Kevin Caulfield

Kevin Caulfield

Managing Director
kcaulfield@compass.com
M: 617-501-3685

Education

Boston College '00
Thayer Academy '96
About Kevin
With over a billion dollars in residential real estate sales and 25 years in the industry, founder Kevin Caulfield owns and operates a premier real estate marketing, consulting and advisory group in Boston and on the South Shore.

A Boston native and Thayer Academy grad, Caulfield played hockey at Boston College before venturing into real estate and founding Caulfield Properties.

Today, Caulfield Properties proudly operates through two specialized business lines: Urban and Estates. Each division is thoughtfully designed and staffed to meet the distinct needs of clients moving between Boston and the South Shore.

The Urban Division is dedicated to high-impact, in-town real estate. Focused on the Back Bay market, this business line leverages deep local knowledge, strategic investment insight and disciplined execution to unlock value in a dynamic, high-demand market.

The Estates Division centers on residential and estate-focused properties on the South Shore, where quality, longevity and thoughtful design take priority. This division reflects our commitment to communities that balance strong investment fundamentals with exceptional living experiences.

Together, the Urban and Estates divisions showcase the breadth of Caulfield Properties—two focused divisions, unified by a commitment to excellence, integrity and long-term value creation.

Kevin Caulfield’s Listings

$5,100,000 | 86 Black Rock Drive, Hingham, MA 02043
$5,100,000 | 86 Black Rock Drive, Hingham, MA 02043
$5,100,000 | 86 Black Rock Drive, Hingham, MA 02043
$5,100,000 | 86 Black Rock Drive, Hingham, MA 02043
$5,100,000 | 86 Black Rock Drive, Hingham, MA 02043
$5,100,000 | 86 Black Rock Drive, Hingham, MA 02043
$5,100,000 | 86 Black Rock Drive, Hingham, MA 02043
$5,100,000 | 86 Black Rock Drive, Hingham, MA 02043
$5,100,000 | 86 Black Rock Drive, Hingham, MA 02043
$5,100,000 | 86 Black Rock Drive, Hingham, MA 02043
$5,100,000 | 86 Black Rock Drive, Hingham, MA 02043
$5,100,000 | 86 Black Rock Drive, Hingham, MA 02043
$5,100,000 | 86 Black Rock Drive, Hingham, MA 02043
$5,100,000 | 86 Black Rock Drive, Hingham, MA 02043
$5,100,000 | 86 Black Rock Drive, Hingham, MA 02043
$5,100,000 | 86 Black Rock Drive, Hingham, MA 02043
$5,100,000 | 86 Black Rock Drive, Hingham, MA 02043
$5,100,000 | 86 Black Rock Drive, Hingham, MA 02043
$5,100,000 | 86 Black Rock Drive, Hingham, MA 02043
$5,100,000 | 86 Black Rock Drive, Hingham, MA 02043
$5,100,000 | 86 Black Rock Drive, Hingham, MA 02043
$5,100,000 | 86 Black Rock Drive, Hingham, MA 02043
$5,100,000 | 86 Black Rock Drive, Hingham, MA 02043
$5,100,000 | 86 Black Rock Drive, Hingham, MA 02043
$5,100,000 | 86 Black Rock Drive, Hingham, MA 02043
$5,100,000 | 86 Black Rock Drive, Hingham, MA 02043
$5,100,000 | 86 Black Rock Drive, Hingham, MA 02043
$5,100,000 | 86 Black Rock Drive, Hingham, MA 02043
$5,100,000 | 86 Black Rock Drive, Hingham, MA 02043
$5,100,000 | 86 Black Rock Drive, Hingham, MA 02043
$5,100,000 | 86 Black Rock Drive, Hingham, MA 02043
$5,100,000 | 86 Black Rock Drive, Hingham, MA 02043
$5,100,000 | 86 Black Rock Drive, Hingham, MA 02043
$5,100,000 | 86 Black Rock Drive, Hingham, MA 02043
$5,100,000 | 86 Black Rock Drive, Hingham, MA 02043
$5,100,000 | 86 Black Rock Drive, Hingham, MA 02043
1/36
Listed By CompassUnder Agreement

$5,100,000

5
Bedrooms
8,378
Square Feet
2.30
Acres

86 Black Rock Drive, Hingham, MA 02043

a aerial view of a house with a yard
a view of a building with a outdoor space
a white building with a white roof and windows
a front view of a building with windows
a black and white photo of a house
a view of house with a yard and balcony
a view of a white house with a sink and wooden floor
a black and white photo of a
unknown
1/9
Listed By Compass

$4,500,000

4
Bedrooms
4,300
Square Feet
2
Acres

96 Black Horse Lane, Cohasset, MA 02025

$2,995,000 | 135 Beach Street, Cohasset, MA 02025
$2,995,000 | 135 Beach Street, Cohasset, MA 02025
$2,995,000 | 135 Beach Street, Cohasset, MA 02025
$2,995,000 | 135 Beach Street, Cohasset, MA 02025
$2,995,000 | 135 Beach Street, Cohasset, MA 02025
$2,995,000 | 135 Beach Street, Cohasset, MA 02025
$2,995,000 | 135 Beach Street, Cohasset, MA 02025
$2,995,000 | 135 Beach Street, Cohasset, MA 02025
$2,995,000 | 135 Beach Street, Cohasset, MA 02025
$2,995,000 | 135 Beach Street, Cohasset, MA 02025
$2,995,000 | 135 Beach Street, Cohasset, MA 02025
$2,995,000 | 135 Beach Street, Cohasset, MA 02025
$2,995,000 | 135 Beach Street, Cohasset, MA 02025
$2,995,000 | 135 Beach Street, Cohasset, MA 02025
$2,995,000 | 135 Beach Street, Cohasset, MA 02025
$2,995,000 | 135 Beach Street, Cohasset, MA 02025
$2,995,000 | 135 Beach Street, Cohasset, MA 02025
$2,995,000 | 135 Beach Street, Cohasset, MA 02025
$2,995,000 | 135 Beach Street, Cohasset, MA 02025
$2,995,000 | 135 Beach Street, Cohasset, MA 02025
$2,995,000 | 135 Beach Street, Cohasset, MA 02025
$2,995,000 | 135 Beach Street, Cohasset, MA 02025
$2,995,000 | 135 Beach Street, Cohasset, MA 02025
$2,995,000 | 135 Beach Street, Cohasset, MA 02025
$2,995,000 | 135 Beach Street, Cohasset, MA 02025
$2,995,000 | 135 Beach Street, Cohasset, MA 02025
$2,995,000 | 135 Beach Street, Cohasset, MA 02025
1/27
Listed By CompassUnder Agreement

$2,995,000

5
Bedrooms
4,600
Square Feet
2.41
Acres

135 Beach Street, Cohasset, MA 02025

a view of backyard with tree
an aerial view of ocean residential house and ocean view
a close up of a vase of flowers sitting on a table
1/3
Listed By Compass

$2,100,000

Unavailable
Bedrooms
Unavailable
Bathrooms
Unavailable
Square Feet
2.73
Acres

98 Black Horse Lane, Cohasset, MA 02025

$1,200,000 | 75 Clarendon Street, Unit 201, Boston, MA 02116
$1,200,000 | 75 Clarendon Street, Unit 201, Boston, MA 02116
$1,200,000 | 75 Clarendon Street, Unit 201, Boston, MA 02116
$1,200,000 | 75 Clarendon Street, Unit 201, Boston, MA 02116
$1,200,000 | 75 Clarendon Street, Unit 201, Boston, MA 02116
$1,200,000 | 75 Clarendon Street, Unit 201, Boston, MA 02116
$1,200,000 | 75 Clarendon Street, Unit 201, Boston, MA 02116
$1,200,000 | 75 Clarendon Street, Unit 201, Boston, MA 02116
$1,200,000 | 75 Clarendon Street, Unit 201, Boston, MA 02116
$1,200,000 | 75 Clarendon Street, Unit 201, Boston, MA 02116
$1,200,000 | 75 Clarendon Street, Unit 201, Boston, MA 02116
$1,200,000 | 75 Clarendon Street, Unit 201, Boston, MA 02116
$1,200,000 | 75 Clarendon Street, Unit 201, Boston, MA 02116
$1,200,000 | 75 Clarendon Street, Unit 201, Boston, MA 02116
$1,200,000 | 75 Clarendon Street, Unit 201, Boston, MA 02116
$1,200,000 | 75 Clarendon Street, Unit 201, Boston, MA 02116
$1,200,000 | 75 Clarendon Street, Unit 201, Boston, MA 02116
1/17
Listed By CompassOpen: 2/5 12:00PM - 01:30PM

$1,200,000

2
Bedrooms
974
Square Feet

75 Clarendon Street, Unit 201, Boston, MA 02116

$1,175,000 | 29 Chief Justice Cushing Highway, Hingham, MA 02043
$1,175,000 | 29 Chief Justice Cushing Highway, Hingham, MA 02043
$1,175,000 | 29 Chief Justice Cushing Highway, Hingham, MA 02043
$1,175,000 | 29 Chief Justice Cushing Highway, Hingham, MA 02043
$1,175,000 | 29 Chief Justice Cushing Highway, Hingham, MA 02043
$1,175,000 | 29 Chief Justice Cushing Highway, Hingham, MA 02043
$1,175,000 | 29 Chief Justice Cushing Highway, Hingham, MA 02043
$1,175,000 | 29 Chief Justice Cushing Highway, Hingham, MA 02043
$1,175,000 | 29 Chief Justice Cushing Highway, Hingham, MA 02043
$1,175,000 | 29 Chief Justice Cushing Highway, Hingham, MA 02043
$1,175,000 | 29 Chief Justice Cushing Highway, Hingham, MA 02043
$1,175,000 | 29 Chief Justice Cushing Highway, Hingham, MA 02043
$1,175,000 | 29 Chief Justice Cushing Highway, Hingham, MA 02043
$1,175,000 | 29 Chief Justice Cushing Highway, Hingham, MA 02043
$1,175,000 | 29 Chief Justice Cushing Highway, Hingham, MA 02043
$1,175,000 | 29 Chief Justice Cushing Highway, Hingham, MA 02043
$1,175,000 | 29 Chief Justice Cushing Highway, Hingham, MA 02043
1/17
Listed By CompassOpen: 2/6 11:00AM - 12:30PM

$1,175,000

3
Bedrooms
2,316
Square Feet
0.29
Acres

29 Chief Justice Cushing Highway, Hingham, MA 02043