| THE KINGSLEY MONTESSORI SCHOOL INC | Boston | — | $19.6M | 6 |
| COMMUNITY PROVIDERS OF ADOLESCENT SERVICES INC | Dorchester | P300 Human Services | $19.6M | 7 |
| SCHOOLS FOR CHILDREN INC | Winchester | B28Z Education | $19.6M | 8 |
| VOLUNTEERS OF AMERICA OF MASSACHUSETTS INC | Jamaica Plain | — | $19.6M | 8 |
| WAYNE J GRIFFIN ELECTRIC INC WELFARE BENEFIT PLAN TRUST | Holliston | Y43 Mutual & Membership Benefit | $19.6M | 0 |
| IBEW LOCAL 104 UNION | Mansfield | — | $19.5M | 16 |
| 350ORG | Boston | C05 Environment | $19.5M | 7 |
| HOPEWELL INC | Dedham | P320 Human Services | $19.5M | 7 |
| CHAPEL HILL-CHAUNCY HALL SCHOOL | Waltham | — | $19.4M | 7 |
| St Jeans Credit Union | Salem | — | $19.4M | 8 |
| ALL HANDS ON DECK NETWORK INC | Northampton | — | $19.4M | 6 |
| VIETNAM VETERANS WORKSHOP INC DBA NEW ENGLAND CENTER AND HOME FOR VETERANS | Boston | L410 Housing & Shelter | $19.4M | 7 |
| ALLIANCE HEALTH OF WRENTHAM INC | Southborough | T20 Philanthropy, Voluntarism & Grantmaking Foundations | $19.4M | 14 |
| CAMBRIDGE COLLEGE INC | Boston | B420 Education | $19.4M | 12 |
| RX FOUNDATION | Hadley | T21 Philanthropy, Voluntarism & Grantmaking Foundations | $19.3M | 1 |
| BETHANY HEALTH CARE CENTER INC | Framingham | — | $19.3M | 7 |
| THE FENN SCHOOL | Concord | — | $19.3M | 7 |
| MASS BAY CREDIT UNION | South Boston | — | $19.3M | 19 |
| BERKSHIRE COMMUNITY ACTION COUNCIL INC | Pittsfield | — | $19.3M | 1 |
| NEW ENGLAND FOUNDATION FOR THE ARTS INCORPORATED | Boston | A120 Arts, Culture & Humanities | $19.2M | 9 |
| MINUTE MAN ARC FOR HUMAN SERVICES INC | Concord | — | $19.1M | 7 |
| VICTORY HUMAN SERVICES INC | Brockton | F33 Mental Health & Crisis Intervention | $19M | 8 |
| COMMUNITY CATALYST INC | Boston | E99 Health Care | $19M | 11 |
| BAIM INSTITUTE FOR CLINICAL RESEARCH INC | Boston | H05 Medical Research | $19M | 20 |
| MASSACHUSETTS SERVICE ALLIANCE INC | Boston | C20Z Environment | $18.9M | 3 |
| THE WINCHENDON SCHOOL INC C/O JANET GELINAS CFO | Winchendon | B200 Education | $18.9M | 6 |
| HENRY C NEVINS HOME INC | Methuen | E91Z Health Care | $18.9M | 7 |
| COMMUNITAS INC | Wakefield | P82Z Human Services | $18.9M | 3 |
| THE PIKE SCHOOL INC | Andover | — | $18.8M | 7 |
| WEBSTER EMERGENCY MEDICAL SERVICES INC | Webster | E62 Health Care | $18.8M | 1 |
| CHELSEA JEWISH NURSING HOME INC | Chelsea | E910 Health Care | $18.8M | 9 |
| The Schooner Foundation c/o Schooner Capital LLC | Boston | T20J Philanthropy, Voluntarism & Grantmaking Foundations | $18.7M | 1 |
| ADVANCED FUNCTIONAL FABRICS OF AMERICA INC | Cambridge | B11 Education | $18.7M | 9 |
| VNA Care Hospice Inc | Worcester | P740 Human Services | $18.7M | 9 |
| PROPRIETORS OF MOUNT AUBURN CEMETERY | Cambridge | — | $18.7M | 11 |
| DEDHAM COUNTRY AND POLO CLUB | Dedham | — | $18.7M | 10 |
| HEALTH IMPERATIVES INC | Brockton | E00Z Health Care | $18.6M | 7 |
| Arbour Way Foundation Inc | Boston | T20 Philanthropy, Voluntarism & Grantmaking Foundations | $18.6M | 0 |
| MASSACHUSETTS BIOTECHNOLOGY COUNCIL INC | Cambridge | — | $18.5M | 9 |
| LOCAL 509 SERVICE EMPLOYEES INTERNATIONAL UNION | Marlborough | — | $18.5M | 39 |
| SOUTH COVE MANOR AT QUINCY POINT REHABILITATION CENTER INC | Quincy | E91 Health Care | $18.5M | 7 |
| AMERICAN METEOROLOGICAL SOCIETY | Boston | U030 Science & Technology | $18.4M | 7 |
| METROWEST YOUNG MEN'S CHRISTIAN ASSOCIATION INC | Framingham | P27Z Human Services | $18.4M | 9 |
| KNOPF FAMILY FOUNDATION INC C/O LIBERTY CHEVROLET | Wakefield | T22 Philanthropy, Voluntarism & Grantmaking Foundations | $18.4M | 0 |
| NEW ENGLAND VILLAGE INC | Pembroke | P820 Human Services | $18.4M | 5 |
| MASSACHUSETTS MUSEUM OF CONTEMPORARY ART FOUNDATION INC | North Adams | B51Z Education | $18.3M | 8 |
| UNITARIAN UNIVERSALIST ASSOCIATION EMPLOYEE BENEFITS TRUST - VEBA | Boston | Y43 Mutual & Membership Benefit | $18.2M | 2 |
| CAMP HARBOR VIEW FOUNDATION INC C/O CONNORS FAMILY OFFICE | Boston | O50 Youth Development | $18.2M | 8 |
| New Bedford Management Systems Inc | Pittsfield | E91 Health Care | $18.2M | 6 |
| UTEC INC | Lowell | O50 Youth Development | $18.1M | 7 |
