| PLANET AID INC | Milford | Q330 International, Foreign Affairs & National Security | $37.3M | 8 |
| HOUSING ASSISTANCE CORPORATION | Hyannis | L20Z Housing & Shelter | $37.1M | 4 |
| ST PATRICK'S MANOR INC | Framingham | E910 Health Care | $37M | 6 |
| COMMUNITY FOUNDATION OF WESTERN | Springfield | T310 Philanthropy, Voluntarism & Grantmaking Foundations | $37M | 5 |
| MINUTEMAN SENIOR SERVICES INC | Burlington | P81Z Human Services | $36.9M | 2 |
| FIDELITY HOUSE INC | Lawrence | P730 Human Services | $36.8M | 8 |
| WORCESTER ACADEMY | Worcester | B200 Education | $36.7M | 5 |
| NATIONAL ELEVATOR INDUSTRY EDUCATIONAL | Attleboro Falls | — | $36.7M | 8 |
| INCOMPASS HUMAN SERVICES INC | Chelmsford | P820 Human Services | $36.6M | 7 |
| THE BOTTOM LINE INC | Jamaica Plain | S99 Community Improvement & Capacity Building | $36.5M | 7 |
| SHADY HILL SCHOOL | Cambridge | B240 Education | $36.3M | 9 |
| DELTA PROJECTS INC | Dedham | P800 Human Services | $36.3M | 8 |
| BOSTON HIGASHI SCHOOL INC | Randolph | B280 Education | $36.2M | 2 |
| THE LONGWOOD COLLECTIVE INC | Boston | E030 Health Care | $36M | 7 |
| THE EDINBURG CENTER INC | Bedford | P20 Human Services | $36M | 8 |
| THE CARROLL SCHOOL | Lincoln | B28Z Education | $35.7M | 9 |
| THE TRUSTEES OF THE CUSHING ACADEMY | Ashburnham | B250 Education | $35.4M | 8 |
| NOTRE DAME HEALTH CARE CENTER INC | Worcester | P700 Human Services | $35.4M | 8 |
| AMERICAN TRAINING INC | Andover | — | $35.3M | 5 |
| CUMMINGS FOUNDATION GRANTS INC (FKA ONEWORLD BOSTON INC) | Woburn | T21 Philanthropy, Voluntarism & Grantmaking Foundations | $35.2M | 0 |
| BRIMMER AND MAY SCHOOL | Chestnut Hill | B200 Education | $35.1M | 6 |
| WHITTIER STREET HEALTH CENTER | Roxbury | E320 Health Care | $34.9M | 8 |
| THE TJX FOUNDATION INC | Framingham | — | $34.9M | 0 |
| IRON WORKERS DISTRICT COUNCIL OF | Dorchester | — | $34.8M | 1 |
| TEAMSTERS LOCAL 653 WELFARE FUND | South Easton | — | $34.7M | 0 |
| MASSACHUSETTS BRICKLAYERS & MASONS | Boston | — | $34.7M | 1 |
| THE FAY SCHOOL INC | Southborough | B200 Education | $34.2M | 7 |
| ALLEN-CHASE FOUNDATION | Deerfield | B250 Education | $34.2M | 7 |
| TUFTS SHARED SERVICES INC | Boston | E220 Health Care | $34.2M | 15 |
| PARK SCHOOL CORPORATION | Brookline | B200 Education | $34.1M | 7 |
| THE ARC OF BRISTOL COUNTY INC | Attleboro | — | $33.9M | 4 |
| THE TRUSTEES OF ANATOLIA COLLEGE | Boston | B420 Education | $33.9M | 7 |
| JEWISH COMMUNITY CENTERS OF | Newton | P280 Human Services | $33.9M | 5 |
| DIMOCK COMMUNITY FOUNDATION INC | Roxbury | T11 Philanthropy, Voluntarism & Grantmaking Foundations | $33.9M | 12 |
| THE GIVING BACK FUND INC | Boston | T700 Philanthropy, Voluntarism & Grantmaking Foundations | $33.8M | 4 |
| 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 | Worcester | — | $33.6M | 1 |
| NEW PROFIT INC | Boston | S50 Community Improvement & Capacity Building | $33.6M | 12 |
| GREATER NEW BEDFORD COMMUNITY HEALTH | New Bedford | — | $33.6M | 10 |
| INTERNATIONAL INSTITUTE OF NEW ENGLAND | Boston | R20Z Civil Rights, Social Action & Advocacy | $33.5M | 9 |
| SOUTH SHORE COMMUNITY ACTION COUNCIL | Plymouth | S20Z Community Improvement & Capacity Building | $33.3M | 6 |
| THE NORTH EAST EDUCATIONAL AND | Andover | P80 Human Services | $33.3M | 7 |
| LIBERTY BAY CREDIT UNION | Braintree | W61Z Public & Societal Benefit | $33.3M | 18 |
| TRI-VALLEY INC | Dudley | E920 Health Care | $33.3M | 2 |
| GREATER BOSTON LEGAL SERVICES INC | Boston | — | $33.2M | 7 |
| TRUST AGREEMENT FOR GPU COMPANIES HEALTH | Heritage Dr N Qu | — | $33.1M | 0 |
| CHMC Cardiovascular Surgical | Boston | — | $33.1M | 8 |
| FRANKLIN W OLIN COLLEGE OF ENGINEERING INC | Needham | B420 Education | $33M | 14 |
| THE FOOD BANK OF WESTERN | Chicopee | — | $33M | 6 |
