| DETECTOGETHER INC FORMERLY KNOWN AS THE 15-40 CONNECTION INC | Westborough | H123 Medical Research | $2.5M | 4 |
| CUNNINGHAM FAMILY FOUNDATION INC | Holden | T20 Philanthropy, Voluntarism & Grantmaking Foundations | $2.5M | 0 |
| JORDAN HEALTH SYSTEMS INC | Charlestown | — | $2.5M | 13 |
| LEHRHAUS CENTER FOR JEWISH LIFE AND LEARNING INC | Somerville | X30 Religion-Related | $2.5M | 1 |
| NANTUCKET LIGHTHOUSE SCHOOL INC | Nantucket | B20 Education | $2.5M | 3 |
| LEAP for Education Inc | Salem | B90 Education | $2.5M | 1 |
| CORTICO CORPORATION | Boston | U40 Science & Technology | $2.5M | 3 |
| JUNIOR ACHIEVEMENT OF GREATER BOSTON INC | Boston | Q320 International, Foreign Affairs & National Security | $2.5M | 4 |
| BROOKLINE FOOD PANTRY INC | Brookline | K31 Food, Agriculture & Nutrition | $2.5M | 1 |
| LOOKOUT FOUNDATION INC C/O GMA FOUNDATIONS | Boston | T20 Philanthropy, Voluntarism & Grantmaking Foundations | $2.5M | 3 |
| CARITAS COMMUNITIES HOLDINGS INC C/O CARITAS COMMUNITIES INC | Braintree | L20 Housing & Shelter | $2.5M | 6 |
| NORTH CHARLES MENTAL HEALTH RESEARCH & TRAINING FOUNDATION INC | Cambridge | F00E Mental Health & Crisis Intervention | $2.5M | 1 |
| NOPI INC | Walpole | W02 Public & Societal Benefit | $2.5M | 4 |
| TRINITY BOSTON CONNECTS INC | Boston | O50 Youth Development | $2.5M | 2 |
| ALL IN ENERGY INC | Roslindale | C60 Environment | $2.5M | 2 |
| TABER CHARITABLE FOUNDATION | Boston | T99 Philanthropy, Voluntarism & Grantmaking Foundations | $2.5M | 0 |
| RESEARCH INSTITUTE FOR LEARNING & DEVELO DEVELOPMENT INC | Lexington | U99 Science & Technology | $2.5M | 4 |
| END MASS OVERDOSE INC | Boston | F20 Mental Health & Crisis Intervention | $2.5M | 1 |
| SEGREGANSETT COUNTRY CLUB INC | Taunton | N50 Recreation & Sports | $2.5M | 0 |
| MASSACHUSETTS ORGANIZATION OF STATE ENGINEERS & SCIENTISTS MOSES | Boston | J40 Employment | $2.5M | 7 |
| SIASCONSET CASINO ASSOCIATION | Siasconset | — | $2.5M | 0 |
| The Ray and Karyn Hendrickson Foundation c/o PKF JND PC | Quincy | T22Z Philanthropy, Voluntarism & Grantmaking Foundations | $2.5M | 0 |
| CAMBRIDGE COMMUNITY CENTER INC | Cambridge | P28Z Human Services | $2.5M | 1 |
| CURIOUS LEARNING A GLOBAL LITERACY PROJECT INC | Amesbury | B90 Education | $2.5M | 4 |
| ADMIRALS HILL ASSISTED LIVING CORP II | Chelsea | L22 Housing & Shelter | $2.5M | 5 |
| JAMES L MCKEOWN BOYS AND GIRLS CLUB OF WOBURN INC | Woburn | O23Z Youth Development | $2.5M | 1 |
| SNOW FARM- THE NEW ENGLAND CRAFT PROGRAM INC | Williamsburg | B60 Education | $2.5M | 1 |
| BROOKVIEW HOUSE INC | Dorchester | P850 Human Services | $2.5M | 3 |
| ZUMIX INC | East Boston | A6BZ Arts, Culture & Humanities | $2.5M | 2 |
| NP BANGERTER CROSSING LLC C/O AEW CAPITAL MANAGEMENT LP | Boston | Y11 Mutual & Membership Benefit | $2.5M | 0 |
| SOUTHERN BERKSHIRE VOLUNTEER AMBULANCE SQUAD INC | Great Barrington | E62Z Health Care | $2.5M | 0 |
| INTERNATIONAL BROTHERHOOD OF ELECTRICAL WORKERS BUILDING CORPORATION | Dorchester | — | $2.5M | 22 |
| COUNCIL OF JUVENILE JUSTICE ADMINISTRATORS INC | Hingham | I21 Crime & Legal-Related | $2.5M | 6 |
| Melrose Day Care Center Inc | Melrose | — | $2.4M | 0 |
| A BETTER CITY INC | Boston | S41 Community Improvement & Capacity Building | $2.4M | 7 |
| SUMMIT AGENCY INC | Worcester | B28 Education | $2.4M | 1 |
| NATIONAL ENVIRONMENTAL POLICY AND LAW CENTER INC | Boston | C013 Environment | $2.4M | 1 |
| SMCWC - Crossroads Housing Inc Crossroads Shelter | East Boston | P20 Human Services | $2.4M | 2 |
| Greenwood Music Camp Inc | Easthampton | N20Z Recreation & Sports | $2.4M | 2 |
| WESTERN AVENUE COMMUNITY FOR THE ARTS INC | Lowell | A20 Arts, Culture & Humanities | $2.4M | 2 |
| BOSTON'S HIGHER GROUND INC | Roxbury | S20 Community Improvement & Capacity Building | $2.4M | 2 |
| FRIENDS OF MVYRADIO INC | West Tisbury | T99 Philanthropy, Voluntarism & Grantmaking Foundations | $2.4M | 1 |
| NEW BEDFORD YACHT CLUB | South Dartmouth | — | $2.4M | 2 |
| POLARIS ACTION INC | Beverly | — | $2.4M | 4 |
| BAYPATH HUMANE SOCIETY OF HOPKINTON INC | Hopkinton | D200 Animal-Related | $2.4M | 1 |
| JANE AND JACK FITZPATRICK TRUST | Stockbridge | A90 Arts, Culture & Humanities | $2.4M | 1 |
| LAWRENCE J AND ANNE RUBENSTEIN CHARITABLE FOUNDATION C/O RIDGEWAY PTRS | Boston | T20 Philanthropy, Voluntarism & Grantmaking Foundations | $2.4M | 0 |
| Foundation For Neurologic Diseases Inc | Newburyport | H960 Medical Research | $2.4M | 3 |
| THE SIXTH AMENDMENT CENTER INCORPORATED | Boston | — | $2.4M | 5 |
| RICHARD SALTONSTALL CHARITABLE FOUNDATION | Boston | T20 Philanthropy, Voluntarism & Grantmaking Foundations | $2.4M | 6 |
