| Old Inn On the Green, LLC | Accommodation and Food Services | $223,000 | $224,049 | 19 | $5.9M |  AI Deep Dive |
| G a Blanco & Sons, INC | Wholesale Trade | $222,500 | $225,578 | 22 | $5.7M | AI Deep Dive |
| The John Dewey Academy INC | Educational Services | $220,432 | $224,473 | 21 | <$5M | AI Deep Dive |
| S & a Supply, Inc. | Wholesale Trade | $220,000 | $222,742 | 21 | $6.4M | AI Deep Dive |
| Gennari Plumbing & Heating, INC | Construction | $214,900 | $217,491 | 12 | <$5M | AI Deep Dive |
| Berkshire Mountain Brewers INC | Manufacturing | $210,435 | $213,220 | 45 | $15.9M | AI Deep Dive |
| Windy Hill Farm Inc. | Administrative and Support and Waste Management | $206,300 | $208,086 | 34 | $7.4M | AI Deep Dive |
| The John Dewey Academy Inc. | Educational Services | $205,977 | $208,700 | 21 | <$5M | AI Deep Dive |
| Community Access to the Arts, Inc. | Health Care and Social Assistance | $198,500 | $137,437 | 11 | <$5M | AI Deep Dive |
| Stockbridge Road Realty LLC | Accommodation and Food Services | $196,829 | $199,568 | 6 | <$5M | AI Deep Dive |
| Mongiardo Studio Inc. | Manufacturing | $196,141 | $197,646 | 18 | <$5M | AI Deep Dive |
| Mongiardo Studio Inc. | Construction | $191,100 | $192,587 | 17 | $5.8M | AI Deep Dive |
| Mahaiwe Performing Arts Center Inc. | Arts, Entertainment, and Recreation | $189,392 | $191,841 | 22 | $5.8M | AI Deep Dive |
| J.p.c. Pops, Inc. | Other Services (except Public Administration) | $187,500 | $188,728 | 15 | <$5M | AI Deep Dive |
| Berkshire Holding Corporation | Manufacturing | $185,100 | $186,200 | 16 | $5.6M | AI Deep Dive |
| Berkshire Bike and Board LLC | Retail Trade | $183,000 | $90,951 | 17 | <$5M | AI Deep Dive |
| Peter Fasano,ltd LLC | Manufacturing | $179,350 | $180,863 | 9 | $8.9M | AI Deep Dive |
| Mahaiwe Performing Arts Center, Inc. | Arts, Entertainment, and Recreation | $173,700 | $165,301 | 15 | <$5M | AI Deep Dive |
| Schmaltz and Pfeffer LLC | Accommodation and Food Services | $172,308 | $173,271 | 14 | <$5M | AI Deep Dive |
| Berkshire Mountain Brewers INC | Accommodation and Food Services | $166,100 | $158,123 | 40 | $7.1M | AI Deep Dive |
| Berkshire Property Agents, LLC | Real Estate and Rental and Leasing | $165,400 | $56,928 | 4 | <$5M | AI Deep Dive |
| Regen Network Development Inc. - Owner | Professional, Scientific, and Technical Services | $158,179 | $160,532 | 8 | <$5M | AI Deep Dive |
| Whalen Nursery INC | Agriculture, Forestry, Fishing and Hunting | $154,120 | $155,995 | 10 | <$5M | AI Deep Dive |
| Regen Network Development, Inc. | Professional, Scientific, and Technical Services | $149,117 | $150,645 | 8 | <$5M | AI Deep Dive |
| Community Access to the Arts Inc. | Educational Services | $148,400 | $149,030 | 11 | <$5M | AI Deep Dive |