| Cape Ann Marina, LLC | Arts, Entertainment, and Recreation | $401,600 | $374,794 | 35 | <$5M |  Research |
| Cape Ann Marina LLC | Arts, Entertainment, and Recreation | $371,645 | $374,763 | 70 | $9.8M | Research |
| Sudbay Chrysler Jeep | Retail Trade | $366,700 | $369,898 | 25 | $6.3M | Research |
| Mile Marker One LLC | Accommodation and Food Services | $361,266 | $364,206 | 101 | $17.9M | Research |
| Common Crow Natural Health Inc. | Retail Trade | $358,100 | $360,050 | 47 | $11.7M | Research |
| Grand Banks Building Products, Inc. | Retail Trade | $351,100 | $353,098 | 27 | $5.6M | Research |
| Cape Ann Medical Center LLC | Health Care and Social Assistance | $350,190 | $352,350 | 23 | <$5M | Research |
| Beauport Hospitality LLC | Accommodation and Food Services | $344,284 | $348,444 | 12 | <$5M | Research |
| Cape Ann Food Pantry, Inc. | Health Care and Social Assistance | $343,700 | $345,781 | 38 | N/A | Research |
| Seven Seas Wharf, Inc. | Accommodation and Food Services | $341,500 | $343,426 | 28 | <$5M | Research |
| Mile Marker One, LLC | Accommodation and Food Services | $332,200 | $335,014 | 30 | $5.3M | Research |
| Tonno LLC | Accommodation and Food Services | $330,680 | $333,552 | 36 | $6.4M | Research |
| Aqua Restaurant Corporation | Accommodation and Food Services | $323,257 | $326,363 | 34 | $6.0M | Research |
| Cape Seafoods INC | Wholesale Trade | $317,773 | $319,540 | 23 | $5.9M | Research |
| Cape Seafoods, Inc. | Wholesale Trade | $317,652 | $320,802 | 23 | $5.9M | Research |
| J&l Welding and Machine Inc. | Manufacturing | $312,500 | $315,035 | 28 | $6.8M | Research |
| J & L Welding and Machine, INC | Manufacturing | $312,500 | $315,182 | 25 | $6.5M | Research |
| Gloucester Marine Genomics | Educational Services | $305,000 | $306,618 | 17 | N/A | Research |
| Mortillaro Lobster INC | Manufacturing | $303,700 | $306,265 | 25 | $8.8M | Research |
| Mortillaro Lobster, Inc. | Manufacturing | $303,700 | $305,472 | 25 | $8.8M | Research |
| Village Silversmith Ltd | Retail Trade | $300,000 | $301,926 | 30 | $8.3M | Research |
| Trio Building, INC | Accommodation and Food Services | $296,500 | $298,174 | 40 | $7.1M | Research |
| Gloucester Marine Genomics Institute Incorporated | Professional, Scientific, and Technical Services | $295,000 | $296,737 | 19 | N/A | Research |
| Wellspring House, Inc. | Health Care and Social Assistance | $294,900 | $297,453 | 69 | N/A | Research |
| Eastern Waste Services LLC | Administrative and Support and Waste Management | $291,500 | $294,303 | 20 | <$5M | Research |