| COMMUNITY CATALYST INC | Boston | E99 Health Care | $19M | 11 |
| BAIM INSTITUTE FOR CLINICAL | Boston | H05 Medical Research | $19M | 20 |
| THE WINCHENDON SCHOOL INC | Winchendon | B200 Education | $18.9M | 6 |
| HENRY C NEVINS HOME INC | Methuen | E91Z Health Care | $18.9M | 7 |
| BOSTON YOUTH SYMPHONY ORCHESTRAS INC | Boston | A690 Arts, Culture & Humanities | $18.9M | 3 |
| COMMUNITAS INC | Wakefield | P82Z Human Services | $18.9M | 3 |
| SIGHTSAVERS INC | Boston | G41 Diseases, Disorders & Medical Disciplines | $18.8M | 1 |
| WEBSTER EMERGENCY MEDICAL SERVICES INC | Webster | E62 Health Care | $18.8M | 1 |
| THE COMMONWEALTH SCHOOL INC | Boston | B250 Education | $18.8M | 6 |
| ADVANCED FUNCTIONAL FABRICS OF | Cambridge | B11 Education | $18.7M | 9 |
| PROPRIETORS OF MOUNT AUBURN CEMETERY | Cambridge | — | $18.7M | 11 |
| DEDHAM COUNTRY AND POLO CLUB | Dedham | — | $18.7M | 10 |
| HEALTH IMPERATIVES INC | Brockton | E00Z Health Care | $18.6M | 7 |
| Arbour Way Foundation Inc | Boston | T20 Philanthropy, Voluntarism & Grantmaking Foundations | $18.6M | 0 |
| BANCROFT SCHOOL | Worcester | B250 Education | $18.6M | 8 |
| MASSACHUSETTS BIOTECHNOLOGY COUNCIL INC | Cambridge | — | $18.5M | 9 |
| VNA CARE HOSPICE INC | Worcester | P740 Human Services | $18.5M | 10 |
| METROWEST YOUNG MEN'S CHRISTIAN | Framingham | P27Z Human Services | $18.4M | 9 |
| NEW ENGLAND VILLAGE INC | Pembroke | P820 Human Services | $18.4M | 5 |
| MASSACHUSETTS MUSEUM OF CONTEMPORARY ART | North Adams | B51Z Education | $18.3M | 8 |
| TEACH PLUS INC | Boston | B90 Education | $18.3M | 12 |
| SOUTH COVE MANOR AT QUINCY POINT | Quincy | E91 Health Care | $18.3M | 7 |
| CAMP HARBOR VIEW FOUNDATION INC | Boston | O50 Youth Development | $18.2M | 8 |
| THE SUNSHINE CHARITABLE FOUNDATION | Boston | T22 Philanthropy, Voluntarism & Grantmaking Foundations | $18.2M | 0 |
| THE FLATLEY FOUNDATION | Braintree | T20 Philanthropy, Voluntarism & Grantmaking Foundations | $18.1M | 0 |
| GOOD SPORTS INC | Braintree | O50 Youth Development | $18.1M | 5 |
| 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 |
| COMMUNITY SERVINGS INC | Jamaica Plain | P80Z Human Services | $18M | 8 |
| GREENTOWN COLLABORATIVE INC | Somerville | C60 Environment | $18M | 11 |
| MARTHA'S VINEYARD | Vineyard Haven | P200 Human Services | $18M | 6 |
| SAGA INNOVATIONS INC | Framingham | B90 Education | $17.9M | 10 |
| CAPE COD FOUNDATION INC | South Yarmouth | B82Z Education | $17.9M | 1 |
| HUMAN SERVICES RESEARCH INSTITUTE INC | Cambridge | V20Z Social Science | $17.9M | 9 |
| BROOKLINE COMMUNITY MENTAL HEALTH | Brookline | — | $17.8M | 11 |
| CHAPEL HILL-CHAUNCY HALL SCHOOL | Waltham | — | $17.8M | 7 |
| MARIAN MANOR FOR THE AGED AND | South Boston | E910 Health Care | $17.7M | 6 |
| Fanny Allen Holdings | Andover | — | $17.7M | 0 |
| ADA Forsyth Institute Inc | Cambridge | T50 Philanthropy, Voluntarism & Grantmaking Foundations | $17.7M | 9 |
| BERKSHIRE FAMILY & INDIVIDUAL | North Adams | P70 Human Services | $17.7M | 2 |
| WALNUT STREET CENTER INC | Medford | P820 Human Services | $17.7M | 8 |
| 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 |
| The Schooner Foundation | Boston | T20J Philanthropy, Voluntarism & Grantmaking Foundations | $17.6M | 1 |
| AMERICAN METEOROLOGICAL SOCIETY | Boston | U030 Science & Technology | $17.5M | 7 |
| New England Donor Services Inc | Waltham | E02 Health Care | $17.5M | 12 |
| DERBY ACADEMY TRUSTEES | Hingham | B200 Education | $17.5M | 7 |
| MASSACHUSETTS SERVICE ALLIANCE INC | Boston | C20Z Environment | $17.5M | 2 |
