| Children's Hospital Ophthalmology | Boston | E30 Health Care | $42.7M | 23 |
| HORACE MANN EDUCATIONAL ASSOCIATES INC | Franklin | P820 Human Services | $42.7M | 7 |
| THE RIVERS SCHOOL CORPORATION | Weston | — | $42.6M | 9 |
| MIDDLESEX SCHOOL | Concord | B250 Education | $42.4M | 11 |
| THE BEAVER COUNTRY DAY SCHOOL INC | Chestnut Hill | B250 Education | $42.3M | 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 |
| STANLEY STREET TREATMENT AND RESOURCES | Fall River | — | $41.5M | 11 |
| CARDINAL CUSHING CENTERS INC | Hanover | — | $41.4M | 7 |
| PATHLIGHT INC | Springfield | — | $41.3M | 8 |
| CARLETON-WILLARD HOMES INC | Bedford | P750 Human Services | $41.2M | 9 |
| LANDMARK SCHOOL INC | Prides Crossing | B280 Education | $41M | 7 |
| FATHER BILL'S & MAINSPRING INC | Brockton | L41 Housing & Shelter | $41M | 7 |
| CERES INC | Boston | C010 Environment | $40.9M | 11 |
| THE FESSENDEN SCHOOL | West Newton | B200 Education | $40.7M | 8 |
| Children's Sports Medicine | Boston | — | $40.6M | 10 |
| VIABILITY INC | Springfield | J30Z Employment | $40.5M | 6 |
| CHARLES RIVER ASSOCIATION FOR RETARDED | Needham | — | $40.3M | 4 |
| ST MARK'S SCHOOL OF SOUTHBOROUGH INC | Southborough | B250 Education | $40.3M | 6 |
| South Shore Young Men's Christian Association | Quincy | P27Z Human Services | $40.2M | 9 |
| PEABODY ESSEX MUSEUM INC | Salem | A500 Arts, Culture & Humanities | $40.1M | 9 |
| ST ANN'S HOME INC | Methuen | — | $40M | 7 |
| CHILDREN'S SERVICES OF ROXBURY INC | Roxbury | P30Z Human Services | $40M | 3 |
| GRANTHAM FOUNDATION FOR THE PROTECTION | Boston | T50Z Philanthropy, Voluntarism & Grantmaking Foundations | $40M | 0 |
| WORCESTER ART MUSEUM | Worcester | A510 Arts, Culture & Humanities | $39.9M | 3 |
| ELDER SERVICES OF WORCESTER AREA | Worcester | E920 Health Care | $39.8M | 3 |
| THE WINSOR SCHOOL | Boston | B200 Education | $39.8M | 8 |
| ASCENTRIA COMMUNITY SERVICES INC | Worcester | P20 Human Services | $39.7M | 11 |
| THE MOSAKOWSKI FAMILY CHARITABLE FOUNDATION | Swampscott | T20 Philanthropy, Voluntarism & Grantmaking Foundations | $39.6M | 1 |
| DOUGLAS A THOM CLINIC INC | Framingham | F320 Mental Health & Crisis Intervention | $39.6M | 7 |
| Social Finance Inc | Boston | P12 Human Services | $39.2M | 13 |
| SYMMES LIFE CARE INC | Lexington | P750 Human Services | $39.2M | 8 |
| Morgan Memorial Goodwill Industries | Boston | J320 Employment | $39.1M | 8 |
| NEIGHBORHOOD ASSISTANCE CORPORATION OF | Boston | — | $38.9M | 7 |
| TEAMSTERS LOCAL 170 HEALTH AND | Worcester | — | $38.7M | 1 |
| Upstream USA Inc | Boston | E21 Health Care | $38.7M | 10 |
| CHILD AND FAMILY SERVICES INC | New Bedford | — | $38.7M | 7 |
| PAINTERS DISTRICT COUNCIL NO 35 | Roslindale | — | $38.6M | 8 |
| PLUMBERS UNION LOCAL 12 WELFARE PLAN | Boston | — | $38.6M | 1 |
| NFI MASSACHUSETTS INC | Danvers | P202 Human Services | $38.3M | 7 |
| MULTICULTURAL COMMUNITY SERVICES OF THE PIONEER VALLEY INC | Springfield | P73Z Human Services | $38.3M | 1 |
| BLUEHUB LOAN FUND INC | Boston | — | $38M | 8 |
| LIFESTREAM INC | New Bedford | E50 Health Care | $37.8M | 5 |
| TRUSTEES OF LAWRENCE ACADEMY | Groton | B250 Education | $37.8M | 9 |
| ALZHEIMER'S DISEASE RESEARCH FOUNDATION | Wellesley Hills | H83 Medical Research | $37.7M | 11 |
| DR MIRIAM & SHELDON G ADELSON | Needham | T990 Philanthropy, Voluntarism & Grantmaking Foundations | $37.6M | 0 |
| FREEDOM CREDIT UNION | Springfield | — | $37.6M | 17 |
| COOPERATIVE FOR HUMAN SERVICES INC | Lexington | P82Z Human Services | $37.5M | 7 |
| EASTERN STATES EXPOSITION | West Springfield | N520 Recreation & Sports | $37.5M | 7 |
| SOMERVILLE-CAMBRIDGE ELDER | Somerville | — | $37.4M | 5 |
