| $350,000–1 million | ALLEGRONE CONSTRUCTION CO., INC. | LENOX, MA | Lee Bank |
| $150,000–350,000 | ALWAYS GROWING LANDSCAPING INC | WASHINGTON, MA | Lee Bank |
| $150,000–350,000 | AMENITEK, INC. | LANESBOROUGH, MA | Lee Bank |
| $150,000–350,000 | ANTERIS SOLUTIONS, INC. | PITTSFIELD, MA | Lee Bank |
| $2–5 million | AUSTEN RIGGS CENTER, INC. | STOCKBRIDGE, MA | Lee Bank |
| $150,000–350,000 | BARRINGTON COFFEE ROASTING CO, INC. | LEE, MA | Lee Bank |
| $150,000–350,000 | BERKSHIRE BIKE, LLC | GREAT BARRINGTON, MA | Lee Bank |
| $150,000–350,000 | BERKSHIRE COMMUNICATORS, INC. | PITTSFIELD, MA | Lee Bank |
| $350,000–1 million | BERKSHIRE COUNTRY DAY SCHOLL | LENOX, MA | Lee Bank |
| $150,000–350,000 | BERKSHIRE MONTESSORI SCHOOL | LENOX DALE, MA | Lee Bank |
| $150,000–350,000 | BERKSHIRE MOUNTAIN BAKERY, INC. | HOUSATONIC, MA | Lee Bank |
| $150,000–350,000 | BERKSHIRE RENTALS, INC. | PITTSFIELD, MA | Lee Bank |
| $150,000–350,000 | BERKSHIRE THEATRE GROUP INC | PITTSFIELD, MA | Lee Bank |
| $350,000–1 million | BOYD CONVERTING COMPANY INC | LEE, MA | Lee Bank |
| $350,000–1 million | BRAZABRA CORPORATION | LEE, MA | Lee Bank |
| $150,000–350,000 | BUTTERNUT BASIN INC | GREAT BARRINGTON, MA | Lee Bank |
| $350,000–1 million | CMC BERKSHIRE, LLC | NEW MARLBOROUGH, MA | Lee Bank |
| $150,000–350,000 | COMMUNITY ACCESS TO THE ARTS, INC. | GREAT BARRINGTON, MA | Lee Bank |
| $150,000–350,000 | CONSERVE THRU CONTROL, INC. | ADAMS, MA | Lee Bank |
| $150,000–350,000 | DETTINGER LUMBER COMPANY INC | PITTSFIELD, MA | Lee Bank |
| $150,000–350,000 | DONOVAN O'CONNOR & DODIG, LLP | NORTH ADAMS, MA | Lee Bank |
| $350,000–1 million | DRESSER HULL COMPANY | LEE, MA | Lee Bank |
| $150,000–350,000 | EDWARDS, KROL AND NAZAROV PC | STOCKBRIDGE, MA | Lee Bank |
| $150,000–350,000 | GARY J OBRIEN PROPERTY SERVICES INC | LEE, MA | Lee Bank |
| $150,000–350,000 | GLAGJR LLC | HILLSDALE, NY | Lee Bank |
| $150,000–350,000 | HENRY'S ELECTRIC INC. | LEE, MA | Lee Bank |
| $150,000–350,000 | JOHN B HULL INC | GREAT BARRINGTON, MA | Lee Bank |
| $150,000–350,000 | KIRKLYN ENTERPRISES INC | LANESBOROUGH, MA | Lee Bank |
| $350,000–1 million | L. P. ADAMS CO., INC. | DALTON, MA | Lee Bank |
| $150,000–350,000 | LAWRENCE V. TOOLE INSURANCE AGENCY, INC. | LEE, MA | Lee Bank |
| $150,000–350,000 | LEE AUDIO 'N' SECURITY INCORPORATED | LEE, MA | Lee Bank |
| $150,000–350,000 | LEPREVOST PLUMBING & HEATING, INC. | LEE, MA | Lee Bank |
| $1–2 million | LOUIS C. ALLEGRONE, INC. | LENOX, MA | Lee Bank |
| $150,000–350,000 | MAIN STREET HOSPITALITY GROUP, LLC | STOCKBRIDGE, MA | Lee Bank |
| $150,000–350,000 | MARTN & OLIVERIA, LLP | PITTSFIELD, MA | Lee Bank |
| $150,000–350,000 | MONGIARDO STUDIO INC. | GREAT BARRINGTON, MA | Lee Bank |
| $150,000–350,000 | MRM HOSPITALITY LLC | PITTSFIELD, MA | Lee Bank |
| $150,000–350,000 | OLD INN ON THE GREEN, LLC | GREAT BARRINGTON, MA | Lee Bank |
| $150,000–350,000 | PETER FASANO,LTD LLC | GREAT BARRINGTON, MA | Lee Bank |
| $150,000–350,000 | R.W.'S INC. | LEE, MA | Lee Bank |
| $150,000–350,000 | RIVERBROOK RESIDENCE, INC. | STOCKBRIDGE, MA | Lee Bank |
| $1–2 million | ROARING LLC | STOCKBRIDGE, MA | Lee Bank |
| $150,000–350,000 | STOCKBRIDGE GOLF CLUB | STOCKBRIDGE, MA | Lee Bank |
| $150,000–350,000 | SUBURBAN INTERNAL MEDICINE INC | LEE, MA | Lee Bank |
| $150,000–350,000 | TETON MANAGEMENT | PITTSFIELD, MA | Lee Bank |
| $150,000–350,000 | THE CHAMBERLAIN GROUP, LLC | GREAT BARRINGTON, MA | Lee Bank |
| $350,000–1 million | THE GREAT BARRINGTON MARKETPLACE INC | SHEFFIELD, MA | Lee Bank |
| $150,000–350,000 | WARD'S NURSERY | GREAT BARRINGTON, MA | Lee Bank |
| $150,000–350,000 | ZOGICS LLC | LENOX, MA | Lee Bank |