| HEALTHCARE ACCESS MARYLAND INC | Baltimore | E99 Health Care | $17.9M | 7 |
| KEY POINT HEALTH SERVICES INC | Aberdeen | — | $17.9M | 15 |
| COMMUNITY LIVING INC | Fredrick | P73Z Human Services | $17.8M | 2 |
| DELMARVA COMMUNITY SERVICES INC | Cambridge | P800 Human Services | $17.8M | 4 |
| PARK WEST HEALTH SYSTEM INC | Baltimore | — | $17.8M | 5 |
| CIVIC WORKS INC | Baltimore | B92 Education | $17.7M | 6 |
| UM FDSP ASSOCIATES PA | Baltimore | — | $17.7M | 7 |
| ATHELAS INSTITUTE INC | Columbia | P820 Human Services | $17.6M | 4 |
| THE AOPA FOUNDATION INC | Frederick | M40 Public Safety, Disaster Preparedness & Relief | $17.5M | 11 |
| VISIT BALTIMORE INC | Baltimore | — | $17.3M | 9 |
| NATURE SACRED | Annapolis | T23 Philanthropy, Voluntarism & Grantmaking Foundations | $17.3M | 2 |
| REBUILD METRO INC | Baltimore | S50Z Community Improvement & Capacity Building | $17.3M | 4 |
| AMERICAN PODIATRIC MEDICAL ASSOCIATION INC | Rockville | — | $17.3M | 19 |
| HOMEFREE USA INC | Landover | T30 Philanthropy, Voluntarism & Grantmaking Foundations | $17.2M | 7 |
| NORA ROBERTS FOUNDATION | Glenn Dale | T22 Philanthropy, Voluntarism & Grantmaking Foundations | $17.1M | 2 |
| KENNEDY KRIEGER FOUNDATION INC | Baltimore | T30 Philanthropy, Voluntarism & Grantmaking Foundations | $17.1M | 7 |
| BLIND INDUSTRIES & SERVICES OF MARYLAND | Baltimore | P86 Human Services | $17M | 12 |
| MARYLAND MEDICINE PA | Baltimore | E21 Health Care | $17M | 5 |
| COMMUNITY FOUNDATION OF THE EASTERN SHOR | Salisbury | T310 Philanthropy, Voluntarism & Grantmaking Foundations | $16.9M | 2 |
| AMERICAN POSTAL WORKERS UNION AFL-CIO HEALTH PLAN HEALTH AND WELFARE TRUST AGREEMENT | Elkridge | — | $16.8M | 6 |
| DEUTSCHER SCHULVEREIN WASHINGTON DC | Potomac | B22Z Education | $16.8M | 6 |
| AMERICAN SOCIETY OF ADDICTION MEDICINE | Rockville | F20 Mental Health & Crisis Intervention | $16.8M | 10 |
| BALTIMORE SYMPHONY ENDOWMENT TRUST | Baltimore | B11 Education | $16.7M | 3 |
| CHILDREN'S INN AT NIH INC | Bethesda | E860 Health Care | $16.7M | 11 |
| GREEN STREET ACADEMY INC | Baltimore | B20 Education | $16.6M | 1 |
| ENERGETICS TECHNOLOGY CENTER INC | Indian Head | U20 Science & Technology | $16.6M | 11 |
| REGINALD S LOURIE CENTER FOR INFANTS AND YOUNG CHILDREN INC | Gaithersburg | P820 Human Services | $16.6M | 11 |
| PROGRESS UNLIMITED INC | Owings Mills | P700 Human Services | $16.6M | 3 |
| Regulatory Affairs Professionals Society | Rockville | W99Z Public & Societal Benefit | $16.6M | 8 |
| NATIONAL ASSOCIATION OF BLACK ACCOUNTANTS INC | Greenbelt | — | $16.5M | 11 |
| STAR-K CERTIFICATION INC | Baltimore | X30Z Religion-Related | $16.5M | 10 |
| ELECTRICAL LOCAL 26 JOINT APPRENTICESHIP AND TRAINING TRUST FUND | Lanham | J22Z Employment | $16.5M | 6 |
| ADAMAH INC | Resisterstown | X302 Religion-Related | $16.5M | 3 |
| THE ARC OF FREDERICK COUNTY INC | Frederick | — | $16.4M | 5 |
| MAN-U SERVICE CONTRACT TRUST FUND | Columbia | — | $16.4M | 0 |
| WESTERN MARYLAND HEALTH CARE CORPORATION | Oakland | — | $16.3M | 9 |
| MID SHORE BEHAVIORAL HEALTH INC | Easton | F99Z Mental Health & Crisis Intervention | $16.3M | 2 |
| ARC OF CARROLL COUNTY INC | Westminster | — | $16.3M | 5 |
| FRIENDS HOUSE RETIREMENT COMMUNITY | Sandy Spring | E91Z Health Care | $16.3M | 7 |
| VOSE RIVER CHARITABLE FUND | Bethesda | E70 Health Care | $16.2M | 0 |
| INSTITUTE FOR OPERATIONS RESEARCH AND THE MANAGEMENT SCIENCES | Catonsville | V22 Social Science | $16.2M | 6 |
| JOHNS HOPKINS HOSPITAL ENDOWMENT FUND INC | Baltimore | E120 Health Care | $16.1M | 0 |
| For the Girls Inc | Wheaton | P85 Human Services | $16M | 1 |
| ALLIANCE FOR THE CHESAPEAKE BAY INC | Annapolis | C010 Environment | $16M | 6 |
| BALTIMORE AFFORDABLE HOUSING DEVELOPMENT INC | Baltimore | L20 Housing & Shelter | $16M | 6 |
| AMERICAN UROLOGICAL ASSOCIATION INC | Linthicum Hts | S41 Community Improvement & Capacity Building | $16M | 22 |
| DDW LLC | Bethesda | — | $16M | 1 |
| 4MyCity Inc | Baltimore | S20 Community Improvement & Capacity Building | $15.9M | 0 |
| CHINESE CULTURE AND COMMUNITY SERVICE CENTER INC | Gaithersburg | A230 Arts, Culture & Humanities | $15.9M | 0 |
| GLENSTONE FOUNDATION | Potomac | A40 Arts, Culture & Humanities | $15.9M | 2 |
