| CHOPTANK COMMUNITY HEALTH SYSTEM INC | Denton | E320 Health Care | $32.8M | 7 |
| SHOCK TRAUMA ASSOCIATES PA | Baltimore | E63Z Health Care | $32.7M | 12 |
| GENERAL GERMAN AGED PEOPLES HOME | Towson | P750 Human Services | $32.6M | 7 |
| Mercy Ridge Inc | Timonium | L220 Housing & Shelter | $32.5M | 5 |
| THE BOYS' LATIN SCHOOL OF MARYLAND INC | Baltimore | B200 Education | $32.3M | 7 |
| CHESAPEAKE BAY FOUNDATION INC | Annapolis | C320 Environment | $32.2M | 11 |
| UNIVERSITY OF MARYLAND ORTHOPAEDIC | Baltimore | B40 Education | $32M | 10 |
| THE VILLAGE AT ORCHARD RIDGE INC | Frederick | L22 Housing & Shelter | $31.9M | 7 |
| KIPP BALTIMORE INC | Baltimore | B29 Education | $31.7M | 6 |
| JEWISH FOUNDATION FOR GROUP HOMES INC | Rockville | P700 Human Services | $31.6M | 8 |
| AFRICAN POPULATION & HEALTH | Rockville | V35 Social Science | $31.6M | 17 |
| COLLINGTON EPISCOPAL LIFE CARE | Mitchellville | P750 Human Services | $31.5M | 8 |
| PENN-MAR ORGANIZATION INC (MD) | Freeland | F33Z Mental Health & Crisis Intervention | $31.5M | 5 |
| LUMINIS HEALTH IMAGING INC | Annapolis | E30Z Health Care | $31.3M | 13 |
| SEVERN SCHOOL INC | Severna Park | B25Z Education | $30.7M | 7 |
| HEALTH CARE FOR THE HOMELESS INC | Baltimore | — | $30.7M | 11 |
| Center for Social Change Inc | Elkridge | Q30 International, Foreign Affairs & National Security | $30.6M | 9 |
| UNIVERSITY OF MARYLAND EMERGENCY | Baltimore | E63Z Health Care | $30.5M | 14 |
| THE ARC OF SOUTHERN MARYLAND INC | Prince Frederick | — | $30.5M | 7 |
| THE MCLEAN SCHOOL OF MARYLAND INC | Potomac | B200 Education | $30.4M | 10 |
| UNIFIED COMMUNITY CONNECTIONS INC | Sparks | G23Z Diseases, Disorders & Medical Disciplines | $30.4M | 9 |
| JOHNS HOPKINS PEDIATRICS AT HOME INC | Baltimore | E60Z Health Care | $30.3M | 19 |
| AMERICAN GASTROENTEROLOGICAL ASSOCIATION | Bethesda | G70Z Diseases, Disorders & Medical Disciplines | $30.3M | 23 |
| IBEW LOCAL UNION NO 26 | Lanham | — | $30.2M | 18 |
| RAST FOUNDATION | Bethesda | T22 Philanthropy, Voluntarism & Grantmaking Foundations | $30.1M | 0 |
| DIGITAL HARBOR FOUNDATION INC | Baltimore | B82 Education | $29.9M | 4 |
| TIME ORGANIZATION INC | Baltimore | I21 Crime & Legal-Related | $29.9M | 1 |
| THE VENETOULIS INSTITUTE FOR | Baltimore | A33 Arts, Culture & Humanities | $29.8M | 13 |
| COMPASS INC | Beltsville | P82 Human Services | $29.8M | 4 |
| PICKERSGILL INC | Towson | P750 Human Services | $29.7M | 6 |
| INTERNATIONAL UNION OF ELEVATOR | Columbia | — | $29.6M | 28 |
| WASHINGTON ADVENTIST UNIVERSITY | Takoma Park | B42Z Education | $29.5M | 6 |
| NORTH EAST REGIONAL BOARD OF DENTAL | Linthicum | — | $29.5M | 29 |
| ANNE ARUNDEL COUNTY MENTAL HEALTH AGENCY INC | Annapolis | F99Z Mental Health & Crisis Intervention | $29.5M | 5 |
| ADVENTIST PHYSICIAN SERVICES INC | Gaithersburg | — | $29.4M | 9 |
| WESTMINSTER PRESBYTERIAN RETIREMENT | Rockville | P750 Human Services | $29.4M | 11 |
| JEWISH COMMUNITY SERVICES INC | Baltimore | P40 Human Services | $29.3M | 8 |
| PEOPLE ENCOURAGING PEOPLE INC | Baltimore | F80Z Mental Health & Crisis Intervention | $29.2M | 13 |
| HEALTHPORT INC | Salisbury | F32 Mental Health & Crisis Intervention | $29.2M | 8 |
| ROLAND PARK PLACE INC | Baltimore | P750 Human Services | $29.2M | 8 |
| MECHANICAL CONTRACTORS ASSOCIATION | Rockville | — | $28.9M | 20 |
| THE LIEBER INSTITUTE INC | Baltimore | H48 Medical Research | $28.9M | 10 |
| BALTIMORE COUNTRY CLUB | Baltimore | — | $28.6M | 10 |
| DISABLED VETERANS NATIONAL FOUNDATION | Lanham | W30 Public & Societal Benefit | $28.6M | 4 |
| ROLAND PARK COUNTRY SCHOOL INC | Baltimore | B200 Education | $28.5M | 8 |
| BROOK LANE HEALTH SERVICES INC | Hagerstown | F31Z Mental Health & Crisis Intervention | $28.5M | 13 |
| SHORE UP INC | Salisbury | — | $28.4M | 1 |
| CHESAPEAKE BAY TRUST | Annapolis | — | $28.4M | 5 |
| HOMEWOOD LIVING MARTINSBURG INC | Williamsport | E91 Health Care | $28.3M | 6 |
| ST VINCENT DE PAUL OF BALTIMORE INC | Baltimore | P200 Human Services | $28.2M | 2 |
