| Kilday Cpas, P. C. | Professional, Scientific, and Technical Services | $37,267 | $37,461 | 2 | <$5M |  AI Deep Dive |
| Kilday Cpas P. C. | Professional, Scientific, and Technical Services | $37,266 | $37,746 | 2 | <$5M | AI Deep Dive |
| 50 West Winery and Vineyards LLC | Accommodation and Food Services | $36,386 | $36,525 | 12 | <$5M | AI Deep Dive |
| Briar Patch LLC | Accommodation and Food Services | $36,361 | $36,662 | 3 | <$5M | AI Deep Dive |
| Middleburg Community Charter School | Educational Services | $36,035 | $36,351 | 5 | N/A | AI Deep Dive |
| Middleburg Tack Exchange Ltd. | Retail Trade | $35,800 | $36,171 | 5 | <$5M | AI Deep Dive |
| O'donnell & Co LLC | Professional, Scientific, and Technical Services | $35,785 | $36,049 | 6 | <$5M | AI Deep Dive |
| Highcliffe Clothiers LLC | Retail Trade | $35,233 | $35,479 | 4 | <$5M | AI Deep Dive |
| Highcliffe Clothiers LLC | Retail Trade | $35,233 | $35,490 | 4 | <$5M | AI Deep Dive |
| Emmanuel Episcopal Church | Other Services (except Public Administration) | $35,130 | $35,333 | 3 | N/A | AI Deep Dive |
| Thomas and Talbot Real Estate, Limited Company | Real Estate and Rental and Leasing | $34,138 | $40,064 | 3 | <$5M | AI Deep Dive |
| Paula Parsons Training Stable LLC | Arts, Entertainment, and Recreation | $33,840 | $34,065 | 5 | <$5M | AI Deep Dive |
| Side Saddle Cafe LLC | Accommodation and Food Services | $33,657 | $33,986 | 5 | <$5M | AI Deep Dive |
| Middleburg Common Grounds LLC | Accommodation and Food Services | $33,500 | $33,725 | 7 | <$5M | AI Deep Dive |
| Thaiverse 2 LLC | Accommodation and Food Services | $32,979 | $33,301 | 6 | <$5M | AI Deep Dive |
| Middleburg Community Center | Health Care and Social Assistance | $32,690 | $33,029 | 10 | N/A | AI Deep Dive |
| Connections4life Professional Therapy Services, PC | Health Care and Social Assistance | $31,750 | $32,040 | 3 | <$5M | AI Deep Dive |
| Emmanuel Episcopal Church | Other Services (except Public Administration) | $31,200 | $33,860 | 3 | N/A | AI Deep Dive |
| Locksley Estate Farmstead Cheese Co., LLC | Manufacturing | $31,000 | $31,245 | 4 | <$5M | AI Deep Dive |
| Windy Hill Foundation | Health Care and Social Assistance | $30,364 | $30,710 | 3 | N/A | AI Deep Dive |
| Mastercraft Homes, Inc. | Construction | $30,200 | $21,061 | 1 | <$5M | AI Deep Dive |
| Fields of Athenry LLC | Retail Trade | $28,600 | $28,965 | 10 | <$5M | AI Deep Dive |
| Middleburg Community Center | Health Care and Social Assistance | $27,500 | $27,709 | 3 | N/A | AI Deep Dive |
| Middleburg Hunt Association INC | Arts, Entertainment, and Recreation | $27,182 | $27,333 | 3 | <$5M | AI Deep Dive |
| Play Ball Inc. | Accommodation and Food Services | $27,181 | $27,337 | 6 | <$5M | AI Deep Dive |