| Fairview Hospital | Health Care and Social Assistance | $5,810,117 | $5,851,504 | 387 | $76.8M |  AI Deep Dive |
| Community Health Programs, Incorporated | Health Care and Social Assistance | $2,202,200 | $2,227,601 | 228 | N/A | AI Deep Dive |
| Community Health Programs Inc. | Health Care and Social Assistance | $2,000,000 | $2,025,918 | 233 | N/A | AI Deep Dive |
| Berkshire Corporation | Manufacturing | $1,072,500 | $1,082,050 | 104 | $103.2M | AI Deep Dive |
| Willowood of Great Barrington INC | Health Care and Social Assistance | $1,069,602 | $1,077,565 | 96 | $16.3M | AI Deep Dive |
| Bear Mountain 320 Operating, LLC | Health Care and Social Assistance | $934,800 | $946,940 | 88 | $15.0M | AI Deep Dive |
| Wheeler & Taylor Inc. | Finance and Insurance | $655,153 | $660,394 | 59 | $30.3M | AI Deep Dive |
| Wheeler and Taylor, Inc. | Real Estate and Rental and Leasing | $655,152 | $659,603 | 47 | $6.8M | AI Deep Dive |
| Catamount Ski Resort LLC | Arts, Entertainment, and Recreation | $436,900 | $443,017 | 30 | <$5M | AI Deep Dive |
| Life Needs Coop Inc. | Health Care and Social Assistance | $425,153 | $429,251 | 67 | N/A | AI Deep Dive |
| Life Needs Coop Inc. | Health Care and Social Assistance | $419,500 | $423,264 | 67 | N/A | AI Deep Dive |
| Berkshire Cooperative Association, Inc. | Retail Trade | $400,000 | $403,518 | 63 | $15.7M | AI Deep Dive |
| Wood Anchor Inc. | Accommodation and Food Services | $341,452 | $345,531 | 16 | <$5M | AI Deep Dive |
| Berkshire South Regional Community Center | Arts, Entertainment, and Recreation | $339,000 | $332,200 | 35 | N/A | AI Deep Dive |
| Berkshire Waldorf School, Inc. | Educational Services | $334,400 | $338,843 | 44 | $5.3M | AI Deep Dive |
| Berkshire South Regional Community Center | Health Care and Social Assistance | $320,035 | $323,647 | 60 | N/A | AI Deep Dive |
| Ward's Nursery | Wholesale Trade | $311,800 | $313,562 | 29 | $7.5M | AI Deep Dive |
| The Chamberlain Group | Manufacturing | $300,601 | $302,248 | 20 | $5.6M | AI Deep Dive |
| Butternut Basin INC | Arts, Entertainment, and Recreation | $275,000 | $276,560 | 24 | <$5M | AI Deep Dive |
| The Chamberlain Group, LLC | Manufacturing | $266,000 | $267,880 | 18 | $5.0M | AI Deep Dive |
| Wood Anchor Restaurant | Accommodation and Food Services | $244,800 | $246,711 | 46 | $8.2M | AI Deep Dive |
| E Caligari and Son | Retail Trade | $239,327 | $241,009 | 23 | <$5M | AI Deep Dive |
| Southern Berkshire Volunteer Ambulance Squad, INC | Health Care and Social Assistance | $231,300 | $234,500 | 33 | N/A | AI Deep Dive |
| John B Hull INC | Retail Trade | $228,200 | $229,469 | 14 | <$5M | AI Deep Dive |
| Gennari Plumbing & Heating Inc. | Construction | $224,900 | $227,792 | 12 | <$5M | AI Deep Dive |