| ASSOCIATED JEWISH CHARITIES OF BALTIMORE | Baltimore | T700 Philanthropy, Voluntarism & Grantmaking Foundations | $56.6M | 7 |
| GILMAN SCHOOL INCORPORATED | Baltimore | B250 Education | $55.6M | 7 |
| MEBA MEDICAL AND BENEFITS PLAN | Baltimore | — | $55.3M | 14 |
| NATIONAL ASSOCIATION OF COMMUNITY HEALTH CENTERS INC | Bethesda | E32C Health Care | $55.2M | 9 |
| THE ARC OF PRINCE GEORGE'S COUNTY INC | Largo | — | $55.1M | 7 |
| COMMUNITY CLINIC INC | Silver Spring | E32Z Health Care | $55M | 11 |
| THE ARC BALTIMORE INC | Baltimore | P82Z Human Services | $54.6M | 11 |
| BEHAVORIAL HEALTH SYSTEMS BALTIMORE | Baltimore | F30Z Mental Health & Crisis Intervention | $54.3M | 14 |
| THE ASSOCIATED JEWISH COMMUNITY FEDERATION OF BALTIMORE INC | Baltimore | T700 Philanthropy, Voluntarism & Grantmaking Foundations | $54.1M | 8 |
| THE HACKERMAN FOUNDATION INC | Towson | T20 Philanthropy, Voluntarism & Grantmaking Foundations | $53.6M | 0 |
| INTERNATIONAL UNION OF PAINTERS AND ALLIED TRADES | Hanover | — | $53.3M | 16 |
| WAY STATION INC | Baltimore | P82Z Human Services | $53.1M | 10 |
| THE CHIMES INC | Baltimore | P730 Human Services | $52.4M | 9 |
| STRATEGIC RESOURCE GROUP INC | Easton | X20 Religion-Related | $52.1M | 2 |
| University of Maryland Baltimore Foundation Inc | Baltimore | B110 Education | $52M | 4 |
| CONGRESSIONAL COUNTRY CLUB INC | Bethesda | — | $51.7M | 11 |
| Chester River Hospital Center Inc | Chestertown | E220 Health Care | $51.7M | 15 |
| BOARD OF CHILD CARE OF THE UNITED METHODIST CHURCH INC | Baltimore | P300 Human Services | $51.6M | 8 |
| HOSPICE OF THE CHESAPEAKE INC | Pasadena | — | $51.4M | 12 |
| MOSAIC COMMUNITY SERVICES INC | Baltimore | S20 Community Improvement & Capacity Building | $51.3M | 10 |
| HOMEWOOD LIVING FREDERICK INC | Williamsport | P750 Human Services | $50.8M | 9 |
| UMGC Ventures Inc | Bethesda | B12 Education | $50.7M | 19 |
| HUGO W MOSER RESEARCH INSTITUTE AT KENNEDY KRIEGER INC | Baltimore | U00Z Science & Technology | $50M | 15 |
| CHILD TRENDS INC | Rockville | P30E Human Services | $49.9M | 12 |
| ENTERPRISE COMMUNITY LOAN FUND INC | Columbia | L20 Housing & Shelter | $49.8M | 14 |
| RISE8 FOUNDATION C/O ACADIA FAMILY OFFICE | Hunt Valley | T20 Philanthropy, Voluntarism & Grantmaking Foundations | $49.4M | 0 |
| CHESAPEAKE REGIONAL INFORMATION SYSTEM FOR OUR PATIENTS INC | Columbia | E02 Health Care | $49.3M | 9 |
| JOHNS HOPKINS HOME CARE GROUP INC | Baltimore | — | $48.3M | 9 |
| LANDON SCHOOL | Bethesda | B200 Education | $47.5M | 8 |
| AMALGAMATED TRANSIT UNION | Silver Spring | — | $47.1M | 26 |
| COMPASS INC | Beltsville | P82 Human Services | $47M | 7 |
| LEGAL AID BUREAU INC | Baltimore | I800 Crime & Legal-Related | $46.4M | 10 |
| TRANSPORTATION COMMUNICATIONS UNIONIAM | Rockville | — | $46.3M | 12 |
| KING FARM PRESBYTERIAN RETIREMENT COMMUNITY INC | Rockville | L22 Housing & Shelter | $46.1M | 11 |
| FOUNDATION FOR ADVANCED EDUCATION IN THE SCIENCES INC | Bethesda | B82Z Education | $45.9M | 8 |
| THE HOLTON ARMS SCHOOL | Bethesda | B250 Education | $45.9M | 8 |
| MEXICAN HASS AVOCADO IMPORTERS ASSOCIATION | Fallston | S41 Community Improvement & Capacity Building | $45.8M | 0 |
| EMERGE INC | Columbia | P820 Human Services | $45.6M | 6 |
| THE VILLAGE AT ROCKVILLE INC | Frederick | P750 Human Services | $45.3M | 7 |
| MADISON STREET PROPERTIES INC | Baltimore | S500 Community Improvement & Capacity Building | $45M | 10 |
| TRUCK DRIVERS & HELPERS LOCAL UNION NO 355 HEALTH & WELFARE PLAN | Baltimore | — | $44.9M | 0 |
| AIRCRAFT OWNERS & PILOTS ASSOCIATION | Frederick | — | $44.8M | 12 |
| UNIVERSITY OF MARYLAND SURGICAL ASSOCIATES PA | Baltimore | E30 Health Care | $44.7M | 10 |
| HANDICAP INTERNATIONAL | Silver Spring | Q30 International, Foreign Affairs & National Security | $44.6M | 1 |
| THE PARK SCHOOL OF BALTIMORE | Baltimore | B200 Education | $44.4M | 8 |
| MASTERS MATES & PILOTS VACATION FUND | Linthicum Heights | — | $44.3M | 14 |
| BELLO MACHRE INC | Glen Burnie | P73Z Human Services | $44.2M | 8 |
| NATIONAL ASSOCIATION FOR THE ADVANCEMENT OF COLORED PEOPLE-GROUP | Baltimore | — | $44.1M | 3 |
| ARC OF WASHINGTON COUNTY INC | Hagerstown | P82Z Human Services | $44M | 2 |
| CHOPTANK COMMUNITY HEALTH SYSTEM INC | Denton | E320 Health Care | $43.8M | 7 |
