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 kitchen with stainless steel appliances kitchen island granite countertop a stove a sink a refrigerator and chairs
a kitchen with stainless steel appliances granite countertop a sink stove and refrigerator
a kitchen with a sink stove top oven and cabinets
a kitchen with stainless steel appliances kitchen island granite countertop a sink and a white cabinets
a kitchen with stainless steel appliances a refrigerator sink and stove
a kitchen with kitchen island granite countertop a stove and a sink
a kitchen with a sink stove and cabinets
a kitchen with granite countertop a sink and a stove next to a window
a view of a dining room with furniture and wooden floor
a dining room with furniture and wooden floor
a living room with furniture and kitchen view
a living room with furniture a large window and a flat screen tv
a living room with furniture flat screen tv and a fireplace
a spacious bedroom with a bed and window
a bedroom with a bed and painting on the wall
a spacious bathroom with a sink a toilet and a mirror
a bathroom with a sink a bathtub and a mirror
a bathroom with a shower and mirror
a spacious bedroom with a bed and a window
a bedroom with a bed a flat screen tv and dresser
a bathroom with a sink a toilet and shower
a view of a roof deck with couches and wooden floor
a view of a roof deck with couches and sky view
a front view of a house
1/24
Listed By CompassUnder Agreement

$1,599,000

2
Bedrooms
1,215
Square Feet

57 Warren Avenue, Unit 3, Boston, MA 02116

$1,489,000 | 19-21 Short Street, Unit 1, Boston, MA 02129
$1,489,000 | 19-21 Short Street, Unit 1, Boston, MA 02129
$1,489,000 | 19-21 Short Street, Unit 1, Boston, MA 02129
$1,489,000 | 19-21 Short Street, Unit 1, Boston, MA 02129
$1,489,000 | 19-21 Short Street, Unit 1, Boston, MA 02129
$1,489,000 | 19-21 Short Street, Unit 1, Boston, MA 02129
$1,489,000 | 19-21 Short Street, Unit 1, Boston, MA 02129
$1,489,000 | 19-21 Short Street, Unit 1, Boston, MA 02129
$1,489,000 | 19-21 Short Street, Unit 1, Boston, MA 02129
$1,489,000 | 19-21 Short Street, Unit 1, Boston, MA 02129
$1,489,000 | 19-21 Short Street, Unit 1, Boston, MA 02129
$1,489,000 | 19-21 Short Street, Unit 1, Boston, MA 02129
$1,489,000 | 19-21 Short Street, Unit 1, Boston, MA 02129
$1,489,000 | 19-21 Short Street, Unit 1, Boston, MA 02129
$1,489,000 | 19-21 Short Street, Unit 1, Boston, MA 02129
$1,489,000 | 19-21 Short Street, Unit 1, Boston, MA 02129
$1,489,000 | 19-21 Short Street, Unit 1, Boston, MA 02129
$1,489,000 | 19-21 Short Street, Unit 1, Boston, MA 02129
$1,489,000 | 19-21 Short Street, Unit 1, Boston, MA 02129
$1,489,000 | 19-21 Short Street, Unit 1, Boston, MA 02129
$1,489,000 | 19-21 Short Street, Unit 1, Boston, MA 02129
$1,489,000 | 19-21 Short Street, Unit 1, Boston, MA 02129
$1,489,000 | 19-21 Short Street, Unit 1, Boston, MA 02129
$1,489,000 | 19-21 Short Street, Unit 1, Boston, MA 02129
$1,489,000 | 19-21 Short Street, Unit 1, Boston, MA 02129
$1,489,000 | 19-21 Short Street, Unit 1, Boston, MA 02129
$1,489,000 | 19-21 Short Street, Unit 1, Boston, MA 02129
$1,489,000 | 19-21 Short Street, Unit 1, Boston, MA 02129
$1,489,000 | 19-21 Short Street, Unit 1, Boston, MA 02129
$1,489,000 | 19-21 Short Street, Unit 1, Boston, MA 02129
$1,489,000 | 19-21 Short Street, Unit 1, Boston, MA 02129
$1,489,000 | 19-21 Short Street, Unit 1, Boston, MA 02129
$1,489,000 | 19-21 Short Street, Unit 1, Boston, MA 02129
$1,489,000 | 19-21 Short Street, Unit 1, Boston, MA 02129
$1,489,000 | 19-21 Short Street, Unit 1, Boston, MA 02129
$1,489,000 | 19-21 Short Street, Unit 1, Boston, MA 02129
1/36
Listed By CompassUnder Agreement

$1,489,000

3
Bedrooms
1,751
Square Feet

19-21 Short Street, Unit 1, Boston, MA 02129

$899,000 | 3 Glover Court, Unit 2, Boston, MA 02127
$899,000 | 3 Glover Court, Unit 2, Boston, MA 02127
$899,000 | 3 Glover Court, Unit 2, Boston, MA 02127
$899,000 | 3 Glover Court, Unit 2, Boston, MA 02127
$899,000 | 3 Glover Court, Unit 2, Boston, MA 02127
$899,000 | 3 Glover Court, Unit 2, Boston, MA 02127
$899,000 | 3 Glover Court, Unit 2, Boston, MA 02127
$899,000 | 3 Glover Court, Unit 2, Boston, MA 02127
$899,000 | 3 Glover Court, Unit 2, Boston, MA 02127
$899,000 | 3 Glover Court, Unit 2, Boston, MA 02127
$899,000 | 3 Glover Court, Unit 2, Boston, MA 02127
$899,000 | 3 Glover Court, Unit 2, Boston, MA 02127
$899,000 | 3 Glover Court, Unit 2, Boston, MA 02127
$899,000 | 3 Glover Court, Unit 2, Boston, MA 02127
$899,000 | 3 Glover Court, Unit 2, Boston, MA 02127
$899,000 | 3 Glover Court, Unit 2, Boston, MA 02127
$899,000 | 3 Glover Court, Unit 2, Boston, MA 02127
$899,000 | 3 Glover Court, Unit 2, Boston, MA 02127
$899,000 | 3 Glover Court, Unit 2, Boston, MA 02127
$899,000 | 3 Glover Court, Unit 2, Boston, MA 02127
$899,000 | 3 Glover Court, Unit 2, Boston, MA 02127
$899,000 | 3 Glover Court, Unit 2, Boston, MA 02127
$899,000 | 3 Glover Court, Unit 2, Boston, MA 02127
$899,000 | 3 Glover Court, Unit 2, Boston, MA 02127
$899,000 | 3 Glover Court, Unit 2, Boston, MA 02127
$899,000 | 3 Glover Court, Unit 2, Boston, MA 02127
$899,000 | 3 Glover Court, Unit 2, Boston, MA 02127
1/27
Listed By CompassUnder Agreement

$899,000

3
Bedrooms
1,439
Square Feet

3 Glover Court, Unit 2, Boston, MA 02127

$849,000 | 29 St Andrew Road, Unit 1, Boston, MA 02128
$849,000 | 29 St Andrew Road, Unit 1, Boston, MA 02128
$849,000 | 29 St Andrew Road, Unit 1, Boston, MA 02128
$849,000 | 29 St Andrew Road, Unit 1, Boston, MA 02128
$849,000 | 29 St Andrew Road, Unit 1, Boston, MA 02128
$849,000 | 29 St Andrew Road, Unit 1, Boston, MA 02128
$849,000 | 29 St Andrew Road, Unit 1, Boston, MA 02128
$849,000 | 29 St Andrew Road, Unit 1, Boston, MA 02128
$849,000 | 29 St Andrew Road, Unit 1, Boston, MA 02128
$849,000 | 29 St Andrew Road, Unit 1, Boston, MA 02128
$849,000 | 29 St Andrew Road, Unit 1, Boston, MA 02128
$849,000 | 29 St Andrew Road, Unit 1, Boston, MA 02128
$849,000 | 29 St Andrew Road, Unit 1, Boston, MA 02128
$849,000 | 29 St Andrew Road, Unit 1, Boston, MA 02128
$849,000 | 29 St Andrew Road, Unit 1, Boston, MA 02128
$849,000 | 29 St Andrew Road, Unit 1, Boston, MA 02128
$849,000 | 29 St Andrew Road, Unit 1, Boston, MA 02128
$849,000 | 29 St Andrew Road, Unit 1, Boston, MA 02128
$849,000 | 29 St Andrew Road, Unit 1, Boston, MA 02128
$849,000 | 29 St Andrew Road, Unit 1, Boston, MA 02128
$849,000 | 29 St Andrew Road, Unit 1, Boston, MA 02128
$849,000 | 29 St Andrew Road, Unit 1, Boston, MA 02128
$849,000 | 29 St Andrew Road, Unit 1, Boston, MA 02128
$849,000 | 29 St Andrew Road, Unit 1, Boston, MA 02128
$849,000 | 29 St Andrew Road, Unit 1, Boston, MA 02128
$849,000 | 29 St Andrew Road, Unit 1, Boston, MA 02128
$849,000 | 29 St Andrew Road, Unit 1, Boston, MA 02128
$849,000 | 29 St Andrew Road, Unit 1, Boston, MA 02128
$849,000 | 29 St Andrew Road, Unit 1, Boston, MA 02128
1/29
Listed By Compass

$849,000

3
Bedrooms
2,257
Square Feet

29 St Andrew Road, Unit 1, Boston, MA 02128

a kitchen with granite countertop a sink stainless steel appliances and cabinets
a kitchen with stainless steel appliances a table chairs and a refrigerator
a view of kitchen with granite countertop cabinets table and chairs
a kitchen with stainless steel appliances granite countertop a sink stove and cabinets
a kitchen with cabinets and window
a living room with furniture and a wooden floor
a living room with furniture ceiling fan and a wooden floor
a living room with furniture and a window
a living room with furniture and a window
a view of a hallway with washer and dryer
a bedroom with a bed and wooden floor
a bedroom with a bed and a window
a bathroom with a sink a toilet and shower
a bedroom with a bed and a window
a bathroom with a sink toilet and shower
a roof deck with a couch and chairs
a city street lined with parked cars and buildings
a view of a park with large trees
a view of a trees in a park
a front view of a house with a yard
1/20
Listed By Compass

$780,000

2
Bedrooms
950
Square Feet

52 O Street, Unit 3, Boston, MA 02127

a kitchen with kitchen island a refrigerator stove and microwave
a kitchen with kitchen island cabinets and chairs in it
a kitchen with a sink stove and refrigerator
a open kitchen with stainless steel appliances granite countertop a stove top oven a sink dishwasher a dining table and chairs with wooden floor
a room with sink washer and dryer
a living room with furniture and a large window
a living room with furniture and large window
a living room with furniture and a flat screen tv
a living room with furniture and a flat screen tv
a living room with furniture and a large window
a view of balcony with furniture
a view of backyard with outdoor seating and trees
a bedroom with a bed and a dresser
a bedroom with a bed and a window
a bathroom with a toilet a sink a glass door a shower and mirror
a spacious bathroom with a toilet sink and mirror
a bathroom with a toilet a sink and a shower
a view of an entryway with sitting area
a view of an entryway with a workspace
a view of a car garage
a view of parking area with parking space
a cars parked in front of a building
a view of a building with a porch
$770,000 | 519 East 2nd Street, Unit 207, Boston, MA 02127
1/24
Listed By Compass

$770,000

1
Bedrooms
773
Square Feet

519 East 2nd Street, Unit 207, Boston, MA 02127