| COMMUNITY HEALTH PROGRAMS INCORPORATED | Great Barrington | — | $33M | 12 |
| YOUNG MEN'S CHRISTIAN ASSOCIATION | Peabody | P270 Human Services | $32.9M | 7 |
| 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 |
| LIFEWORKS INCORPORATED | Westwood | P80Z Human Services | $32.1M | 7 |
| ROCA INC | Chelsea | O99Z Youth Development | $32.1M | 8 |
| Outer Cape Health Services Inc | Harwich Port | E39Z Health Care | $32M | 9 |
| EDGEWOOD RETIREMENT COMMUNITY INC | North Andover | P750 Human Services | $31.8M | 7 |
| KENNEDY-DONOVAN CENTER INC | Foxboro | P800 Human Services | $31.8M | 8 |
| QUINCY CREDIT UNION | Quincy | — | $31.7M | 8 |
| THE WILLIAM F CONNELL CHARITABLE TRUST | Boston | — | $31.5M | 0 |
| BENJAMIN FRANKLIN CUMMINGS INSTITUTE OF | Boston | B40 Education | $31.4M | 7 |
| JEWISH FAMILY & CHILDREN'S SERVICE INC | Waltham | — | $31.3M | 7 |
| GOSNOLD INC | Falmouth | — | $31.3M | 13 |
| Boston Plastic and Oral Surgery | 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 |
| MASSACHUSETTS PUBLIC EMPLOYEES | Peabody | E81Z Health Care | $31M | 4 |
| Heading Home Inc | Boston | L40Z Housing & Shelter | $30.9M | 4 |
| 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 |
| THE LEARNING CENTER FOR THE DEAF INC | Framingham | — | $30.8M | 6 |
| GUIDEWIRE INC | Chicopee | P820 Human Services | $30.6M | 5 |
| PRX Inc | Cambridge | A34 Arts, Culture & Humanities | $30.6M | 14 |
| 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 |
| PINNACLE WEST CAPITAL CORPORATION UNION | Heritage Dr N Qu | Y43 Mutual & Membership Benefit | $30.4M | 0 |
| THE JAKET FOUNDATION | Boston | T22 Philanthropy, Voluntarism & Grantmaking Foundations | $30.3M | 0 |
| HOLOCAUST LEGACY FOUNDATION INC | Boston | A54 Arts, Culture & Humanities | $30.2M | 1 |
| EVERGREEN CENTER INC | Milford | G84Z Diseases, Disorders & Medical Disciplines | $30.2M | 7 |
| HOUSING FAMILIES INC | Malden | P85Z Human Services | $29.9M | 4 |
| Hebrew Senior Life Inc | Boston | T02 Philanthropy, Voluntarism & Grantmaking Foundations | $29.8M | 19 |
| THE COUNTRY CLUB | Chestnut Hill | — | $29.8M | 8 |
| THE ROXBURY LATIN SCHOOL | West Roxbury | B250 Education | $29.6M | 9 |
| THE ROBERT AND MICHELLE COOKE ATCHINSON | Winchester | T22 Philanthropy, Voluntarism & Grantmaking Foundations | $29.6M | 0 |
| COMMUNITY HEALTH CENTER OF CAPE COD | Mashpee | E30 Health Care | $29.6M | 8 |
| BAY STATE COMMUNITY SERVICES INC | Quincy | — | $29.5M | 5 |
| MARY ANN MORSE HEALTHCARE CORP | Framingham | — | $29.4M | 10 |
| MIRA CHARITABLE FOUNDATION | Boston | T20 Philanthropy, Voluntarism & Grantmaking Foundations | $29.3M | 0 |
| THE BRIEN CENTER FOR MENTAL HEALTH AND | Pittsfield | F80Z Mental Health & Crisis Intervention | $29.3M | 8 |
| THE BOSTON ATHLETIC ASSOCIATION | Boston | — | $29.3M | 10 |
| CATHOLIC MEMORIAL HOME INC | Fall River | E91Z Health Care | $29.3M | 5 |
| GROWALD CLIMATE FUND INC | Brookline | T20 Philanthropy, Voluntarism & Grantmaking Foundations | $29.3M | 1 |
| NUPATH INC | Woburn | P82Z Human Services | $29.2M | 7 |
