| The Shared Living Collaborative Inc | Merrimac | P80 Human Services | $18.1M | 1 |
| CATHOLIC SCHOOLS FOUNDATION INC | Boston | B820 Education | $18.1M | 3 |
| ICATHOLIC MEDIA INC | Watertown | X800 Religion-Related | $18M | 7 |
| GREENTOWN COLLABORATIVE INC | Somerville | C60 Environment | $18M | 11 |
| MARTHA'S VINEYARD COMMUNITY SERVICES INC | Vineyard Haven | P200 Human Services | $18M | 6 |
| SUNSHINE VILLAGE INC | Chicopee | P820 Human Services | $17.9M | 6 |
| SAGA INNOVATIONS INC | Framingham | B90 Education | $17.9M | 10 |
| AMERICAN CONSUMER CREDIT COUNSELING INC | Auburndale | P51 Human Services | $17.9M | 19 |
| HUMAN SERVICES RESEARCH INSTITUTE INC | Cambridge | V20Z Social Science | $17.9M | 9 |
| BROOKLINE COMMUNITY MENTAL HEALTH CENTER INC | Brookline | — | $17.8M | 11 |
| HUNTINGTON THEATRE CO INC | Boston | A650 Arts, Culture & Humanities | $17.8M | 7 |
| TRUSTEES OF THE PUBLIC LIBRARY OF THE CITY OF BOSTON | Boston | B110 Education | $17.8M | 9 |
| BOSTON LATIN SCHOOL ASSOCIATION | Boston | B820 Education | $17.8M | 5 |
| LUTHERAN HOUSING CORPORATION - BROCKTON | Worcester | F33 Mental Health & Crisis Intervention | $17.7M | 14 |
| Fanny Allen Holdings | Andover | — | $17.7M | 3 |
| ADA Forsyth Institute Inc | Cambridge | T50 Philanthropy, Voluntarism & Grantmaking Foundations | $17.7M | 9 |
| BERKSHIRE FAMILY & INDIVIDUAL RESOURCES INC | North Adams | P70 Human Services | $17.7M | 2 |
| WALNUT STREET CENTER INC | Medford | P820 Human Services | $17.7M | 8 |
| ITALIAN HOME FOR CHILDREN INC | Jamaica Plain | F33Z Mental Health & Crisis Intervention | $17.7M | 4 |
| PROJECT BREAD-THE WALK FOR HUNGER INC | East Boston | K30J Food, Agriculture & Nutrition | $17.6M | 8 |
| COMPASS WORKING CAPITAL INC | Boston | — | $17.6M | 6 |
| DEDHAM COUNTRY DAY SCHOOL | Dedham | B240 Education | $17.6M | 7 |
| NANTUCKET CONSERVATION FOUNDATION INC | Nantucket | C300 Environment | $17.5M | 6 |
| New England Donor Services Inc | Waltham | E02 Health Care | $17.5M | 12 |
| DERBY ACADEMY TRUSTEES | Hingham | B200 Education | $17.5M | 7 |
| Integritus Healthcare Mgmt Services Inc formerly BHCS Management Services Inc | Pittsfield | E91Z Health Care | $17.5M | 6 |
| COMMUNITY ACTION PROGRAMS INTER-CITY IN | Chelsea | — | $17.4M | 4 |
| LA COLABORATIVA INC | Chelsea | P20B Human Services | $17.3M | 2 |
| East Longmeadow Management Systems Inc | Pittsfield | E91Z Health Care | $17.3M | 6 |
| AMERICAN ACADEMY OF ARTS & SCIENCES | Cambridge | V300 Social Science | $17.3M | 7 |
| STEPPINGSTONE FOUNDATION INC | Boston | B280 Education | $17.3M | 6 |
| ACTION FOR THE CLIMATE EMERGENCY | Charlestown | C05 Environment | $17.3M | 6 |
| HOPEFUL JOURNEYS EDUCATIONAL CENTER INC | Beverly | B28 Education | $17.2M | 11 |
| THE TECHNICAL ASSISTANCE COLLABORATIVE INC | Boston | Z99Z Unknown | $17.2M | 11 |
| BRAE BURN COUNTRY CLUB | West Newton | — | $17.1M | 8 |
| NEVILLE COMMUNITIES HOME INC | Cambridge | L20 Housing & Shelter | $17.1M | 5 |
| EASTERN EDUCATIONAL TELEVISION NETWORK INC | Boston | A320 Arts, Culture & Humanities | $17.1M | 12 |
| Salem State University Alumni Association and Foundation Inc | Salem | B110 Education | $17.1M | 1 |
| SPRINGFIELD DAY NURSERY CORPORATION | Springfield | P33 Human Services | $17.1M | 3 |
| ALL CARE VISITING NURSE ASSOCIATION OF GREATER LYNN INC | Lynn | — | $17M | 7 |
| SPRINGFIELD RESCUE MISSION | Springfield | P600 Human Services | $17M | 1 |
| Bourne Management Systems Inc | Pittsfield | E91 Health Care | $17M | 5 |
| THE MASSACHUSETTS GREEN HIGH PERFORMANCE COMPUTING CENTER INC | Holyoke | B19 Education | $17M | 21 |
| LEO INC | Lynn | P400 Human Services | $16.9M | 7 |
| HEAT & FROST INSULATORS AND ALLIED WORKERS LOCAL 6 HEALTH AND WELFARE FUND | Quincy | — | $16.9M | 2 |
| INTERNATIONAL UNION OF OPERATING ENGINEERS LOCAL 98 HEALTH & WELFARE FUND | Southwick | — | $16.9M | 5 |
| Peabody Management Systems Inc | Pittsfield | E91Z Health Care | $16.7M | 6 |
| HISTORIC DEERFIELD INC | Deerfield | A540 Arts, Culture & Humanities | $16.7M | 6 |
| Phemus Corporation | Boston | B110 Education | $16.7M | 3 |
| MASSACHUSETTS SOCIETY FOR THE PREVENTION OF CRUELTY TO CHILDREN | Lexington | I030 Crime & Legal-Related | $16.7M | 8 |
