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

a living room with furniture and a rug
a living room with furniture and a flat screen tv
a kitchen with stainless steel appliances a refrigerator and a stove top oven
a kitchen with stainless steel appliances granite countertop a stove and a refrigerator
a hallway with a sink a washer and dryer
a kitchen with a sink and a refrigerator
a kitchen with stainless steel appliances a stove and a refrigerator
a living room with furniture and a fireplace
a view of a dining room with furniture and wooden floor
a living room with furniture and a fireplace
a bathroom with a sink and a mirror
a view of a living room and dining room
a spacious bedroom with a bed and walk in closet
a spacious bedroom with a bed and a night stand
a bedroom with a bed and a window
a spacious bedroom with a bed and a window
a balcony view with a outdoor seating space
a view of a balcony with furniture
a bathroom with a double vanity sink and a mirror
a bathroom with a shower
a room with toys and dresser
a living room with baby crib furniture and a book shelf
a living room with furniture and a baby crib
a bathroom with a toilet sink and mirror
a bath tub sitting next to a white sink and vanity
a living room with a couch and a flat screen tv
a living room with furniture and a window
a view of a livingroom with furniture and wooden floor
a bathroom with a sink and a toilet
a bedroom with furniture and stairs
a view of balcony and patio
a city view with sitting space
a terrace view with sitting space
a view of a roof deck with couches
a view of roof deck with seating space
a view of a roof deck with couches
a view of a terrace with couches
a city view with lot of high rise buildings
a front view of a brick building with glass windows
a building view
1/40
Compass Coming Soon

$2,500,000

3
Bedrooms
1,688
Square Feet

54 Appleton Street, Unit 4, Boston, MA 02116

a kitchen with stainless steel appliances kitchen island a table chairs in it and wooden floors
a kitchen with refrigerator cabinets and wooden floor
a kitchen with stainless steel appliances granite countertop a sink stove and refrigerator
a kitchen with kitchen island stainless steel appliances a dining table chairs sink and white cabinets
a kitchen with a sink appliances and a living room
a kitchen with stainless steel appliances granite countertop a stove and a wooden floors
a living room with furniture and a fireplace
a living room with furniture a flat screen tv and a fireplace
a view of a dining room with furniture and wooden floor
a view of a dining room with furniture and wooden floor
a bedroom with a large bed and a window
a spacious bedroom with a bed and a couch
a bedroom with a bed and a chair
a bathroom with a double vanity sink and a mirror
a bathroom with a granite countertop sink two mirror and shower
a bathroom with a shower
a bedroom with a bed and wooden floor
a bathroom with a sink toilet and vanity
a view of a room with gym equipment and equipment
a view of a room with gym equipment and wooden floor
a view of storage and utility room
a car parked in front of a building
a view of an chairs and tables in the balcony
a car parked in front of a building
1/24
Listed By Compass

$1,149,000

2
Bedrooms
1,602
Square Feet

858 East 2nd Street, Unit 2, Boston, MA 02127

$1,075,000 | 488 Columbus Avenue, Unit 5, Boston, MA 02118
$1,075,000 | 488 Columbus Avenue, Unit 5, Boston, MA 02118
$1,075,000 | 488 Columbus Avenue, Unit 5, Boston, MA 02118
$1,075,000 | 488 Columbus Avenue, Unit 5, Boston, MA 02118
$1,075,000 | 488 Columbus Avenue, Unit 5, Boston, MA 02118
$1,075,000 | 488 Columbus Avenue, Unit 5, Boston, MA 02118
$1,075,000 | 488 Columbus Avenue, Unit 5, Boston, MA 02118
$1,075,000 | 488 Columbus Avenue, Unit 5, Boston, MA 02118
$1,075,000 | 488 Columbus Avenue, Unit 5, Boston, MA 02118
$1,075,000 | 488 Columbus Avenue, Unit 5, Boston, MA 02118
$1,075,000 | 488 Columbus Avenue, Unit 5, Boston, MA 02118
$1,075,000 | 488 Columbus Avenue, Unit 5, Boston, MA 02118
$1,075,000 | 488 Columbus Avenue, Unit 5, Boston, MA 02118
$1,075,000 | 488 Columbus Avenue, Unit 5, Boston, MA 02118
$1,075,000 | 488 Columbus Avenue, Unit 5, Boston, MA 02118
$1,075,000 | 488 Columbus Avenue, Unit 5, Boston, MA 02118
$1,075,000 | 488 Columbus Avenue, Unit 5, Boston, MA 02118
$1,075,000 | 488 Columbus Avenue, Unit 5, Boston, MA 02118
$1,075,000 | 488 Columbus Avenue, Unit 5, Boston, MA 02118
$1,075,000 | 488 Columbus Avenue, Unit 5, Boston, MA 02118
$1,075,000 | 488 Columbus Avenue, Unit 5, Boston, MA 02118
$1,075,000 | 488 Columbus Avenue, Unit 5, Boston, MA 02118
$1,075,000 | 488 Columbus Avenue, Unit 5, Boston, MA 02118
$1,075,000 | 488 Columbus Avenue, Unit 5, Boston, MA 02118
1/24
Listed By CompassUnder Agreement

$1,075,000

1
Bedrooms
785
Square Feet

488 Columbus Avenue, Unit 5, Boston, MA 02118

$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 CompassUnder Agreement

$899,000

2
Bedrooms
1,028
Square Feet

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

a kitchen with stainless steel appliances a refrigerator a stove a microwave and island with wooden floor
a kitchen with white cabinets and stainless steel appliances
a kitchen with stainless steel appliances a table and chairs in it
a kitchen with a sink and refrigerator
a view of a livingroom and dining room
a view of a dining room with furniture and wooden floor
a living room with furniture and a window
a living room with furniture and a flat screen tv
a living room with furniture and a flat screen tv
a bedroom with a bed and a window
a bedroom with a bed and a dresser
a bathroom with a sink toilet and shower
a view of an empty room with a window and workspace
a spacious bathroom with a tub and shower
a bathroom with a sink a toilet and shower
a utility room with dryer and washer
a view of outdoor space and yard
a view of parking garage with cars parked
a view of parking space with parked cars
a view of utility room
a view of a backyard with sitting area
a view of a building with a large window
a view of a building with a large windows
a view of a car parked in front of a building
a car parked in front of a building
$775,000 | 320 Maverick Street, Unit 209, Boston, MA 02128
1/26
Listed By Compass

$775,000

2
Bedrooms
1,108
Square Feet

320 Maverick Street, Unit 209, Boston, MA 02128

$575,000 | 25 South Street, Unit 4, Boston, MA 02135
$575,000 | 25 South Street, Unit 4, Boston, MA 02135
$575,000 | 25 South Street, Unit 4, Boston, MA 02135
$575,000 | 25 South Street, Unit 4, Boston, MA 02135
$575,000 | 25 South Street, Unit 4, Boston, MA 02135
$575,000 | 25 South Street, Unit 4, Boston, MA 02135
$575,000 | 25 South Street, Unit 4, Boston, MA 02135
$575,000 | 25 South Street, Unit 4, Boston, MA 02135
$575,000 | 25 South Street, Unit 4, Boston, MA 02135
$575,000 | 25 South Street, Unit 4, Boston, MA 02135
$575,000 | 25 South Street, Unit 4, Boston, MA 02135
$575,000 | 25 South Street, Unit 4, Boston, MA 02135
$575,000 | 25 South Street, Unit 4, Boston, MA 02135
$575,000 | 25 South Street, Unit 4, Boston, MA 02135
$575,000 | 25 South Street, Unit 4, Boston, MA 02135
$575,000 | 25 South Street, Unit 4, Boston, MA 02135
$575,000 | 25 South Street, Unit 4, Boston, MA 02135
$575,000 | 25 South Street, Unit 4, Boston, MA 02135
$575,000 | 25 South Street, Unit 4, Boston, MA 02135
$575,000 | 25 South Street, Unit 4, Boston, MA 02135
$575,000 | 25 South Street, Unit 4, Boston, MA 02135
$575,000 | 25 South Street, Unit 4, Boston, MA 02135
$575,000 | 25 South Street, Unit 4, Boston, MA 02135
$575,000 | 25 South Street, Unit 4, Boston, MA 02135
$575,000 | 25 South Street, Unit 4, Boston, MA 02135
$575,000 | 25 South Street, Unit 4, Boston, MA 02135
$575,000 | 25 South Street, Unit 4, Boston, MA 02135
$575,000 | 25 South Street, Unit 4, Boston, MA 02135
$575,000 | 25 South Street, Unit 4, Boston, MA 02135
$575,000 | 25 South Street, Unit 4, Boston, MA 02135
$575,000 | 25 South Street, Unit 4, Boston, MA 02135
1/31
Listed By Compass

$575,000

1
Bedrooms
980
Square Feet

25 South Street, Unit 4, Boston, MA 02135

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 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 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 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 view of swimming pool with outdoor seating

$5,500

2
Bedrooms

9 Joy Street, Unit PH, Boston, MA 02114

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