| Caledonia Haulers, Inc. | Transportation and Warehousing | $4,155,100 | $4,209,116 | 275 | $55.4M |  Research |
| Winona Controls Inc. | Construction | $782,415 | $785,675 | 44 | $13.9M | Research |
| Winona Controls INC | Construction | $782,400 | $789,116 | 39 | $12.3M | Research |
| 425 N Badger Street Caledonia Opco LLC | Health Care and Social Assistance | $460,757 | $463,256 | 71 | $12.1M | Research |
| Staggemeyer Stave Co. Inc. | Manufacturing | $404,162 | $406,455 | 28 | $27.8M | Research |
| Sno Pac Foods, Inc. | Wholesale Trade | $350,574 | $353,671 | 55 | $14.2M | Research |
| Precision Stainless, Inc. | Manufacturing | $318,200 | $320,390 | 34 | $8.9M | Research |
| Kittleson Masonry INC | Construction | $315,590 | $317,189 | 27 | <$5M | Research |
| Joe Rud Trucking Inc. | Transportation and Warehousing | $302,643 | $303,861 | 28 | $5.6M | Research |
| Joe Rud Trucking, Inc. | Transportation and Warehousing | $287,731 | $289,946 | 23 | <$5M | Research |
| Tactacam LLC | Retail Trade | $224,085 | $225,598 | 16 | <$5M | Research |
| Caledonia Implement Company | Wholesale Trade | $169,912 | $170,700 | 10 | <$5M | Research |
| Caledonia Implement Company | Wholesale Trade | $169,900 | $171,236 | 14 | <$5M | Research |
| Church of St. Mary | Other Services (except Public Administration) | $145,400 | $146,446 | 30 | N/A | Research |
| Caledonia Veterinary Clinic, P.a. | Professional, Scientific, and Technical Services | $132,400 | $133,209 | 14 | <$5M | Research |
| Claddagh Senior Living, LLC | Health Care and Social Assistance | $128,891 | $129,686 | 29 | <$5M | Research |
| Koch Dairy, Inc. | Agriculture, Forestry, Fishing and Hunting | $124,600 | $125,732 | 13 | <$5M | Research |
| Bonanza Grain Inc. | Mining, Quarrying, and Oil and Gas Extraction | $122,367 | $122,903 | 12 | <$5M | Research |
| Bonanza Grain, Inc. | Transportation and Warehousing | $122,300 | $123,439 | 9 | <$5M | Research |
| Independent Choices Assistance If Needed, LLC | Health Care and Social Assistance | $112,421 | $113,083 | 21 | <$5M | Research |
| Caledonia Lumber Co., Inc. | Retail Trade | $105,000 | $105,581 | 14 | <$5M | Research |
| Family Dental Center of Caledonia LLC | Health Care and Social Assistance | $99,800 | $100,410 | 9 | <$5M | Research |
| Family Dental Center of Caledonia LLC | Health Care and Social Assistance | $99,800 | $100,160 | 9 | <$5M | Research |
| Hoscheit Dairy Farms L.l.c. | Agriculture, Forestry, Fishing and Hunting | $90,200 | $90,677 | 9 | <$5M | Research |
| Murphy Law Office Pllp | Professional, Scientific, and Technical Services | $85,600 | $86,347 | 11 | <$5M | Research |