Google street view image for 106 Old Orchard Rd, Chestnut Hill, MA 02467

Off market

$4,171,983

•

6.5 ba

•

5,287

sq ft

106 Old Orchard Rd, Chestnut Hill, MA 02467

About this home

106 Old Orchard Rd is a 5,287 square foot house on a 0.52 acre lot with 6 bedrooms and 6.5 bathrooms. Based on Redfin's Chestnut Hill data, we estimate the home's value is $4,171,983.

Single-familyProperty Type

1989Year Built

0.52 acresLot Size

$789Est. Price/Sq.Ft.

Source:Public Records

Redfin Estimate

$4,171,983

$43K since October

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 11.9% higher than the average sale price ($3.73M) 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 NOV 2, 2026
$4,300,000
B
4 beds4.5 baths5,229 sq ft
7 Monadnock Rd, Chestnut Hill, MA 02467
SOLD JUN 12, 2026
$4,805,000
C
6 beds5.5 baths4,918 sq ft
75 Dalton Rd, Newton, MA 02459
SOLD AUG 18, 2026
$3,250,000
D
6 beds4.5 baths5,150 sq ft
49 Buswell Park, Newton, MA 02458
SOLD SEP 24, 2026
$3,855,000
E
5 beds5.5 baths8,000 sq ft
85 Gate House Rd, Chestnut Hill, MA 02467
SOLD AUG 4, 2026
$2,775,000
F
5 beds3.5 baths4,276 sq ft
99 Huntington Rd, Newton, MA 02458

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Earn from this home

Sell

$3,964,220

Est. take-home

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Rent

$7,379/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

97.1%

2.3% MoM

Median sale price

$1.6M

$69K MoM

Avg. days on market

83d

42 days MoM

Recently sold homes

15 MoM

New listings for sale

NEW 19 HRS AGO
$1,299,000
2 beds2.5 baths1,514 sq ft
321 Hammond Pond Pkwy #201, Chestnut Hill, MA 02467
$4,475,000
6 beds5.5 baths4,015 sq ft
23 Circuit Rd, Chestnut Hill, MA 02467
EARLY ACCESS
Unknown
2 beds2 baths884 sq ft
99 Florence St, Chestnut Hill, MA 02467
VIDEO TOUR
$1,995,000
5 beds4.5 baths3,812 sq ft
91 Spooner Rd, Chestnut Hill, MA 02467
OPEN TODAY, 12:30PM TO 2PM
$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
See all

Provided by Redfin

Sale history for 106 Old Orchard Rd

As the MLS and public records start to fill up, we'll list the details here.

Tax history for 106 Old Orchard Rd

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

Property details

Interior

Basement Information
Basement Sq. Ft: 1,914
Basement Type: Partial

Bathroom Information
# of Full Baths: 6
# of 1/2 Baths: 1

Heating & Cooling
Heating Type: Forced Air

Fireplace Information
# of Fireplaces: 5
Has Fireplace

Room Information
# of Rooms: 12

Exterior

Exterior Information
Physical Condition: Average
Building Style Type: Colonial
Construction Type: Concrete
Exterior Wall: Wood Siding/Shingle
Roof Shape Type: Hip

Property Information
Living Sq. Ft: 5,287
Gross Sq. Ft: 10,905
Ground Floor Sq. Ft: 3,549
# of Units: 1
# of Stories: 2

Parking & Garage Information
Parking Type: Basement Garage
Garage / Carport Type: Basement

Lot Information
# of Buildings: 1
Land Sq. Ft: 22,651
Municipality Name: NEWTON
Acres: 0.52
Zoning Code: SR1
State Use Description: 1-FAMILY RESIDENCE

Financial

Assessor Information
Assessment Year: 2026

Public facts

Beds: 6
Baths: 6.5
Sq. Ft.: 5,287
Stories: 2.0
Lot Size: 0.52 acres
Style: Single Family Residential
Year Built: 1989
Year Renovated: —
County: Middlesex County
APN: 2389420

Home facts updated by county records on Apr 25, 2026

Around this home

Schools

K - 12
Preschool & daycare

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
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

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)

34°

21°

36°

22°

51°

33°

59°

42°

68°

52°

80°

62°

84°

66°

79°

61°

74°

57°

63°

48°

52°

38°

39°

26°

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

Try the sun simulator tool to see how light moves across the property at different times of day and year.

Provided by Shadowmap

Estimated sale price

$3.96M – $4.80M

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Nearby similar homes

$4,475,000

6 beds5.5 baths4,015 sq ft

23 Circuit Rd, Chestnut Hill, MA 02467

French doors • Dual walk-in closets • 0.28 acre lot

OPEN TODAY, 12:30PM TO 2PM

$3,200,000

6 beds5.5 baths4,730 sq ft

67 Moody St, Chestnut Hill, MA 02467

Exquisite millwork • Soaring ceilings • White oak floors

3D WALKTHROUGH

$2,999,000

7 beds4 baths7,006 sq ft

945 Beacon St, Newton, MA 02459

Victorian home • Hand-carved details • 0.43 acre lot

$4,980,000

5 beds5.5 baths5,919 sq ft

90 Suffolk Rd, Chestnut Hill, MA 02467

Private acre • Cooks kitchen • In-law suite

$2,450,000

5 beds4 baths4,715 sq ft

127 Commonwealth Ave, Chestnut Hill, MA 02467

Chestnut hill • Green b line • Colonial estate

$2,550,000

6 beds5 baths4,112 sq ft

22 Bracebridge Rd, Newton, MA 02459

Large foyer • Period details • Fireplace

New listings for sale in 02467

NEW 19 HRS AGO

$1,299,000

2 beds2.5 baths1,514 sq ft

321 Hammond Pond Pkwy #201, Chestnut Hill, MA 02467

Open floor plan • Hardwood floors • Custom closets

$4,475,000

6 beds5.5 baths4,015 sq ft

23 Circuit Rd, Chestnut Hill, MA 02467

French doors • Dual walk-in closets • 0.28 acre lot

EARLY ACCESSCOLDWELL BANKER REALTY COMING SOON

Unknown

2 beds2 baths884 sq ft

99 Florence St, Chestnut Hill, MA 02467

Updated kitchen • Granite countertop • Renovated bathrooms

VIDEO TOUR

$1,995,000

5 beds4.5 baths3,812 sq ft

91 Spooner Rd, Chestnut Hill, MA 02467

Interior courtyard • Fireplace office • 0.8 acre lot

OPEN TODAY, 12:30PM TO 2PM

$3,200,000

6 beds5.5 baths4,730 sq ft

67 Moody St, Chestnut Hill, MA 02467

Exquisite millwork • Soaring ceilings • White oak floors

$16,000,000

5 beds6 baths6,640 sq ft

154 Woodland Rd, Chestnut Hill, MA 02467

New construction • Golf course views • Limestone façade

Home values near 106 Old Orchard Rd

Data from public records.

Address	Redfin Estimate
81 Old Orchard Rd, Chestnut Hill, MA 5 Beds \| 4.5 Baths \| 4207 Sq. Ft.	$3,075,399
119 Old Orchard Rd, Chestnut Hill, MA 6 Beds \| 4 Baths \| 3395 Sq. Ft.	$2,568,588
26 Old Orchard Rd, Chestnut Hill, MA 8 Beds \| 3.5 Baths \| 4488 Sq. Ft.	$3,170,296
109 Old Orchard Rd, Chestnut Hill, MA 4 Beds \| 3.5 Baths \| 2856 Sq. Ft.	$2,443,208
14 Old Orchard Rd, Chestnut Hill, MA 6 Beds \| 7 Baths \| 7102 Sq. Ft.	$6,234,533
37 Woodman Rd, Chestnut Hill, MA 5 Beds \| 5.5 Baths \| 4711 Sq. Ft.	$3,630,762
9 Woodman Rd, Chestnut Hill, MA 6 Beds \| 7 Baths \| 7016 Sq. Ft.	$5,197,892

Address	Redfin Estimate
101 Old Orchard Rd, Chestnut Hill, MA 3 Beds \| 2.5 Baths \| 2924 Sq. Ft.	$3,154,948
116 Old Orchard Rd, Chestnut Hill, MA 6 Beds \| 5.5 Baths \| 5165 Sq. Ft.	$3,415,902
26 Old Orchard Rd, Chestnut Hill, MA 2 Beds \| 1 Baths \| 1410 Sq. Ft.	$535,510
116 Old Orchard Rd, Chestnut Hill, MA 6 Beds \| 5.5 Baths \| 4442 Sq. Ft.	$3,323,674
81 Old Orchard Rd, Chestnut Hill, MA 5 Beds \| 3.5 Baths \| 4207 Sq. Ft.	$2,780,472
17 Old England Rd, Chestnut Hill, MA 8 Beds \| 5.5 Baths \| 5609 Sq. Ft.	$3,498,646
23 Woodman Rd, Chestnut Hill, MA 4 Beds \| 3.5 Baths \| 3003 Sq. Ft.	$2,325,132

Address	Redfin Estimate
109 Old Orchard Rd, Chestnut Hill, MA 5 Beds \| 3.5 Baths \| 3656 Sq. Ft.	$2,495,257
14 Old Orchard Rd, Chestnut Hill, MA 6 Beds \| 7 Baths \| 9010 Sq. Ft.	$6,012,850
101 Old Orchard Rd, Chestnut Hill, MA 4 Beds \| 3 Baths \| 2924 Sq. Ft.	$2,737,106
119 Old Orchard Rd, Chestnut Hill, MA 4 Beds \| 3.5 Baths \| 3810 Sq. Ft.	$2,599,893
25 Old Orchard Rd, Chestnut Hill, MA 5 Beds \| 3.5 Baths \| 4153 Sq. Ft.	$3,375,699
25 Old England Rd, Chestnut Hill, MA 5 Beds \| 5 Baths \| 3582 Sq. Ft.	$3,617,732
263 Hammond St, Chestnut Hill, MA 7 Beds \| 6.5 Baths \| - Sq. Ft.	$5,880,544

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