| COMMONWEALTH ZOOLOGICAL CORPORATION D/B/A ZOO NEW ENGLAND | Boston | D500 Animal-Related | $29.1M | 12 |
| ROOT CAPITAL INC | Cambridge | Q123 International, Foreign Affairs & National Security | $29.1M | 11 |
| Gordon-Conwell Theological Seminary Inc | South Hamilton | B500 Education | $28.8M | 7 |
| PLANNED PARENTHOOD LEAGUE OF MASSACHUSETTS INC | Boston | E420 Health Care | $28.7M | 11 |
| HOCKOMOCK YOUNG MEN'S CHRISTIAN ASSOCIATION INC | North Attleboro | P27Z Human Services | $28.6M | 9 |
| NEW BALANCE FOUNDATION | Boston | — | $28.5M | 0 |
| Massachusetts and Northern New England Laborers District Council | Hopkinton | — | $28.5M | 13 |
| LATHAM CENTERS INC | Yarmouth | — | $28.4M | 7 |
| THE ACHIEVEMENT NETWORK LTD | Boston | B90 Education | $28.3M | 13 |
| BELLWETHER EDUCATION PARTNERS INC | Boston | B60 Education | $28.3M | 11 |
| JEWISH HEALTHCARE CENTER INC | Worcester | E910 Health Care | $28.3M | 5 |
| TURNING POINT INC AND AFFILIATES | Newburyport | L410 Housing & Shelter | $28.2M | 9 |
| WALKER INC | Needham | B28Z Education | $28.1M | 8 |
| VISITING NURSE ASSOCIATION & HOSPICE OF WESTERN NEW ENGLAND INC | West Springfield | — | $28.1M | 16 |
| UHealthSolutions INC | Shrewsbury | E60 Health Care | $28.1M | 10 |
| JEWISH VOCATIONAL SERVICE INC | Boston | J210 Employment | $28.1M | 7 |
| Luk Crisis Center Inc | Fitchburg | — | $28M | 8 |
| LIGHTHOUSE SCHOOL INC | North Chelmsford | B28Z Education | $27.9M | 8 |
| ALIGN CREDIT UNION | Lowell | — | $27.9M | 11 |
| Orchard Cove Inc | Canton | P75 Human Services | $27.9M | 20 |
| MANET COMMUNITY HEALTH CENTER INC | North Quincy | E32Z Health Care | $27.9M | 8 |
| SHERRILL HOUSE INC | Boston | E910 Health Care | $27.7M | 9 |
| THE PINGREE SCHOOL INC | South Hamilton | B250 Education | $27.5M | 7 |
| Children's Urological Foundation Inc | Boston | E240 Health Care | $27.5M | 17 |
| River Valley Counseling Center Inc | Holyoke | F32 Mental Health & Crisis Intervention | $27.5M | 10 |
| KRUPP FAMILY FOUNDATION | Boston | T202 Philanthropy, Voluntarism & Grantmaking Foundations | $27.5M | 0 |
| HUNTINGTON THEATRE CO INC | Boston | A650 Arts, Culture & Humanities | $27.5M | 7 |
| THE AMERICAN IRELAND FUND (DBA THE IRELAND FUNDS AMERICA/THE IRELAND FUNDS) | Boston | — | $27.3M | 7 |
| BAYSTATE HEALTH INC | Springfield | E210 Health Care | $27.3M | 8 |
| Hillcrest Extended Care Services Inc Formerly Berkshire Missouri Inc | Pittsfield | E91Z Health Care | $27.3M | 6 |
| NORTH END COMMUNITY HEALTH COMMITTEE | Boston | E300 Health Care | $27.2M | 10 |
| LIFEPATH INC | Greenfield | P44Z Human Services | $27M | 4 |
| NORTH SHORE COMMUNITY HEALTH INC | Salem | E320 Health Care | $26.9M | 12 |
| TUFTS MEDICAL CENTER PHYSICIANS ORGANIZATION INC | Boston | E31 Health Care | $26.8M | 19 |
| REACH OUT AND READ INC | Boston | B920 Education | $26.8M | 8 |
| JUDGE BAKER CHILDREN'S CENTER | Boston | P300 Human Services | $26.7M | 8 |
| South Boston Community Health Center In | South Boston | E300 Health Care | $26.7M | 9 |
| CHELSEA JEWISH GREEN HOUSE INC | Chelsea | E92 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 |
| WILBRAHAM AND MONSON ACADEMY | Wilbraham | — | $26.7M | 9 |
| DEUTSCHES ALTENHEIM INC | West Roxbury | P73 Human Services | $26.4M | 10 |
| VINFEN CORPORATION OF CONNECTICUT INC | Cambridge | P700 Human Services | $26.4M | 6 |
| ADDGENE INC | Watertown | H30 Medical Research | $26.3M | 11 |
| NATIONAL ASSOCIATION OF GOVERNMENT EMPLOYEES | Quincy | — | $26.3M | 52 |
| SLOUGH FARM FOUNDATION | Edgartown | K19 Food, Agriculture & Nutrition | $26.2M | 1 |
| FACING HISTORY AND OURSELVES INC | Boston | A70Z Arts, Culture & Humanities | $26.2M | 12 |
| CENTERBOARD INC | Lynn | — | $26.2M | 2 |
| THE KRUPP FOUNDATION | Boston | T30J Philanthropy, Voluntarism & Grantmaking Foundations | $26M | 0 |
| AUSTEN RIGGS CENTER INC | Stockbridge | F300 Mental Health & Crisis Intervention | $26M | 16 |
