| William H Russell | Construction | $70,656 | $71,391 | 6 | <$5M |  AI Deep Dive |
| Sanford Nadelstein Dds,cags,p.c. | Health Care and Social Assistance | $70,416 | $70,850 | 8 | <$5M | AI Deep Dive |
| Rocco's, LLC | Accommodation and Food Services | $70,000 | $70,237 | 9 | <$5M | AI Deep Dive |
| Island Transport | Administrative and Support and Waste Management | $69,200 | $69,945 | 17 | $5.4M | AI Deep Dive |
| Offshore Engineering Inc. | Construction | $69,199 | $69,860 | 4 | <$5M | AI Deep Dive |
| Shirley's Hardware Inc. | Retail Trade | $68,500 | $68,954 | 7 | <$5M | AI Deep Dive |
| David Finkelstein Od & Ryan Shea Od LLC | Health Care and Social Assistance | $67,150 | $67,654 | 4 | <$5M | AI Deep Dive |
| Trian Enterprises | Manufacturing | $65,701 | $66,207 | 6 | <$5M | AI Deep Dive |
| Dukes County Regional Housing Authority | Public Administration | $63,700 | $64,156 | 4 | N/A | AI Deep Dive |
| Ppm Ventures Inc. | Real Estate and Rental and Leasing | $63,160 | $63,848 | 6 | <$5M | AI Deep Dive |
| Woody's Auto Supply, Inc. | Retail Trade | $63,100 | $63,512 | 5 | <$5M | AI Deep Dive |
| Marek Tree and Land INC | Administrative and Support and Waste Management | $62,900 | $52,553 | 4 | <$5M | AI Deep Dive |
| Martha's Vineyard Furniture Company LLC | Retail Trade | $62,495 | $63,130 | 7 | <$5M | AI Deep Dive |
| Martha's Vineyard Playhouse Inc. | Arts, Entertainment, and Recreation | $62,300 | $38,172 | 6 | <$5M | AI Deep Dive |
| Martha's Vineyard Hebrew Center | Other Services (except Public Administration) | $61,800 | $62,150 | 7 | N/A | AI Deep Dive |
| Peter James Breese Architects INC | Professional, Scientific, and Technical Services | $60,800 | $61,393 | 3 | <$5M | AI Deep Dive |
| Iriescapes Mv INC | Construction | $60,686 | $61,436 | 7 | <$5M | AI Deep Dive |
| Grace Episcopal Church | Other Services (except Public Administration) | $59,700 | $60,470 | 4 | <$5M | AI Deep Dive |
| Peter James Breese Architects Inc. | Professional, Scientific, and Technical Services | $59,335 | $59,639 | 3 | <$5M | AI Deep Dive |
| Martha's Vineyard Dry Cleaners LLC | Other Services (except Public Administration) | $58,900 | $50,571 | 6 | <$5M | AI Deep Dive |
| Martha's Vineyard Vacation Rentals & Real Estate Sales INC | Real Estate and Rental and Leasing | $58,685 | $59,218 | 5 | <$5M | AI Deep Dive |
| Mv Vacation Rentals & Real Estate | Real Estate and Rental and Leasing | $58,682 | $59,135 | 4 | <$5M | AI Deep Dive |
| Marthas Vineyard Family Campground INC | Accommodation and Food Services | $58,213 | $58,808 | 2 | <$5M | AI Deep Dive |
| Martha's Vineyard Film Society INC | Information | $57,500 | $57,857 | 6 | <$5M | AI Deep Dive |
| Little House Cafe | Accommodation and Food Services | $57,400 | $56,464 | 10 | <$5M | AI Deep Dive |