| Bennington College Corporation | Educational Services | $5,945,442 | $6,023,559 | 370 | N/A |  Research |
| United Counseling Service of Bennington County INC | Health Care and Social Assistance | $2,746,500 | $2,778,028 | 279 | N/A | Research |
| Mount Anthony Housing Corporation | Health Care and Social Assistance | $1,866,712 | $0 | 183 | N/A | Research |
| Cm Healthcare LLC | Health Care and Social Assistance | $744,985 | $753,006 | 96 | $16.3M | Research |
| Southern Vermont Nursing and Rehabilitation LLC | Health Care and Social Assistance | $706,045 | $721,288 | 80 | $13.6M | Research |
| Abacus Automation | Manufacturing | $648,037 | $653,383 | 35 | $9.2M | Research |
| Abacus Automation, Inc. | Manufacturing | $648,037 | $652,465 | 37 | $9.7M | Research |
| Jbm Sherman Carmel INC | Manufacturing | $646,400 | $650,987 | 60 | $14.7M | Research |
| Porta-Brace, Inc. | Manufacturing | $545,700 | $550,305 | 47 | $13.1M | Research |
| Bennington Auto Mart, Inc. | Retail Trade | $515,200 | $520,112 | 46 | $11.6M | Research |
| Porta-Brace, Inc. | Manufacturing | $509,828 | $512,384 | 43 | $15.2M | Research |
| The Pharmacy INC | Retail Trade | $458,900 | $462,911 | 47 | $8.2M | Research |
| Bennington Furniture Inc. | Retail Trade | $410,527 | $414,450 | 34 | $6.2M | Research |
| Bennington Furniture, Inc. | Retail Trade | $410,500 | $413,693 | 33 | $6.0M | Research |
| Town of Bennington Rescue Squad INC | Health Care and Social Assistance | $386,100 | $391,019 | 43 | N/A | Research |
| M S & K INC | Professional, Scientific, and Technical Services | $350,229 | $354,691 | 21 | <$5M | Research |
| Advanced Eyecare, INC | Health Care and Social Assistance | $334,300 | $336,284 | 22 | $5.2M | Research |
| Advanced Eyecare, INC | Health Care and Social Assistance | $312,978 | $315,070 | 28 | $8.8M | Research |
| Family Footwear Center, Inc. | Retail Trade | $305,400 | $307,131 | 38 | $10.5M | Research |
| M S & K, INC | Real Estate and Rental and Leasing | $304,500 | $308,446 | 18 | <$5M | Research |
| Sierra Enterprises INC | Accommodation and Food Services | $303,902 | $306,241 | 30 | $5.3M | Research |
| Bennington Nissan | Retail Trade | $298,640 | $292,056 | 24 | $6.0M | Research |
| Global- Z International INC | Administrative and Support and Waste Management | $275,530 | $278,919 | 13 | <$5M | Research |
| Global- Z International INC | Administrative and Support and Waste Management | $275,500 | $277,582 | 13 | <$5M | Research |
| Sunrise Family Resource Center INC | Health Care and Social Assistance | $248,300 | $250,545 | 26 | N/A | Research |