| River View at the Point LLC | Accommodation and Food Services | $39,000 | $39,402 | 8 | <$5M | AI Deep Dive |
| Nichols Lawn & Landscape LLC | Administrative and Support and Waste Management | $38,800 | $39,165 | 10 | <$5M | AI Deep Dive |
| Will Brown's Truck Repaair Inc. | Transportation and Warehousing | $38,531 | $38,760 | 4 | <$5M | AI Deep Dive |
| Carlton Transport INC | Other Services (except Public Administration) | $37,885 | $38,031 | 5 | <$5M | AI Deep Dive |
| Carlton Transport, Inc. | Transportation and Warehousing | $37,800 | $38,117 | 6 | <$5M | AI Deep Dive |
| First Baptist Church of Cambridge | Other Services (except Public Administration) | $37,700 | $38,098 | 7 | N/A | AI Deep Dive |
| Charles C Powell INC | Real Estate and Rental and Leasing | $37,648 | $37,792 | 3 | <$5M | AI Deep Dive |
| A & D Friends LLC | Accommodation and Food Services | $37,645 | $37,931 | 12 | <$5M | AI Deep Dive |
| Bernard Johnson | Administrative and Support and Waste Management | $37,125 | $37,603 | 25 | $5.4M | AI Deep Dive |
| Harrington & Merryweather | Professional, Scientific, and Technical Services | $36,100 | $36,399 | 3 | <$5M | AI Deep Dive |
| Cambridge Marketplace, LLC | Real Estate and Rental and Leasing | $35,000 | $34,150 | 4 | <$5M | AI Deep Dive |
| Will Brown's Truck Repair, Inc. | Other Services (except Public Administration) | $34,900 | $35,507 | 3 | <$5M | AI Deep Dive |
| Lil Bitta Bull Bbq LLC | Accommodation and Food Services | $34,244 | $34,452 | 8 | <$5M | AI Deep Dive |
| Choptank Bowling Center, Inc. | Arts, Entertainment, and Recreation | $33,929 | $34,193 | 11 | <$5M | AI Deep Dive |
| Choptank Oyster Mortgage LLC | Finance and Insurance | $33,800 | $34,166 | 6 | <$5M | AI Deep Dive |
| Generation III Marina LLC | Arts, Entertainment, and Recreation | $33,527 | $33,757 | 6 | <$5M | AI Deep Dive |
| Sharon Real Estate PC | Real Estate and Rental and Leasing | $33,500 | $33,825 | 3 | <$5M | AI Deep Dive |
| Elliott's Baking Company | Accommodation and Food Services | $32,303 | $32,594 | 13 | <$5M | AI Deep Dive |
| Dorchester County Pawn, INC | Finance and Insurance | $32,013 | $32,341 | 8 | <$5M | AI Deep Dive |
| Robert S Collison PA | Professional, Scientific, and Technical Services | $31,918 | $32,049 | 3 | <$5M | AI Deep Dive |
| Rusticana Cambridge LLC | Accommodation and Food Services | $31,723 | $32,075 | 14 | <$5M | AI Deep Dive |
| Bereket, Inc. | Accommodation and Food Services | $31,632 | $32,077 | 10 | <$5M | AI Deep Dive |
| Cc West Salem Va LLC | Other Services (except Public Administration) | $31,500 | $31,819 | 13 | <$5M | AI Deep Dive |
| Handley Construction, Inc. | Construction | $31,283 | $31,608 | 4 | <$5M | AI Deep Dive |
| Robert S. Collison, P.a. | Professional, Scientific, and Technical Services | $31,138 | $28,594 | 4 | <$5M | AI Deep Dive |