| Rosewater Wine & Spirits LLC | Retail Trade | $30,400 | $30,731 | 5 | <$5M |  AI Deep Dive |
| The Boneyard LLC | Retail Trade | $30,332 | $30,652 | 6 | <$5M | AI Deep Dive |
| Vic Mv Hotel LLC | Accommodation and Food Services | $30,200 | $30,368 | 4 | <$5M | AI Deep Dive |
| Paul Bettencourt Electrician | Construction | $29,900 | $30,074 | 4 | <$5M | AI Deep Dive |
| Paul a Bettencourt | Construction | $29,900 | $30,290 | 1 | <$5M | AI Deep Dive |
| Martha's Vineyard Spear Point Oysters LLC | Agriculture, Forestry, Fishing and Hunting | $29,473 | $29,628 | 2 | <$5M | AI Deep Dive |
| Boneyard LLC | Retail Trade | $28,945 | $29,149 | 24 | $7.3M | AI Deep Dive |
| Animal Shelter of Martha's Vineyard | Finance and Insurance | $28,900 | $29,158 | 2 | N/A | AI Deep Dive |
| J.e. Kelleher Plumbing & Mechanical, Inc. | Construction | $28,800 | $24,747 | 3 | <$5M | AI Deep Dive |
| The Christina Gallery, Inc. | Retail Trade | $28,700 | $28,887 | 2 | <$5M | AI Deep Dive |
| Ihay INC | Administrative and Support and Waste Management | $27,936 | $28,263 | 2 | <$5M | AI Deep Dive |
| Kg Events & Design LLC | Arts, Entertainment, and Recreation | $27,500 | $27,678 | 4 | <$5M | AI Deep Dive |
| United Methodist Church of Martha's Vineyard | Other Services (except Public Administration) | $27,200 | $18,166 | 1 | N/A | AI Deep Dive |
| Marques Construction Limited Partnership | Construction | $26,840 | $27,194 | 2 | <$5M | AI Deep Dive |
| Tesoro Charters Ltd | Arts, Entertainment, and Recreation | $26,405 | $26,706 | 2 | <$5M | AI Deep Dive |
| Land Works Landscaping LLC | Administrative and Support and Waste Management | $26,400 | $26,748 | 2 | <$5M | AI Deep Dive |
| The Light Keeper's Inn LLC | Administrative and Support and Waste Management | $26,317 | $26,587 | 5 | <$5M | AI Deep Dive |
| Vineyard Arts Project Limited | Arts, Entertainment, and Recreation | $26,058 | $26,282 | 3 | N/A | AI Deep Dive |
| Brian Sylvia Electric | Construction | $25,852 | $26,034 | 2 | <$5M | AI Deep Dive |
| Brian Sylvia | Construction | $25,852 | $25,992 | 2 | <$5M | AI Deep Dive |
| Katydid Inc. | Retail Trade | $25,662 | $25,857 | 3 | <$5M | AI Deep Dive |
| Edgartown Pizza INC | Accommodation and Food Services | $24,900 | $25,044 | 4 | <$5M | AI Deep Dive |
| Donna Goodale | Retail Trade | $24,600 | $11,348 | 2 | <$5M | AI Deep Dive |
| Fish Chappy LLC | Retail Trade | $24,300 | $16,472 | 4 | <$5M | AI Deep Dive |
| Recycled Bicycles of Gainsville, INC | Retail Trade | $24,000 | $24,162 | 13 | <$5M | AI Deep Dive |