| Marion's Pie Shop | Manufacturing | $42,500 | $42,943 | 9 | <$5M |  AI Deep Dive |
| The Old Harbor Inn | Accommodation and Food Services | $41,900 | $42,186 | 3 | <$5M | AI Deep Dive |
| The Blue Coral Seaside Cuisine & Spirits, LLC | Accommodation and Food Services | $41,100 | $41,377 | 50 | $8.9M | AI Deep Dive |
| Chatham Health Club INC | Arts, Entertainment, and Recreation | $40,210 | $40,637 | 23 | <$5M | AI Deep Dive |
| Diane E. F. Co. Inc. | Accommodation and Food Services | $40,192 | $40,774 | 15 | <$5M | AI Deep Dive |
| Windwalker Enterprises, Ltd | Accommodation and Food Services | $40,000 | $40,384 | 3 | <$5M | AI Deep Dive |
| Riley & Norcross LLC | Professional, Scientific, and Technical Services | $39,573 | $39,833 | 4 | <$5M | AI Deep Dive |
| Tale of the Cod | Retail Trade | $39,387 | $39,598 | 6 | <$5M | AI Deep Dive |
| Wise Living LLC | Real Estate and Rental and Leasing | $39,325 | $39,841 | 3 | <$5M | AI Deep Dive |
| Chatham Cookware LLC | Accommodation and Food Services | $38,968 | $39,341 | 8 | <$5M | AI Deep Dive |
| Fisherman's Daughter LLC | Retail Trade | $38,879 | $39,182 | 18 | $5.4M | AI Deep Dive |
| Sheila Hadawar | Retail Trade | $38,695 | $39,011 | 5 | <$5M | AI Deep Dive |
| Seaside Designs INC | Professional, Scientific, and Technical Services | $38,360 | $39,090 | 4 | <$5M | AI Deep Dive |
| If the Shoe Fits, LLC | Retail Trade | $38,304 | $38,689 | 5 | <$5M | AI Deep Dive |
| Muriel Underhill | Other Services (except Public Administration) | $37,595 | $37,958 | 5 | <$5M | AI Deep Dive |
| Clark Engineering-Sba Small 7a Term | Professional, Scientific, and Technical Services | $37,195 | $37,546 | 2 | <$5M | AI Deep Dive |
| The Trading Company of Chatham, Inc. | Retail Trade | $37,000 | $37,298 | 2 | <$5M | AI Deep Dive |
| Mcdonald Landscaping LLC | Administrative and Support and Waste Management | $36,900 | $37,245 | 7 | <$5M | AI Deep Dive |
| Eric Linder | Retail Trade | $36,789 | $37,159 | 3 | <$5M | AI Deep Dive |
| Old Wharf Village LLC Old Wharf Village LLC | Accommodation and Food Services | $35,980 | $0 | 2 | <$5M | AI Deep Dive |
| The Trading Company of Chatham Inc. | Retail Trade | $35,111 | $35,419 | 2 | <$5M | AI Deep Dive |
| Diane Ef Co INC | Accommodation and Food Services | $34,800 | $35,293 | 25 | <$5M | AI Deep Dive |
| Thomas Electrical Services Inc. | Construction | $34,257 | $34,434 | 4 | <$5M | AI Deep Dive |
| Robert Bianchi | Professional, Scientific, and Technical Services | $32,653 | $33,044 | 2 | <$5M | AI Deep Dive |
| Pilgrim Village of Chatham | Accommodation and Food Services | $31,772 | $32,041 | 5 | <$5M | AI Deep Dive |