| Chesapeake Cnc Manufacturing Center INC | Manufacturing | $200,700 | $202,361 | 19 | <$5M |  Research |
| Living at Home Health Services, LLC | Health Care and Social Assistance | $194,500 | $196,163 | 37 | $6.3M | Research |
| Living at Home Health Services LLC | Health Care and Social Assistance | $194,500 | $195,848 | 38 | $6.5M | Research |
| Blue Heron Contracting LLC | Construction | $191,133 | $193,044 | 19 | $5.8M | Research |
| Blue Heron Contracting LLC | Construction | $191,130 | $192,255 | 26 | $7.9M | Research |
| Drs Shanahan and Ferguson PC | Health Care and Social Assistance | $186,200 | $187,560 | 20 | $6.3M | Research |
| Worton Creek Marina, LLC | Arts, Entertainment, and Recreation | $180,485 | $181,855 | 14 | <$5M | Research |
| Eastern Shore Events LLC | Real Estate and Rental and Leasing | $180,461 | $176,607 | 9 | <$5M | Research |
| Eastern Shore Family Foot Care LLC | Administrative and Support and Waste Management | $179,800 | $181,488 | 13 | <$5M | Research |
| Goose Pointe LLC | Accommodation and Food Services | $176,068 | $177,770 | 48 | $8.5M | Research |
| Chestertown Cardiology LLC | Health Care and Social Assistance | $175,000 | $83,448 | 6 | <$5M | Research |
| E. L. B. Incorporated | Other Services (except Public Administration) | $162,323 | $157,218 | 12 | <$5M | Research |
| Eastern Shore Events LLC | Real Estate and Rental and Leasing | $161,829 | $162,534 | 16 | $7.2M | Research |
| Fair Hill Farms, Inc. | Agriculture, Forestry, Fishing and Hunting | $156,385 | $157,413 | 15 | <$5M | Research |
| E. L. B. Incorporated | Other Services (except Public Administration) | $156,200 | $157,791 | 12 | <$5M | Research |
| Sultana Education Foundation | Educational Services | $139,895 | $141,248 | 9 | N/A | Research |
| Stoltzfus Brothers Shore Construction LLC | Construction | $137,600 | $138,527 | 14 | <$5M | Research |
| Tideland Gardens INC | Agriculture, Forestry, Fishing and Hunting | $136,100 | $137,389 | 21 | <$5M | Research |
| Macleod Law Group, LLC | Professional, Scientific, and Technical Services | $132,740 | $133,780 | 9 | <$5M | Research |
| Macleod Law Group LLC | Professional, Scientific, and Technical Services | $132,740 | $133,496 | 9 | <$5M | Research |
| Anthony, Judge & Ware, LLC | Professional, Scientific, and Technical Services | $128,200 | $128,909 | 11 | <$5M | Research |
| Sunrise Solar INC | Utilities | $125,800 | $127,003 | 10 | N/A | Research |
| Sultana Education Foundation, INC | Educational Services | $124,912 | $126,230 | 17 | N/A | Research |
| Sado Inc. | Accommodation and Food Services | $123,192 | $124,157 | 20 | <$5M | Research |
| Production Sciences, Inc. | Manufacturing | $122,600 | $123,725 | 17 | $16.9M | Research |