| SPOONFULS | Newton | K193 Food, Agriculture & Nutrition | $14.9M | 5 |
| EDUCATION RESOURCE STRATEGIES INC | Watertown | B90 Education | $14.7M | 11 |
| GLENMEADOW INC | Longmeadow | L22 Housing & Shelter | $14.7M | 4 |
| ELIZABETH SETON RESIDENCE INC | Wellesley Hills | — | $14.7M | 6 |
| MASSHIRE HAMPDEN COUNTY WORKFORCE BOARD | Springfield | — | $14.6M | 4 |
| NORTHEAST REGIONAL COUNCIL OF SMART | Dorchester | J40 Employment | $14.6M | 27 |
| IBEW LOCAL 104 UNION | Mansfield | — | $14.6M | 13 |
| OVERLOOK COMMUNITIES INC | Charlton | L22 Housing & Shelter | $14.6M | 7 |
| TAPESTRY HEALTH SYSTEMS INC | Springfield | E42Z Health Care | $14.5M | 3 |
| MASSACHUSETTS MARITIME ACADEMY | Buzzards Bay | B42I Education | $14.5M | 0 |
| LUTHERAN HOME OF JAMAICA PLAIN INC | Jaimaica Plain | — | $14.5M | 13 |
| COMMONWEALTH OF MASSACHUSETTSNAGE | Quincy | — | $14.5M | 1 |
| ADULT & TEEN CHALLENGE NEW ENGLAND | Brockton | F330 Mental Health & Crisis Intervention | $14.5M | 3 |
| Bourne Management Systems Inc | Pittsfield | E91 Health Care | $14.4M | 3 |
| WEST SUBURBAN YOUNG MEN'S CHRISTIAN ASSOCIATION | Newton | P27Z Human Services | $14.4M | 5 |
| ENERGY FEDERATION INC | Marlborough | — | $14.4M | 18 |
| Joy In Childhood Foundation Inc | Canton | T990 Philanthropy, Voluntarism & Grantmaking Foundations | $14.4M | 0 |
| HOME FOR AGED WOMEN INC | Brookline | P750 Human Services | $14.4M | 3 |
| Integrate Health Inc | Medway | G12 Diseases, Disorders & Medical Disciplines | $14.3M | 5 |
| LUMINOS FUND | Boston | B20 Education | $14.3M | 8 |
| GREATER BOSTON CHINESE GOLDEN AGE CENTER | Boston | P81Z Human Services | $14.3M | 5 |
| SEMCOA INC DBA SOUTHEAST MASSACHUSETTS | New Bedford | Z99Z Unknown | $14.2M | 2 |
| CAST INC | Lynnfield | P820 Human Services | $14.2M | 12 |
| GREEN ENERGY CONSUMERS | Jamaica Plain | L820 Housing & Shelter | $14.2M | 1 |
| THE CENTER FOR EFFECTIVE PHILANTHROPY | Cambridge | T02 Philanthropy, Voluntarism & Grantmaking Foundations | $14.2M | 13 |
| AMERICAN CONSUMER CREDIT | Auburndale | P51 Human Services | $14.2M | 19 |
| MATTAPAN COMMUNITY HEALTH CENTER INC | Mattapan | — | $14.2M | 8 |
| FSG INC | Boston | S05 Community Improvement & Capacity Building | $14.1M | 8 |
| BRANDON RESIDENTIAL TREATMENT | Natick | F33Z Mental Health & Crisis Intervention | $14.1M | 4 |
| SCHOOL FOR FIELD STUDIES INC | Pittsfield | — | $14.1M | 3 |
| CUTCHINS PROGRAMS FOR CHILDREN | Northampton | F33Z Mental Health & Crisis Intervention | $14.1M | 4 |
| ADOPT A STUDENT FOUNDATION | Boston | B82Z Education | $14.1M | 0 |
| WOODLAND GOLF CLUB OF AUBURNDALE | Auburndale | — | $14.1M | 6 |
| ANIMAL RESCUE LEAGUE OF BOSTON | Dedham | D200 Animal-Related | $14M | 8 |
| SOUTH SHORE HEALTH EXPRESS INC | South Weymouth | H19 Medical Research | $14M | 11 |
| LEXINGTON CHRISTIAN ACADEMY | Lexington | B25Z Education | $14M | 3 |
| SHORE COUNTRY DAY SCHOOL | Beverly | — | $14M | 8 |
| TREMONT CREDIT UNION | Milton | W60 Public & Societal Benefit | $14M | 4 |
| TBL CHARITABLE FOUNDATION | Newtonville | T22 Philanthropy, Voluntarism & Grantmaking Foundations | $14M | 0 |
| MASSACHUSETTS LIBRARY SYSTEM INC | Marlborough | B70 Education | $13.9M | 3 |
| PUBLISHERS INTERNATIONAL LINKING | Lynnfield | B70 Education | $13.9M | 8 |
| CATHOLIC CHARITIES OF THE DIOCESE OF FALL RIVER MASSACHUSETTS INC | Fall River | — | $13.9M | 4 |
| INLY SCHOOL INC | Scituate | — | $13.9M | 4 |
| MONTROSE FOUNDATION INC | Medfield | B24Z Education | $13.9M | 6 |
| NORTHEAST LEGAL AID INC | Lawrence | I80Z Crime & Legal-Related | $13.8M | 5 |
| SOUTH COASTAL COUNTIES LEGAL SERVICES | Fall River | I80 Crime & Legal-Related | $13.8M | 8 |
| Edgar P Benjamin Healthcare Center Inc | Roxbury Crossing | E91Z Health Care | $13.8M | 6 |
| DISABILITY RIGHTS FUND INC | Boston | Q30 International, Foreign Affairs & National Security | $13.7M | 5 |
| BAYSTATE HEALTH FOUNDATION INC | Springfield | E11 Health Care | $13.7M | 11 |
| GREATER WORCESTER COMMUNITY FOUNDATION | Worcester | T310 Philanthropy, Voluntarism & Grantmaking Foundations | $13.7M | 4 |
