| JUMPSTART FOR YOUNG CHILDREN INC | Boston | B21 Education | $20.4M | 10 |
| LEAGUE SCHOOL FOR AUTISM INC | Walpole | B28Z Education | $20.3M | 8 |
| HARVARD STREET NEIGHBORHOOD HEALTH | Dorchester | E32Z Health Care | $20.3M | 6 |
| THE MURRAY BURNSTINE CHARITABLE TRUST | Stoneham | A20 Arts, Culture & Humanities | $20.3M | 2 |
| POINT32HEALTH FOUNDATION INC | Canton | E12 Health Care | $20.2M | 19 |
| CAMPUS CHILD CARE INC | Cambridge | P33Z Human Services | $20.2M | 6 |
| SCHOOLS FOR CHILDREN INC | Winchester | B28Z Education | $20.2M | 5 |
| RANDI & JOEL CUTLER FAMILY FOUNDATION | Boston | T20 Philanthropy, Voluntarism & Grantmaking Foundations | $20.2M | 0 |
| LOOMIS COMMUNITIES INC | South Hadley | P750 Human Services | $20.2M | 7 |
| TEAMSTERS HEALTH SERVICES & INSURANCE | Springfield | — | $20.2M | 4 |
| EF EDUCATIONAL FOUNDATION FOR | Cambridge | Q230 International, Foreign Affairs & National Security | $20.2M | 13 |
| COTTING SCHOOL INC | Lexington | B200 Education | $20.1M | 8 |
| THE BOSTON HOME INC | Boston | E910 Health Care | $20M | 8 |
| SAINT VINCENT'S SERVICES INC | Fall River | P730 Human Services | $20M | 3 |
| EMPOWER LGA INC | Canton | B22Z Education | $20M | 6 |
| ROXBURY TENANTS OF HARVARD | Boston | P200 Human Services | $19.9M | 16 |
| HomeStart Inc | Boston | S31 Community Improvement & Capacity Building | $19.9M | 6 |
| VNA CARE MANAGEMENT RESOURCES INC | Worcester | E92Z Health Care | $19.9M | 10 |
| The Irene E and George A Davis Foundation | Springfield | T22 Philanthropy, Voluntarism & Grantmaking Foundations | $19.9M | 0 |
| BELMONT DAY SCHOOL INC | Belmont | B21Z Education | $19.9M | 9 |
| LIFE-SKILLS INC | Sturbridge | E50Z Health Care | $19.8M | 6 |
| CLERMONT FOUNDATION | Boston | T21J Philanthropy, Voluntarism & Grantmaking Foundations | $19.8M | 1 |
| BETH ISRAEL LAHEY HEALTH PRIMARY CARE | Charlestown | — | $19.7M | 20 |
| CHRISTOPHER HOUSE INC | Worcester | — | $19.7M | 6 |
| FAIR HAVENS INC | West Brookfield | — | $19.6M | 13 |
| THE KINGSLEY MONTESSORI SCHOOL INC | Boston | — | $19.6M | 6 |
| COMMUNITY PROVIDERS OF ADOLESCENT | Dorchester | P300 Human Services | $19.6M | 7 |
| VOLUNTEERS OF AMERICA OF | Jamaica Plain | — | $19.6M | 8 |
| 350ORG | Boston | C05 Environment | $19.5M | 7 |
| St Jeans Credit Union | Salem | — | $19.4M | 8 |
| ENTREPRENEURIAL VENTURES IN EDUCATION | Quincy | B90 Education | $19.4M | 13 |
| ALL HANDS ON DECK NETWORK INC | Northampton | — | $19.4M | 6 |
| ALLIANCE HEALTH OF BROCKTON INC | Southborough | E910 Health Care | $19.4M | 15 |
| VIETNAM VETERANS WORKSHOP INC DBA | Boston | L410 Housing & Shelter | $19.4M | 7 |
| ALLIANCE HEALTH OF WRENTHAM INC | Southborough | T20 Philanthropy, Voluntarism & Grantmaking Foundations | $19.4M | 14 |
| CAMBRIDGE COLLEGE INC | Boston | B420 Education | $19.4M | 12 |
| HORIZONS FOR HOMELESS CHILDREN | Roxbury | P330 Human Services | $19.4M | 5 |
| RX FOUNDATION | Hadley | T21 Philanthropy, Voluntarism & Grantmaking Foundations | $19.3M | 1 |
| BETHANY HEALTH CARE CENTER INC | Framingham | — | $19.3M | 7 |
| THE FENN SCHOOL | Concord | — | $19.3M | 7 |
| BERKSHIRE COMMUNITY ACTION COUNCIL INC | Pittsfield | — | $19.3M | 1 |
| ISABELLA STEWART GARDNER MUSEUM INC | Boston | A510 Arts, Culture & Humanities | $19.3M | 7 |
| PERFECT SEAS FOUNDATION INC | Boston | P20 Human Services | $19.2M | 0 |
| MI Nursing Restorative Center Inc | Lawrence | E910 Health Care | $19.2M | 6 |
| NEW ENGLAND FOUNDATION FOR THE ARTS | Boston | A120 Arts, Culture & Humanities | $19.2M | 9 |
| NEW ENGLAND INTERSTATE WATER | Lowell | C012 Environment | $19.2M | 7 |
| Care Central VNA & Hospice Inc | Gardner | E92 Health Care | $19.1M | 7 |
| VISITING NURSE ASSOCIATION OF | Worcester | E920 Health Care | $19.1M | 10 |
| TUFTS VETERINARY EMERGENCY TREATMENT | North Grafton | E20Z Health Care | $19M | 11 |
| VICTORY HUMAN SERVICES INC | Brockton | F33 Mental Health & Crisis Intervention | $19M | 8 |
