| The Fantastical LLC | Professional, Scientific, and Technical Services | $170,125 | $171,689 | 9 | <$5M |  AI Deep Dive |
| Resilient Ops INC | Professional, Scientific, and Technical Services | $164,052 | $53,449 | 3 | <$5M | AI Deep Dive |
| Resilient Ops INC | Information | $164,052 | $90,917 | 3 | <$5M | AI Deep Dive |
| Salone Estetica, Inc. | Other Services (except Public Administration) | $159,775 | $160,667 | 13 | <$5M | AI Deep Dive |
| Winchester After School Program, INC | Health Care and Social Assistance | $159,021 | $161,256 | 20 | N/A | AI Deep Dive |
| Little Flippers Swim School of Winchester, Inc. | Educational Services | $155,650 | $156,454 | 24 | <$5M | AI Deep Dive |
| Christopher Kokoras Insurance Agency INC | Finance and Insurance | $151,262 | $152,770 | 14 | $7.2M | AI Deep Dive |
| St. Mary School | Educational Services | $150,955 | $152,469 | 13 | N/A | AI Deep Dive |
| Bespoke Woodwrights LLC | Manufacturing | $149,762 | $150,866 | 10 | <$5M | AI Deep Dive |
| Associated Reporting Sys Inc-Sba Small 7a Term | Unknown | $148,910 | $149,839 | 15 | N/A | AI Deep Dive |
| First House, LLC | Accommodation and Food Services | $148,800 | $149,999 | 16 | <$5M | AI Deep Dive |
| Salone Estetica Inc. | Other Services (except Public Administration) | $147,778 | $149,219 | 9 | <$5M | AI Deep Dive |
| John a Pierce Ins Agency INC | Unknown | $146,338 | $147,849 | 6 | N/A | AI Deep Dive |
| Stirling, Inc. | Professional, Scientific, and Technical Services | $142,150 | $143,856 | 12 | <$5M | AI Deep Dive |
| Winchester After School Program INC | Health Care and Social Assistance | $140,041 | $141,031 | 17 | N/A | AI Deep Dive |
| Ashton Law PC | Professional, Scientific, and Technical Services | $134,579 | $135,408 | 9 | <$5M | AI Deep Dive |
| Insite Contracting INC | Construction | $128,500 | $129,732 | 9 | <$5M | AI Deep Dive |
| Insite Contracting Incorporated | Construction | $128,500 | $129,204 | 9 | <$5M | AI Deep Dive |
| Barrett & Scibelli, LLC | Professional, Scientific, and Technical Services | $127,500 | $129,051 | 9 | <$5M | AI Deep Dive |
| Janis Moriarty Dmd PC | Health Care and Social Assistance | $127,020 | $128,079 | 17 | <$5M | AI Deep Dive |
| Pragya Systems Corp. | Information | $125,600 | $126,987 | 7 | <$5M | AI Deep Dive |
| Gloria's Pizzeria, Inc. | Accommodation and Food Services | $125,000 | $120,082 | 25 | <$5M | AI Deep Dive |
| Milford Swim School Corporation | Educational Services | $123,000 | $124,172 | 77 | $10.0M | AI Deep Dive |
| Boston Basins, Inc. | Wholesale Trade | $122,985 | $124,188 | 9 | <$5M | AI Deep Dive |
| Associated Reporting Sys INC | Administrative and Support and Waste Management | $122,605 | $123,531 | 10 | <$5M | AI Deep Dive |