| Aquamarine Builders, Inc. | Construction | $99,600 | $100,091 | 6 | <$5M |  AI Deep Dive |
| Vineyard Pool & Spa Inc. | Construction | $99,361 | $99,631 | 8 | <$5M | AI Deep Dive |
| Terrace at the Charlotte Inn LLC | Accommodation and Food Services | $97,303 | $98,154 | 7 | <$5M | AI Deep Dive |
| Thornton Chandler Construction Inc. | Construction | $96,800 | $97,460 | 6 | <$5M | AI Deep Dive |
| Martha's Vineyard Colonial Inn, LLC | Accommodation and Food Services | $95,500 | $96,329 | 14 | <$5M | AI Deep Dive |
| Brewer Tree & Land Company Inc. | Agriculture, Forestry, Fishing and Hunting | $95,000 | $95,502 | 4 | <$5M | AI Deep Dive |
| Summer Shades, INC | Retail Trade | $94,606 | $95,292 | 8 | <$5M | AI Deep Dive |
| Daves Handyman Services INC | Construction | $93,000 | $44,841 | 5 | <$5M | AI Deep Dive |
| Waterfront Builders, Inc. | Construction | $92,000 | $35,463 | 7 | <$5M | AI Deep Dive |
| Airport Fish House Inc. | Retail Trade | $91,708 | $92,580 | 8 | <$5M | AI Deep Dive |
| Itc Distributors LLC | Wholesale Trade | $90,383 | $91,007 | 7 | <$5M | AI Deep Dive |
| 19 Raw LLC | Accommodation and Food Services | $90,173 | $91,027 | 15 | <$5M | AI Deep Dive |
| Hagerty Tree INC | Administrative and Support and Waste Management | $90,000 | $90,348 | 7 | <$5M | AI Deep Dive |
| Hagerty Tree INC | Administrative and Support and Waste Management | $90,000 | $90,463 | 7 | <$5M | AI Deep Dive |
| Foam Insulation Technology INC | Construction | $89,000 | $89,801 | 6 | <$5M | AI Deep Dive |
| Atlanta Island Auto Rentals INC | Real Estate and Rental and Leasing | $89,000 | $89,566 | 10 | <$5M | AI Deep Dive |
| Thornton Chandler Construction INC | Construction | $88,493 | $89,584 | 6 | <$5M | AI Deep Dive |
| Espresso Love INC | Manufacturing | $88,000 | $89,218 | 10 | <$5M | AI Deep Dive |
| Signature Oysters LLC | Agriculture, Forestry, Fishing and Hunting | $86,800 | $17,319 | 5 | <$5M | AI Deep Dive |
| Point B Realty, LLC | Real Estate and Rental and Leasing | $85,600 | $86,439 | 6 | <$5M | AI Deep Dive |
| Edgartown Meat and Fish Market, Inc. | Retail Trade | $84,700 | $85,476 | 12 | <$5M | AI Deep Dive |
| Among the Flowers, INC | Accommodation and Food Services | $83,157 | $83,936 | 11 | <$5M | AI Deep Dive |
| Jms Waterman INC | Wholesale Trade | $81,800 | $82,387 | 6 | <$5M | AI Deep Dive |
| Serpa Brotherspartnership | Construction | $78,700 | $79,067 | 4 | <$5M | AI Deep Dive |
| Brewer Tree & Land Co INC | Agriculture, Forestry, Fishing and Hunting | $77,293 | $78,199 | 4 | <$5M | AI Deep Dive |