Caulfield Properties's Profile Photo

Caulfield Properties

caulfieldproperties@compass.com
M: 617-501-3685
About Caulfield Properties
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.

Team Agents

Caulfield Properties’ Listings

an aerial view of a houses with a lake view
1/27
Listed By Compass

$4,500,000

4
Bedrooms
5,617
Square Feet
1.39
Acres

5 Seal Cove Lane, Hingham, MA 02043

$2,995,000 | 131 Mt Vernon Street, Unit 2, Boston, MA 02108
1/13
Listed By Compass

$2,995,000

4
Bedrooms
2,183
Square Feet

131 Mt Vernon Street, Unit 2, Boston, MA 02108

a view of a kitchen with large windows and a kitchen view
1/13
Listed By Compass

$2,900,000

3
Bedrooms
2,380
Square Feet

118 B Street, Unit 501, Boston, MA 02127

an aerial view of ocean residential house and ocean view
1/5
Listed By Compass

$2,400,000

Unavailable
Bedrooms
Unavailable
Bathrooms
Unavailable
Square Feet
2
Acres

96 Black Horse Lane, Cohasset, MA 02025

an aerial view of a house with garden
1/21
Listed By Compass

$2,295,000

2
Bedrooms
2,878
Square Feet
Unavailable
Acres

24 Black Rock Drive, Unit 24, Hingham, MA 02043

a front view of a house with a garden
1/16
Compass Coming Soon

$2,200,000

4
Bedrooms
3,420
Square Feet
0.47
Acres

28 Ledge Way, Cohasset, MA 02025

$1,995,000 | 19 Ellisville Road, Plymouth, MA 02360
1/11
Listed By Compass

$1,995,000

3
Bedrooms
2,739
Square Feet
2.26
Acres

19 Ellisville Road, Plymouth, MA 02360

$1,650,000 | 5 Home Meadows Lane, Hingham, MA 02043
1/4
Listed By CompassUnder Agreement

$1,650,000

Unavailable
Bedrooms
Unavailable
Bathrooms
Unavailable
Square Feet
1.50
Acres

5 Home Meadows Lane, Hingham, MA 02043

a outdoor kitchen with granite countertop a stove a sink a dining table and chairs with wooden floor
1/12
Listed By Compass

$1,325,000

1
Bedrooms
1,460
Square Feet

35 Channel Center Street, Unit 206, Boston, MA 02210

unknown
1/3
Listed By CompassPending

$1,299,000

Unavailable
Bedrooms
Unavailable
Bathrooms
Unavailable
Square Feet
Unavailable
Acres

7 Fawn Lane, Nantucket, MA 02554

front view of a house with a yard
1/3
Listed By CompassPending

$1,199,000

Unavailable
Bedrooms
Unavailable
Bathrooms
Unavailable
Square Feet
Unavailable
Acres

9 Fawn Lane, Nantucket, MA 02554

a living room with furniture and a table
1/13
Listed By Compass

$1,150,000

2
Bedrooms
1,143
Square Feet

118 B Street, Unit 204, Boston, MA 02127

$1,150,000 | 767 Grove Street, Norwell, MA 02061
1/35
Listed By CompassVirtual Tour

$1,150,000

4
Bedrooms
2,288
Square Feet
1.19
Acres

767 Grove Street, Norwell, MA 02061

a view of a chairs and table in the balcony
1/13
Listed By Compass

$1,125,000

2
Bedrooms
1,232
Square Feet

118 B Street, Unit 302, Boston, MA 02127

a view of a chairs and table in the balcony
1/13
Listed By Compass

$1,099,000

2
Bedrooms
1,096
Square Feet

118 B Street, Unit 203, Boston, MA 02127

a living room with furniture and a large window
1/10
Listed By CompassUnder Agreement

$810,000

1
Bedrooms
747
Square Feet

118 B Street, Unit 307, Boston, MA 02127

a front view of a building with street view
1/10
Listed By Compass

$789,000

1
Bedrooms
747
Square Feet

118 B Street, Unit 26, Boston, MA 02127

a living room with furniture and a large window
1/8
Listed By CompassUnder Agreement

$699,000

1
Bedrooms
713
Square Feet

118 B Street, Unit 201, Boston, MA 02127

Caulfield Properties’ 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

$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

$7,800,000 | 350 S Collier Blvd, Unit PH202

$7,800,000

350 S Collier Blvd, Unit PH202

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
3.5
Bathrooms

26 Holyoke St

Boston

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

$6,500,000

5
Bedrooms
3
Bathrooms

40 Hancock St

Dorchester

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

$6,450,000

6
Bedrooms
5
Bathrooms

51 Chestnut St

Boston

$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

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

$6,000,000

4
Bedrooms
2
Bathrooms

144 W Canton St

South End

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

$5,500,000

3
Bedrooms
5
Bathrooms

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

-

13
Bedrooms

52 Beacon Street, Boston, MA 02108

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 a fireplace and a potted plant

$9,500

4
Bedrooms

49 Verndale Street, Unit 1, Brookline, MA 02446

front view of a building

$8,500

1
Bedrooms

40 Trinity Place, Unit 24F, Boston, MA 02116

a terrace view with seating space

$7,700

1
Bedrooms

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

a front view of a building

$7,700

3
Bedrooms

200 St Paul Street, Unit 1, Brookline, MA 02446

front view of house with a yard

$7,500

4
Bedrooms

93 Woodcliff Road, Chestnut Hill, MA 02467

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 kitchen with a sink stove and cabinets

$7,300

2
Bedrooms

133 Seaport Boulevard, Unit 1703, Boston, MA 02210

a living room with furniture and a flat screen tv

$7,000

2
Bedrooms

16 Follen Street, Unit 1, Boston, MA 02116

front view of house with a yard

$7,000

4
Bedrooms

93 Woodcliff Road, Brookline, MA 02467

$6,600 | 0 Dorchester Street, Unit 1, Boston, MA 02127

$6,600

5
Bedrooms

0 Dorchester Street, Unit 1, Boston, MA 02127

a front view of a house with a yard

$6,550

4
Bedrooms

112 Newton Street, Unit 112, Brookline, MA 02445

front view of a brick building

$6,500

2
Bedrooms

333 Beacon Street, Unit 3, Boston, MA 02116

front view of a house with a yard

$6,500

3
Bedrooms

69 Thomas Park, Unit 3, Boston, MA 02127