| B & D Productions Inc. | Educational Services | $40,683 | $45,649 | 6 | <$5M | AI Deep Dive |
| Beginning Years Child Dev. Ctr. at Medfield High School LLC | Health Care and Social Assistance | $40,574 | $40,769 | 7 | <$5M | AI Deep Dive |
| Blazing Hearth Pizza LLC | Accommodation and Food Services | $40,428 | $40,832 | 3 | <$5M | AI Deep Dive |
| Cambridge Fund Raising Assoc | Information | $40,355 | $40,616 | 3 | <$5M | AI Deep Dive |
| Cambridge Fundraising Associates, LLC | Information | $40,355 | $40,703 | 3 | <$5M | AI Deep Dive |
| Group 7 Design INC | Professional, Scientific, and Technical Services | $40,162 | $40,515 | 2 | <$5M | AI Deep Dive |
| Compass Environmental Professtionals, LLC | Other Services (except Public Administration) | $40,000 | $40,182 | 2 | <$5M | AI Deep Dive |
| Almar LLC | Construction | $40,000 | $40,386 | 6 | <$5M | AI Deep Dive |
| Victorem Partners INC | Unknown | $39,196 | $39,532 | 2 | N/A | AI Deep Dive |
| Kristine Lilly Heavey | Arts, Entertainment, and Recreation | $39,022 | $20,927 | 1 | <$5M | AI Deep Dive |
| Tc Building Incorporated | Construction | $38,790 | $38,992 | 5 | <$5M | AI Deep Dive |
| Tc Building Incorporated | Unknown | $38,789 | $39,058 | 5 | N/A | AI Deep Dive |
| Rogan Robbins Advertising LLC | Professional, Scientific, and Technical Services | $38,477 | $38,650 | 2 | <$5M | AI Deep Dive |
| J. Foster Co., Inc. | Construction | $37,500 | $37,699 | 3 | <$5M | AI Deep Dive |
| Hurley-Testa Construction Company Inc. | Construction | $37,495 | $37,671 | 3 | <$5M | AI Deep Dive |
| Hurley-Testa Construction Company, Inc. | Construction | $37,494 | $37,571 | 3 | <$5M | AI Deep Dive |
| Uva Wahoos, LLC | Arts, Entertainment, and Recreation | $37,200 | $37,447 | 10 | <$5M | AI Deep Dive |
| Life's a Pooch LLC | Unknown | $35,300 | $21,013 | 4 | N/A | AI Deep Dive |
| Cornerstone Search | Administrative and Support and Waste Management | $34,510 | $34,417 | 3 | <$5M | AI Deep Dive |
| Charles River Contracting | Construction | $34,200 | $25,666 | 6 | $6.8M | AI Deep Dive |
| Beginning Years On Pleasant Street | Health Care and Social Assistance | $34,000 | $24,637 | 4 | <$5M | AI Deep Dive |
| Cornerstone Search Associates, INC | Administrative and Support and Waste Management | $33,928 | $34,191 | 3 | <$5M | AI Deep Dive |
| Faggioli's Pizza Inc. | Accommodation and Food Services | $33,780 | $34,225 | 8 | <$5M | AI Deep Dive |
| Ronnie Armany | Real Estate and Rental and Leasing | $33,200 | $33,603 | 4 | <$5M | AI Deep Dive |
| Cmd INC DBA Nicholas Christies Day Spa | Other Services (except Public Administration) | $32,852 | $32,950 | 5 | <$5M | AI Deep Dive |