| BERKSHIRE TACONIC COMMUNITY FOUNDATION INC | Sheffield | T310 Philanthropy, Voluntarism & Grantmaking Foundations | $16.6M | 6 |
| ROOFERS UNION LOCAL NO 33 THRIFT FUND | Stoughton | — | $16.6M | 0 |
| BETTER COMMUNITY LIVING INC | North Dartmouth | F33Z Mental Health & Crisis Intervention | $16.6M | 2 |
| SEED GLOBAL HEALTH | Boston | B82 Education | $16.5M | 10 |
| CROSSROADS CONTINUUM INC | Hudson | B21 Education | $16.4M | 6 |
| SENIORCARE INC | Gloucester | P44Z Human Services | $16.4M | 1 |
| TEACH PLUS INC | Boston | B90 Education | $16.4M | 11 |
| BANCROFT SCHOOL | Worcester | B250 Education | $16.4M | 7 |
| REFUGEPOINT INC | Boston | Q33 International, Foreign Affairs & National Security | $16.4M | 9 |
| Berkshire Retirement Community Inc | Pittsfield | P750 Human Services | $16.4M | 4 |
| EASTER SEALS MASSACHUSETTS INC | Worcester | E50 Health Care | $16.3M | 7 |
| WESTERN MASSACHUSETTS TRAINING CONSORTIUM INC | Holyoke | P020 Human Services | $16.3M | 1 |
| EMANUEL DEVELOPMENT CORPORATION | Brighton | P75 Human Services | $16.3M | 14 |
| 'SCONSET TRUST INC | Siasconset | C340 Environment | $16.3M | 2 |
| ALLIANCE HEALTH OF BROCKTON INC | Southborough | E910 Health Care | $16.3M | 14 |
| PINE BROOK COUNTRY CLUB INC | Weston | — | $16.2M | 6 |
| EYOL INC | Watertown | B99 Education | $16.2M | 2 |
| DEPLOYUS INC | Boston | C35 Environment | $16.2M | 8 |
| ECONOMIC MOBILITY PATHWAYS INC | Boston | E40 Health Care | $16.2M | 9 |
| THE GROUNDTRUTH PROJECT INC | Boston | J22 Employment | $16.1M | 8 |
| NEW ENGLAND HISTORIC GENEALOGICAL SOCIETY | Boston | — | $16M | 8 |
| Old Colony Hospice Inc | West Bridgewater | P74 Human Services | $16M | 6 |
| TUFTS MEDICINE INC | Burlington | E02 Health Care | $15.9M | 22 |
| THE WORKERS COMPENSATION RATING & INSPECTION BUREAU OF MASSACHUSETTS | Boston | — | $15.9M | 11 |
| Brockton Visiting Nurse Association Inc | Brockton | E92Z Health Care | $15.9M | 7 |
| COLLEGE YEAR IN ATHENS INC | Cambridge | Q220 International, Foreign Affairs & National Security | $15.9M | 1 |
| MICAH PHILANTHROPIES | Agawam | T20 Philanthropy, Voluntarism & Grantmaking Foundations | $15.9M | 3 |
| TAPESTRY HEALTH SYSTEMS INC | Springfield | E42Z Health Care | $15.9M | 5 |
| Children's Hospital Pathology Foundation Inc | Boston | G97Z Diseases, Disorders & Medical Disciplines | $15.8M | 13 |
| THE SIDNEY AND DEANNA WOLK FAMILY FOUNDATION | Medford | T22 Philanthropy, Voluntarism & Grantmaking Foundations | $15.8M | 0 |
| OVERLOOK COMMUNITIES INC | Charlton | L22 Housing & Shelter | $15.8M | 10 |
| FUND FOR THE PUBLIC INTEREST INC | Boston | — | $15.7M | 11 |
| BUZZARDS BAY COALITION | New Bedford | C320 Environment | $15.7M | 5 |
| THE HOUSING PARTNERSHIP NETWORK INC | Boston | L99 Housing & Shelter | $15.7M | 9 |
| BUILD HEALTH INTERNATIONAL INC | Beverly | T23 Philanthropy, Voluntarism & Grantmaking Foundations | $15.6M | 1 |
| American Hockey League | Springfield | — | $15.6M | 6 |
| LUTHERAN HOME OF JAMAICA PLAIN INC | Jaimaica Plain | — | $15.5M | 14 |
| THE NILENDU AND RENU SRIVASTAVA FAMILY FOUNDATION | Lynnfield | T20 Philanthropy, Voluntarism & Grantmaking Foundations | $15.4M | 0 |
| Stamps Family Charitable Foundation Inc | Boston | T20 Philanthropy, Voluntarism & Grantmaking Foundations | $15.4M | 0 |
| HOLYOKE CREDIT UNION | Holyoke | — | $15.3M | 7 |
| DUFFY HEALTH CENTER INC | Hyannis | E99 Health Care | $15.3M | 9 |
| WORCESTER CENTER FOR PERFORMING ARTS INC | Worcester | A20 Arts, Culture & Humanities | $15.3M | 5 |
| MASSACHUSETTS LIBRARY SYSTEM INC | Marlborough | B70 Education | $15.3M | 4 |
| CHARLES RIVER COUNTRY CLUB INC | Newton Centre | — | $15.3M | 8 |
| THE ARC OF THE SOUTH SHORE INC | Hingham | P82Z Human Services | $15.3M | 6 |
| GREENLIGHT FUND INC | Boston | S50 Community Improvement & Capacity Building | $15.3M | 8 |
| GIRL SCOUTS OF EASTERN MASSACHUSETTS INC | Waltham | O42 Youth Development | $15.3M | 7 |
| CENTER FOR APPLIED BEHAVIORAL INSTRUCTION INC | Worcester | B99 Education | $15.3M | 6 |
| PRO-DEMOCRACY CAMPAIGN C/O VERDOLINO & LOWEY PC | Foxborough | R19 Civil Rights, Social Action & Advocacy | $15.3M | 2 |
| ALLIANCE HEALTH OF MASSACHUSETTS INC | Southborough | L22 Housing & Shelter | $15.2M | 14 |
