| 10 Putnam Street LLC | Accommodation and Food Services | $134,400 | $136,024 | 19 | <$5M |  AI Deep Dive |
| Winthrop Arms, Inc. | Accommodation and Food Services | $132,600 | $134,169 | 31 | $9.7M | AI Deep Dive |
| 10 Putnam Street LLC | Accommodation and Food Services | $124,145 | $125,924 | 79 | $14.0M | AI Deep Dive |
| Sticky Molasses LLC | Accommodation and Food Services | $120,300 | $120,841 | 20 | <$5M | AI Deep Dive |
| Ticket Academy Corp. | Professional, Scientific, and Technical Services | $120,000 | $120,750 | 5 | <$5M | AI Deep Dive |
| Odyssey Early Learning Academy LLC | Health Care and Social Assistance | $119,255 | $119,895 | 23 | <$5M | AI Deep Dive |
| Streeter Plumbing & Heating, INC | Construction | $117,100 | $118,297 | 9 | <$5M | AI Deep Dive |
| 19 Crest Avenue Food Services, Inc. | Accommodation and Food Services | $116,095 | $117,427 | 21 | <$5M | AI Deep Dive |
| Joel Rubiera | Real Estate and Rental and Leasing | $115,153 | $116,894 | 6 | <$5M | AI Deep Dive |
| Winthrop Hospitality LLC | Accommodation and Food Services | $108,770 | $109,581 | 13 | <$5M | AI Deep Dive |
| Odyssey Grill INC | Accommodation and Food Services | $107,800 | $90,530 | 4 | <$5M | AI Deep Dive |
| Essex St Food Services I | Accommodation and Food Services | $105,000 | $105,613 | 11 | <$5M | AI Deep Dive |
| Select Parking INC | Other Services (except Public Administration) | $103,372 | $104,080 | 15 | <$5M | AI Deep Dive |
| Select Parking INC | Other Services (except Public Administration) | $103,000 | $93,553 | 9 | <$5M | AI Deep Dive |
| Corolla Company INC | Construction | $100,388 | $101,838 | 9 | <$5M | AI Deep Dive |
| Corolla Company, Inc. | Construction | $100,300 | $101,297 | 9 | <$5M | AI Deep Dive |
| Shepherd Pmc LLC | Construction | $98,459 | $99,017 | 3 | <$5M | AI Deep Dive |
| Shepherd Pmc, LLC | Accommodation and Food Services | $98,459 | $99,526 | 4 | <$5M | AI Deep Dive |
| D'parma Ristorante Inc. | Accommodation and Food Services | $95,739 | $96,516 | 30 | $5.3M | AI Deep Dive |
| Helco Safety Equipment Corp | Wholesale Trade | $93,988 | $95,268 | 10 | <$5M | AI Deep Dive |
| Woodside Hardware Co., Inc. | Retail Trade | $92,792 | $93,504 | 20 | <$5M | AI Deep Dive |
| Eagle Restoration and Contracting Inc. | Construction | $91,530 | $91,962 | 7 | <$5M | AI Deep Dive |
| Eagle Restoration & Contracting, Inc. | Construction | $91,530 | $92,168 | 7 | <$5M | AI Deep Dive |
| Winthrop Yacht Club | Other Services (except Public Administration) | $90,400 | $91,415 | 31 | N/A | AI Deep Dive |
| Stafford Painting LLC | Construction | $86,300 | $87,198 | 5 | <$5M | AI Deep Dive |