| Pcc Industries INC | Administrative and Support and Waste Management | $20,832 | $0 | 1 | <$5M |  AI Deep Dive |
| Terry Porter | Accommodation and Food Services | $20,720 | $0 | 1 | <$5M | AI Deep Dive |
| George Hill | Health Care and Social Assistance | $20,052 | $20,088 | 1 | <$5M | AI Deep Dive |
| Pine Plains Truck and Auto, LLC | Other Services (except Public Administration) | $16,700 | $16,913 | 3 | <$5M | AI Deep Dive |
| Inn at Pine Plains Ltd | Accommodation and Food Services | $16,620 | $16,746 | 15 | <$5M | AI Deep Dive |
| Mike George Plumbing and Heating | Construction | $16,250 | $16,484 | 3 | <$5M | AI Deep Dive |
| Casazza Construction INC | Construction | $15,463 | $15,590 | 4 | <$5M | AI Deep Dive |
| Brighterviews Inc. | Administrative and Support and Waste Management | $15,458 | $15,574 | 1 | <$5M | AI Deep Dive |
| Brighterviews INC | Administrative and Support and Waste Management | $15,457 | $15,545 | 1 | <$5M | AI Deep Dive |
| Denardis Plumbing & Heating Inc. | Construction | $15,297 | $15,419 | 3 | <$5M | AI Deep Dive |
| Richard Pelletier | Construction | $14,635 | $14,721 | 1 | <$5M | AI Deep Dive |
| William Reinert Associates, Inc. | Professional, Scientific, and Technical Services | $13,937 | $14,056 | 1 | <$5M | AI Deep Dive |
| Christina Coughlin | Other Services (except Public Administration) | $13,342 | $13,439 | 1 | <$5M | AI Deep Dive |
| The Church Street Bar Inc. | Accommodation and Food Services | $13,287 | $13,396 | 4 | <$5M | AI Deep Dive |
| Prospect Hill Farmstead LLC | Retail Trade | $13,020 | $13,290 | 1 | <$5M | AI Deep Dive |
| Prospect Hill Farmstead LLC | Agriculture, Forestry, Fishing and Hunting | $12,760 | $12,835 | 1 | <$5M | AI Deep Dive |
| Timothy Jones | Professional, Scientific, and Technical Services | $12,500 | $12,657 | 1 | <$5M | AI Deep Dive |
| Jose Santiago | Other Services (except Public Administration) | $12,327 | $12,416 | 1 | <$5M | AI Deep Dive |
| Jz Enterprises INC | Manufacturing | $11,250 | $11,313 | 1 | <$5M | AI Deep Dive |
| Nature Walk Farm LLC | Agriculture, Forestry, Fishing and Hunting | $10,200 | $10,297 | 1 | <$5M | AI Deep Dive |
| Moose On the Loose, LLC | Retail Trade | $9,855 | $9,900 | 6 | <$5M | AI Deep Dive |
| Full Circus Farm LLC | Agriculture, Forestry, Fishing and Hunting | $9,400 | $9,438 | 2 | <$5M | AI Deep Dive |
| Pine Plains Liquor Corporation | Retail Trade | $8,317 | $8,462 | 3 | <$5M | AI Deep Dive |
| Homestead Improvements & Water Systems INC | Construction | $8,175 | $8,240 | 1 | <$5M | AI Deep Dive |
| Church of the Regeneration | Other Services (except Public Administration) | $7,560 | $7,592 | 1 | N/A | AI Deep Dive |