| Chesapeake Crewing L.l.c. | Transportation and Warehousing | $1,711,605 | $1,721,902 | 137 | $34.7M |  AI Deep Dive |
| The Key School | Educational Services | $1,700,000 | $1,712,901 | 168 | N/A | AI Deep Dive |
| Continental Contractors, Inc. | Construction | $1,678,357 | $1,698,083 | 83 | $94.6M | AI Deep Dive |
| Continental Contractors Inc. | Construction | $1,678,357 | $1,695,554 | 62 | $70.6M | AI Deep Dive |
| Annapolis Pediatrics PA | Health Care and Social Assistance | $1,627,200 | $1,637,454 | 133 | $41.7M | AI Deep Dive |
| Constellation Software Engineering Corp | Information | $1,598,457 | $1,612,492 | 98 | $16.5M | AI Deep Dive |
| Chesapeake Open Mri LLC | Health Care and Social Assistance | $1,586,390 | $1,599,777 | 174 | $40.3M | AI Deep Dive |
| Chesapeake Open Mri, LLC | Health Care and Social Assistance | $1,586,390 | $1,608,469 | 127 | $29.4M | AI Deep Dive |
| Immersion Consulting LLC | Administrative and Support and Waste Management | $1,544,580 | $1,562,557 | 96 | $15.1M | AI Deep Dive |
| The Ravens Group INC | Professional, Scientific, and Technical Services | $1,462,697 | $1,475,721 | 76 | $10.6M | AI Deep Dive |
| Pyramid INC | Construction | $1,445,196 | $1,458,323 | 90 | $27.3M | AI Deep Dive |
| Criswell Performance Cars of Annapolis, Inc. | Retail Trade | $1,426,000 | $1,437,963 | 120 | $30.2M | AI Deep Dive |
| Criswell Performance Imports | Retail Trade | $1,417,100 | $1,491,823 | 118 | $29.7M | AI Deep Dive |
| Criswell Performance Cars of Annapolis Inc. | Retail Trade | $1,385,467 | $1,398,206 | 100 | $25.2M | AI Deep Dive |
| Langton Green, INC | Health Care and Social Assistance | $1,343,350 | $1,361,531 | 205 | N/A | AI Deep Dive |
| Fosterthomas Inc. | Professional, Scientific, and Technical Services | $1,334,027 | $1,342,214 | 101 | $10.5M | AI Deep Dive |
| Annapolis Motors, LLC | Retail Trade | $1,321,500 | $1,337,937 | 111 | $28.0M | AI Deep Dive |
| Compass Marketing INC | Information | $1,321,200 | $1,346,596 | 48 | $8.1M | AI Deep Dive |
| Compass Marketing INC | Professional, Scientific, and Technical Services | $1,278,938 | $1,296,594 | 48 | <$5M | AI Deep Dive |
| Bay Capital Mortgage Corporation | Finance and Insurance | $1,270,300 | $1,290,519 | 76 | $39.0M | AI Deep Dive |
| Koons Ford of Annapolis, Inc. | Retail Trade | $1,256,500 | $1,265,691 | 149 | $37.5M | AI Deep Dive |
| Anne Arundel Urology, P.a. | Health Care and Social Assistance | $1,237,700 | $1,255,028 | 90 | $28.2M | AI Deep Dive |
| Orbis Technologies Inc. | Information | $1,234,287 | $1,252,397 | 59 | $9.9M | AI Deep Dive |
| Wyetech, LLC | Professional, Scientific, and Technical Services | $1,181,500 | $1,191,444 | 51 | $6.3M | AI Deep Dive |
| Severn Management Company, LLC | Real Estate and Rental and Leasing | $1,172,900 | $1,187,301 | 114 | $20.9M | AI Deep Dive |