| Chesapeake Charter, Inc. | Transportation and Warehousing | $409,682 | $412,757 | 50 | $19.2M |  AI Deep Dive |
| Wh-Annapolis Food LLC | Accommodation and Food Services | $409,591 | $412,509 | 42 | $7.5M | AI Deep Dive |
| Bestgate Engineering, LLC | Professional, Scientific, and Technical Services | $403,700 | $408,102 | 16 | <$5M | AI Deep Dive |
| Alliance for the Chesapeake Bay, Inc. | Other Services (except Public Administration) | $402,900 | $405,452 | 36 | $6.9M | AI Deep Dive |
| Concourse Advisory Group | Real Estate and Rental and Leasing | $402,620 | $405,245 | 26 | <$5M | AI Deep Dive |
| Mavenspire, Inc. | Professional, Scientific, and Technical Services | $400,000 | $403,079 | 21 | <$5M | AI Deep Dive |
| New Energy Equity LLC | Construction | $399,800 | $402,099 | 21 | $6.5M | AI Deep Dive |
| Chesapeake Women's Care PA | Health Care and Social Assistance | $397,652 | $400,267 | 45 | $14.1M | AI Deep Dive |
| Berla Corporation | Professional, Scientific, and Technical Services | $396,905 | $398,217 | 22 | <$5M | AI Deep Dive |
| The Northeast Maglev LLC | Professional, Scientific, and Technical Services | $396,600 | $401,227 | 14 | <$5M | AI Deep Dive |
| Michael S. Neall & Associates P.c. | Professional, Scientific, and Technical Services | $396,482 | $401,338 | 29 | $7.0M | AI Deep Dive |
| Michael S. Neall and Wynel S. P.c. | Professional, Scientific, and Technical Services | $396,400 | $401,859 | 29 | $7.0M | AI Deep Dive |
| Southern Kitchens LLC | Accommodation and Food Services | $396,000 | $401,240 | 68 | $12.1M | AI Deep Dive |
| Lisa Renfro MD PA | Health Care and Social Assistance | $394,218 | $398,484 | 39 | $12.2M | AI Deep Dive |
| Shippers' Choice of Virginia, Inc. | Educational Services | $391,261 | $395,377 | 44 | $5.9M | AI Deep Dive |
| Naval Academy Primary School | Educational Services | $391,220 | $393,176 | 50 | N/A | AI Deep Dive |
| Megalos Corporation | Accommodation and Food Services | $390,300 | $395,593 | 60 | $10.7M | AI Deep Dive |
| Annapolitan Care Center, INC | Health Care and Social Assistance | $389,167 | $394,381 | 58 | $9.9M | AI Deep Dive |
| Ken's Creative Kitchen Inc. | Accommodation and Food Services | $386,169 | $389,925 | 50 | $9.3M | AI Deep Dive |
| Mavenspire Inc. | Professional, Scientific, and Technical Services | $385,875 | $387,590 | 21 | <$5M | AI Deep Dive |
| Annapolis Internal Medicine | Health Care and Social Assistance | $385,311 | $387,698 | 43 | $7.8M | AI Deep Dive |
| Edgewater Tire Center INC | Other Services (except Public Administration) | $381,300 | $386,829 | 38 | $7.4M | AI Deep Dive |
| First Class Plumbing, LLC | Construction | $380,800 | $383,972 | 27 | $8.5M | AI Deep Dive |
| First Class Plumbing LLC | Construction | $380,800 | $383,815 | 25 | $7.9M | AI Deep Dive |
| Carpaccio Tuscan Grille Inc. | Accommodation and Food Services | $379,523 | $384,940 | 74 | $13.1M | AI Deep Dive |