| Keefe Piccolo Co., Inc. | Manufacturing | $34,986 | $35,077 | 5 | <$5M | AI Deep Dive |
| Tumblekids USA | Educational Services | $34,900 | $35,263 | 6 | <$5M | AI Deep Dive |
| Tumble Kids USA INC | Educational Services | $34,900 | $35,101 | 5 | <$5M | AI Deep Dive |
| John G. Crowe Associates, Inc. | Professional, Scientific, and Technical Services | $34,768 | $35,169 | 2 | <$5M | AI Deep Dive |
| Budget Lock, Inc. | Administrative and Support and Waste Management | $34,500 | $34,817 | 2 | <$5M | AI Deep Dive |
| Budget Lock Inc. | Administrative and Support and Waste Management | $34,500 | $34,690 | 2 | <$5M | AI Deep Dive |
| The Baldwin Companies | Construction | $34,375 | $34,780 | 2 | <$5M | AI Deep Dive |
| Winchester School of Chinese Culture INC | Educational Services | $34,162 | $34,620 | 10 | N/A | AI Deep Dive |
| Kristen Rivoli Interior Design LLC | Professional, Scientific, and Technical Services | $34,120 | $34,433 | 2 | <$5M | AI Deep Dive |
| Paul Bourgeois | Finance and Insurance | $33,929 | $34,127 | 12 | $6.2M | AI Deep Dive |
| Elenis Mediterranean Grille INC | Accommodation and Food Services | $33,865 | $33,956 | 5 | <$5M | AI Deep Dive |
| Winchester Seniors Association Inc. | Health Care and Social Assistance | $33,250 | $33,413 | 5 | N/A | AI Deep Dive |
| Town Pantry INC | Retail Trade | $32,567 | $32,711 | 5 | <$5M | AI Deep Dive |
| Jbbd Inc. | Professional, Scientific, and Technical Services | $32,500 | $32,722 | 1 | <$5M | AI Deep Dive |
| Crawford Memorial United Methodist Church | Other Services (except Public Administration) | $31,957 | $32,107 | 11 | N/A | AI Deep Dive |
| Smart Tax Corporation | Professional, Scientific, and Technical Services | $31,702 | $31,959 | 2 | <$5M | AI Deep Dive |
| A + Insurance Agency, LLC | Finance and Insurance | $31,700 | $31,880 | 4 | <$5M | AI Deep Dive |
| Saha Corp (7-Eleven Franchise) | Retail Trade | $31,270 | $31,606 | 9 | <$5M | AI Deep Dive |
| New England Physical Therapy Network | Health Care and Social Assistance | $31,089 | $31,303 | 2 | <$5M | AI Deep Dive |
| Jeevendra Martyn Business | Health Care and Social Assistance | $30,800 | $4,348 | 1 | <$5M | AI Deep Dive |
| Jeevendra Martyn | Health Care and Social Assistance | $30,800 | $17,848 | 1 | <$5M | AI Deep Dive |
| O'connell Design Build Ltd | Construction | $30,770 | $31,011 | 3 | <$5M | AI Deep Dive |
| O'connell Design Build Ltd | Construction | $30,770 | $31,038 | 3 | <$5M | AI Deep Dive |
| Charles River Eye Associates | Health Care and Social Assistance | $30,512 | $30,738 | 4 | <$5M | AI Deep Dive |
| Jack Greiner | Health Care and Social Assistance | $30,512 | $30,716 | 3 | <$5M | AI Deep Dive |