| Belizimo Salon | Other Services (except Public Administration) | $29,200 | $29,546 | 4 | <$5M |  AI Deep Dive |
| Hawkins House INC | Retail Trade | $29,200 | $29,379 | 5 | <$5M | AI Deep Dive |
| Belizimo Salon | Other Services (except Public Administration) | $29,200 | $29,390 | 5 | <$5M | AI Deep Dive |
| Michael Mahar | Construction | $28,707 | $28,812 | 2 | <$5M | AI Deep Dive |
| Bennington Pizza House LLC | Accommodation and Food Services | $28,600 | $28,988 | 11 | <$5M | AI Deep Dive |
| China Wok Family INC | Accommodation and Food Services | $28,500 | $28,718 | 7 | <$5M | AI Deep Dive |
| Sperber Tool Works INC | Manufacturing | $28,200 | $28,350 | 3 | <$5M | AI Deep Dive |
| Kateryna Latypova Dmd | Health Care and Social Assistance | $27,440 | $27,595 | 4 | <$5M | AI Deep Dive |
| Second Congregational Church Inc., Bennington, Vt | Other Services (except Public Administration) | $27,100 | $27,229 | 6 | <$5M | AI Deep Dive |
| Bringing You Vermont LLC | Accommodation and Food Services | $26,598 | $26,760 | 13 | <$5M | AI Deep Dive |
| Windylea Farm LLC | Agriculture, Forestry, Fishing and Hunting | $26,100 | $26,339 | 3 | <$5M | AI Deep Dive |
| The Avocado Pit LLC | Accommodation and Food Services | $25,785 | $26,205 | 15 | <$5M | AI Deep Dive |
| Bennington Dental Center PC | Health Care and Social Assistance | $25,595 | $25,987 | 7 | <$5M | AI Deep Dive |
| Sarah E Wilson, Attorney at Law | Professional, Scientific, and Technical Services | $24,805 | $25,204 | 3 | <$5M | AI Deep Dive |
| Open Sesame, Inc. | Retail Trade | $24,800 | $24,956 | 5 | <$5M | AI Deep Dive |
| One World Environmental DBA 802 Restroo | Real Estate and Rental and Leasing | $24,600 | $24,735 | 4 | <$5M | AI Deep Dive |
| One World Environmental DBA 802 Restrooms | Real Estate and Rental and Leasing | $24,600 | $24,773 | 10 | <$5M | AI Deep Dive |
| Kimberley Benner | Accommodation and Food Services | $24,400 | $24,585 | 9 | <$5M | AI Deep Dive |
| Brian K. Marthage | Professional, Scientific, and Technical Services | $24,367 | $24,519 | 2 | <$5M | AI Deep Dive |
| Brian Marthage | Professional, Scientific, and Technical Services | $24,367 | $24,566 | 2 | <$5M | AI Deep Dive |
| E-Enable INC | Professional, Scientific, and Technical Services | $24,300 | $24,461 | 3 | <$5M | AI Deep Dive |
| Open Sesame, Inc. | Retail Trade | $24,268 | $24,460 | 4 | <$5M | AI Deep Dive |
| James F Thibodeau, State Farm Insurance | Finance and Insurance | $24,100 | $24,286 | 2 | <$5M | AI Deep Dive |
| Steele Rose, LLC | Accommodation and Food Services | $24,004 | $0 | 8 | <$5M | AI Deep Dive |
| Bennington County Association Against Child Abuse | Health Care and Social Assistance | $23,800 | $23,952 | 2 | N/A | AI Deep Dive |