| COMMUNITIES FOR PEOPLE INC | Boston | F33Z Mental Health & Crisis Intervention | $21.8M | 8 |
| Northeast Gas Association Inc | Westborough | — | $21.8M | 5 |
| Boston Firefighters Credit Union | Dorchester | — | $21.8M | 13 |
| SANCTA MARIA HOSPITAL INC | Cambridge | — | $21.8M | 7 |
| ROSIE'S PLACE INC | Boston | L410 Housing & Shelter | $21.7M | 7 |
| THE ARC OF OPPORTUNITY IN NORTH CENTRAL MASSACHUSETTS INC | Fitchburg | — | $21.7M | 7 |
| JACOB'S PILLOW DANCE FESTIVAL INC | Becket | A620 Arts, Culture & Humanities | $21.6M | 6 |
| NATIONAL CONSUMER LAW CENTER INC | Boston | I80Z Crime & Legal-Related | $21.6M | 13 |
| MASSACHUSETTS NURSES ASSOCIATION | Canton | — | $21.5M | 22 |
| MI Nursing Restorative Center Inc | Lawrence | E910 Health Care | $21.5M | 6 |
| TRANSIT EMPLOYEES HEALTH AND WELFARE FUND | Boston | Y43 Mutual & Membership Benefit | $21.5M | 1 |
| Northampton Management Systems Inc | Pittsfield | E91 Health Care | $21.4M | 6 |
| BOYS & GIRLS CLUBS OF DORCHESTER INC | Dorchester | O210 Youth Development | $21.4M | 5 |
| YOUNG MEN'S CHRISTIAN ASSOCIATION SOUTHCOAST INC | New Bedford | — | $21.4M | 6 |
| IntegriNurse Inc | Pittsfield | E112 Health Care | $21.4M | 6 |
| COMMUNITY SYSTEMS INC | Plymouth | P73Z Human Services | $21.2M | 9 |
| AFSCME COUNCIL 93 | Boston | — | $21.2M | 43 |
| YOUTHBUILD USA INC | Roxbury | J20 Employment | $21.2M | 9 |
| HIGHLAND VALLEY ELDER SERVICES INC | Florence | — | $21.2M | 2 |
| MASSACHUSETTS BAY HEALTH CARE TRUST FUND | Lexington | — | $21.1M | 0 |
| HEALTH AND SOCIAL SERVICES CONSORTIUM INC | Walpole | — | $21M | 1 |
| NORTH ADAMS REGIONAL HOSPITAL | Pittsfield | E20 Health Care | $21M | 7 |
| FAIR HAVENS INC | West Brookfield | — | $20.9M | 14 |
| VIRGINIA LIFE ACCIDENT AND SICKNESS INSURANCE GUARANTY ASSOCIATION | Hampden | — | $20.7M | 0 |
| SOLDIER ON INC | Pittsfield | W30 Public & Societal Benefit | $20.7M | 9 |
| LAST MILE HEALTH | Boston | E60 Health Care | $20.7M | 10 |
| Boston Pediatric Neurosurgical Foundation Inc | Boston | G9BZ Diseases, Disorders & Medical Disciplines | $20.6M | 10 |
| THE SUMMER ISLE FOUNDATION | Woburn | T12 Philanthropy, Voluntarism & Grantmaking Foundations | $20.6M | 0 |
| BOSTON ARCHITECTURAL COLLEGE | Boston | — | $20.5M | 10 |
| THE INSTITUTE OF CONTEMPORARY ART INC | Boston | A510 Arts, Culture & Humanities | $20.4M | 10 |
| JUMPSTART FOR YOUNG CHILDREN INC | Boston | B21 Education | $20.4M | 10 |
| Care Central VNA & Hospice Inc | Gardner | E92 Health Care | $20.3M | 7 |
| LEAGUE SCHOOL FOR AUTISM INC | Walpole | B28Z Education | $20.3M | 8 |
| HARVARD STREET NEIGHBORHOOD HEALTH CENTER INC | Dorchester | E32Z Health Care | $20.3M | 6 |
| THE MURRAY BURNSTINE CHARITABLE TRUST | Stoneham | A20 Arts, Culture & Humanities | $20.3M | 2 |
| POINT32HEALTH FOUNDATION INC | Canton | E12 Health Care | $20.2M | 19 |
| EF EDUCATIONAL FOUNDATION FOR FOREIGN STUDY A NON-PROFIT CORPORATION | Cambridge | Q230 International, Foreign Affairs & National Security | $20.2M | 13 |
| COTTING SCHOOL INC | Lexington | B200 Education | $20.1M | 7 |
| THE BOSTON HOME INC | Boston | E910 Health Care | $20M | 8 |
| SAINT VINCENT'S SERVICES INC | Fall River | P730 Human Services | $20M | 3 |
| EMPOWER LGA INC | Canton | B22Z Education | $20M | 6 |
| PEABODY ESSEX MUSEUM INC | Salem | A500 Arts, Culture & Humanities | $20M | 8 |
| ROXBURY TENANTS OF HARVARD ASSOCIATION INC | Boston | P200 Human Services | $19.9M | 16 |
| HomeStart Inc | Boston | S31 Community Improvement & Capacity Building | $19.9M | 6 |
| VNA CARE MANAGEMENT RESOURCES INC | Worcester | E92Z Health Care | $19.9M | 10 |
| The Irene E and George A Davis Foundation | Springfield | T22 Philanthropy, Voluntarism & Grantmaking Foundations | $19.9M | 0 |
| COMMUNITY SERVINGS INC | Jamaica Plain | P80Z Human Services | $19.9M | 8 |
| LIFE-SKILLS INC | Sturbridge | E50Z Health Care | $19.8M | 6 |
| BETH ISRAEL LAHEY HEALTH PRIMARY CARE | Charlestown | — | $19.7M | 20 |
| CHRISTOPHER HOUSE INC | Worcester | — | $19.7M | 6 |
