| FAMILYAID BOSTON INC | Boston | — | $24.2M | 7 |
| CITY OF BOSTON CREDIT UNION | South Boston | — | $24.2M | 16 |
| TUFTS VETERINARY EMERGENCY TREATMENT & SPECIALTIES INC | North Grafton | E20Z Health Care | $24.2M | 12 |
| ALLIANCE HEALTH OF QUINCY INC | Southborough | E110 Health Care | $24.2M | 15 |
| MIDDLESEX HUMAN SERVICE AGENCY INC | Waltham | L41Z Housing & Shelter | $24.1M | 6 |
| INTERNATIONAL BROTHERHOOD OF ELECTRICAL WORKERS LOCAL 103 | Dorchester | — | $24.1M | 26 |
| CHARLES RIVER COMMUNITY HEALTH INC | Brighton | E32Z Health Care | $24M | 9 |
| The Once Here Foundation | Cambridge | T20 Philanthropy, Voluntarism & Grantmaking Foundations | $24M | 0 |
| MISS HALL'S SCHOOL INC | Pittsfield | B250 Education | $24M | 5 |
| NEW ENGLAND LIFE PLAN COMMUNITIES CORP | Lincoln | L22 Housing & Shelter | $23.9M | 0 |
| LYCEE INTERNATIONAL DE BOSTON INTERNATIONAL SCHOOL OF BOSTON INC | Cambridge | B240 Education | $23.9M | 7 |
| ROOT CAPITAL INC | Cambridge | Q123 International, Foreign Affairs & National Security | $23.8M | 12 |
| CARDINAL BROOK TRUST | Boston | T20 Philanthropy, Voluntarism & Grantmaking Foundations | $23.7M | 0 |
| The McCance Foundation | North Scituate | T99Z Philanthropy, Voluntarism & Grantmaking Foundations | $23.6M | 1 |
| HEALTH & WELFARE TRUST FD IUOE LOCAL 877 & 70 | Norwood | — | $23.5M | 0 |
| CAMPUS CHILD CARE INC | Cambridge | P33Z Human Services | $23.5M | 6 |
| SCHOOL OF LEADERSHIP-AFGHANISTAN INC | Boston | — | $23.5M | 2 |
| NASHOBA LEARNING GROUP INC | Bedford | B28 Education | $23.5M | 8 |
| HORIZONS FOR HOMELESS CHILDREN | Roxbury | P330 Human Services | $23.5M | 5 |
| OVERLOOK MASONIC HEALTH CENTER INC | Charlton | E910 Health Care | $23.5M | 9 |
| CAPE ABILITIES INC | Hyannis | P820 Human Services | $23.4M | 7 |
| BELMONT DAY SCHOOL INC | Belmont | B21Z Education | $23.4M | 9 |
| SAINT FRANCIS HOUSE INC | Boston | P85Z Human Services | $23.4M | 7 |
| THE NEW COMMONWEALTH RACIAL EQUITY AND SOCIAL JUSTICE FUND INC | Roxbury | R30 Civil Rights, Social Action & Advocacy | $23.4M | 1 |
| THE BOTTOM LINE INC | Jamaica Plain | S99 Community Improvement & Capacity Building | $23.4M | 13 |
| NORTH ATLANTIC STATES CARPENTERS TRAINING FUND | Millbury | J220 Employment | $23.4M | 7 |
| TINKER ISLAND FOUNDATION | Boston | T20 Philanthropy, Voluntarism & Grantmaking Foundations | $23.3M | 1 |
| MERCY LIFE INC | West Springfield | — | $23.2M | 14 |
| CRITERION CHILD ENRICHMENT INC | Milford | P300 Human Services | $23.1M | 7 |
| NORTH ATLANTIC STATES CARPENTERS VACATION FUND | Wilmington | — | $23.1M | 6 |
| LOOMIS COMMUNITIES INC | South Hadley | P750 Human Services | $23.1M | 8 |
| SOUTH SHORE SUPPORT SERVICES INC | Weymouth | P820 Human Services | $22.8M | 1 |
| MASSACHUSETTS HOUSING INVESTMENT CORPORATION | Boston | L120 Housing & Shelter | $22.6M | 9 |
| THE JAKET FOUNDATION | Boston | T22 Philanthropy, Voluntarism & Grantmaking Foundations | $22.5M | 0 |
| TEAMSTERS HEALTH SERVICES & INSURANCE PLAN OF LOCAL UNION 404 | Springfield | — | $22.5M | 4 |
| MERRIMACK VALLEY YOUNG MEN'S CHRISTIAN ASSOCIATION INC | Lawrence | O55Z Youth Development | $22.4M | 6 |
| COMMUNITY LEGAL AID INC | Worcester | I99 Crime & Legal-Related | $22.4M | 5 |
| ISABELLA STEWART GARDNER MUSEUM INC | Boston | A510 Arts, Culture & Humanities | $22.3M | 7 |
| HEALTHFIRST FAMILY CARE CENTER INC | Fall River | E320 Health Care | $22.3M | 9 |
| Technology Review Inc | Cambridge | A33 Arts, Culture & Humanities | $22.3M | 16 |
| MASSACHUSETTS HOUSING AND SHELTER ALLIANCE INC | Boston | P850 Human Services | $22.3M | 5 |
| THE CAMBRIDGE SCHOOL OF WESTON INC | Weston | B200 Education | $22.3M | 9 |
| COMMUNITY CONNECTIONS INC | South Yarmouth | P82Z Human Services | $22.2M | 5 |
| Worcester City Campus Corporation Group | Westborough | B19 Education | $22.2M | 6 |
| WORCESTER COUNTY FOOD BANK INC | Shrewsbury | K31Z Food, Agriculture & Nutrition | $22.2M | 1 |
| JA WORLDWIDE INC | Boston | B82 Education | $22.1M | 10 |
| MASS DESIGN GROUP LTD | Boston | Q30 International, Foreign Affairs & National Security | $22.1M | 12 |
| TENACRE COUNTRY DAY SCHOOL CORPORATION | Wellesley | B21Z Education | $22M | 7 |
| WELLESLEY COUNTRY CLUB | Wellesley | — | $21.9M | 7 |
| ANIMAL RESCUE LEAGUE OF BOSTON | Dedham | D200 Animal-Related | $21.9M | 10 |
