| Figueroa and Sons INC | Other Services (except Public Administration) | $133,400 | $134,789 | 9 | <$5M | AI Deep Dive |
| Why Not Corp | Accommodation and Food Services | $129,415 | $131,284 | 13 | <$5M | AI Deep Dive |
| Callahan Plumbing and Heating INC | Construction | $129,200 | $129,968 | 6 | <$5M | AI Deep Dive |
| Hospice of Martha's Vineyard | Health Care and Social Assistance | $128,900 | $112,577 | 11 | N/A | AI Deep Dive |
| David J Schwab Electrical Contractor, Inc. | Construction | $128,400 | $120,926 | 6 | <$5M | AI Deep Dive |
| Richard T. Olsen & Son INC | Construction | $125,000 | $77,090 | 6 | <$5M | AI Deep Dive |
| Hospice of Marthas Vineyard INC | Health Care and Social Assistance | $123,600 | $124,091 | 11 | N/A | AI Deep Dive |
| Waterwheel Inc. | Manufacturing | $122,418 | $0 | 8 | <$5M | AI Deep Dive |
| Leroux Associated Stores Ma, Inc. | Retail Trade | $121,155 | $121,815 | 11 | <$5M | AI Deep Dive |
| Sanford Nadelstein Dds,cags,p.c. | Health Care and Social Assistance | $121,100 | $103,180 | 7 | <$5M | AI Deep Dive |
| Fe Leslie Druggist INC | Retail Trade | $120,700 | $121,381 | 7 | <$5M | AI Deep Dive |
| Henrietta Brewer House, Inc., the | Health Care and Social Assistance | $115,393 | $116,200 | 15 | <$5M | AI Deep Dive |
| Trian Enterprises Inc. | Manufacturing | $114,900 | $66,481 | 6 | <$5M | AI Deep Dive |
| Daniele's Fuel INC | Accommodation and Food Services | $113,500 | $114,526 | 10 | <$5M | AI Deep Dive |
| Mone Insurance Agency INC | Finance and Insurance | $112,905 | $113,409 | 8 | <$5M | AI Deep Dive |
| Santoro Seafood INC | Retail Trade | $112,900 | $114,147 | 29 | <$5M | AI Deep Dive |
| E. West Enterprises, Inc. | Retail Trade | $112,875 | $114,367 | 8 | <$5M | AI Deep Dive |
| Seven Gates Farm Corporation | Agriculture, Forestry, Fishing and Hunting | $111,700 | $0 | 5 | <$5M | AI Deep Dive |
| Sourati Engineering Group, LLC | Professional, Scientific, and Technical Services | $110,900 | $111,812 | 6 | <$5M | AI Deep Dive |
| Copper Wok INC | Accommodation and Food Services | $110,699 | $112,080 | 7 | <$5M | AI Deep Dive |
| Leroux Assoc Stores Ma INC | Retail Trade | $108,977 | $109,949 | 11 | <$5M | AI Deep Dive |
| Martha's Vineyard Plumbing & Heating INC | Construction | $107,800 | $108,537 | 6 | <$5M | AI Deep Dive |
| Cb Stark Silversmith | Retail Trade | $107,622 | $108,722 | 15 | <$5M | AI Deep Dive |
| Vineyard Montessori School Inc. | Educational Services | $106,078 | $106,522 | 11 | N/A | AI Deep Dive |
| Mone Insurance Agency INC | Finance and Insurance | $103,700 | $104,655 | 9 | <$5M | AI Deep Dive |