| Stuart Jones LLC | Accommodation and Food Services | $693,361 | $699,630 | 87 | $15.4M |  Research |
| Iron Rooster-Annapolis, LLC | Accommodation and Food Services | $631,046 | $635,904 | 51 | $9.1M | Research |
| Chapelwood Enterprises, LLC | Health Care and Social Assistance | $559,000 | $565,646 | 137 | $23.5M | Research |
| Childs Landscape Contractors, INC | Professional, Scientific, and Technical Services | $511,772 | $514,715 | 59 | $11.9M | Research |
| Robert W. Childs Landscape Contractors Inc. | Administrative and Support and Waste Management | $511,722 | $515,020 | 59 | $12.8M | Research |
| Stuart Jones, LLC | Accommodation and Food Services | $495,258 | $501,337 | 87 | $15.4M | Research |
| Compass Pointe Consulting LLC | Professional, Scientific, and Technical Services | $450,577 | $453,994 | 30 | <$5M | Research |
| Tull Behling and Decere Pediatric Dentistry | Health Care and Social Assistance | $417,115 | $419,561 | 28 | $6.5M | Research |
| Mother's Peninsula Grille LLC | Accommodation and Food Services | $401,545 | $404,361 | 40 | $7.1M | Research |
| Televere Systems, LLC | Finance and Insurance | $389,468 | $393,822 | 27 | $13.9M | Research |
| Televere Systems LLC | Professional, Scientific, and Technical Services | $389,467 | $393,394 | 29 | $6.0M | Research |
| The Young Women's Christian Association of Annapolis and Ann | Other Services (except Public Administration) | $327,800 | $329,784 | 41 | N/A | Research |
| Eco Interior Maintenance | Other Services (except Public Administration) | $304,722 | $308,596 | 33 | $6.3M | Research |
| Mothers Peninsula Grille, LLC | Accommodation and Food Services | $299,000 | $301,982 | 21 | <$5M | Research |
| Ophthalmology Associates of Greater Annapolis, INC | Health Care and Social Assistance | $289,325 | $292,700 | 20 | <$5M | Research |
| Opthalmology Associates of Greater Annapolis PA | Health Care and Social Assistance | $289,325 | $291,315 | 39 | $12.2M | Research |
| Whitsend III INC | Administrative and Support and Waste Management | $277,800 | $280,974 | 20 | <$5M | Research |
| Whits End III INC | Administrative and Support and Waste Management | $277,800 | $281,347 | 20 | <$5M | Research |
| Tull Behling and Decere Pediatric Dentistry | Health Care and Social Assistance | $264,315 | $265,322 | 34 | $7.9M | Research |
| Thrive Gym LLC | Educational Services | $250,932 | $254,109 | 61 | $7.9M | Research |
| Thrive Gym LLC | Educational Services | $250,000 | $252,555 | 56 | $7.3M | Research |
| Maryland Coalition Against Sexual Assault | Other Services (except Public Administration) | $234,415 | $140,718 | 25 | N/A | Research |
| Atlas Marble & Tile INC | Construction | $231,500 | $233,701 | 19 | <$5M | Research |
| Amtek Company, Incorporated | Educational Services | $219,900 | $222,362 | 9 | <$5M | Research |
| Locus, LLC | Professional, Scientific, and Technical Services | $218,100 | $219,239 | 14 | <$5M | Research |