| Kitchen Porch Ltd | Accommodation and Food Services | $399,400 | $401,424 | 30 | $5.6M |  AI Deep Dive |
| Swordfish Enterprises LLC | Accommodation and Food Services | $245,807 | $124,767 | 48 | $15.0M | AI Deep Dive |
| Swordfish Enterprises LLC | Accommodation and Food Services | $221,395 | $223,296 | 19 | $5.9M | AI Deep Dive |
| Kitchen Porch Ltd | Accommodation and Food Services | $220,000 | $220,934 | 15 | <$5M | AI Deep Dive |
| Menemsha Homeport INC | Accommodation and Food Services | $188,488 | $190,064 | 39 | $6.9M | AI Deep Dive |
| Tea Lane Nursery & Farms, Inc. | Administrative and Support and Waste Management | $187,000 | $189,434 | 13 | <$5M | AI Deep Dive |
| Robert A. Young Jr. Electrical Contractor INC | Construction | $137,500 | $125,340 | 8 | <$5M | AI Deep Dive |
| Menemsha Homeport, Inc. | Accommodation and Food Services | $114,150 | $115,330 | 48 | $8.5M | AI Deep Dive |
| Grey Barn Farm Enterprises, LLC | Manufacturing | $107,800 | $108,571 | 12 | <$5M | AI Deep Dive |
| The Yard, Inc. | Arts, Entertainment, and Recreation | $106,500 | $107,720 | 9 | N/A | AI Deep Dive |
| Conroy & Company Real Estate, INC | Real Estate and Rental and Leasing | $106,500 | $20,931 | 1 | <$5M | AI Deep Dive |
| Chilmark General Store LLC | Accommodation and Food Services | $104,100 | $258,642 | 58 | $10.3M | AI Deep Dive |
| See the World Productions | Information | $100,400 | $101,129 | 7 | N/A | AI Deep Dive |
| Chilmark Town Affairs Council | Health Care and Social Assistance | $100,301 | $100,922 | 85 | N/A | AI Deep Dive |
| Elevate INC | Administrative and Support and Waste Management | $87,780 | $88,312 | 10 | <$5M | AI Deep Dive |
| Chilmark Restaurant Group, LLC | Accommodation and Food Services | $86,800 | $87,594 | 12 | <$5M | AI Deep Dive |
| Fenner Construction LLC | Construction | $86,600 | $87,122 | 40 | $12.4M | AI Deep Dive |
| Martha Elizabeth Management Services LLC | Agriculture, Forestry, Fishing and Hunting | $83,849 | $84,186 | 12 | <$5M | AI Deep Dive |
| Elevate, Inc. | Administrative and Support and Waste Management | $82,528 | $63,884 | 9 | <$5M | AI Deep Dive |
| The Yard INC | Arts, Entertainment, and Recreation | $80,000 | $80,796 | 6 | N/A | AI Deep Dive |
| Fullbro Trust | Retail Trade | $42,920 | $43,392 | 8 | <$5M | AI Deep Dive |
| Rebecca J Potter | Administrative and Support and Waste Management | $40,100 | $40,493 | 2 | <$5M | AI Deep Dive |
| Fullerbro Trust | Retail Trade | $38,400 | $38,898 | 4 | <$5M | AI Deep Dive |
| C. Kurth and Sons | Construction | $36,000 | $36,345 | 3 | <$5M | AI Deep Dive |
| Morgan Stone and Landscaping Inc. | Administrative and Support and Waste Management | $31,200 | $31,556 | 1 | <$5M | AI Deep Dive |