| New England Natural Bakers Inc. | Manufacturing | $496,815 | $502,205 | 30 | $10.6M | AI Deep Dive |
| Two Fathers LLC | Retail Trade | $492,925 | $497,827 | 36 | $9.1M | AI Deep Dive |
| Clayton D Davenport Trucking INC | Transportation and Warehousing | $476,100 | $481,931 | 30 | <$5M | AI Deep Dive |
| New England Natural Bakers, Inc. | Manufacturing | $464,700 | $337,576 | 44 | $15.5M | AI Deep Dive |
| Connecticut Valley Oral Surgery Associates, PC | Health Care and Social Assistance | $460,000 | $462,561 | 39 | $9.0M | AI Deep Dive |
| Greenfield Carmart, LLC | Retail Trade | $449,000 | $530,338 | 30 | $7.6M | AI Deep Dive |
| Applied Dynamics Corporation | Manufacturing | $448,510 | $451,668 | 36 | $9.4M | AI Deep Dive |
| Wood & Wood INC | Construction | $435,421 | $440,407 | 35 | $11.9M | AI Deep Dive |
| Applied Dynamics Corporation | Other Services (except Public Administration) | $417,539 | $420,411 | 32 | $6.9M | AI Deep Dive |
| Crocker Communications, Inc. | Information | $410,656 | $413,829 | 38 | $6.4M | AI Deep Dive |
| Two Fathers, LLC | Retail Trade | $393,000 | $463,793 | 36 | $9.1M | AI Deep Dive |
| Community Young Men S Christian Assoc of Greenfield | Health Care and Social Assistance | $388,478 | $392,533 | 85 | $13.8M | AI Deep Dive |
| Forza Autogroup Inc. | Retail Trade | $387,312 | $391,056 | 32 | $8.1M | AI Deep Dive |
| Dillon Chevrolet, Inc. | Retail Trade | $367,000 | $369,373 | 33 | $8.3M | AI Deep Dive |
| The Community Young Men's Christian Association of Greenfiel | Arts, Entertainment, and Recreation | $365,000 | $369,340 | 135 | $18.9M | AI Deep Dive |
| Lifepath INC | Other Services (except Public Administration) | $358,600 | $361,675 | 140 | N/A | AI Deep Dive |
| Hitpoint, Inc. | Information | $356,591 | $358,611 | 26 | <$5M | AI Deep Dive |
| Greenfield Glass Co INC | Manufacturing | $353,018 | $354,584 | 29 | $28.8M | AI Deep Dive |
| Fosters Super Market, Inc. | Retail Trade | $325,000 | $328,455 | 61 | $15.2M | AI Deep Dive |
| Hospice of Franklin County INC | Health Care and Social Assistance | $321,307 | $322,860 | 29 | <$5M | AI Deep Dive |
| Fox Hopyard Golf Club LLC | Arts, Entertainment, and Recreation | $291,875 | $293,874 | 299 | $41.9M | AI Deep Dive |
| Fox Hopyard Golf Club, LLC | Arts, Entertainment, and Recreation | $291,800 | $294,766 | 32 | <$5M | AI Deep Dive |
| Hangar of Greenfield INC | Accommodation and Food Services | $288,214 | $292,257 | 41 | $7.3M | AI Deep Dive |
| Australis Aquaculture, LLC | Wholesale Trade | $287,113 | $289,874 | 14 | <$5M | AI Deep Dive |
| Greenfield Center School INC | Educational Services | $262,313 | $263,965 | 19 | N/A | AI Deep Dive |