| THE ARC OF BRISTOL COUNTY INC | Attleboro | — | $33.9M | 4 |
| THE GIVING BACK FUND INC | Boston | T700 Philanthropy, Voluntarism & Grantmaking Foundations | $33.8M | 4 |
| BRIMMER AND MAY SCHOOL | Chestnut Hill | B200 Education | $33.8M | 6 |
| OBSERVATORY HILL FOUNDATION | Boston | T20 Philanthropy, Voluntarism & Grantmaking Foundations | $33.7M | 0 |
| WESTMASS ELDERCARE INC | Holyoke | P810 Human Services | $33.7M | 4 |
| CENTRAL MASSACHUSETTS HOUSING ALLIANCE INC | Worcester | — | $33.6M | 1 |
| NEW PROFIT INC | Boston | S50 Community Improvement & Capacity Building | $33.6M | 12 |
| GREATER NEW BEDFORD COMMUNITY HEALTH CENTER INC | New Bedford | — | $33.6M | 10 |
| THE TINA SNIDER FOUNDATION | Gloucester | T22 Philanthropy, Voluntarism & Grantmaking Foundations | $33.5M | 1 |
| INTERNATIONAL INSTITUTE OF NEW ENGLAND INC | Boston | R20Z Civil Rights, Social Action & Advocacy | $33.5M | 9 |
| SOUTH SHORE COMMUNITY ACTION COUNCIL INC | Plymouth | S20Z Community Improvement & Capacity Building | $33.3M | 6 |
| WALKER INC | Needham | B28Z Education | $33.3M | 8 |
| GREATER BOSTON LEGAL SERVICES INC | Boston | — | $33.2M | 7 |
| THE BRIEN CENTER FOR MENTAL HEALTH AND SUBSTANCE ABUSE SERVICES | Pittsfield | F80Z Mental Health & Crisis Intervention | $33.1M | 9 |
| CHMC Cardiovascular Surgical Foundation Inc | Boston | — | $33.1M | 8 |
| THE FOOD BANK OF WESTERN MASSACHUSETTS INC | Chicopee | — | $33M | 6 |
| GUILD OF SAINT AGNES OF WORCESTER | Worcester | P33Z Human Services | $32.8M | 2 |
| WANG THEATRE INC | Boston | A610 Arts, Culture & Humanities | $32.8M | 10 |
| COOPERATIVE PRODUCTION INC | North Dighton | P80 Human Services | $32.6M | 9 |
| Woodwell Climate Research Center Inc | Falmouth | U300 Science & Technology | $32.6M | 10 |
| RTH MISSION PARK REALTY CORPORATION | Boston | L11 Housing & Shelter | $32.2M | 5 |
| SOUTHCOAST HEALTH SYSTEM INC | New Bedford | E210 Health Care | $32.2M | 12 |
| THE ROBERT AND MICHELLE COOKE ATCHINSON FOUNDATION | Winchester | T22 Philanthropy, Voluntarism & Grantmaking Foundations | $32.2M | 0 |
| ROCA INC | Chelsea | O99Z Youth Development | $32.1M | 8 |
| THE LYNCH FOUNDATION | Boston | T900 Philanthropy, Voluntarism & Grantmaking Foundations | $32M | 2 |
| GOSNOLD INC | Falmouth | — | $31.9M | 11 |
| UNIVERSITY OF MASSACHUSETTS AMHERST FOUNDATION INC | Amherst | B12 Education | $31.9M | 14 |
| EDGEWOOD RETIREMENT COMMUNITY INC | North Andover | P750 Human Services | $31.8M | 7 |
| MASSACHUSETTS PUBLIC EMPLOYEES HEALTH AND WELFARE FUND | Peabody | E81Z Health Care | $31.8M | 3 |
| FACING HISTORY & OURSELVES INC | Boston | A70Z Arts, Culture & Humanities | $31.8M | 14 |
| THE ROXBURY LATIN SCHOOL | West Roxbury | B250 Education | $31.8M | 8 |
| ALZHEIMER'S DISEASE RESEARCH FOUNDATION | Wellesley Hills | H83 Medical Research | $31.8M | 11 |
| QUINCY CREDIT UNION | Quincy | — | $31.7M | 8 |
| MANET COMMUNITY HEALTH CENTER INC | North Quincy | E32Z Health Care | $31.6M | 9 |
| INQUILINOS BORICUAS EN ACCION INC | Boston | — | $31.6M | 7 |
| NORTH SHORE COMMUNITY HEALTH INC | Salem | E320 Health Care | $31.6M | 11 |
| THE WILLIAM F CONNELL CHARITABLE TRUST | Boston | T20 Philanthropy, Voluntarism & Grantmaking Foundations | $31.5M | 0 |
| BENJAMIN FRANKLIN CUMMINGS INSTITUTE OF TECHNOLOGY | Boston | B40 Education | $31.4M | 7 |
| JEWISH FAMILY & CHILDREN'S SERVICE INC | Waltham | — | $31.3M | 7 |
| Boston Plastic and Oral Surgery Foundation Inc | Boston | B99Z Education | $31.3M | 9 |
| KRIPALU CENTER FOR YOGA & HEALTH | Stockbridge | P54Z Human Services | $31.1M | 7 |
| NURTURY INC | Roxbury | — | $31.1M | 6 |
| POLISH NATIONAL CREDIT UNION | Chicopee | — | $31M | 9 |
| GROTON HILL MUSIC INC | Groton | A680 Arts, Culture & Humanities | $30.9M | 4 |
| NEW ENGLAND WILDLIFE CENTER INC | South Weymouth | D340 Animal-Related | $30.8M | 5 |
| THE NEW ENGLAND COLLEGE OF OPTOMETRY | Boston | — | $30.8M | 14 |
| ST MARK'S SCHOOL OF SOUTHBOROUGH INC | Southborough | B250 Education | $30.6M | 6 |
| VICTORY PROGRAMS INC | Boston | F22Z Mental Health & Crisis Intervention | $30.6M | 9 |
| YMCA of Central Massachusetts (2909) | Worcester | P270 Human Services | $30.5M | 5 |
| CRYSTAL SPRINGS INC | Assonet | P800 Human Services | $30.4M | 5 |
