| Baystate Engineering Corp | Construction | $350,785 | $353,279 | 24 | $9.0M |  AI Deep Dive |
| Tree Specialists, Inc. | Administrative and Support and Waste Management | $335,410 | $337,069 | 21 | <$5M | AI Deep Dive |
| Baystate Engineering Corp. | Construction | $333,770 | $336,301 | 30 | $11.2M | AI Deep Dive |
| Liberating Technologies, Inc. | Manufacturing | $315,000 | $0 | 16 | <$5M | AI Deep Dive |
| D. Masters Enterprises, Inc. | Construction | $307,390 | $310,242 | 24 | $7.3M | AI Deep Dive |
| Titan Contractors Inc. | Construction | $303,217 | $305,028 | 17 | $5.3M | AI Deep Dive |
| Titan Contractors, Inc. | Construction | $302,990 | $304,640 | 19 | $7.1M | AI Deep Dive |
| Fore Kicks INC | Arts, Entertainment, and Recreation | $279,647 | $282,001 | 39 | $5.5M | AI Deep Dive |
| Murray Paving and Reclamation INC | Construction | $267,510 | $269,791 | 11 | <$5M | AI Deep Dive |
| Autogen INC | Manufacturing | $262,801 | $264,745 | 9 | <$5M | AI Deep Dive |
| Kramers Custom Kitchens & Woodworking Inc. | Manufacturing | $255,000 | $221,981 | 21 | $5.5M | AI Deep Dive |
| Protective Solutions INC | Professional, Scientific, and Technical Services | $253,371 | $255,523 | 17 | <$5M | AI Deep Dive |
| First Congregational Church of Holliston | Other Services (except Public Administration) | $249,250 | $251,666 | 41 | N/A | AI Deep Dive |
| Autogen, Inc. | Manufacturing | $247,700 | $250,218 | 14 | <$5M | AI Deep Dive |
| Cadwell Products Company INC | Manufacturing | $242,980 | $245,130 | 21 | $5.9M | AI Deep Dive |
| Heffernan Lawn Management | Administrative and Support and Waste Management | $240,656 | $242,522 | 20 | <$5M | AI Deep Dive |
| Fore Kicks Inc. | Arts, Entertainment, and Recreation | $239,800 | $241,279 | 14 | <$5M | AI Deep Dive |
| Rodenhiser Excavating, INC | Construction | $237,127 | $238,528 | 16 | <$5M | AI Deep Dive |
| Abbess Instruments and Systems, Inc. | Manufacturing | $234,450 | $236,352 | 18 | <$5M | AI Deep Dive |
| Abbess Instruments and Systems, Inc. | Manufacturing | $234,450 | $235,388 | 17 | <$5M | AI Deep Dive |
| Eric Enterprises INC | Administrative and Support and Waste Management | $232,627 | $234,418 | 24 | $5.2M | AI Deep Dive |
| Murray Paving & Reclamation, Inc. | Construction | $226,910 | $228,467 | 12 | <$5M | AI Deep Dive |
| New England Household Moving & Storage INC | Transportation and Warehousing | $226,580 | $229,834 | 19 | <$5M | AI Deep Dive |
| New England Household Moving | Transportation and Warehousing | $226,580 | $228,537 | 15 | <$5M | AI Deep Dive |
| Starburst Printing and Graphics INC | Manufacturing | $218,741 | $221,232 | 17 | $16.9M | AI Deep Dive |