| NEW ENGLAND LABORERS TRAINING TRUST FUND | Hopkinton | J120 Employment | $27.1M | 8 |
| LIFEPATH INC | Greenfield | P44Z Human Services | $27M | 4 |
| Collaborative for Regional Educational Services and Training | Andover | B28 Education | $27M | 8 |
| AGING SERVICES OF NORTH CENTRAL MASSACHUSETTS INC | Leominster | P810 Human Services | $26.9M | 4 |
| THE AMERICAN UNIVERSITY OF GREECE FOUNDATION | Boston | T11 Philanthropy, Voluntarism & Grantmaking Foundations | $26.9M | 7 |
| TUFTS MEDICAL CENTER PHYSICIANS ORGANIZATION INC | Boston | E31 Health Care | $26.8M | 19 |
| REACH OUT AND READ INC | Boston | B920 Education | $26.8M | 8 |
| LATHAM CENTERS INC | Yarmouth | — | $26.8M | 7 |
| South Boston Community Health Center In | South Boston | E300 Health Care | $26.7M | 9 |
| HOLYOKE-CHICOPEE-SPRINGFIELD HEAD START INC | Springfield | — | $26.7M | 5 |
| JEWISH NURSING HOME OF WESTERN MASSACHUSETTS INC | Longmeadow | P31Z Human Services | $26.7M | 9 |
| CENTRAL CATHOLIC HIGH SCHOOL OF LAWRENCE INC | Lawrence | — | $26.7M | 6 |
| THE REEDER FOUNDATION C/O PAR CAPITAL MANAGEMENT | Boston | T20 Philanthropy, Voluntarism & Grantmaking Foundations | $26.7M | 0 |
| Eastern nazarene college | Quincy | B430 Education | $26.6M | 4 |
| SALEM COMMUNITY CORPORATION | Worcester | P750 Human Services | $26.6M | 5 |
| DEUTSCHES ALTENHEIM INC | West Roxbury | P73 Human Services | $26.4M | 10 |
| Addgene Inc | Watertown | H30 Medical Research | $26.4M | 11 |
| LASELL VILLAGE INC | Auburndale | L22Z Housing & Shelter | $26.3M | 11 |
| NATIONAL ASSOCIATION OF GOVERNMENT EMPLOYEES | Quincy | — | $26.3M | 52 |
| CATHOLIC MEMORIAL HOME INC | Fall River | E91Z Health Care | $26.3M | 5 |
| SLOUGH FARM FOUNDATION | Edgartown | K19 Food, Agriculture & Nutrition | $26.2M | 1 |
| VETERANS INC | Worcester | S20Z Community Improvement & Capacity Building | $26.2M | 5 |
| WALNUT HILL CENTER FOR THE ARTS INC | Natick | B200 Education | $26.1M | 5 |
| NEW ENGLAND INTERSTATE WATER POLLUTION CONTROL COMMISSION | Lowell | C012 Environment | $26.1M | 7 |
| THE KRUPP FOUNDATION | Boston | T30J Philanthropy, Voluntarism & Grantmaking Foundations | $26M | 0 |
| STATE STREET FOUNDATION INC | Boston | T20 Philanthropy, Voluntarism & Grantmaking Foundations | $26M | 0 |
| AUSTEN RIGGS CENTER INC | Stockbridge | F300 Mental Health & Crisis Intervention | $26M | 16 |
| THE SALEM FOUNDATION | Boston | T21 Philanthropy, Voluntarism & Grantmaking Foundations | $26M | 0 |
| FAMILY SERVICE ASSOCIATION OF GREATER FALL RIVER INC | Fall River | — | $25.9M | 5 |
| AMERICAN REPERTORY THEATRE CO INC | Cambridge | A650 Arts, Culture & Humanities | $25.9M | 13 |
| THE DIMITRIS BERTSIMAS - GEORGIA PERAKIS FOUNDATION | Belmont | A54 Arts, Culture & Humanities | $25.7M | 0 |
| HOSPICE OF THE GOOD SHEPHERD INC | Newton | P74Z Human Services | $25.6M | 8 |
| CLARENDON EARLY EDUCATION SERVICES INC | Lawrence | P33Z Human Services | $25.6M | 3 |
| JEWISH REHABILITATION CENTER FOR THE AGED OF THE NORTH SHORE INC | Peabody | E91Z Health Care | $25.6M | 9 |
| COMMUNITY RESEARCH INITIATIVE OF NEW ENGLAND INC | Boston | G81Z Diseases, Disorders & Medical Disciplines | $25.5M | 5 |
| BEAVERBROOK STEP INC | Watertown | P820 Human Services | $25.3M | 7 |
| FISHER COLLEGE | Boston | B420 Education | $25.3M | 12 |
| RANDI & JOEL CUTLER FAMILY FOUNDATION | Boston | T20 Philanthropy, Voluntarism & Grantmaking Foundations | $25.1M | 0 |
| RESIST INC | Jamaica Plain | — | $24.9M | 10 |
| HARVARD FEDERAL CREDIT UNION | Cambridge | — | $24.9M | 9 |
| THE POSSIBLE PROJECT INC | Boston | B80 Education | $24.8M | 19 |
| MEADOWBROOK SCHOOL OF WESTON INCORPORATED | Weston | B200 Education | $24.7M | 10 |
| ESSEX COUNTY COMMUNITY FOUNDATION INC | Beverly | T31 Philanthropy, Voluntarism & Grantmaking Foundations | $24.7M | 5 |
| Boston Children's Network Specialty Physicians Inc | Boston | E03 Health Care | $24.6M | 18 |
| HOBART AMES FOUNDATION | Boston | Z99Z Unknown | $24.6M | 4 |
| SEVEN HILLS FOUNDATION | Worcester | P82Z Human Services | $24.6M | 12 |
| JOSLIN CLINIC INC | Charlestown | E300 Health Care | $24.5M | 13 |
| LAB CENTRAL INC | Cambridge | U02 Science & Technology | $24.5M | 10 |
| Community Action Inc | Haverhill | S21Z Community Improvement & Capacity Building | $24.4M | 1 |
| EAGLE HILL FOUNDATION OF MASSACHUSETTSINC | Hardwick | — | $24.3M | 8 |
