| D. Best Construction | Construction | $250,000 | $251,329 | 17 | $5.2M |  AI Deep Dive |
| Two Brothers and a Sister INC | Accommodation and Food Services | $243,534 | $245,969 | 16 | <$5M | AI Deep Dive |
| The Martha's Vineyard Museum, Inc. | Arts, Entertainment, and Recreation | $238,342 | $239,772 | 26 | N/A | AI Deep Dive |
| Tisbury Inn | Accommodation and Food Services | $231,200 | $232,695 | 23 | $7.2M | AI Deep Dive |
| Brennan & Co., LLC | Construction | $227,500 | $230,423 | 20 | $6.3M | AI Deep Dive |
| Electronic Security Systems, LLC | Administrative and Support and Waste Management | $214,499 | $217,281 | 17 | <$5M | AI Deep Dive |
| Mv Times Corp | Information | $210,323 | $212,120 | 20 | <$5M | AI Deep Dive |
| Clmv LLC | Administrative and Support and Waste Management | $195,042 | $198,033 | 15 | <$5M | AI Deep Dive |
| Brissette Electric INC | Construction | $187,900 | $189,017 | 18 | $5.9M | AI Deep Dive |
| Waterside Market Group Inc. | Accommodation and Food Services | $183,100 | $184,101 | 25 | <$5M | AI Deep Dive |
| Two Brothers and a Sister INC | Accommodation and Food Services | $173,953 | $176,069 | 16 | <$5M | AI Deep Dive |
| Cove Road Inn LLC | Accommodation and Food Services | $172,091 | $173,331 | 12 | <$5M | AI Deep Dive |
| Island Grown Initiative Ltd. | Agriculture, Forestry, Fishing and Hunting | $171,400 | $172,353 | 19 | N/A | AI Deep Dive |
| Tate Builders INC | Construction | $161,601 | $69,127 | 7 | <$5M | AI Deep Dive |
| Friends of Mvyradio INC | Information | $155,080 | $156,135 | 21 | N/A | AI Deep Dive |
| Island Propane INC | Retail Trade | $150,524 | $151,740 | 9 | <$5M | AI Deep Dive |
| Friends of Mvy Radio Inc. | Information | $150,042 | $151,017 | 9 | N/A | AI Deep Dive |
| Tashmoo Insurance Agency INC | Finance and Insurance | $147,400 | $135,624 | 8 | <$5M | AI Deep Dive |
| Vineyard Medical Care LLC | Health Care and Social Assistance | $145,800 | $89,315 | 10 | <$5M | AI Deep Dive |
| Among the Flowers INC | Accommodation and Food Services | $142,051 | $143,235 | 17 | <$5M | AI Deep Dive |
| A.p. Fortes Plumbing & Heating, Inc. | Construction | $137,500 | $138,250 | 9 | <$5M | AI Deep Dive |
| Schofield, Barbini & Hoehn, Inc. | Professional, Scientific, and Technical Services | $136,805 | $138,667 | 10 | <$5M | AI Deep Dive |
| Maciel and Sons | Administrative and Support and Waste Management | $136,800 | $137,657 | 9 | <$5M | AI Deep Dive |
| Educomp INC | Retail Trade | $136,700 | $138,569 | 9 | <$5M | AI Deep Dive |
| Sheriffs Meadow Foundation | Arts, Entertainment, and Recreation | $135,100 | $135,888 | 7 | N/A | AI Deep Dive |