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

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 patio with couch and outdoor seating
a dining hall with stainless steel appliances a dining table and chairs
a living room with furniture large windows and a flat screen tv
1/3
Listed By CompassUnder Agreement

$2,900,000

3
Bedrooms
2,490
Square Feet

118 B Street, Unit 502, Boston, MA 02127

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

$1,925,000 | 41 Peach Orchard Road, Burlington, MA 01803
$1,925,000 | 41 Peach Orchard Road, Burlington, MA 01803
$1,925,000 | 41 Peach Orchard Road, Burlington, MA 01803
$1,925,000 | 41 Peach Orchard Road, Burlington, MA 01803
$1,925,000 | 41 Peach Orchard Road, Burlington, MA 01803
$1,925,000 | 41 Peach Orchard Road, Burlington, MA 01803
$1,925,000 | 41 Peach Orchard Road, Burlington, MA 01803
$1,925,000 | 41 Peach Orchard Road, Burlington, MA 01803
$1,925,000 | 41 Peach Orchard Road, Burlington, MA 01803
$1,925,000 | 41 Peach Orchard Road, Burlington, MA 01803
$1,925,000 | 41 Peach Orchard Road, Burlington, MA 01803
$1,925,000 | 41 Peach Orchard Road, Burlington, MA 01803
$1,925,000 | 41 Peach Orchard Road, Burlington, MA 01803
$1,925,000 | 41 Peach Orchard Road, Burlington, MA 01803
$1,925,000 | 41 Peach Orchard Road, Burlington, MA 01803
1/15
Compass Coming Soon

$1,925,000

6
Bedrooms
6,516
Square Feet
0.58
Acres

41 Peach Orchard Road, Burlington, MA 01803

a front view of a house with a yard and garage
a front view of a house with a yard
a living room with furniture and a window
a view of a dining room with furniture window and wooden floor
a kitchen with stainless steel appliances granite countertop a stove top oven a sink and dishwasher with white cabinets
a living room with furniture a flat screen tv and a fireplace
a view of a dining room with furniture and a potted plant
a living room with furniture and a large window
a bathroom with a sink and a mirror
a utility room with dryer and washer
a spacious bedroom with a bed and wooden floor
a bathroom with a sink toilet and shower
a bedroom with a bed and a window
a bathroom with a granite countertop sink and a mirror
a en suite bathroom with a sink and a mirror
a spacious bedroom with a bed and a chandelier
a view of deck and patio
a view of a swimming pool with an outdoor space and seating area
an aerial view of multiple house
1/19
Listed By CompassUnder Agreement

$1,799,000

4
Bedrooms
2,817
Square Feet
0.37
Acres

43 Park View Drive, Hingham, MA 02043

$1,280,000 | 118 B Street, Unit 408, Boston, MA 02127
$1,280,000 | 118 B Street, Unit 408, Boston, MA 02127
$1,280,000 | 118 B Street, Unit 408, Boston, MA 02127
$1,280,000 | 118 B Street, Unit 408, Boston, MA 02127
$1,280,000 | 118 B Street, Unit 408, Boston, MA 02127
$1,280,000 | 118 B Street, Unit 408, Boston, MA 02127
$1,280,000 | 118 B Street, Unit 408, Boston, MA 02127
$1,280,000 | 118 B Street, Unit 408, Boston, MA 02127
$1,280,000 | 118 B Street, Unit 408, Boston, MA 02127
$1,280,000 | 118 B Street, Unit 408, Boston, MA 02127
$1,280,000 | 118 B Street, Unit 408, Boston, MA 02127
1/11
Listed By CompassContingent

$1,280,000

2
Bedrooms
1,193
Square Feet

118 B Street, Unit 408, Boston, MA 02127

a living room with furniture and a table
a living room with furniture kitchen view and kitchen view
a bedroom with a bed and a large window
a bedroom with a bed and a couch
a view of a dresser
a bathroom with a sink toilet and shower
a bedroom with a bed and painting on the wall
a bathroom with a sink toilet and shower
a view of a chairs and table in the balcony
a front view of a brick building with many windows
a view of a building with a street
1/11
Listed By Compass

$1,249,000

2
Bedrooms
1,143
Square Feet

118 B Street, Unit 204, Boston, MA 02127

$1,165,000 | 118 B Street, Unit 303, Boston, MA 02127
$1,165,000 | 118 B Street, Unit 303, Boston, MA 02127
$1,165,000 | 118 B Street, Unit 303, Boston, MA 02127
$1,165,000 | 118 B Street, Unit 303, Boston, MA 02127
$1,165,000 | 118 B Street, Unit 303, Boston, MA 02127
$1,165,000 | 118 B Street, Unit 303, Boston, MA 02127
$1,165,000 | 118 B Street, Unit 303, Boston, MA 02127
$1,165,000 | 118 B Street, Unit 303, Boston, MA 02127
$1,165,000 | 118 B Street, Unit 303, Boston, MA 02127
$1,165,000 | 118 B Street, Unit 303, Boston, MA 02127
$1,165,000 | 118 B Street, Unit 303, Boston, MA 02127
$1,165,000 | 118 B Street, Unit 303, Boston, MA 02127
1/12
Listed By CompassVirtual Tour

$1,165,000

2
Bedrooms
1,096
Square Feet

118 B Street, Unit 303, Boston, MA 02127

a living room with furniture kitchen view and kitchen view
a living room with furniture and a table
a bedroom with a bed and a large window
a bedroom with a bed and a couch
a bathroom with a sink toilet and shower
a view of a dresser
a bedroom with a bed and painting on the wall
a bathroom with a sink toilet and shower
a view of a chairs and table in the balcony
a front view of a brick building with many windows
a view of a building with a street
1/11
Listed By CompassUnder Agreement

$1,165,000

2
Bedrooms
1,031
Square Feet

118 B Street, Unit 409, Boston, MA 02127

a living room with furniture kitchen view and kitchen view
a living room with furniture and a table
a bedroom with a bed and a large window
a bedroom with a bed and a couch
a bathroom with a sink toilet and shower
a view of a dresser
a bedroom with a bed and painting on the wall
a bathroom with a sink toilet and shower
a view of a chairs and table in the balcony
a front view of a brick building with many windows
a view of a building with a street
1/11
Listed By CompassContingent

$1,145,000

2
Bedrooms
1,031
Square Feet

118 B Street, Unit 309, Boston, MA 02127

a living room with furniture kitchen view and kitchen view
a living room with furniture and a table
a bedroom with a bed and a large window
a bedroom with a bed and a couch
a bathroom with a sink toilet and shower
a view of a dresser
a bedroom with a bed and painting on the wall
a bathroom with a sink toilet and shower
a view of a chairs and table in the balcony
a front view of a brick building with many windows
a view of a building with a street
1/11
Listed By Compass

$1,135,000

2
Bedrooms
1,031
Square Feet

118 B Street, Unit 209, Boston, MA 02127

a living room with furniture fireplace and flat screen tv
a view of a dining room with furniture and chandelier
a kitchen with stainless steel appliances a sink dishwasher a stove and a microwave oven with cabinets
a bedroom with a bed and a chandelier
a living room with furniture and a window
a bathroom with a granite countertop sink a toilet and a mirror
$1,125,000 | 75 Clarendon Street, Unit 201, Boston, MA 02116
$1,125,000 | 75 Clarendon Street, Unit 201, Boston, MA 02116
$1,125,000 | 75 Clarendon Street, Unit 201, Boston, MA 02116
$1,125,000 | 75 Clarendon Street, Unit 201, Boston, MA 02116
$1,125,000 | 75 Clarendon Street, Unit 201, Boston, MA 02116
$1,125,000 | 75 Clarendon Street, Unit 201, Boston, MA 02116
1/12
Listed By CompassVirtual Tour

$1,125,000

2
Bedrooms
974
Square Feet

75 Clarendon Street, Unit 201, Boston, MA 02116

a living room with furniture and a large window
a living room with furniture and floor to ceiling windows
a living room with furniture and a large window
a bedroom with a bed and a painting on the wall
a bedroom with a bed and a window
a en suite bathroom with a sink
a view of a dining room with furniture and wooden floor
a kitchen with sink stove and refrigerator
a room with kitchen island granite countertop a sink and a stove top oven
a kitchen with a sink cabinets and appliances
a bathroom with a double vanity sink toilet and shower
a living room with furniture and large windows
a dining room with furniture and window
a living room with furniture and large windows
a living room with furniture and a chandelier
a living room with furniture flat screen tv and chandelier
a dining room with stainless steel appliances kitchen island granite countertop furniture and a rug
a living room with furniture and a flat screen tv
a living room with couches and a fireplace
a living room with furniture and a chandelier
a view of a a dining room kitchen and living room
a living room with furniture and a flat screen tv
a large bathroom with a large tub and sink
a view of a roof deck with couches and potted plants
a roof deck with couches and potted plants
a swimming pool with outdoor seating and yard
a view of roof deck with table and chairs
1/27
Listed By Compass

$949,000

1
Bedrooms
937
Square Feet

100 Shawmut Avenue, Unit 201, Boston, MA 02118

$829,000 | 118 B Street, Unit 406, Boston, MA 02127
$829,000 | 118 B Street, Unit 406, Boston, MA 02127
$829,000 | 118 B Street, Unit 406, Boston, MA 02127
$829,000 | 118 B Street, Unit 406, Boston, MA 02127
$829,000 | 118 B Street, Unit 406, Boston, MA 02127
$829,000 | 118 B Street, Unit 406, Boston, MA 02127
$829,000 | 118 B Street, Unit 406, Boston, MA 02127
$829,000 | 118 B Street, Unit 406, Boston, MA 02127
$829,000 | 118 B Street, Unit 406, Boston, MA 02127
1/9
Listed By CompassUnder Agreement

$829,000

1
Bedrooms
747
Square Feet

118 B Street, Unit 406, Boston, MA 02127

$820,000 | 118 B Street, Unit 407, Boston, MA 02127
$820,000 | 118 B Street, Unit 407, Boston, MA 02127
$820,000 | 118 B Street, Unit 407, Boston, MA 02127
$820,000 | 118 B Street, Unit 407, Boston, MA 02127
$820,000 | 118 B Street, Unit 407, Boston, MA 02127
$820,000 | 118 B Street, Unit 407, Boston, MA 02127
$820,000 | 118 B Street, Unit 407, Boston, MA 02127
$820,000 | 118 B Street, Unit 407, Boston, MA 02127
$820,000 | 118 B Street, Unit 407, Boston, MA 02127
1/9
Listed By CompassContingent

$820,000

1
Bedrooms
747
Square Feet

118 B Street, Unit 407, Boston, MA 02127

$819,000 | 118 B Street, Unit 401, Boston, MA 02127
$819,000 | 118 B Street, Unit 401, Boston, MA 02127
$819,000 | 118 B Street, Unit 401, Boston, MA 02127
$819,000 | 118 B Street, Unit 401, Boston, MA 02127
$819,000 | 118 B Street, Unit 401, Boston, MA 02127
$819,000 | 118 B Street, Unit 401, Boston, MA 02127
$819,000 | 118 B Street, Unit 401, Boston, MA 02127
$819,000 | 118 B Street, Unit 401, Boston, MA 02127
$819,000 | 118 B Street, Unit 401, Boston, MA 02127
1/9
Listed By CompassContingent

$819,000

1
Bedrooms
713
Square Feet

118 B Street, Unit 401, Boston, MA 02127

a living room with furniture and a large window
a kitchen with stainless steel appliances a table chairs and white cabinets
a view of a dining room with furniture
a bedroom with bed and a window
a bathroom with a double vanity sink mirror and shower
a view of closet
a balcony with wooden floor and glass top table
a view of a building with a street
a front view of a brick building with many windows
1/9
Listed By Compass

$810,000

1
Bedrooms
747
Square Feet

118 B Street, Unit 307, Boston, MA 02127

a front view of a residential apartment building with a yard
a kitchen with granite countertop white cabinets stainless steel appliances and sink
a kitchen with stainless steel appliances a refrigerator sink and microwave
a kitchen with a refrigerator a microwave a stove and a dining table with wooden floor
a living room with furniture and a wooden floor
a bedroom with a bed and a window
a bathroom with a sink a toilet and shower
a front view of a building with lot of cars and trees
1/8
Listed By CompassContingent

$579,000

1
Bedrooms
640
Square Feet

576 East Broadway, Unit 3, Boston, MA 02127

Kevin Caulfield’s Transactions

Past Sales
$27,250,000 | 776 Boylston St, Unit PH2-A and PH1-E | Boston

$27,250,000

776 Boylston St, Unit PH2-A and PH1-E

Boston

a black and white photo of a house

$15,750,000

4
Bedrooms
5,050
Square Feet

40 Beacon Street, Unit 3, Boston, MA 02108

a living room with furniture and a fireplace

$14,500,000

4
Bedrooms
5,320
Square Feet

35 Commonwealth Avenue, Unit PH, Boston, MA 02116

a living room with furniture and a flat screen tv

$14,131,000

3
Bedrooms
3,753
Square Feet

682 Atlantic Avenue, Unit PH(E), Boston, MA 02111

$13,500,000 | 52 Beacon Street, Boston, MA 02108

$13,500,000

13
Bedrooms
14,500
Square Feet
0.07
Acres

52 Beacon Street, Boston, MA 02108

$10,200,000 | 222 Commonwealth Avenue, Unit PH, Boston, MA 02116

$10,200,000

3
Bedrooms
4,540
Square Feet

222 Commonwealth Avenue, Unit PH, Boston, MA 02116

a large kitchen with stainless steel appliances granite countertop a large center island and a stove

$8,750,000

4
Bedrooms
3,469
Square Feet

45 Temple Street, Unit PH1, Boston, MA 02114

$8,000,000 | 45 Temple Street, Unit PH2, Boston, MA 02114

$8,000,000

2
Bedrooms
2,940
Square Feet

45 Temple Street, Unit PH2, Boston, MA 02114

a front view of a building

$7,875,000

4
Bedrooms
3,892
Square Feet
0.04
Acres

102 Chestnut Street, Boston, MA 02108

a view of a street with potted plants

$6,950,000

3
Bedrooms
3,347
Square Feet

128 Beacon Street, Unit H, Boston, MA 02116

$6,750,000 | 26 Holyoke St | Boston

$6,750,000

5
Bedrooms

26 Holyoke St

Boston

$6,500,000 | 40 Hancock St | Dorchester

$6,500,000

5
Bedrooms

40 Hancock St

Dorchester

$6,450,000 | 51 Chestnut St | Boston

$6,450,000

6
Bedrooms

51 Chestnut St

Boston

$6,000,000 | 144 W Canton St | South End

$6,000,000

4
Bedrooms

144 W Canton St

South End

$6,000,000 | 37 Sheafe Street, Boston, MA 02113

$6,000,000

23
Bedrooms
7,424
Square Feet
0.05
Acres

37 Sheafe Street, Boston, MA 02113

$5,500,000 | 82 Mt Vernon, Unit 2 | Beacon Hill

$5,500,000

3
Bedrooms

82 Mt Vernon, Unit 2

Beacon Hill

a front view of a house with a garden and plants

$5,400,000

6
Bedrooms
5,355
Square Feet
0.29
Acres

460 Walnut Street, Brookline, MA 02445

$5,315,000 | 45 Temple Street, Unit 203, Boston, MA 02114

$5,315,000

3
Bedrooms
2,797
Square Feet

45 Temple Street, Unit 203, Boston, MA 02114

Past Rentals
a view of a house with pool and yard

$15,000

4
Bedrooms

193 East Street, Unit 193, Hingham, MA 02043

$12,000 | 144 West Canton Street, Unit 1, Boston, MA 02118

$12,000

3
Bedrooms

144 West Canton Street, Unit 1, Boston, MA 02118

a living room with furniture fireplace and flat screen tv

$10,000

2
Bedrooms

342 Marlborough Street, Unit 1, Boston, MA 02115

$10,000 | 144 West Canton Street, Unit 1, Boston, MA 02118

$10,000

3
Bedrooms

144 West Canton Street, Unit 1, Boston, MA 02118

$9,800 | 163 Marlborough Street, Unit 3, Boston, MA 02116

$9,800

2
Bedrooms

163 Marlborough Street, Unit 3, Boston, MA 02116

a living room with furniture flat screen tv and a large window

$7,500

4
Bedrooms

14 West Broadway, Unit 701, Boston, MA 02127

a front view of a house with a yard

$6,550

4
Bedrooms

112 Newton Street, Unit 112, Brookline, MA 02445

$6,500 | 300 Pier 4 Blvd., Unit 2J, Boston, MA 02210

$6,500

1
Bedrooms

300 Pier 4 Blvd., Unit 2J, Boston, MA 02210

$6,400 | 687 East 2nd Street, Unit 7, Boston, MA 02127

$6,400

4
Bedrooms

687 East 2nd Street, Unit 7, Boston, MA 02127

$6,400 | 300 Pier 4 Blvd., Unit 2J, Boston, MA 02210

$6,400

1
Bedrooms

300 Pier 4 Blvd., Unit 2J, Boston, MA 02210

$6,300 | 30 Union Park Street, Unit 305, Boston, MA 02118

$6,300

2
Bedrooms

30 Union Park Street, Unit 305, Boston, MA 02118

$6,100 | 304 Shawmut Avenue, Unit 1, Boston, MA 02118

$6,100

4
Bedrooms

304 Shawmut Avenue, Unit 1, Boston, MA 02118

$5,500 | 15 Sleeper Street, Unit 204, Boston, MA 02210

$5,500

2
Bedrooms

15 Sleeper Street, Unit 204, Boston, MA 02210

$5,300 | 216 West Canton Street, Unit 1, Boston, MA 02116

$5,300

3
Bedrooms

216 West Canton Street, Unit 1, Boston, MA 02116

$5,200 | 110 Beverly St, Unit 1024 | Greater Boston

$5,200

110 Beverly St, Unit 1024

Greater Boston

$5,000 | 416 Commonwealth Avenue, Unit 319, Boston, MA 02215

$5,000

2
Bedrooms

416 Commonwealth Avenue, Unit 319, Boston, MA 02215

a kitchen with stainless steel appliances a table chairs and a refrigerator

$5,000

2
Bedrooms

15 Sleeper Street, Unit 204, Boston, MA 02210

$4,800 | 296 Marlborough Street, Unit 6, Boston, MA 02116

$4,800

3
Bedrooms

296 Marlborough Street, Unit 6, Boston, MA 02116