| Cardinal Hayes Home for Children | Other Services (except Public Administration) | $2,731,875 | $193,237 | 325 | N/A |  AI Deep Dive |
| Millbrook School | Educational Services | $2,033,500 | $2,055,729 | 149 | N/A | AI Deep Dive |
| Dutchess Day School | Educational Services | $576,277 | $581,408 | 40 | N/A | AI Deep Dive |
| Structure Works Construction Inc. | Construction | $404,983 | $407,480 | 21 | $6.4M | AI Deep Dive |
| Structure Works Construction Inc. | Construction | $404,983 | $407,868 | 26 | $8.2M | AI Deep Dive |
| Mackey Butts and Wise, LLP | Professional, Scientific, and Technical Services | $343,950 | $346,457 | 27 | $6.6M | AI Deep Dive |
| Cornell Cooperative Extension DC | Agriculture, Forestry, Fishing and Hunting | $323,200 | $326,919 | 56 | N/A | AI Deep Dive |
| Cornell Cooperative Extension Dutchesss County | Agriculture, Forestry, Fishing and Hunting | $322,500 | $325,610 | 60 | N/A | AI Deep Dive |
| Millbrook Physical Therapy PC | Health Care and Social Assistance | $292,700 | $295,571 | 20 | $5.4M | AI Deep Dive |
| Millbrook Physical Therapy, P.c. | Health Care and Social Assistance | $292,700 | $296,782 | 39 | $10.5M | AI Deep Dive |
| Tamarack Preserve, Ltd. | Arts, Entertainment, and Recreation | $250,000 | $252,226 | 26 | <$5M | AI Deep Dive |
| Twin Brooks Garden Center INC | Agriculture, Forestry, Fishing and Hunting | $249,800 | $252,134 | 12 | <$5M | AI Deep Dive |
| Millbrook Winery | Manufacturing | $217,680 | $218,873 | 24 | $8.5M | AI Deep Dive |
| Crisp Architects | Professional, Scientific, and Technical Services | $187,500 | $189,190 | 14 | <$5M | AI Deep Dive |
| Reardon Briggs Co. INC | Retail Trade | $184,476 | $185,391 | 22 | <$5M | AI Deep Dive |
| Tankfarm LLC | Unknown | $184,187 | $0 | 15 | N/A | AI Deep Dive |
| Dutchess Land Conservancy | Other Services (except Public Administration) | $161,910 | $162,877 | 13 | N/A | AI Deep Dive |
| Millbrook Equine Veterinary Clinic, PC | Professional, Scientific, and Technical Services | $155,926 | $157,951 | 12 | <$5M | AI Deep Dive |
| 17a-4 LLC | Professional, Scientific, and Technical Services | $148,890 | $149,518 | 10 | <$5M | AI Deep Dive |
| 17a-4, LLC | Professional, Scientific, and Technical Services | $148,800 | $149,880 | 10 | <$5M | AI Deep Dive |
| Millbrook Kitchen Project LLC | Manufacturing | $145,000 | $147,940 | 22 | $7.8M | AI Deep Dive |
| The Millbrook Kitchen Project | Manufacturing | $130,705 | $132,406 | 20 | $7.1M | AI Deep Dive |
| New Dimension Construction Inc. | Construction | $125,350 | $126,033 | 15 | <$5M | AI Deep Dive |
| New Dimension Construction Inc. | Construction | $125,300 | $126,069 | 13 | <$5M | AI Deep Dive |
| Macina, LLC | Accommodation and Food Services | $112,500 | $113,291 | 12 | <$5M | AI Deep Dive |