| Cove Road Inn LLC | Accommodation and Food Services | $116,400 | $117,739 | 20 | $6.3M |  AI Deep Dive |
| 7 a Foods LLC | Accommodation and Food Services | $104,528 | $105,478 | 10 | <$5M | AI Deep Dive |
| Misty Meadows Equine Learning Center, Inc. | Educational Services | $88,300 | $88,775 | 10 | N/A | AI Deep Dive |
| Haynes Plumbing & Caretaking, Inc. | Construction | $85,700 | $86,593 | 5 | <$5M | AI Deep Dive |
| Sea Smoke Barbeque, Corp | Accommodation and Food Services | $77,602 | $78,387 | 12 | <$5M | AI Deep Dive |
| Bernier's Up-Island Market INC | Retail Trade | $75,000 | $75,504 | 8 | <$5M | AI Deep Dive |
| Vineyard Engineering INC | Professional, Scientific, and Technical Services | $72,800 | $73,327 | 7 | <$5M | AI Deep Dive |
| 7a Foods, LLC | Accommodation and Food Services | $71,200 | $71,879 | 14 | <$5M | AI Deep Dive |
| Plane View INC | Accommodation and Food Services | $70,407 | $71,123 | 8 | <$5M | AI Deep Dive |
| The Font Bureau INC | Professional, Scientific, and Technical Services | $67,000 | $67,422 | 10 | <$5M | AI Deep Dive |
| Breth Corporation | Accommodation and Food Services | $65,700 | $66,177 | 13 | <$5M | AI Deep Dive |
| Tdr Landscaping & Irrigation INC | Administrative and Support and Waste Management | $64,800 | $65,443 | 25 | $5.4M | AI Deep Dive |
| Contact Stone INC | Construction | $62,700 | $63,287 | 3 | <$5M | AI Deep Dive |
| Laurence Clancy Construction, Inc. | Construction | $53,685 | $54,453 | 3 | <$5M | AI Deep Dive |
| William a Dreyer III Builder LLC | Construction | $53,200 | $53,697 | 2 | <$5M | AI Deep Dive |
| Radius Construction INC | Construction | $52,600 | $52,888 | 4 | <$5M | AI Deep Dive |
| Roy C Hope | Administrative and Support and Waste Management | $47,800 | $48,123 | 10 | <$5M | AI Deep Dive |
| Radius Construction Inc. | Construction | $46,255 | $46,496 | 4 | <$5M | AI Deep Dive |
| Dukes County Builders INC | Construction | $43,300 | $43,765 | 3 | <$5M | AI Deep Dive |
| John C. Anderson | Construction | $43,031 | $43,435 | 3 | <$5M | AI Deep Dive |
| Stedman Construction Inc. | Construction | $41,600 | $41,809 | 2 | <$5M | AI Deep Dive |
| Sports Initiatives LLC | Professional, Scientific, and Technical Services | $41,600 | $20,943 | 2 | <$5M | AI Deep Dive |
| Stedman Construction Inc. | Construction | $41,600 | $42,010 | 2 | <$5M | AI Deep Dive |
| Kfb & Associates Consulting Inc. | Professional, Scientific, and Technical Services | $41,000 | $41,269 | 3 | <$5M | AI Deep Dive |
| Mid-Island Repair INC | Other Services (except Public Administration) | $39,200 | $39,392 | 5 | <$5M | AI Deep Dive |