| SCHOOL FOR FIELD STUDIES INC | Pittsfield | — | $14.1M | 3 |
| CUTCHINS PROGRAMS FOR CHILDREN & FAMILIES INC | Northampton | F33Z Mental Health & Crisis Intervention | $14.1M | 4 |
| ADOPT A STUDENT FOUNDATION C/O CATHEDRAL HIGH SCHOOL | Boston | B82Z Education | $14.1M | 0 |
| ST BONIFACE HAITI FOUNDATION INC | Newton | P200 Human Services | $14.1M | 6 |
| WOODLAND GOLF CLUB OF AUBURNDALE | Auburndale | — | $14.1M | 6 |
| ASCENTRIA CARE ALLIANCE INC | Worcester | P20Z Human Services | $14.1M | 14 |
| MONTSERRAT COLLEGE OF ART INC | Beverly | B40Z Education | $14M | 3 |
| SOUTH SHORE HEALTH EXPRESS INC | South Weymouth | H19 Medical Research | $14M | 11 |
| LEXINGTON CHRISTIAN ACADEMY | Lexington | B25Z Education | $14M | 3 |
| SHORE COUNTRY DAY SCHOOL | Beverly | — | $14M | 8 |
| PUBLISHERS INTERNATIONAL LINKING ASSOCIATION INC | Lynnfield | B70 Education | $13.9M | 8 |
| ICIVICS INC | Cambridge | B90 Education | $13.9M | 8 |
| CATHOLIC CHARITIES OF THE DIOCESE OF FALL RIVER MASSACHUSETTS INC | Fall River | — | $13.9M | 4 |
| NORTH ATLANTIC STATES CARPENTERS LABOR MANAGEMENT PROGRAM | Boston | — | $13.9M | 2 |
| CENTER OF HOPE FOUNDATION INC | Southbridge | P820 Human Services | $13.9M | 4 |
| MONTROSE FOUNDATION INC | Medfield | B24Z Education | $13.9M | 6 |
| Edgar P Benjamin Healthcare Center Inc | Roxbury Crossing | E91Z Health Care | $13.8M | 6 |
| GAAMHA INC | Gardner | — | $13.8M | 3 |
| DISABILITY RIGHTS FUND INC | Boston | Q30 International, Foreign Affairs & National Security | $13.7M | 5 |
| BAYSTATE HEALTH FOUNDATION INC | Springfield | E11 Health Care | $13.7M | 11 |
| GREATER WORCESTER COMMUNITY FOUNDATION INC | Worcester | T310 Philanthropy, Voluntarism & Grantmaking Foundations | $13.7M | 4 |
| LOOMIS SENIOR LIVING INC | Springfield | S50 Community Improvement & Capacity Building | $13.7M | 8 |
| THE CHESTNUT HILL SCHOOL | Chestnut Hill | B21Z Education | $13.7M | 8 |
| AUTOMOBILE INSURERS BUREAU OF MASSACHUSETTS | Boston | — | $13.7M | 13 |
| NEW ENGLAND FUTBOL CLUB INC | Mendon | N64 Recreation & Sports | $13.7M | 5 |
| ROOFERS-UNION LOCAL NO 33 INSURANCE FUND | Stoughton | — | $13.7M | 1 |
| SATTLER COLLEGE | Boston | B42 Education | $13.7M | 5 |
| BROOKWOOD SCHOOL INCORPORATED | Manchester | B240 Education | $13.7M | 8 |
| SHIPLEY FOUNDATION INC #0755496 | Boston | T22 Philanthropy, Voluntarism & Grantmaking Foundations | $13.7M | 0 |
| MASSACHUSETTS HEALTH & HOSPITAL ASSOC INC | Burlington | — | $13.6M | 9 |
| IMPACTISRAEL INC | Needham | Q11 International, Foreign Affairs & National Security | $13.5M | 4 |
| THE BELL FOUNDATION INC | Needham | — | $13.5M | 7 |
| Pittsfield Management Systems Inc | Pittsfield | L22 Housing & Shelter | $13.5M | 2 |
| BASS RIVER DAY ACTIVITY PROGRAM INC | Beverly | — | $13.5M | 1 |
| ENERGY FEDERATION INC | Franklin | — | $13.5M | 16 |
| LIH MEMORIAL GRANT FUND | Brookline Village | B82 Education | $13.4M | 0 |
| THE NASHAWTUC COUNTRY CLUB INC | Concord | — | $13.4M | 7 |
| HERITAGE MUSEUMS AND GARDENS INC | Sandwich | A540 Arts, Culture & Humanities | $13.4M | 4 |
| OVERLOOK VISITING NURSE ASSOCIATION INC | Charlton | E92 Health Care | $13.4M | 10 |
| COMMONWEALTH CANCER CONSORTIUM INC | Cambridge | — | $13.4M | 12 |
| ALS THERAPY DEVELOPMENT FOUNDATION INC | Watertown | H80 Medical Research | $13.4M | 6 |
| MASTER TRUST AGREEMENT FOR WELFARE BENEFITS | Somerville | Y43 Mutual & Membership Benefit | $13.3M | 1 |
| VINCENT MEMORIAL HOSPITAL FOUNDATION INC C/O WILLIAM R BAKER JR | Boston | E110 Health Care | $13.3M | 0 |
| Hebrew Seniorlife Hospice Care Inc | Boston | P74 Human Services | $13.3M | 20 |
| SOUTH SHORE STARS INC | Weymouth | P33Z Human Services | $13.3M | 6 |
| BOSTON TEACHER UNION HLTH & WELFARE FND | Boston | — | $13.3M | 2 |
| 2LIFE PARTNERS INC | Brighton | S20 Community Improvement & Capacity Building | $13.3M | 5 |
| ADULT & TEEN CHALLENGE NEW ENGLAND AND NEW JERSEY INC | Brockton | F330 Mental Health & Crisis Intervention | $13.3M | 2 |
| NAISMITH MEMORIAL BASKETBALL HALL OF FAME | Springfield | A500 Arts, Culture & Humanities | $13.3M | 8 |
| THE KRAFT FAMILY FOUNDATION INC | Foxborough | T20 Philanthropy, Voluntarism & Grantmaking Foundations | $13.2M | 0 |
