| Cripple Creek Golf & Country Club | Arts, Entertainment, and Recreation | $344,323 | $347,011 | 62 | $8.7M |  Research |
| Auto Works Collision Center LLC | Other Services (except Public Administration) | $309,265 | $311,289 | 29 | $5.7M | Research |
| Auto Works Collision Center LLC | Other Services (except Public Administration) | $294,090 | $295,653 | 27 | $5.3M | Research |
| Carey Insurance Group INC | Finance and Insurance | $261,430 | $262,841 | 29 | $14.9M | Research |
| Claim to Fame Stable, LLC | Arts, Entertainment, and Recreation | $250,000 | $172,182 | 9 | <$5M | Research |
| Brafman Family Dentistry, P.a. | Health Care and Social Assistance | $245,124 | $248,193 | 18 | <$5M | Research |
| Brafman Family Dentistry P.a. | Health Care and Social Assistance | $226,472 | $229,543 | 21 | <$5M | Research |
| Culver & Pierson, LLC | Real Estate and Rental and Leasing | $223,752 | $225,318 | 21 | <$5M | Research |
| Ocean View Plumbing & Heating Inc. | Construction | $222,223 | $224,174 | 15 | <$5M | Research |
| Blades Hvac Services, Inc. | Construction | $171,602 | $173,934 | 20 | $6.3M | Research |
| Marvel's Portable Welding INC | Agriculture, Forestry, Fishing and Hunting | $150,000 | $150,617 | 15 | <$5M | Research |
| Tuckahoe Acres Camping Resort INC | Accommodation and Food Services | $145,200 | $146,777 | 7 | <$5M | Research |
| Bunting's Garage, Inc. | Other Services (except Public Administration) | $134,245 | $135,668 | 17 | <$5M | Research |
| Shore Water and Dagsboro Electric, INC | Construction | $127,400 | $128,214 | 11 | <$5M | Research |
| Cf Zeiler LLC | Construction | $125,000 | $126,295 | 5 | <$5M | Research |
| Reliable Home Maintenance LLC | Construction | $123,077 | $123,778 | 12 | <$5M | Research |
| Shore Water & Dagsboro Electric INC | Construction | $122,900 | $123,450 | 11 | <$5M | Research |
| North Star Heating & Air Conditioning, Inc. | Construction | $119,695 | $120,541 | 13 | <$5M | Research |
| Reliable Home Maintenance LLC | Construction | $110,800 | $111,874 | 13 | <$5M | Research |
| Lighthouse Christian School Inc. | Educational Services | $105,692 | $106,223 | 8 | <$5M | Research |
| Michael R Butterworth, Dds, INC | Health Care and Social Assistance | $101,790 | $102,504 | 7 | <$5M | Research |
| Eastern Shore Motors LLC | Retail Trade | $95,603 | $96,075 | 12 | <$5M | Research |
| Eastern Shore Motors LLC | Retail Trade | $90,800 | $88,782 | 13 | <$5M | Research |
| Cave Construction INC | Construction | $88,833 | $89,356 | 10 | <$5M | Research |
| David Hamm | Agriculture, Forestry, Fishing and Hunting | $82,783 | $83,953 | 1 | <$5M | Research |