| O'connell Oil Associates, Inc. | Retail Trade | $654,196 | $658,012 | 59 | $14.1M | AI Deep Dive |
| Lipton INC | Retail Trade | $652,680 | $661,335 | 111 | $37.1M | AI Deep Dive |
| Berkshire Retirement Home, Inc. | Health Care and Social Assistance | $650,000 | $656,500 | 92 | N/A | AI Deep Dive |
| Berkshire Precision Tool LLC | Manufacturing | $646,715 | $653,253 | 57 | $14.9M | AI Deep Dive |
| Edm Services Inc. | Professional, Scientific, and Technical Services | $642,342 | $651,071 | 36 | <$5M | AI Deep Dive |
| Berkshire Precision Tool, LLC | Manufacturing | $630,100 | $637,730 | 53 | $13.9M | AI Deep Dive |
| Edm Services, Inc. | Professional, Scientific, and Technical Services | $621,800 | $629,449 | 53 | $6.5M | AI Deep Dive |
| Pittsfield Pipers, INC | Construction | $569,053 | $576,973 | 29 | $9.2M | AI Deep Dive |
| Brilliant Graphics Group LLC | Professional, Scientific, and Technical Services | $564,337 | $570,552 | 16 | <$5M | AI Deep Dive |
| Laurin Publishing Co., Inc. | Information | $558,500 | $565,156 | 46 | $7.7M | AI Deep Dive |
| Ucp of Western Massachusetts, INC | Health Care and Social Assistance | $515,900 | $493,965 | 83 | N/A | AI Deep Dive |
| Brilliant Graphics Group L.l.c. | Manufacturing | $515,407 | $520,971 | 16 | $15.9M | AI Deep Dive |
| Goodwill of the Berkshires and Southern Vermont, INC | Retail Trade | $506,530 | $509,820 | 127 | $24.1M | AI Deep Dive |
| Goodwill of the Berkshires and Southern Vermont, INC | Retail Trade | $506,530 | $509,680 | 108 | $20.5M | AI Deep Dive |
| Dns Enterprises, Ltd | Health Care and Social Assistance | $505,500 | $509,207 | 122 | $19.8M | AI Deep Dive |
| Sampco Inc. | Manufacturing | $499,100 | $505,253 | 18 | <$5M | AI Deep Dive |
| Sampco Inc. | Manufacturing | $494,114 | $499,529 | 40 | $11.2M | AI Deep Dive |
| Mountain View Home Care. Inc. | Health Care and Social Assistance | $477,400 | $480,448 | 85 | $14.6M | AI Deep Dive |
| Berkshire Young Men's Christian Association | Health Care and Social Assistance | $444,003 | $446,402 | 148 | N/A | AI Deep Dive |
| Barrington Stage Company INC | Arts, Entertainment, and Recreation | $440,052 | $443,126 | 23 | N/A | AI Deep Dive |
| Pediatric Development Center INC | Health Care and Social Assistance | $437,700 | $443,086 | 40 | N/A | AI Deep Dive |
| Pediatric Development Center INC | Health Care and Social Assistance | $435,100 | $440,950 | 40 | N/A | AI Deep Dive |
| Berkshire Housing Services, Inc. | Health Care and Social Assistance | $434,000 | $436,901 | 42 | N/A | AI Deep Dive |
| Dns Enterprises Ltd | Health Care and Social Assistance | $427,900 | $429,944 | 99 | $17.0M | AI Deep Dive |
| Pittsfield Motors INC | Retail Trade | $416,800 | $422,053 | 29 | $7.3M | AI Deep Dive |