Jamie Gaines's Profile Photo

Jamie Gaines

Real Estate Advisor
jamie.gaines@compass.com
M: 617-595-6961

Specialties

Sales & Rentals 

Education

Gettysburg College
About Jamie

Jamie Gaines is the Founder of The Gaines Group, a premier real estate team at Compass in Boston, dedicated to providing an exceptional client experience. With over 7.5 years of industry expertise and more than $200 million in real estate transactions under her belt — including hundreds of successful rental agreements — Jamie has built a reputation for her sharp attention to detail, market knowledge, and unwavering commitment to her clients. Whether working with a first-time homebuyer navigating the process or a seasoned investor, Jamie approaches every client and transaction with the same level of care, transparency, and professionalism.

Jamie founded The Gaines Group with the mission of delivering elevated service and expert guidance, ensuring that every client, regardless of budget or deal size, feels supported and informed throughout their real estate journey. Her ability to simplify complex transactions, combined with her strong negotiation skills, has consistently led to successful outcomes for her clients and lasting relationships.

In addition to her work in real estate, Jamie serves as the Philanthropy Chair for the Compass Young Professionals, New England chapter, where she is passionate about giving back to her community. She also loves exploring Boston, particularly the South End, where she enjoys discovering new restaurants, local businesses, and connecting with her community. 

Jamie currently lives in a brownstone condo in the South End, giving her a deep appreciation for Boston’s architecture, history, and neighborhood charm — something she enjoys sharing with her clients as they navigate finding their own perfect space. 

A proud Bostonian, Jamie has completed the Boston Marathon twice, embracing new challenges in the city she loves. Deeply connected to her community, she’s always seeking ways to give back and support the place she calls home.

Jamie’s unwavering dedication, market expertise, and people-first approach have made her a trusted advisor and top producer in the Boston real estate market. Whether you're buying, selling, or investing, Jamie and The Gaines Group are committed to making your real estate journey seamless, informed, and enjoyable.


Jamie Gaines’ Listings

$899,000 | 101 North Beacon Street, Unit 309, Watertown, MA 02472
$899,000 | 101 North Beacon Street, Unit 309, Watertown, MA 02472
$899,000 | 101 North Beacon Street, Unit 309, Watertown, MA 02472
$899,000 | 101 North Beacon Street, Unit 309, Watertown, MA 02472
$899,000 | 101 North Beacon Street, Unit 309, Watertown, MA 02472
$899,000 | 101 North Beacon Street, Unit 309, Watertown, MA 02472
$899,000 | 101 North Beacon Street, Unit 309, Watertown, MA 02472
$899,000 | 101 North Beacon Street, Unit 309, Watertown, MA 02472
$899,000 | 101 North Beacon Street, Unit 309, Watertown, MA 02472
$899,000 | 101 North Beacon Street, Unit 309, Watertown, MA 02472
$899,000 | 101 North Beacon Street, Unit 309, Watertown, MA 02472
$899,000 | 101 North Beacon Street, Unit 309, Watertown, MA 02472
$899,000 | 101 North Beacon Street, Unit 309, Watertown, MA 02472
$899,000 | 101 North Beacon Street, Unit 309, Watertown, MA 02472
$899,000 | 101 North Beacon Street, Unit 309, Watertown, MA 02472
$899,000 | 101 North Beacon Street, Unit 309, Watertown, MA 02472
$899,000 | 101 North Beacon Street, Unit 309, Watertown, MA 02472
$899,000 | 101 North Beacon Street, Unit 309, Watertown, MA 02472
$899,000 | 101 North Beacon Street, Unit 309, Watertown, MA 02472
$899,000 | 101 North Beacon Street, Unit 309, Watertown, MA 02472
$899,000 | 101 North Beacon Street, Unit 309, Watertown, MA 02472
$899,000 | 101 North Beacon Street, Unit 309, Watertown, MA 02472
$899,000 | 101 North Beacon Street, Unit 309, Watertown, MA 02472
$899,000 | 101 North Beacon Street, Unit 309, Watertown, MA 02472
$899,000 | 101 North Beacon Street, Unit 309, Watertown, MA 02472
$899,000 | 101 North Beacon Street, Unit 309, Watertown, MA 02472
$899,000 | 101 North Beacon Street, Unit 309, Watertown, MA 02472
$899,000 | 101 North Beacon Street, Unit 309, Watertown, MA 02472
$899,000 | 101 North Beacon Street, Unit 309, Watertown, MA 02472
$899,000 | 101 North Beacon Street, Unit 309, Watertown, MA 02472
1/30
Listed By Compass

$899,000

2
Bedrooms
1,028
Square Feet

101 North Beacon Street, Unit 309, Watertown, MA 02472

$699,000 | 691 East 8th Street, Unit 1, Boston, MA 02127
$699,000 | 691 East 8th Street, Unit 1, Boston, MA 02127
$699,000 | 691 East 8th Street, Unit 1, Boston, MA 02127
$699,000 | 691 East 8th Street, Unit 1, Boston, MA 02127
$699,000 | 691 East 8th Street, Unit 1, Boston, MA 02127
$699,000 | 691 East 8th Street, Unit 1, Boston, MA 02127
$699,000 | 691 East 8th Street, Unit 1, Boston, MA 02127
$699,000 | 691 East 8th Street, Unit 1, Boston, MA 02127
$699,000 | 691 East 8th Street, Unit 1, Boston, MA 02127
$699,000 | 691 East 8th Street, Unit 1, Boston, MA 02127
$699,000 | 691 East 8th Street, Unit 1, Boston, MA 02127
$699,000 | 691 East 8th Street, Unit 1, Boston, MA 02127
$699,000 | 691 East 8th Street, Unit 1, Boston, MA 02127
$699,000 | 691 East 8th Street, Unit 1, Boston, MA 02127
$699,000 | 691 East 8th Street, Unit 1, Boston, MA 02127
$699,000 | 691 East 8th Street, Unit 1, Boston, MA 02127
$699,000 | 691 East 8th Street, Unit 1, Boston, MA 02127
$699,000 | 691 East 8th Street, Unit 1, Boston, MA 02127
$699,000 | 691 East 8th Street, Unit 1, Boston, MA 02127
$699,000 | 691 East 8th Street, Unit 1, Boston, MA 02127
$699,000 | 691 East 8th Street, Unit 1, Boston, MA 02127
$699,000 | 691 East 8th Street, Unit 1, Boston, MA 02127
$699,000 | 691 East 8th Street, Unit 1, Boston, MA 02127
$699,000 | 691 East 8th Street, Unit 1, Boston, MA 02127
$699,000 | 691 East 8th Street, Unit 1, Boston, MA 02127
$699,000 | 691 East 8th Street, Unit 1, Boston, MA 02127
1/26
Listed By CompassUnder Agreement

$699,000

2
Bedrooms
880
Square Feet

691 East 8th Street, Unit 1, Boston, MA 02127

Jamie Gaines’ Transactions

Past Sales
a view of a terrace with furniture

$3,350,000

3
Bedrooms
2,340
Square Feet

32 Derne Street, Unit 3A, Boston, MA 02114

a view of a building

$2,760,000

7
Bedrooms
2,937
Square Feet

54 Burbank Street, Boston, MA 02115

a living room with furniture and a table

$2,650,000

3
Bedrooms
2,300
Square Feet

46 Clarendon Street, Unit 1, Boston, MA 02116

a kitchen with a stove a refrigerator and a fireplace

$2,605,000

3
Bedrooms
2,725
Square Feet

10 Holyoke Street, Unit 1, Boston, MA 02116

a view of a dining room with furniture a chandelier and wooden floor

$2,530,000

3
Bedrooms
1,778
Square Feet

10 Greenwich Park, Unit 2, Boston, MA 02118

a kitchen with a stove a table and chairs

$2,525,000

3
Bedrooms
1,750
Square Feet

14 Wellington Street, Unit 2, Boston, MA 02118

a kitchen with stainless steel appliances kitchen island granite countertop a table chairs and a refrigerator

$2,499,000

3
Bedrooms
2,190
Square Feet

11 Isabella Street, Unit 1, Boston, MA 02116

a car parked in front of a building

$2,425,000

3
Bedrooms
2,385
Square Feet

96 Pembroke Street, Unit A, Boston, MA 02118

a large kitchen with a table and chairs in it

$2,425,000

4
Bedrooms
2,280
Square Feet

37 Rutland Square, Unit 1, Boston, MA 02118

a living room with furniture a fireplace and a chandelier

$2,415,000

3
Bedrooms
2,270
Square Feet

38 Concord Square, Unit 1, Boston, MA 02118

a front view of a house with a yard and garage

$2,367,000

4
Bedrooms
5,866
Square Feet
0.29
Acres

41 Brewster Road, Hingham, MA 02043

a living room with furniture and a flat screen tv

$2,300,000

3
Bedrooms
2,107
Square Feet

112 West Concord Street, Unit 3, Boston, MA 02118

a living room with furniture and a window

$2,260,000

3
Bedrooms
1,795
Square Feet

144 West Concord Street, Unit 3, Boston, MA 02118

a living room with stainless steel appliances kitchen island granite countertop furniture and a wooden floor

$2,226,000

2
Bedrooms
1,437
Square Feet

116 Charles Street, Unit 3, Boston, MA 02114

a living room with furniture and windows

$2,200,000

3
Bedrooms
1,729
Square Feet

164 West Brookline Street, Unit 1, Boston, MA 02118

a living room with furniture and a flat screen tv

$2,175,000

2
Bedrooms
1,300
Square Feet

249 Marlborough Street, Unit 3, Boston, MA 02116

a living room with furniture and a table

$2,150,000

4
Bedrooms
1,902
Square Feet

33 Commercial Wharf, Unit A, Boston, MA 02110

a living room with furniture and a wooden floor

$2,125,000

3
Bedrooms
1,619
Square Feet

36 Upton Street, Unit 3, Boston, MA 02118

Past Rentals
a living room with furniture a fireplace and a table

$16,500

3
Bedrooms

133 Seaport Boulevard, Unit PH1A, Boston, MA 02210

a living room with furniture and a flat screen tv

$10,500

5
Bedrooms

4 East Concord Street, Unit SF, Boston, MA 02118

a living room with furniture and large windows

$10,500

3
Bedrooms

380 Harrison Avenue, Unit 1008, Boston, MA 02118

a kitchen with stainless steel appliances a sink cabinets and a refrigerator

$10,000

3
Bedrooms

380 Harrison Avenue, Unit PH2H, Boston, MA 02118

a living room with furniture and a large window

$8,500

3
Bedrooms

97 West Springfield Street, Unit 2, Boston, MA 02118

a kitchen with stainless steel appliances granite countertop a refrigerator a oven a stove and a dining table with wooden floor

$8,200

3
Bedrooms

2 Union Park, Unit 1, Boston, MA 02118

a living room with furniture and a fireplace

$6,950

3
Bedrooms

150 Vassal Lane, Cambridge, MA 02138

a view of a dining room with furniture window and outside view

$6,800

3
Bedrooms

148 Commonwealth Avenue, Unit 201, Boston, MA 02116

a front view of a building

$6,595

2
Bedrooms

100 Shawmut Avenue, Unit 310, Boston, MA 02118

$6,300 | 615 East 6th Street, Unit 2, Boston, MA 02127

$6,300

3
Bedrooms

615 East 6th Street, Unit 2, Boston, MA 02127

a view of a building

$6,200

2
Bedrooms

71 Appleton Street, Unit 1, Boston, MA 02116

a kitchen with stainless steel appliances granite countertop a stove top oven a sink dishwasher a dining table and chairs with wooden floor

$6,000

2
Bedrooms

62 Pinckney Street, Unit 4, Boston, MA 02114

a kitchen with a table chairs a oven a counter space and cabinets

$6,000

4
Bedrooms

12 Emmet Street, Boston, MA 02127

a living room with furniture and a flat screen tv

$6,000

2
Bedrooms

99 Pembroke Street, Unit 2, Boston, MA 02118

a kitchen with a refrigerator and a stove top oven

$5,800

3
Bedrooms

266 Lamartine Street, Unit 2, Boston, MA 02130

a view of an empty room with a fireplace and a window

$5,500

3
Bedrooms

20 Winfield Street, Unit 1, Boston, MA 02127

a open kitchen with stainless steel appliances granite countertop a stove and a refrigerator

$5,500

4
Bedrooms

29 Woodford Street, Unit 3, Boston, MA 02125

a view of swimming pool with outdoor seating

$5,500

2
Bedrooms

9 Joy Street, Unit PH, Boston, MA 02114