| Salvatore J. Sciangula | Professional, Scientific, and Technical Services | $25,000 | $25,303 | 1 | <$5M |  AI Deep Dive |
| The Catskill Mountain Country Store | Retail Trade | $24,604 | $24,774 | 21 | <$5M | AI Deep Dive |
| St Theresas of the Child Jesus | Other Services (except Public Administration) | $23,400 | $23,555 | 5 | N/A | AI Deep Dive |
| Desgaches and Associates Inc. | Accommodation and Food Services | $23,000 | $23,115 | 7 | <$5M | AI Deep Dive |
| St Theresa of the Child Jesus Church | Other Services (except Public Administration) | $22,950 | $23,141 | 4 | N/A | AI Deep Dive |
| Casa Neapolis LLC | Accommodation and Food Services | $21,068 | $21,313 | 3 | <$5M | AI Deep Dive |
| Belgian Trucking & Excavating, LLC | Construction | $20,000 | $20,132 | 4 | <$5M | AI Deep Dive |
| Windham Area Recreation Foundation | Arts, Entertainment, and Recreation | $19,300 | $19,524 | 4 | <$5M | AI Deep Dive |
| Robert Edward Forte | Construction | $19,282 | $0 | 4 | <$5M | AI Deep Dive |
| Brabazon Agency, Inc. | Finance and Insurance | $18,300 | $18,514 | 3 | <$5M | AI Deep Dive |
| Windham Convenience INC | Retail Trade | $17,600 | $17,812 | 4 | <$5M | AI Deep Dive |
| Windham Ventures INC | Real Estate and Rental and Leasing | $16,732 | $16,879 | 7 | <$5M | AI Deep Dive |
| Windham Hardware, Inc. | Retail Trade | $16,000 | $16,118 | 3 | <$5M | AI Deep Dive |
| Windham Ventures | Information | $15,600 | $15,747 | 4 | <$5M | AI Deep Dive |
| Thyme and Place, Ltd. | Retail Trade | $15,560 | $15,756 | 4 | <$5M | AI Deep Dive |
| John T Moss CPA | Professional, Scientific, and Technical Services | $14,600 | $14,707 | 3 | <$5M | AI Deep Dive |
| Right Beginnings, Inc. | Health Care and Social Assistance | $14,480 | $14,612 | 10 | <$5M | AI Deep Dive |
| John Landi | Construction | $14,322 | $14,416 | 1 | <$5M | AI Deep Dive |
| Windham Local LLC | Accommodation and Food Services | $14,049 | $14,221 | 10 | <$5M | AI Deep Dive |
| Xcel LLC | Real Estate and Rental and Leasing | $12,900 | $12,975 | 1 | <$5M | AI Deep Dive |
| Sva Enterprises INC | Other Services (except Public Administration) | $12,500 | $12,664 | 1 | <$5M | AI Deep Dive |
| Jtm Wealth Managment, Inc. | Finance and Insurance | $12,215 | $12,326 | 1 | <$5M | AI Deep Dive |
| Decker Gulino Inc. | Other Services (except Public Administration) | $12,036 | $12,104 | 3 | <$5M | AI Deep Dive |
| Decker-Gulino Inc. | Other Services (except Public Administration) | $12,000 | $12,127 | 1 | <$5M | AI Deep Dive |
| Windham Mt Real Estate, Building & Development LLC | Real Estate and Rental and Leasing | $11,993 | $12,121 | 2 | <$5M | AI Deep Dive |