| The Waterfield Design Group, Inc. | Professional, Scientific, and Technical Services | $95,400 | $96,354 | 6 | <$5M |  AI Deep Dive |
| Strong Landscaping, Inc. | Administrative and Support and Waste Management | $95,100 | $89,287 | 9 | <$5M | AI Deep Dive |
| Streamline Health Care Solutions | Professional, Scientific, and Technical Services | $94,947 | $87,859 | 7 | <$5M | AI Deep Dive |
| Stage Music Center | Educational Services | $94,378 | $95,264 | 18 | <$5M | AI Deep Dive |
| G.r. Nowell & Son, Inc. | Transportation and Warehousing | $94,115 | $94,787 | 10 | <$5M | AI Deep Dive |
| First Congregational Church in Winchester | Other Services (except Public Administration) | $93,802 | $94,354 | 11 | N/A | AI Deep Dive |
| Pkm Landscape Design Inc. | Administrative and Support and Waste Management | $93,600 | $94,159 | 9 | <$5M | AI Deep Dive |
| Parish of the Epiphany | Other Services (except Public Administration) | $91,500 | $92,105 | 15 | N/A | AI Deep Dive |
| Cbs Exotic Stones Inc. | Retail Trade | $91,400 | $90,391 | 7 | <$5M | AI Deep Dive |
| Winchester Optical Inc. | Retail Trade | $91,076 | $92,015 | 7 | <$5M | AI Deep Dive |
| Fresh Touch Cleaners INC | Other Services (except Public Administration) | $90,972 | $91,637 | 14 | <$5M | AI Deep Dive |
| Fresh Touch Cleaners Inc. | Other Services (except Public Administration) | $90,972 | $91,515 | 8 | <$5M | AI Deep Dive |
| Winchester Optical INC | Retail Trade | $90,898 | $91,456 | 7 | <$5M | AI Deep Dive |
| M & M Landscaping & Rubbish Removal Inc. | Administrative and Support and Waste Management | $90,864 | $91,694 | 12 | <$5M | AI Deep Dive |
| Scotti & Company, Inc. | Finance and Insurance | $90,600 | $91,757 | 6 | <$5M | AI Deep Dive |
| M & M Landscaping & Rubbish Removal, Inc. | Administrative and Support and Waste Management | $90,488 | $91,385 | 9 | <$5M | AI Deep Dive |
| Winchester Unitarian Society | Other Services (except Public Administration) | $90,000 | $89,890 | 22 | N/A | AI Deep Dive |
| Scotti Insurance Agency, Inc. | Finance and Insurance | $89,100 | $71,215 | 5 | <$5M | AI Deep Dive |
| Strong Landscaping Inc. | Administrative and Support and Waste Management | $88,564 | $89,275 | 9 | <$5M | AI Deep Dive |
| Driscoll Skating & Skills LLC | Arts, Entertainment, and Recreation | $87,500 | $20,932 | 10 | <$5M | AI Deep Dive |
| Principal Street Capital Advisors, LLC | Finance and Insurance | $87,005 | $88,259 | 4 | <$5M | AI Deep Dive |
| Patricia Wu Dmd PC | Health Care and Social Assistance | $86,596 | $83,388 | 6 | <$5M | AI Deep Dive |
| Shockwave LLC | Accommodation and Food Services | $86,544 | $86,917 | 9 | <$5M | AI Deep Dive |
| Asthma & Allergy Specialists PC | Health Care and Social Assistance | $86,250 | $86,654 | 4 | <$5M | AI Deep Dive |
| Asthma & Allergy Specialists PC | Health Care and Social Assistance | $86,250 | $86,957 | 4 | <$5M | AI Deep Dive |