Off market feb 2007 for $795K

$1,791,644

Est. refi paymentEst. refi $4,062/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

$597Est. 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 minute ago

•Source:MLS PIN #70505288

Redfin Estimate

$1,791,644

$996K since sold in February 2007$8,000 since October

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 9.2% higher than the average sale price ($1.64M) of 6 comparable homes.

SOLD OCT 29, 2026
$1,450,000
A
3 beds2 baths2,100 sq ft
109 Wallis Rd, Chestnut Hill, MA 02467
SOLD JUL 1, 2026
$1,735,000
B
5 beds3 baths2,909 sq ft
25 Clearwater Rd, Chestnut Hill, MA 02467
SOLD SEP 15, 2026
$1,940,000
C
4 beds2.5 baths3,123 sq ft
142 Beverly Rd, Chestnut Hill, MA 02467
SOLD AUG 3, 2026
$1,355,000
D
3 beds2.5 baths2,590 sq ft
291 Russett Rd, Chestnut Hill, MA 02467
SOLD MAY 29, 2026
$1,690,000
E
4 beds2.5 baths2,511 sq ft
55 Bellingham Rd, Chestnut Hill, MA 02467
SOLD JUN 29, 2026
$1,670,000
F
4 beds2.5 baths2,408 sq ft
87 Payson Rd, Chestnut Hill, MA 02467

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Earn from this home

Sell

$1,396,850

Est. take-home

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Refinance

Est. cash available

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Rent

$5,532/mo

Redfin rental estimate

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Market trends in 02467, MA

Last updated October 2026

Buyer's Market

Seller's Market

Balanced market

Sale-to-list price

99.4%

0.1% MoM

Median sale price

$1.6M

$50K MoM

Avg. days on market

41d

15 days MoM

Recently sold homes

11 MoM

New listings for sale

EARLY ACCESS
$4,450,000
6 beds6 baths4,015 sq ft
23 Circuit Rd, Chestnut Hill, MA 02467
$3,200,000
6 beds5.5 baths4,730 sq ft
67 Moody St, Chestnut Hill, MA 02467
$16,000,000
5 beds6 baths6,640 sq ft
154 Woodland Rd, Chestnut Hill, MA 02467
$550,000
1 bed1.5 baths899 sq ft
250 Hammond Pond Pkwy Unit 310N, Chestnut Hill, MA 02467
EARLY ACCESS
$4,600,000
6 beds6 baths11,834 sq ft
106 Crafts Rd, Chestnut Hill, MA 02467
VIDEO TOUR
$1,599,000
3 beds2 baths2,114 sq ft
209 Commonwealth Ave Unit 2A, 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

K - 12
Preschool & daycare

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

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...
1 month ago • Brookline
Benjamin Ginsburg
Redfin Premier agent
155 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

0.31% 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

$1.70M – $2.06M

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Home values near 66 Woodcliff Rd

Data from public records.

Address	Redfin Estimate
46 Woodcliff Road, Chestnut Hill, MA 5 Beds \| 4 Baths \| 3360 Sq. Ft.	$2,609,467
54 Woodcliff Road, Chestnut Hill, MA 5 Beds \| 4 Baths \| 2575 Sq. Ft.	$1,674,406
80 Woodcliff Road, Chestnut Hill, MA 3 Beds \| 2.5 Baths \| 2065 Sq. Ft.	$1,652,989
43 Woodcliff Road, Chestnut Hill, MA 3 Beds \| 2.5 Baths \| 1839 Sq. Ft.	$1,499,825
65 Woodcliff Road, Chestnut Hill, MA 4 Beds \| 3 Baths \| 2581 Sq. Ft.	$1,716,790
85 Woodcliff Road, Chestnut Hill, MA 4 Beds \| 3.5 Baths \| 2747 Sq. Ft.	$1,845,178
861 W Roxbury Pkwy, Chestnut Hill, MA 4 Beds \| 2.5 Baths \| 2928 Sq. Ft.	$1,810,343

Address	Redfin Estimate
85 Woodcliff Road, Chestnut Hill, MA 4 Beds \| 3 Baths \| 3352 Sq. Ft.	$1,947,177
60 Woodcliff Road, Chestnut Hill, MA 4 Beds \| 3 Baths \| 3582 Sq. Ft.	$2,259,777
86 Woodcliff Road, Chestnut Hill, MA 4 Beds \| 3 Baths \| 4064 Sq. Ft.	$2,391,305
51 Woodcliff Road, Chestnut Hill, MA 3 Beds \| 2.5 Baths \| 1756 Sq. Ft.	$1,395,579
73 Woodcliff Road, Chestnut Hill, MA 4 Beds \| 3 Baths \| 1507 Sq. Ft.	$1,329,603
43 Woodcliff Road, Chestnut Hill, MA 6 Beds \| 3 Baths \| 2626 Sq. Ft.	$2,026,825
851 W Roxbury Pkwy, Chestnut Hill, MA 4 Beds \| 2 Baths \| 2912 Sq. Ft.	$1,749,537

Address	Redfin Estimate
46 Woodcliff Road, Chestnut Hill, MA 3 Beds \| 2.5 Baths \| 1980 Sq. Ft.	$1,372,195
74 Woodcliff Road, Chestnut Hill, MA 3 Beds \| 2.5 Baths \| 2050 Sq. Ft.	$1,395,213
92 Woodcliff Road, Chestnut Hill, MA 3 Beds \| 2.5 Baths \| - Sq. Ft.	$1,339,428
59 Woodcliff Road, Chestnut Hill, MA 3 Beds \| 3 Baths \| 2775 Sq. Ft.	$1,788,211
79 Woodcliff Road, Chestnut Hill, MA 3 Beds \| 2.5 Baths \| 1794 Sq. Ft.	$1,743,576
869 W Roxbury Pkwy, Chestnut Hill, MA 4 Beds \| 3.5 Baths \| 2455 Sq. Ft.	$1,920,295
882 W Roxbury Pkwy, Chestnut Hill, MA 4 Beds \| 2.5 Baths \| 2521 Sq. Ft.	$1,703,512

Property information provided by MLS PIN when last listed in 2007. This data may not show owner updates. Learn more.

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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

Local insights from Redfin agents

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