| HOMES FOR OUR TROOPS INC | Taunton | L99 Housing & Shelter | $44.6M | 7 |
| HORACE MANN EDUCATIONAL ASSOCIATES INC | Franklin | P820 Human Services | $44.3M | 8 |
| CITIZENS FOR CITIZENS INC | Fall River | S200 Community Improvement & Capacity Building | $44M | 5 |
| MINUTEMAN SENIOR SERVICES INC | Burlington | P81Z Human Services | $43.9M | 2 |
| SOUTH SHORE ELDER SERVICES INC | Braintree | K36Z Food, Agriculture & Nutrition | $43.9M | 5 |
| FLOCK INC | Boston | T22 Philanthropy, Voluntarism & Grantmaking Foundations | $43.9M | 0 |
| Norwell Visiting Nurse Association Inc | Norwell | — | $43.8M | 7 |
| NATIONAL ELEVATOR INDUSTRY EDUCATIONAL PROGRAM | Attleboro Falls | — | $43.8M | 8 |
| WORCESTER COMMUNITY ACTION COUNCIL INC | Worcester | P20Z Human Services | $43.4M | 3 |
| UHealthSolutions INC | Shrewsbury | E60 Health Care | $43.4M | 11 |
| South Shore Mental Health Center Inc | Braintree | F33 Mental Health & Crisis Intervention | $43.2M | 8 |
| TUFTS MEDICINE CARE AT HOME INC | Lawrence | P74Z Human Services | $43M | 14 |
| Heading Home Inc | Boston | L40Z Housing & Shelter | $42.8M | 7 |
| Children's Hospital Ophthalmology Foundation Inc | Boston | E30 Health Care | $42.7M | 23 |
| THE NORTH EAST EDUCATIONAL AND DEVELOPMENTAL SUPPORTS CENTER INC | Andover | P80 Human Services | $42.6M | 7 |
| THE BEAVER COUNTRY DAY SCHOOL INC | Chestnut Hill | B250 Education | $42.3M | 9 |
| ASCENTRIA COMMUNITY SERVICES INC | Worcester | P20 Human Services | $42.1M | 11 |
| ST ANN'S HOME INC | Methuen | — | $42M | 9 |
| JORDAN PHYSICIAN ASSOCIATES INC | Charlestown | E31 Health Care | $42M | 19 |
| THE UNION OF CONCERNED SCIENTISTS INC | Cambridge | Q055 International, Foreign Affairs & National Security | $41.9M | 14 |
| ST PATRICK'S MANOR INC | Framingham | E910 Health Care | $41.9M | 6 |
| THE FESSENDEN SCHOOL | West Newton | B200 Education | $41.8M | 8 |
| THE RIVERS SCHOOL CORPORATION | Weston | — | $41.6M | 11 |
| CONSERVATION LAW FOUNDATION INC | Boston | C013 Environment | $41.6M | 7 |
| STANLEY STREET TREATMENT AND RESOURCES INC | Fall River | — | $41.5M | 11 |
| Morgan Memorial Goodwill Industries Inc | Boston | J320 Employment | $41.5M | 8 |
| FATHER BILL'S & MAINSPRING INC | Brockton | L41 Housing & Shelter | $41.4M | 7 |
| CARDINAL CUSHING CENTERS INC | Hanover | — | $41.4M | 7 |
| CARLETON-WILLARD HOMES INC | Bedford | P750 Human Services | $41.2M | 9 |
| THE WINSOR SCHOOL | Boston | B200 Education | $41.2M | 9 |
| DIMOCK COMMUNITY FOUNDATION INC | Roxbury | T11 Philanthropy, Voluntarism & Grantmaking Foundations | $41.1M | 9 |
| LANDMARK SCHOOL INC | Prides Crossing | B280 Education | $41M | 7 |
| NELLIE MAE EDUCATION FOUNDATION INC | Quincy | B120 Education | $40.9M | 24 |
| CERES INC | Boston | C010 Environment | $40.9M | 11 |
| FIDELITY HOUSE INC | Lawrence | P730 Human Services | $40.9M | 8 |
| Children's Sports Medicine Foundation Inc | Boston | — | $40.6M | 10 |
| VIABILITY INC | Springfield | J30Z Employment | $40.5M | 6 |
| SOMERVILLE-CAMBRIDGE ELDER SERVICES INCORPORATED | Somerville | — | $40.3M | 7 |
| South Shore Young Men's Christian Association | Quincy | P27Z Human Services | $40.2M | 9 |
| WORCESTER ART MUSEUM | Worcester | A510 Arts, Culture & Humanities | $39.9M | 3 |
| THE MOSAKOWSKI FAMILY CHARITABLE FOUNDATION | Swampscott | T20 Philanthropy, Voluntarism & Grantmaking Foundations | $39.6M | 1 |
| THE TRUSTEES OF ANATOLIA COLLEGE | Boston | B420 Education | $39.5M | 7 |
| Social Finance Inc | Boston | P12 Human Services | $39.2M | 13 |
| LIBERTY BAY CREDIT UNION | Braintree | W61Z Public & Societal Benefit | $39.2M | 18 |
| SYMMES LIFE CARE INC D/B/A BROOKHAVEN AT LEXINGTON | Lexington | P750 Human Services | $39.2M | 8 |
| Outer Cape Health Services Inc | Harwich Port | E39Z Health Care | $39M | 10 |
| FRANKLIN W OLIN COLLEGE OF ENGINEERING INC | Needham | B420 Education | $39M | 17 |
| COOPERATIVE FOR HUMAN SERVICES INC | Lexington | P82Z Human Services | $38.9M | 8 |
| NEIGHBORHOOD ASSISTANCE CORPORATION OF AMERICA | Boston | — | $38.9M | 7 |
| NEW HOPE COMMUNITY CAPITAL INC | Boston | L21 Housing & Shelter | $38.9M | 0 |
