OFF MARKET

Off Market Apr 2020 for $3.2M

$4,293,369

Est. refi paymentEst. refi $5,836/mo

•

7,422

sq ft

106 Old Orchard Rd, Chestnut Hill, MA 02467

About this home

Stunning brick colonial in desired Chestnut Hill community with over 7,000 sf of living space on 1/2 acre. Enter the grand foyer featuring marble, radiant heated floors and bridal staircase. Home flows into a chef’s kitchen equipped with top of the line appliances, custom cabinets and granite countertops. Sun drenched family room boasts stone fireplace and wet bar. Formal living room with palladium windows and fireplace opens to a sophisticated office with built in bookcase. French doors lead to 4 season sunroom, stone patio and private yard. Second floor offers master suite with deck, fireplace, en-suite bathroom with Jacuzzi, sauna and custom built walk in closet. Upper level has three additional large bedrooms, au-pair suite and playroom. Finished basement with theater room, bar, wine cellar, exercise room, laundry and abundant storage. 3 car garage direct entry into mudroom with built in storage. Minutes to shops and restaurants, T stop and renowned school system.

Single-familyProperty Type

1989Year Built

0.52 acresLot Size

$578Est. Price/Sq.Ft.

3 garage spacesParking

Listed by Michael Carucci • Gibson Sotheby's International Realty

Bought with Amy Lipton • Coldwell Banker Residential Brokerage - Brookline

Redfin checked: a minute ago

•Source:MLS PIN #72624462

Redfin Estimate

$4,293,369

$1.0M since sold in April 2020$46K since August

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 5.9% higher than the average sale price ($4.05M) of 6 comparable homes.

SOLD JUL 28, 2026
$3,375,000
A
5 beds4.5 baths4,922 sq ft
171 Hobart Rd, Newton, MA 02459
SOLD JUN 12, 2026
$4,805,000
B
6 beds5.5 baths4,918 sq ft
75 Dalton Rd, Newton, MA 02459
SOLD AUG 4, 2026
$4,500,000
C
5 beds6 baths7,522 sq ft
66 Montrose St, Newton, MA 02458
SOLD AUG 4, 2026
$5,750,000
D
5 beds7.5 baths7,359 sq ft
124 Chestnut Hill Rd, Chestnut Hill, MA 02467
SOLD AUG 18, 2026
$3,250,000
E
6 beds4.5 baths5,150 sq ft
49 Buswell Park, Newton, MA 02458
SOLD JUL 23, 2026
$2,650,000
F
5 beds4.5 baths6,260 sq ft
81 Brackett Rd, Newton, MA 02458

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Earn from this home

Sell

$1,801,590

Est. take-home

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Refinance

Est. cash available

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Rent

$6,911/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

99.4%

+1.0% MoM

Median sale price

$1.5M

$85K MoM

Avg. days on market

31d

2 days MoM

Recently sold homes

11 MoM

New listings for sale

NEW 4 HRS AGO
$799,000
2 beds2 baths1,551 sq ft
280 Boylston St #411, Chestnut Hill, MA 02467
OPEN TODAY, 10AM TO 11AM
$3,995,000
4 beds4.5 baths4,884 sq ft
17 Glenoe Rd, Brookline, MA 02445
OPEN TODAY, 11:30AM TO 12:30PM
$3,100,000
5 beds4.5 baths3,913 sq ft
284 Woodland Rd, Chestnut Hill, MA 02467
OPEN TODAY, 11:30AM TO 1PM
$1,699,000
3 beds2 baths2,607 sq ft
154 Bellingham Rd, Chestnut Hill, MA 02467
NEW 11 HRS AGO
$3,750,000
4 beds4.5 baths4,500 sq ft
63-65 Commonwealth Ave #65, Chestnut Hill, MA 02467
NEW 11 HRS AGO
$3,750,000
4 beds4.5 baths4,500 sq ft
65 Commonwealth Ave, Chestnut Hill, MA 02467
OPEN SAT, 12PM TO 1:30PM
$795,000
2 beds2 baths1,495 sq ft
20 Hammond Pond Pkwy #504, Chestnut Hill, MA 02467
NEW 34 HRS AGO
$2,765,000
5 beds3.5 baths4,028 sq ft
401 Heath St, Chestnut Hill, MA 02467
OPEN FRI, 5:30PM TO 6:30PM
$1,790,000
4 beds3 baths2,500 sq ft
133 Wolcott Rd, Chestnut Hill, MA 02467
$698,000
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2430 Beacon St #104, Chestnut Hill, MA 02467
See all

Provided by Redfin

Redfin agents who toured

Large and multiple windows letting in a lot of light throughout the home. Many nice renovations and upgrades including kitchen and baths. Half of backyard area is a bit of a hill and other half is flatter offering more space suitable for outdoor...
7 years ago• May not reflect the current state of the home
Annie Bergen
Redfin agent

Sale history for 106 Old Orchard Rd

Date

Event

Price

MLS PIN #72624462

Apr 10, 2020

Sold

$3,260,000

$439/sq ft

Mar 6, 2020

Pending

—

Feb 21, 2020

Listed

$3,699,000

$498/sq ft

MLS PIN #71136623

May 13, 2011

Sold

$2,548,000

$343/sq ft

Feb 28, 2011

Contingent

—

Oct 26, 2010

Price Changed

$2,900,000

$391/sq ft

Sep 14, 2010

Listed

$3,095,000

$417/sq ft

Olde Chestnut Hill. Constructed in 1989 this exquisite 13 room brick French country style colonial is sited on a half acre lot. The 5,800 +/- square foot residence provides splendid architectural detail and masterful workmanship. There are grand formal rooms, inviting family rooms and 5+ bedrooms. Expansive family room with a stone hearth and chimney leading to a solarium and library. Fabulous cook's kitchen featuring an AGA Stove. Three car garage.

Public Records

Jun 20, 1991

Sold

$975,000

$131/sq ft

Public Records

Jun 21, 1988

Sold

$420,000

$57/sq ft

Year

Property tax

Land + Additions

Assessment*

2026

$39,035 (+3.8%)

$2,097,800 + $1,930,600

$4,028,400

2025

$37,599 (+3.4%)

$1,997,900 + $1,838,700

$3,836,600

2024

$36,355 (+3.6%)

$1,939,700 + $1,785,200

$3,724,900

2023

$35,085 (+5.2%)

$1,528,600 + $1,917,900

$3,446,500

2022

$33,359 (−1.3%)

$1,486,100 + $1,684,900

$3,171,000

2021

$33,798 (+3.1%)

$1,402,000 + $1,739,100

$3,141,100

2020

$32,793 (+2.9%)

$1,402,000 + $1,739,100

$3,141,100

2019

$31,868 (−14.3%)

$1,361,200 + $1,688,400

$3,049,600

2018

$37,197 (+3.1%)

$1,164,700 + $2,273,100

$3,437,800

2017

$36,064 (+4.6%)

$1,098,800 + $2,144,400

$3,243,200

2016

$34,493 (+4.9%)

$1,026,900 + $2,004,100

$3,031,000

2015

$32,888 (+9.4%)

$959,700 + $1,873,000

$2,832,700

2014

$30,053 (+5.5%)

$874,900 + $1,604,700

$2,479,600

2013

$28,491 (+2.9%)

$874,900 + $1,604,700

$2,479,600

2012

$27,697 (+21.9%)

$874,900 + $1,604,700

$2,479,600

2011

$22,728 (+2.6%)

$864,100 + $1,221,000

$2,085,100

2010

$22,149 (+2.4%)

$881,700 + $1,246,000

$2,127,700

2009

$21,624

$899,700 + $1,271,400

$2,171,100

Tax history for 106 Old Orchard Rd

Year

Property tax

Land + Additions

Assessment*

2026

$39,035 (+3.8%)

$2,097,800 + $1,930,600

$4,028,400

2025

$37,599 (+3.4%)

$1,997,900 + $1,838,700

$3,836,600

2024

$36,355 (+3.6%)

$1,939,700 + $1,785,200

$3,724,900

2023

$35,085 (+5.2%)

$1,528,600 + $1,917,900

$3,446,500

2022

$33,359 (−1.3%)

$1,486,100 + $1,684,900

$3,171,000

2021

$33,798 (+3.1%)

$1,402,000 + $1,739,100

$3,141,100

2020

$32,793 (+2.9%)

$1,402,000 + $1,739,100

$3,141,100

2019

$31,868 (−14.3%)

$1,361,200 + $1,688,400

$3,049,600

2018

$37,197 (+3.1%)

$1,164,700 + $2,273,100

$3,437,800

2017

$36,064 (+4.6%)

$1,098,800 + $2,144,400

$3,243,200

2016

$34,493 (+4.9%)

$1,026,900 + $2,004,100

$3,031,000

2015

$32,888 (+9.4%)

$959,700 + $1,873,000

$2,832,700

2014

$30,053 (+5.5%)

$874,900 + $1,604,700

$2,479,600

2013

$28,491 (+2.9%)

$874,900 + $1,604,700

$2,479,600

2012

$27,697 (+21.9%)

$874,900 + $1,604,700

$2,479,600

2011

$22,728 (+2.6%)

$864,100 + $1,221,000

$2,085,100

2010

$22,149 (+2.4%)

$881,700 + $1,246,000

$2,127,700

2009

$21,624

$899,700 + $1,271,400

$2,171,100

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

Public record

Beds

Baths

6.5

Stories

Lot width

—

Lot depth

—

Lot size

22,670

Year renovated

2021

Sq. Ft.

7,422

Year built

1989

Style

Single Family Residential

County

Middlesex County

APN

2389420S

Parking Spaces

Basement

Yes

Accessible

HOA Dues

—

Garage

Yes

Features

Pool

Last updated by owner on Aug 19, 2022.

Property details

Parking

Parking Information
Has Garage
# of Garage Spaces: 3
# of Covered Spaces: 3
Parking Spaces: 4
AttachedGarageYN: Yes
Parking Features: Attached

Interior

Bathroom Information
# of Bathrooms (Full): 6
# of Bathrooms (Half): 1
Master Bathroom Features: Yes

Basement Information
Basement: Partially Finished

Fireplace Information
Has Fireplace
# of Fireplaces (Total): 5

Interior Features
# of Rooms (Total): 16

Exterior

Building Information
Building Area (Total): 7,422
Year Built Source: Public Records
Year Built Details: Actual
Lead Paint: None

Property Information
PropertySubType: Single Family Residence

Lot Information
Lot Size (Acres): 0.52
Lot Features: Corner Lot

Financial

Tax Information
Tax Annual Amount: $31,868
Tax Year: 2019

Utilities

Utility Information
Sewer: Public Sewer
Water Source: Public

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

Location

Location Information
Directions: Hammond Street to Old Orchard Road.
UnparsedAddress: 106 Old Orchard Rd, Newton MA 02467

Community Information
Senior CommunityYN: No

Public facts

Beds: 6
Baths: 6.5
Sq. Ft.: 7,422
Stories: 2.0
Parking Spaces: 6
Basement: Yes
Accessible: No
Lot Size: 0.52 acres
Style: Single Family Residential
Year Built: 1989
Year Renovated: 2021
County: Middlesex County
APN: 2389420S
HOA Dues: —
Garage: Yes
Features: Pool

Home facts updated by owner on Aug 19, 2022

Other

Listing Information
StandardStatus: Closed

Around this home

Schools

Bowen

Public K-5 • Assigned • 1.0mi

8/10

Oak Hill Middle School

Public 6-8 • Assigned • 1.6mi

8/10

Newton South High School

Public 9-12 • Assigned • 1.4mi

10/10

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

Local insights from Redfin agents

Comprising 13 distinct 'villages,' Newton remains a fiercely competitive Seller's market. With restrictive zoning, multiple T stops, and a suburban setting near Boston, this highly desirable, built-out city lacks new buildable land, ensuring new...
2 months ago • Newton
Benjamin Ginsburg
Redfin Premier agent
153 deals
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Climate risks

1/10 Flood Factor

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

1/10 Fire Factor

Unlikely to be in a wildfire in next 30 years

5/10 Heat Factor

7 days above 96° expected this year, 14 days in 30 years

6/10 Wind Factor

54% chance of strong winds in next 30 years

2/10 Air Factor

1 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

$4.08M – $4.94M

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Home values near 106 Old Orchard Rd

Data from public records.

Address	Redfin Estimate
25 Old Orchard Road, Chestnut Hill, MA 5 Beds \| 3.5 Baths \| 4330 Sq. Ft.	$3,833,810
109 Old Orchard Road, Chestnut Hill, MA 5 Beds \| 3.5 Baths \| 3656 Sq. Ft.	$2,756,084

Address	Redfin Estimate
81 Old Orchard Road, Chestnut Hill, MA 5 Beds \| 4.5 Baths \| 4207 Sq. Ft.	$3,347,545
119 Old Orchard Road, Chestnut Hill, MA 6 Beds \| 4 Baths \| 3395 Sq. Ft.	$2,730,072

Address	Redfin Estimate
101 Old Orchard Road, Chestnut Hill, MA 3 Beds \| 2.5 Baths \| 2924 Sq. Ft.	$3,302,941
116 Old Orchard Road, Chestnut Hill, MA 6 Beds \| 5.5 Baths \| 5165 Sq. Ft.	$3,590,499

Property information provided by MLS PIN when last listed in 2020. 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

Redfin agents who toured

Sale history for 106 Old Orchard Rd

Tax history for 106 Old Orchard 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 106 Old Orchard Rd

More real estate resources