| Kevin Oliver Caretaking Inc. | Real Estate and Rental and Leasing | $28,200 | $28,367 | 3 | <$5M | AI Deep Dive |
| Parry Windows & Doors LLC | Construction | $27,300 | $27,440 | 3 | <$5M | AI Deep Dive |
| Stanley Starzell Cfp | Finance and Insurance | $27,083 | $27,298 | 2 | <$5M | AI Deep Dive |
| Parry Windows & Doors LLC | Manufacturing | $26,910 | $27,035 | 3 | <$5M | AI Deep Dive |
| Cybele Benton Mccormick | Accommodation and Food Services | $26,489 | $26,805 | 6 | <$5M | AI Deep Dive |
| Krishana Collins | Agriculture, Forestry, Fishing and Hunting | $25,100 | $25,371 | 3 | <$5M | AI Deep Dive |
| Jmg Sports Agency INC | Arts, Entertainment, and Recreation | $24,600 | $24,914 | 3 | <$5M | AI Deep Dive |
| Krishana Collins | Agriculture, Forestry, Fishing and Hunting | $24,072 | $24,352 | 3 | <$5M | AI Deep Dive |
| Ellen Wingard | Professional, Scientific, and Technical Services | $23,600 | $23,819 | 1 | <$5M | AI Deep Dive |
| Friends of the Chilmark Preschool, INC | Public Administration | $23,100 | $23,373 | 3 | N/A | AI Deep Dive |
| Foggy. Bottom Company LLC | Administrative and Support and Waste Management | $22,000 | $15,166 | 3 | <$5M | AI Deep Dive |
| Island Interiors LLC | Professional, Scientific, and Technical Services | $20,833 | $21,062 | 1 | <$5M | AI Deep Dive |
| Jennifer a Jamgochian | Administrative and Support and Waste Management | $20,833 | $20,956 | 1 | <$5M | AI Deep Dive |
| The Garfinkel Group LLC | Professional, Scientific, and Technical Services | $20,832 | $20,913 | 1 | <$5M | AI Deep Dive |
| Rebecca Conroy | Real Estate and Rental and Leasing | $20,800 | $20,938 | 1 | <$5M | AI Deep Dive |
| Jill Alman-Bernstein | Real Estate and Rental and Leasing | $20,800 | $20,920 | 2 | <$5M | AI Deep Dive |
| Rebecca Potter | Administrative and Support and Waste Management | $20,700 | $20,858 | 8 | <$5M | AI Deep Dive |
| Rumi Sumaq LLC | Manufacturing | $20,600 | $20,706 | 2 | <$5M | AI Deep Dive |
| Gustavo Simoes | Construction | $19,200 | $19,343 | 3 | <$5M | AI Deep Dive |
| Russell Maloney Real Estate LLC | Real Estate and Rental and Leasing | $18,000 | $11,843 | 1 | <$5M | AI Deep Dive |
| Martha's Vineyard Fishermen's Preservation Trust | Manufacturing | $16,300 | $16,409 | 1 | N/A | AI Deep Dive |
| Our Island Club | Other Services (except Public Administration) | $16,000 | $4,229 | 3 | <$5M | AI Deep Dive |
| Maida Caretaking | Real Estate and Rental and Leasing | $15,000 | $12,089 | 1 | <$5M | AI Deep Dive |
| Bodnar Fine Homebuilding, LLC | Construction | $15,000 | $15,161 | 1 | <$5M | AI Deep Dive |
| Island Stone & Granite INC | Construction | $13,750 | $13,840 | 2 | <$5M | AI Deep Dive |