About Caulfield Properties
With over a billion dollars in real estate sales, Caulfield Properties is a premier real estate advising group in Boston and Hingham. Consistently ranked as the Wall Street Journal’s “The Thousand” and Boston Magazine's "Top Producers," founder Kevin Caulfield has built a business around real relationships and an unending obsession with success for his clients.

A Hyde Park native and Thayer Academy grad, Caulfield played hockey at Boston College before venturing into real estate. In 2003, Caulfield founded Charlesgate Realty Group and then went on to serve as Vice President at Coldwell Banker and Vice President at Campion and Company.

In 2016, Caulfield moved to Compass to give his clients a smarter, more intuitive real estate experience. Since then he has led his team to increased sales volume year-over-year.

A long-time resident of the South End, Caulfield now resides in Hingham with his wife and three girls. On the side, Caulfield mentors the Boston College Student-Athlete Mentor Program and serves on the Board of Thayer Academy's Alumni Association.

Team Agents

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
a living room with furniture and a fireplace

$14,500,000

4
Bedrooms
5,320
Square Feet
a living room with furniture and a flat screen tv

$14,131,000

3
Bedrooms
3,753
Square Feet
$10,200,000 | 222 Commonwealth Avenue, Unit PH, Boston, MA 02116

$10,200,000

3
Bedrooms
4,540
Square Feet
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
$8,000,000 | 45 Temple Street, Unit PH2, Boston, MA 02114

$8,000,000

2
Bedrooms
2,940
Square Feet
a front view of a building

$7,875,000

4
Bedrooms
3,892
Square Feet
0.04
Acres
$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
$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
$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

-

13
Bedrooms
Past Rentals
a view of a house with pool and yard

$15,000

4
Bedrooms
$12,000 | 144 West Canton Street, Unit 1, Boston, MA 02118

$12,000

3
Bedrooms
$10,000 | 144 West Canton Street, Unit 1, Boston, MA 02118

$10,000

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

$9,800

2
Bedrooms
a living room with furniture a fireplace and a potted plant

$9,500

4
Bedrooms
front view of a building

$8,500

1
Bedrooms
a terrace view with seating space

$7,700

1
Bedrooms
a front view of a building

$7,700

3
Bedrooms
a living room with furniture flat screen tv and a large window

$7,500

4
Bedrooms
front view of house with a yard

$7,500

4
Bedrooms
a kitchen with a sink stove and cabinets

$7,300

2
Bedrooms
a living room with furniture and a flat screen tv

$7,000

2
Bedrooms
front view of house with a yard

$7,000

4
Bedrooms
$6,600 | 0 Dorchester Street, Unit 1, Boston, MA 02127

$6,600

5
Bedrooms
a front view of a house with a yard

$6,550

4
Bedrooms
front view of a house with a yard

$6,500

3
Bedrooms
front view of a brick building

$6,500

2
Bedrooms