| St. Michael's Parish | Other Services (except Public Administration) | $208,300 | $210,748 | 29 | N/A |  AI Deep Dive |
| Southern Maryland Towing Inc. | Transportation and Warehousing | $108,232 | $108,650 | 16 | <$5M | AI Deep Dive |
| True Chesapeake Oyster Company LLC | Agriculture, Forestry, Fishing and Hunting | $104,175 | $32,314 | 3 | <$5M | AI Deep Dive |
| Southern Maryland Towing, Inc. | Transportation and Warehousing | $77,762 | $78,420 | 13 | <$5M | AI Deep Dive |
| Point Lookout Marine Properties | Arts, Entertainment, and Recreation | $33,862 | $34,178 | 7 | <$5M | AI Deep Dive |
| True Chesapeake Oyster Company LLC | Agriculture, Forestry, Fishing and Hunting | $32,540 | $32,867 | 5 | <$5M | AI Deep Dive |
| Dameron Contracting LLC | Construction | $31,563 | $31,837 | 7 | <$5M | AI Deep Dive |
| Dameron Contracting LLC | Construction | $31,562 | $31,802 | 7 | <$5M | AI Deep Dive |
| Swanendele Inn LLC | Accommodation and Food Services | $30,000 | $30,329 | 6 | <$5M | AI Deep Dive |
| Tennyson Heating & Cooling, Inc. | Construction | $25,710 | $26,051 | 2 | <$5M | AI Deep Dive |
| Tennyson Heating & Cooling Inc. | Construction | $23,057 | $23,169 | 3 | <$5M | AI Deep Dive |
| Swanendele Inn LLC | Accommodation and Food Services | $21,192 | $21,341 | 6 | <$5M | AI Deep Dive |
| Robert Woodburn | Agriculture, Forestry, Fishing and Hunting | $20,833 | $20,923 | 1 | <$5M | AI Deep Dive |
| Joseph Henderson | Arts, Entertainment, and Recreation | $18,302 | $18,357 | 1 | <$5M | AI Deep Dive |
| Woodlawn Farm | Agriculture, Forestry, Fishing and Hunting | $17,500 | $17,558 | 2 | <$5M | AI Deep Dive |
| Sunset Cove, LLC | Accommodation and Food Services | $16,674 | $16,830 | 7 | <$5M | AI Deep Dive |
| Q Street Catering and Culinary Arts LLC | Accommodation and Food Services | $13,590 | $10,035 | 8 | <$5M | AI Deep Dive |
| Bluheven Piers LLC | Finance and Insurance | $13,515 | $12,138 | 2 | <$5M | AI Deep Dive |
| Point Lookout INC | Retail Trade | $12,396 | $12,598 | 2 | <$5M | AI Deep Dive |
| Q Street Catering and Culinary Arts, LLC | Accommodation and Food Services | $11,162 | $11,271 | 7 | <$5M | AI Deep Dive |
| Toil LLC | Administrative and Support and Waste Management | $7,500 | $7,593 | 2 | <$5M | AI Deep Dive |
| Georgina Perez | Accommodation and Food Services | $7,455 | $7,483 | 1 | <$5M | AI Deep Dive |
| Ridge Post 255 American-Legion Incorporated | Other Services (except Public Administration) | $6,250 | $6,314 | 2 | N/A | AI Deep Dive |
| Buzz's Marina | Arts, Entertainment, and Recreation | $5,861 | $5,907 | 1 | <$5M | AI Deep Dive |
| Cynthia Milstead | Health Care and Social Assistance | $4,125 | $4,142 | 1 | <$5M | AI Deep Dive |