| Ipswich Junior Sailing | Educational Services | $40,000 | $40,350 | 20 | N/A |  AI Deep Dive |
| Roman Catholic Archbishop of Boston | Other Services (except Public Administration) | $39,800 | $40,054 | 8 | N/A | AI Deep Dive |
| Fahey Construction | Construction | $39,487 | $39,920 | 3 | <$5M | AI Deep Dive |
| Heart & Soul Cafe, INC | Accommodation and Food Services | $39,477 | $39,784 | 9 | <$5M | AI Deep Dive |
| Chelsea Morning Produce Inc. | Wholesale Trade | $39,272 | $39,596 | 6 | <$5M | AI Deep Dive |
| 42 North, LLC | Accommodation and Food Services | $37,500 | $20,662 | 3 | <$5M | AI Deep Dive |
| Partners in Development INC | Other Services (except Public Administration) | $37,395 | $37,701 | 6 | N/A | AI Deep Dive |
| Pomo Ice Cream, Inc. | Accommodation and Food Services | $36,179 | $36,504 | 10 | <$5M | AI Deep Dive |
| R Bouley Inc. | Accommodation and Food Services | $35,800 | $36,271 | 12 | <$5M | AI Deep Dive |
| Little Wolf Coffee | Accommodation and Food Services | $35,582 | $35,920 | 3 | <$5M | AI Deep Dive |
| Rest Stop, LLC | Administrative and Support and Waste Management | $35,500 | $20,663 | 2 | <$5M | AI Deep Dive |
| Ipswich Inn Inc. | Accommodation and Food Services | $35,122 | $35,351 | 10 | <$5M | AI Deep Dive |
| Windhill Realty, LLC | Real Estate and Rental and Leasing | $34,642 | $34,855 | 2 | <$5M | AI Deep Dive |
| North Shore Forms Co, Inc. | Construction | $33,020 | $30,418 | 2 | <$5M | AI Deep Dive |
| Rescue Force Inc. | Construction | $33,000 | $33,415 | 2 | <$5M | AI Deep Dive |
| Ellen Rose | Professional, Scientific, and Technical Services | $32,995 | $33,300 | 4 | <$5M | AI Deep Dive |
| Windhill Realty, LLC | Real Estate and Rental and Leasing | $32,900 | $33,222 | 2 | <$5M | AI Deep Dive |
| Atlantic Atm LLC | Finance and Insurance | $32,500 | $32,671 | 2 | <$5M | AI Deep Dive |
| Atlantic Atm LLC | Finance and Insurance | $32,500 | $32,812 | 2 | <$5M | AI Deep Dive |
| Happy May INC DBA | Accommodation and Food Services | $32,500 | $32,779 | 7 | <$5M | AI Deep Dive |
| Scl Home Services Llc-Sba Small 7a Term | Unknown | $32,462 | $32,779 | 2 | N/A | AI Deep Dive |
| Clean Soils Environmental Ltd | Professional, Scientific, and Technical Services | $31,537 | $31,851 | 4 | <$5M | AI Deep Dive |
| Gallery Byzantium INC | Retail Trade | $31,300 | $31,605 | 4 | <$5M | AI Deep Dive |
| Upwire Electric, LLC | Construction | $31,200 | $31,433 | 4 | <$5M | AI Deep Dive |
| A.p. Marcorelle Co., Inc. | Retail Trade | $31,100 | $31,468 | 7 | <$5M | AI Deep Dive |