| Seafood Shanty Restaurant Management INC | Accommodation and Food Services | $1,925,100 | $1,935,490 | 54 | $9.6M |  Research |
| Donaroma's Nursery & Landscaping Services, INC | Administrative and Support and Waste Management | $1,026,100 | $1,037,823 | 89 | $19.3M | Research |
| Boathouse Bar LLC | Accommodation and Food Services | $800,000 | $804,340 | 36 | $6.4M | Research |
| Atria Mv Corporation | Accommodation and Food Services | $679,455 | $688,194 | 23 | <$5M | Research |
| Third Door Media INC | Administrative and Support and Waste Management | $678,625 | $682,269 | 30 | $5.7M | Research |
| Accounting Automation Consultants INC | Professional, Scientific, and Technical Services | $662,500 | $667,764 | 34 | <$5M | Research |
| Ps Kelley House Management Company, LLC | Accommodation and Food Services | $521,311 | $526,467 | 125 | $39.1M | Research |
| Landscope, Inc. | Administrative and Support and Waste Management | $484,235 | $487,746 | 32 | $6.9M | Research |
| Walter Smith Plumbing & Heating, Inc. | Construction | $481,452 | $487,711 | 23 | $7.3M | Research |
| 19 Raw LLC | Accommodation and Food Services | $473,277 | $477,799 | 43 | $7.6M | Research |
| Island Health Plan INC | Public Administration | $471,687 | $475,709 | 41 | N/A | Research |
| Morning Glory Farm, Inc. | Agriculture, Forestry, Fishing and Hunting | $436,700 | $393,896 | 174 | $8.7M | Research |
| The Seafood Shanty Restaurant Management Inc. | Accommodation and Food Services | $416,100 | $419,702 | 54 | $9.6M | Research |
| Brunos Rolloff Inc. | Administrative and Support and Waste Management | $403,753 | $406,926 | 35 | $6.6M | Research |
| Vineyard Gazette LLC | Information | $398,553 | $401,850 | 33 | $5.5M | Research |
| Vineyard Gazette, LLC | Information | $398,500 | $401,142 | 35 | $5.9M | Research |
| Nelson Mechanical Design, Inc. | Manufacturing | $373,400 | $377,032 | 24 | $6.3M | Research |
| Reynolds Rappaport Kaplan & Hackney LLC | Professional, Scientific, and Technical Services | $348,800 | $350,864 | 19 | <$5M | Research |
| Island Health, Inc. | Public Administration | $338,441 | $341,910 | 30 | N/A | Research |
| A On Main Fine Dining LLC | Accommodation and Food Services | $337,110 | $340,924 | 21 | <$5M | Research |
| Lavalon INC | Accommodation and Food Services | $328,632 | $331,654 | 24 | <$5M | Research |
| Boathouse Bar LLC | Accommodation and Food Services | $317,700 | $319,885 | 33 | $5.9M | Research |
| Fullin & Bettencourt Plumbing & Heating INC | Construction | $264,880 | $266,830 | 17 | $5.4M | Research |
| Greenhouse LLC | Accommodation and Food Services | $246,213 | $249,475 | 12 | <$5M | Research |
| Island Pools & Spas INC | Construction | $236,800 | $240,024 | 15 | $5.1M | Research |