| TEAMSTERS LOCAL 170 HEALTH AND WELFARE FUND | Worcester | — | $38.7M | 1 |
| Upstream USA Inc | Boston | E21 Health Care | $38.7M | 10 |
| PAINTERS DISTRICT COUNCIL NO 35 HEALTH BENEFITS FUND | Roslindale | — | $38.6M | 8 |
| PLUMBERS UNION LOCAL 12 WELFARE PLAN HEALTH AND WELFARE FUND | Boston | — | $38.6M | 1 |
| BROOKS SCHOOL | North Andover | B250 Education | $38.4M | 7 |
| NFI MASSACHUSETTS INC | Danvers | P202 Human Services | $38.3M | 7 |
| MULTICULTURAL COMMUNITY SERVICES OF THE PIONEER VALLEY INC | Springfield | P73Z Human Services | $38.3M | 1 |
| THE EDINBURG CENTER INC | Bedford | P20 Human Services | $38.3M | 7 |
| CHARLES RIVER ASSOCIATION FOR RETARDED CITIZENS INC | Needham | — | $38.2M | 8 |
| THE LONGWOOD COLLECTIVE INC | Boston | E030 Health Care | $38.1M | 7 |
| BLUEHUB LOAN FUND INC | Boston | — | $38M | 8 |
| LIFEWORKS INCORPORATED | Westwood | P80Z Human Services | $37.9M | 8 |
| LIFESTREAM INC | New Bedford | E50 Health Care | $37.8M | 5 |
| TRUSTEES OF LAWRENCE ACADEMY AT GROTON MA CORP | Groton | B250 Education | $37.8M | 9 |
| ALLEN-CHASE FOUNDATION DBA EAGLEBROOK SCHOOL | Deerfield | B250 Education | $37.6M | 7 |
| DR MIRIAM & SHELDON G ADELSON MEDICAL RESEARCH FOUNDATION | Needham | T990 Philanthropy, Voluntarism & Grantmaking Foundations | $37.6M | 0 |
| FREEDOM CREDIT UNION | Springfield | — | $37.6M | 17 |
| DOTHOUSE HEALTH INC | Dorchester | E30Z Health Care | $37.5M | 10 |
| EASTERN STATES EXPOSITION | West Springfield | N520 Recreation & Sports | $37.5M | 7 |
| PLANET AID INC | Milford | Q330 International, Foreign Affairs & National Security | $37.3M | 8 |
| THE TRUSTEES OF THE CUSHING ACADEMY | Ashburnham | B250 Education | $37.3M | 8 |
| COMMUNITY FOUNDATION OF WESTERN MASSACHUSETTS | Springfield | T310 Philanthropy, Voluntarism & Grantmaking Foundations | $37M | 5 |
| WORCESTER ACADEMY | Worcester | B200 Education | $36.7M | 5 |
| Whittier Street Health Center Committee Inc | Roxbury | E320 Health Care | $36.7M | 8 |
| SHADY HILL SCHOOL | Cambridge | B240 Education | $36.3M | 9 |
| BAY STATE COMMUNITY SERVICES INC | Quincy | — | $36.3M | 7 |
| DELTA PROJECTS INC | Dedham | P800 Human Services | $36.3M | 8 |
| BOSTON HIGASHI SCHOOL INC | Randolph | B280 Education | $36.2M | 2 |
| GUIDEWIRE INC | Chicopee | P820 Human Services | $36M | 6 |
| TRI-VALLEY INC | Dudley | E920 Health Care | $35.8M | 2 |
| TRUST AGREEMENT FOR GPU COMPANIES HEALTH CARE PLAN FOR EMPLOYEES | Heritage Dr N Qu | — | $35.8M | 0 |
| JAMES S MCDONNELL FAMILY FOUNDATION INC | Lincoln | T20 Philanthropy, Voluntarism & Grantmaking Foundations | $35.4M | 2 |
| NOTRE DAME HEALTH CARE CENTER INC | Worcester | P700 Human Services | $35.4M | 8 |
| KENNEDY-DONOVAN CENTER INC | Foxboro | P800 Human Services | $35.3M | 7 |
| AMERICAN TRAINING INC | Andover | — | $35.3M | 5 |
| THE BOSTON ATHLETIC ASSOCIATION | Boston | — | $35.1M | 11 |
| THE FAY SCHOOL INC | Southborough | B200 Education | $35.1M | 7 |
| IRON WORKERS DISTRICT COUNCIL OF NEW ENGLAND HEALTH AND WELFARE FUND | Dorchester | — | $35.1M | 1 |
| YOUNG MEN'S CHRISTIAN ASSOCIATION OF METRO NORTH INC | Peabody | P270 Human Services | $35M | 7 |
| THE AMERICAN IRELAND FUND (DBA THE IRELAND FUNDS AMERICA/THE IRELAND FUNDS) | Boston | — | $34.9M | 7 |
| TEAMSTERS LOCAL 653 WELFARE FUND | South Easton | — | $34.7M | 0 |
| COMMUNITY HEALTH PROGRAMS INCORPORATED | Great Barrington | — | $34.7M | 11 |
| MASSACHUSETTS BRICKLAYERS & MASONS HEALTH & WELFARE FUND | Boston | — | $34.7M | 1 |
| Massachusetts and Northern New England Laborers District Council | Hopkinton | — | $34.4M | 7 |
| MASSACHUSETTS LEAGUE OF COMMUNITY HEALTH CENTERS INC | Boston | — | $34.4M | 11 |
| TURNING POINT INC AND AFFILIATES | Newburyport | L410 Housing & Shelter | $34.4M | 9 |
| THE CARROLL SCHOOL | Lincoln | B28Z Education | $34.4M | 9 |
| THE TJX FOUNDATION INC | Framingham | T20 Philanthropy, Voluntarism & Grantmaking Foundations | $34.4M | 0 |
| TUFTS SHARED SERVICES INC | Boston | E220 Health Care | $34.2M | 15 |
| PARK SCHOOL CORPORATION | Brookline | B200 Education | $34.1M | 7 |
