| Jay Rhind Builders Inc. | Construction | $39,638 | $39,845 | 6 | <$5M |  AI Deep Dive |
| Stockbridge General Store | Accommodation and Food Services | $39,100 | $39,573 | 17 | <$5M | AI Deep Dive |
| Berkshire Whole Health, PC | Health Care and Social Assistance | $38,630 | $38,931 | 2 | <$5M | AI Deep Dive |
| Green-Land Market LLC | Retail Trade | $35,000 | $35,314 | 5 | <$5M | AI Deep Dive |
| Pilling Landscaping Inc. | Administrative and Support and Waste Management | $33,700 | $33,869 | 5 | <$5M | AI Deep Dive |
| Williams and Sons County Store Inc. | Retail Trade | $32,388 | $32,615 | 15 | <$5M | AI Deep Dive |
| Williams & Sons Country Store, Inc. | Retail Trade | $32,300 | $32,625 | 10 | <$5M | AI Deep Dive |
| Camp Wagalot Berkshire T.l.c. for Pets Inc. | Other Services (except Public Administration) | $30,752 | $31,165 | 5 | <$5M | AI Deep Dive |
| Camp Wagalot Berkshire T.l.c. for Pets Inc. | Other Services (except Public Administration) | $30,752 | $31,145 | 4 | <$5M | AI Deep Dive |
| Notre Reve INC | Accommodation and Food Services | $29,940 | $30,138 | 10 | <$5M | AI Deep Dive |
| Stockbridge Gas Co, Inc. | Utilities | $29,700 | $29,894 | 4 | N/A | AI Deep Dive |
| Stockbridge Health Center | Health Care and Social Assistance | $28,542 | $27,098 | 1 | <$5M | AI Deep Dive |
| Raposo Industries LLC | Accommodation and Food Services | $27,828 | $28,034 | 9 | <$5M | AI Deep Dive |
| Vlada Boutique | Retail Trade | $25,912 | $25,982 | 8 | <$5M | AI Deep Dive |
| Robert Anderson | Administrative and Support and Waste Management | $25,135 | $25,246 | 3 | <$5M | AI Deep Dive |
| Garden Visions | Other Services (except Public Administration) | $25,100 | $25,206 | 3 | <$5M | AI Deep Dive |
| Berkshire Roofing & Gutter LLC | Construction | $24,652 | $24,899 | 2 | <$5M | AI Deep Dive |
| Berkshire Roofing & Gutter LLC | Construction | $24,600 | $24,868 | 2 | <$5M | AI Deep Dive |
| Heirlooms Jewelry | Retail Trade | $24,500 | $21,078 | 1 | <$5M | AI Deep Dive |
| Faber Landscape Maintenance Co. | Professional, Scientific, and Technical Services | $23,120 | $23,238 | 4 | <$5M | AI Deep Dive |
| Patricia Andrew | Administrative and Support and Waste Management | $22,034 | $22,082 | 2 | <$5M | AI Deep Dive |
| Ilm, LLC | Real Estate and Rental and Leasing | $20,904 | $21,008 | 7 | <$5M | AI Deep Dive |
| Changing Tastes LLC | Professional, Scientific, and Technical Services | $20,833 | $21,001 | 2 | <$5M | AI Deep Dive |
| Heirlooms Jewelry | Retail Trade | $20,833 | $20,923 | 1 | <$5M | AI Deep Dive |
| Arlin Wasserman | Professional, Scientific, and Technical Services | $20,832 | $20,978 | 1 | <$5M | AI Deep Dive |