| St. Andrew's United Methodist Church of Annapolis (and Schoo | Educational Services | $455,231 | $458,636 | 49 | N/A |  Research |
| Premier Nursery & Garden Center | Retail Trade | $277,900 | $281,258 | 45 | $9.3M | Research |
| The Brewery at the Farm at Broad Run | Manufacturing | $107,400 | $108,516 | 9 | <$5M | Research |
| Millbrook Quarries LLC | Agriculture, Forestry, Fishing and Hunting | $79,713 | $0 | 10 | <$5M | Research |
| Meriwether Vineyard INC | Manufacturing | $76,707 | $77,145 | 6 | <$5M | Research |
| Shanes Signs INC | Other Services (except Public Administration) | $73,445 | $74,159 | 4 | <$5M | Research |
| Shanes Signs Inc. | Manufacturing | $73,445 | $73,953 | 4 | <$5M | Research |
| J.e. Miller Construction Inc. | Construction | $70,160 | $70,638 | 5 | <$5M | Research |
| Gro Getters INC | Wholesale Trade | $62,895 | $63,233 | 6 | <$5M | Research |
| Millbrook Quarries LLC | Agriculture, Forestry, Fishing and Hunting | $57,773 | $58,144 | 8 | <$5M | Research |
| Simply Elite Home Team, LLC | Real Estate and Rental and Leasing | $53,725 | $54,299 | 4 | <$5M | Research |
| Pearmund Cellars LLC | Manufacturing | $50,445 | $50,768 | 6 | <$5M | Research |
| Gro Getters INC | Unknown | $47,227 | $47,580 | 7 | N/A | Research |
| The Magus Group, LLC | Educational Services | $47,146 | $42,520 | 2 | <$5M | Research |
| Wilson Service Company LLC | Construction | $40,415 | $40,638 | 5 | <$5M | Research |
| Hedden's Electric, LLC | Construction | $39,298 | $39,701 | 4 | <$5M | Research |
| Accurate Towing and Storage INC | Transportation and Warehousing | $38,803 | $39,277 | 3 | <$5M | Research |
| Accurate Towing and Storage INC | Transportation and Warehousing | $35,400 | $37,173 | 4 | <$5M | Research |
| The Magus Group LLC | Educational Services | $31,876 | $32,045 | 2 | <$5M | Research |
| Pace Communications LLC | Agriculture, Forestry, Fishing and Hunting | $30,000 | $30,320 | 3 | <$5M | Research |
| Eastern Shore Green Clean, LLC | Administrative and Support and Waste Management | $29,887 | $30,078 | 9 | <$5M | Research |
| Mkm Support Services, LLC | Construction | $23,500 | $23,932 | 3 | <$5M | Research |
| Bull Run Mountains Conservancy INC | Arts, Entertainment, and Recreation | $21,378 | $21,651 | 2 | N/A | Research |
| Fallen Dragon Studios LLC | Public Administration | $20,833 | $21,001 | 2 | N/A | Research |
| Quality Propertyspec, LLC | Professional, Scientific, and Technical Services | $20,560 | $20,713 | 1 | <$5M | Research |