| Tom Farley Land Design Inc. | Professional, Scientific, and Technical Services | $113,509 | $114,140 | 12 | <$5M |  AI Deep Dive |
| Michaels of Stockbridge, Inc. | Accommodation and Food Services | $103,564 | $103,956 | 19 | <$5M | AI Deep Dive |
| Tom Farley Land Design, Inc. | Professional, Scientific, and Technical Services | $102,030 | $102,574 | 10 | <$5M | AI Deep Dive |
| James Obanhein Electric, Inc. | Construction | $90,500 | $90,954 | 8 | <$5M | AI Deep Dive |
| James Obanhein Electric Inc. | Construction | $89,922 | $90,343 | 8 | <$5M | AI Deep Dive |
| Doers LLC | Accommodation and Food Services | $88,700 | $89,361 | 10 | <$5M | AI Deep Dive |
| Michaels of Stockbridge, Inc. | Accommodation and Food Services | $88,370 | $87,857 | 25 | <$5M | AI Deep Dive |
| Oryan INC | Accommodation and Food Services | $76,930 | $77,497 | 15 | <$5M | AI Deep Dive |
| Pamela Sandler Architect LLC | Professional, Scientific, and Technical Services | $75,490 | $75,931 | 4 | <$5M | AI Deep Dive |
| Is183, Inc. | Educational Services | $74,800 | $65,991 | 9 | <$5M | AI Deep Dive |
| Is183 Inc. | Educational Services | $72,682 | $73,281 | 17 | <$5M | AI Deep Dive |
| Native Habitat Resotration LLC | Agriculture, Forestry, Fishing and Hunting | $64,700 | $65,136 | 5 | <$5M | AI Deep Dive |
| Hart Marketing Enterprises, LLC | Information | $60,400 | $45,807 | 3 | <$5M | AI Deep Dive |
| Hart Marketing Enterprises, LLC | Professional, Scientific, and Technical Services | $60,368 | $60,665 | 3 | <$5M | AI Deep Dive |
| Schantz Galleries | Retail Trade | $56,982 | $57,382 | 4 | <$5M | AI Deep Dive |
| Schantz Galleries | Retail Trade | $55,000 | $55,473 | 5 | <$5M | AI Deep Dive |
| Oryan INC | Accommodation and Food Services | $54,900 | $55,452 | 12 | <$5M | AI Deep Dive |
| Berkshire Waldorf High School INC | Educational Services | $53,100 | $53,553 | 9 | <$5M | AI Deep Dive |
| Stockbridge Library Association | Information | $51,902 | $52,249 | 8 | N/A | AI Deep Dive |
| Stockbridge Library Association | Information | $48,800 | $49,265 | 10 | N/A | AI Deep Dive |
| Pilling Landscaping Inc. | Other Services (except Public Administration) | $47,979 | $48,190 | 6 | <$5M | AI Deep Dive |
| St. Pauls Episcopal Church | Other Services (except Public Administration) | $47,530 | $47,672 | 4 | <$5M | AI Deep Dive |
| Jay Rhind Builders INC | Construction | $47,020 | $47,361 | 10 | <$5M | AI Deep Dive |
| Marconica, INC | Administrative and Support and Waste Management | $45,820 | $46,027 | 9 | <$5M | AI Deep Dive |
| Notre Reve INC | Accommodation and Food Services | $44,107 | $44,304 | 18 | $5.6M | AI Deep Dive |