| THE INSTITUTE OF CONTEMPORARY ART INC | Boston | A510 Arts, Culture & Humanities | $23.2M | 9 |
| CRITERION CHILD ENRICHMENT INC | Milford | P300 Human Services | $23.1M | 7 |
| NORTH ATLANTIC STATES CARPENTERS | Wilmington | — | $23.1M | 6 |
| EDWARD C JOHNSON FUND | Boston | — | $22.9M | 3 |
| Technology Review Inc | Cambridge | A33 Arts, Culture & Humanities | $22.9M | 18 |
| Worcester City Campus Corporation Group | Shrewsbury | — | $22.8M | 6 |
| SOUTH SHORE SUPPORT SERVICES INC | Weymouth | P820 Human Services | $22.8M | 1 |
| CAPE ABILITIES INC | Hyannis | P820 Human Services | $22.7M | 6 |
| EASTERN NAZARENE COLLEGE | Quincy | B430 Education | $22.6M | 4 |
| WAYNE J GRIFFIN ELECTRIC INC WELFARE | Holliston | Y43 Mutual & Membership Benefit | $22.5M | 0 |
| CARL & RUTH SHAPIRO FAMILY FOUNDATION | Wellesley | T20 Philanthropy, Voluntarism & Grantmaking Foundations | $22.5M | 0 |
| MERRIMACK VALLEY YOUNG MEN'S | Lawrence | O55Z Youth Development | $22.4M | 6 |
| AGING SERVICES OF NORTH CENTRAL | Leominster | P810 Human Services | $22.3M | 3 |
| MASSACHUSETTS HOUSING AND SHELTER | Boston | P850 Human Services | $22.3M | 5 |
| THE CAMBRIDGE SCHOOL OF WESTON INC | Weston | B200 Education | $22.3M | 9 |
| COMMUNITY CONNECTIONS INC | South Yarmouth | P82Z Human Services | $22.2M | 5 |
| WORCESTER COUNTY FOOD BANK INC | Shrewsbury | K31Z Food, Agriculture & Nutrition | $22.2M | 1 |
| JA WORLDWIDE INC | Boston | B82 Education | $22.1M | 10 |
| TENACRE COUNTRY DAY SCHOOL CORPORATION | Wellesley | B21Z Education | $22M | 7 |
| WELLESLEY COUNTRY CLUB | Wellesley | — | $21.9M | 7 |
| INQUILINOS BORICUAS EN ACCION INC | Boston | — | $21.9M | 6 |
| HEALTHFIRST FAMILY CARE CENTER INC | Fall River | E320 Health Care | $21.9M | 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 | 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 |
| TRANSIT EMPLOYEES HEALTH AND WELFARE | Boston | Y43 Mutual & Membership Benefit | $21.5M | 1 |
| MASSACHUSETTS BAY HEALTH CARE TRUST FUND | Lexington | — | $21.5M | 0 |
| 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 | New Bedford | — | $21.4M | 6 |
| NELLIE MAE EDUCATION FOUNDATION INC | Quincy | B120 Education | $21.4M | 26 |
| IntegriNurse Inc | Pittsfield | E112 Health Care | $21.4M | 6 |
| LABOURE COLLEGE OF HEALTHCARE INC | Milton | — | $21.2M | 11 |
| AFSCME COUNCIL 93 | Boston | — | $21.2M | 43 |
| YOUTHBUILD USA INC | Roxbury | J20 Employment | $21.2M | 9 |
| MEADOWBROOK SCHOOL OF WESTON | Weston | B200 Education | $21.2M | 8 |
| HIGHLAND VALLEY ELDER SERVICES INC | Florence | — | $21.2M | 2 |
| NORTH ADAMS REGIONAL HOSPITAL | Pittsfield | E20 Health Care | $21M | 7 |
| COMMUNITIES FOR PEOPLE INC | Boston | F33Z Mental Health & Crisis Intervention | $20.8M | 6 |
| MIDDLESEX HUMAN SERVICE AGENCY INC | Waltham | L41Z Housing & Shelter | $20.8M | 7 |
| VIRGINIA LIFE ACCIDENT AND SICKNESS | Hampden | — | $20.7M | 0 |
| COMMUNITY LEGAL AID INC | Worcester | I99 Crime & Legal-Related | $20.7M | 5 |
| Boston Pediatric Neurosurgical | Boston | G9BZ Diseases, Disorders & Medical Disciplines | $20.6M | 10 |
| COMMUNITY SYSTEMS INC | Plymouth | P73Z Human Services | $20.6M | 9 |
| BOSTON ARCHITECTURAL COLLEGE | Boston | — | $20.5M | 10 |
