| Natalie Grewal | Accommodation and Food Services | $29,338 | $29,482 | 2 | <$5M |  AI Deep Dive |
| Midland Plumbing & Heating Inc. | Construction | $29,233 | $29,391 | 2 | <$5M | AI Deep Dive |
| Anne D Foley | Accommodation and Food Services | $29,167 | $29,438 | 1 | <$5M | AI Deep Dive |
| Seaver INC | Administrative and Support and Waste Management | $28,980 | $29,163 | 4 | <$5M | AI Deep Dive |
| Seaver INC | Administrative and Support and Waste Management | $28,980 | $29,214 | 4 | <$5M | AI Deep Dive |
| Vineyard Tennis Center INC | Arts, Entertainment, and Recreation | $28,927 | $29,140 | 5 | <$5M | AI Deep Dive |
| Sourati Engineering, INC | Professional, Scientific, and Technical Services | $28,900 | $29,132 | 2 | <$5M | AI Deep Dive |
| Sail Martha's Vineyard | Arts, Entertainment, and Recreation | $28,400 | $28,595 | 2 | <$5M | AI Deep Dive |
| Life at Humphreys INC | Accommodation and Food Services | $28,400 | $28,648 | 19 | <$5M | AI Deep Dive |
| Sarka Havlatkova Greene | Other Services (except Public Administration) | $27,926 | $28,221 | 3 | <$5M | AI Deep Dive |
| A1 Mv Cleaning Services | Administrative and Support and Waste Management | $27,800 | $27,984 | 2 | <$5M | AI Deep Dive |
| Midland Plumbing & Heating, Inc. | Construction | $27,300 | $27,492 | 2 | <$5M | AI Deep Dive |
| Autoeuropa of Martha's Vineyard Inc. | Other Services (except Public Administration) | $27,200 | $27,381 | 2 | <$5M | AI Deep Dive |
| Kristen Beaumont Reimann, Landscape Architect | Professional, Scientific, and Technical Services | $27,000 | $27,246 | 2 | <$5M | AI Deep Dive |
| Bobbi Flake Reed, Inc. | Real Estate and Rental and Leasing | $27,000 | $27,248 | 2 | <$5M | AI Deep Dive |
| Jr Construction & Sons INC | Construction | $26,812 | $27,046 | 3 | <$5M | AI Deep Dive |
| The Vineyard House INC | Other Services (except Public Administration) | $26,370 | $26,517 | 3 | N/A | AI Deep Dive |
| Worth and Wing | Professional, Scientific, and Technical Services | $26,300 | $12,716 | 2 | <$5M | AI Deep Dive |
| Island Home Medical | Wholesale Trade | $26,000 | $26,339 | 2 | <$5M | AI Deep Dive |
| Vineyard House INC | Other Services (except Public Administration) | $26,000 | $26,178 | 3 | N/A | AI Deep Dive |
| Stina Sayre Designs LLC | Manufacturing | $25,822 | $25,948 | 2 | <$5M | AI Deep Dive |
| Jessica Buckley | Accommodation and Food Services | $25,600 | $25,773 | 6 | <$5M | AI Deep Dive |
| Coastwise Wharf Co Inc. | Arts, Entertainment, and Recreation | $25,326 | $25,521 | 5 | <$5M | AI Deep Dive |
| Armstrong, Inc. | Professional, Scientific, and Technical Services | $25,300 | $25,417 | 2 | <$5M | AI Deep Dive |
| Coulter Brown LLC | Retail Trade | $25,000 | $25,246 | 4 | <$5M | AI Deep Dive |