| Coogan Family INC | Accommodation and Food Services | $236,667 | $239,566 | 16 | <$5M |  AI Deep Dive |
| Island Epicure INC | Accommodation and Food Services | $228,600 | $230,936 | 18 | <$5M | AI Deep Dive |
| Martha's Vineyard Construction Co INC | Construction | $219,808 | $221,200 | 10 | <$5M | AI Deep Dive |
| Willett Electric INC | Construction | $216,891 | $218,704 | 11 | <$5M | AI Deep Dive |
| Rosewater Mv LLC | Accommodation and Food Services | $216,841 | $219,336 | 7 | <$5M | AI Deep Dive |
| Depot Corner INC | Retail Trade | $207,114 | $208,980 | 19 | $6.4M | AI Deep Dive |
| Rosewater Mv LLC | Accommodation and Food Services | $197,600 | $199,885 | 12 | <$5M | AI Deep Dive |
| Granite Stores of M.v. Inc. | Retail Trade | $193,600 | $194,565 | 14 | <$5M | AI Deep Dive |
| William Mueller Plumbing INC | Construction | $188,900 | $190,737 | 11 | <$5M | AI Deep Dive |
| Atria Mv Corporation | Accommodation and Food Services | $182,741 | $184,269 | 12 | <$5M | AI Deep Dive |
| Harborside Triangle Liquors, Ltd | Retail Trade | $179,130 | $180,697 | 39 | $6.0M | AI Deep Dive |
| Willett Electric INC | Construction | $177,000 | $179,337 | 11 | <$5M | AI Deep Dive |
| Greenhouse LLC | Accommodation and Food Services | $175,867 | $178,134 | 12 | <$5M | AI Deep Dive |
| Harborside Inn Condominium Trust | Accommodation and Food Services | $175,000 | $176,731 | 43 | $13.4M | AI Deep Dive |
| Edgartown Hardware, INC | Retail Trade | $173,286 | $174,624 | 20 | <$5M | AI Deep Dive |
| Detente LLC | Accommodation and Food Services | $170,496 | $172,485 | 8 | <$5M | AI Deep Dive |
| Martha's Vineyard Preservation Trust, INC | Real Estate and Rental and Leasing | $164,282 | $165,578 | 20 | N/A | AI Deep Dive |
| Marthas Vineyard Preservation Trust INC | Arts, Entertainment, and Recreation | $164,282 | $165,313 | 24 | N/A | AI Deep Dive |
| Island Epicure INC | Accommodation and Food Services | $163,300 | $164,495 | 10 | <$5M | AI Deep Dive |
| Bad Martha Farmers Brewery LLC | Manufacturing | $161,500 | $163,018 | 19 | $6.7M | AI Deep Dive |
| Vineyard Cantina INC | Accommodation and Food Services | $157,583 | $160,095 | 8 | <$5M | AI Deep Dive |
| Chappaquiddick Ferry, INC | Transportation and Warehousing | $153,200 | $154,644 | 10 | <$5M | AI Deep Dive |
| Edgartown Art Gallery INC | Accommodation and Food Services | $152,858 | $154,192 | 9 | <$5M | AI Deep Dive |
| Big Sky, Inc. | Real Estate and Rental and Leasing | $147,153 | $148,478 | 8 | <$5M | AI Deep Dive |
| Rosbeck Builders Corp | Construction | $146,700 | $148,625 | 7 | <$5M | AI Deep Dive |