| Evergreen Excavating LLC | Construction | $44,987 | $45,161 | 5 | <$5M | AI Deep Dive |
| Columbia Tile LLC | Construction | $42,500 | $40,587 | 4 | <$5M | AI Deep Dive |
| One Thousand Percent LLC | Information | $41,667 | $41,886 | 2 | <$5M | AI Deep Dive |
| Justin Madsen | Construction | $40,905 | $41,104 | 2 | <$5M | AI Deep Dive |
| Madpiper, LLC | Accommodation and Food Services | $40,800 | $41,230 | 10 | <$5M | AI Deep Dive |
| Louis F. Payn Foundation for Aged People | Health Care and Social Assistance | $39,400 | $39,558 | 15 | N/A | AI Deep Dive |
| Flint Law Firm PC | Professional, Scientific, and Technical Services | $38,019 | $38,326 | 3 | <$5M | AI Deep Dive |
| Chatham Film Club Inc. | Information | $37,480 | $37,686 | 11 | <$5M | AI Deep Dive |
| Chatham Real Food Market Co-Op Inc. | Retail Trade | $35,420 | $35,698 | 12 | <$5M | AI Deep Dive |
| Nancyscans Corp. | Professional, Scientific, and Technical Services | $34,799 | $35,197 | 2 | <$5M | AI Deep Dive |
| Nancyscans Corp. | Manufacturing | $34,799 | $35,126 | 3 | <$5M | AI Deep Dive |
| Upstate Scenic Inc. | Arts, Entertainment, and Recreation | $33,052 | $33,407 | 6 | <$5M | AI Deep Dive |
| Chatham Tax Service INC | Professional, Scientific, and Technical Services | $32,885 | $33,091 | 12 | <$5M | AI Deep Dive |
| Chatham Flowers & Gifts, LLC | Retail Trade | $32,703 | $32,975 | 12 | <$5M | AI Deep Dive |
| Mutual Arising Mental Health Counseling, Pllc | Health Care and Social Assistance | $32,500 | $25,249 | 2 | <$5M | AI Deep Dive |
| Wunderburger, Inc. | Accommodation and Food Services | $32,153 | $32,413 | 10 | <$5M | AI Deep Dive |
| James Kleinbaum, Attorney at Law PC | Professional, Scientific, and Technical Services | $31,700 | $31,985 | 3 | <$5M | AI Deep Dive |
| Gmb 36 LLC | Unknown | $28,200 | $28,535 | 10 | N/A | AI Deep Dive |
| Chatham Kids Club Inc. | Health Care and Social Assistance | $27,917 | $28,048 | 9 | N/A | AI Deep Dive |
| Chatham Tax Sverice Inc. | Professional, Scientific, and Technical Services | $26,197 | $26,386 | 12 | <$5M | AI Deep Dive |
| Chatham Film Club, Inc. | Arts, Entertainment, and Recreation | $26,080 | $26,323 | 19 | <$5M | AI Deep Dive |
| Suzanne Trevellyan | Professional, Scientific, and Technical Services | $25,518 | $25,647 | 1 | <$5M | AI Deep Dive |
| Trevellyan.biz | Professional, Scientific, and Technical Services | $25,500 | $25,675 | 1 | <$5M | AI Deep Dive |
| Shear Images | Other Services (except Public Administration) | $24,200 | $24,455 | 4 | <$5M | AI Deep Dive |
| Camphill Association of North America | Health Care and Social Assistance | $23,350 | $23,500 | 2 | N/A | AI Deep Dive |