| SEAFARERS INTERNATIONAL UNION OF NORTH A | Camp Springs | — | $24.5M | 21 |
| COURTLAND GARDENS NURSING AND REHABILITATION CENTER INC | Baltimore | E91Z Health Care | $24.3M | 4 |
| CATHOLIC LEGAL IMMIGRATION NETWORK INC | Silver Spring | R20 Civil Rights, Social Action & Advocacy | $24.2M | 7 |
| MEDSOURCE COMMUNITY SERVICES INC | Hagerstown | P20Z Human Services | $24.2M | 10 |
| CONSTELLATION ENERGY FOUNDATION INC CFND01 | Baltimore | — | $24.1M | 0 |
| ADVENTIST HOME HEALTH SERVICES INC | Gaithersburg | — | $23.7M | 16 |
| ALLIANCE INC | Timonium | J300 Employment | $23.7M | 4 |
| PROJECT REDIRECT-DC | Silver Spring | P44 Human Services | $23.5M | 1 |
| YOUNG MENS CHRISTIAN ASSOCIATION OF THE CHESAPEAKE INC | Easton | — | $23.3M | 3 |
| NORWOOD SCHOOL INC | Bethesda | B240 Education | $23.3M | 7 |
| THE JEMICY SCHOOL INC | Owings Mills | B280 Education | $23.1M | 8 |
| THE HEIGHTS INC | Potomac | — | $23.1M | 7 |
| THE KEY SCHOOL INC | Annapolis | B200 Education | $23.1M | 7 |
| THE KEITH CAMPBELL FOUNDATION FOR THE ENVIRONMENT INC | Bethesda | T20 Philanthropy, Voluntarism & Grantmaking Foundations | $23.1M | 1 |
| GEICO PHILANTHROPIC FOUNDATION | Chevy Chase | T20 Philanthropy, Voluntarism & Grantmaking Foundations | $22.9M | 0 |
| SAINT JAMES SCHOOL | Hagerstown | B200 Education | $22.9M | 2 |
| SEAFARERS HARRY LUNDEBERG SCHOOL OF SEAMANSHIP | Camp Springs | — | $22.7M | 0 |
| PRIMARY CARE COALITION OF MONTGOMERY COUNTY MARYLAND INC | Silver Spring | E70 Health Care | $22.5M | 6 |
| THE MORNINGSTAR PHILANTHROPIC FOUNDATION D/B/A THE MORNINGSTAR FOUNDATION | Bethesda | — | $22.4M | 0 |
| JERROLD VAN WINTER CHARITABLE FOUNDATION | Rockville | T20 Philanthropy, Voluntarism & Grantmaking Foundations | $22.2M | 0 |
| EDITORIAL PROJECTS IN EDUCATION INC | Bethesda | A330 Arts, Culture & Humanities | $22.2M | 9 |
| PENN-MAR ORGANIZATION INC (PA) | Freeland | P82Z Human Services | $22.1M | 5 |
| THE SEED SCHOOL OF MARYLAND | Baltimore | B25 Education | $22M | 7 |
| JENKINS MEMORIAL NURSING HOME INC | Timonium | — | $22M | 3 |
| AUTO CARE ASSOCIATION | Bethesda | S41 Community Improvement & Capacity Building | $22M | 12 |
| STA OF BALTIMORE-ILA VACATION AND HOLIDAY FUND | Baltimore | J40 Employment | $21.9M | 3 |
| THE COMMUNITY FOUNDATION OF FREDERICK COUNTY MARYLAND INC | Frederick | T31 Philanthropy, Voluntarism & Grantmaking Foundations | $21.7M | 5 |
| AMERICAN ASSOCIATION OF COLLEGES OF OSTEOPATHIC MEDICINE | Bethesda | B54C Education | $21.7M | 11 |
| MARYLAND ZOOLOGICAL SOCIETY INC | Baltimore | D500 Animal-Related | $21.6M | 7 |
| THE NATIONAL FEDERATION OF THE BLIND | Baltimore | G41Z Diseases, Disorders & Medical Disciplines | $21.5M | 5 |
| Association for Financial Professionals | Rockville | — | $21.5M | 11 |
| KABOOM INC | Bethesda | N320 Recreation & Sports | $21.5M | 7 |
| ASBURY COMMUNITIES INC | Frederick | E19 Health Care | $21.4M | 21 |
| BRIDGINGLIFE INC | Westminster | — | $21.4M | 10 |
| UNIVERSITY OF MARYLAND OBSTETRICAL AND GYNECOLOGICAL ASSOCIATES PA | Baltimore | — | $21.4M | 7 |
| MELVIN J BERMAN HEBREW ACADEMY | Rockville | X30P Religion-Related | $21.3M | 9 |
| J Willard and Alice S Marriott Foundation | Bethesda | T20 Philanthropy, Voluntarism & Grantmaking Foundations | $21.3M | 2 |
| FUND FOR EDUCATIONAL EXCELLENCE INC | Baltimore | B20 Education | $21.3M | 8 |
| HIAS FOUNDATION INC | Silver Spring | Q12 International, Foreign Affairs & National Security | $21.2M | 1 |
| PLANNED PARENTHOOD OF MARYLAND INC | Baltimore | E420 Health Care | $21.1M | 8 |
| HOMEWOOD AT WILLIAMSPORT MD INC | Williamsport | L22Z Housing & Shelter | $21.1M | 10 |
| WAREHOUSE EMPLOYEES LOCAL NO 570 TRUST FUND | Baltimore | — | $21.1M | 2 |
| VNA INC | Calverton | E020 Health Care | $21M | 12 |
| INTERNATIONAL MASONRY INSTITUTE | Bowie | — | $21M | 9 |
| AMERICAN ASSOCIATION OF ZOOLOGICAL PARKS AND AQUARIUMS INC | Silver Spring | D030 Animal-Related | $20.9M | 8 |
| THE KAHLERT FOUNDATION INC | Sykesville | — | $20.9M | 3 |
| Dimensions Healthcare Associates Inc | Upper Marlboro | E99Z Health Care | $20.8M | 13 |
| THE AFFILIATED SANTE GROUP | Silver Spring | F99Z Mental Health & Crisis Intervention | $20.7M | 10 |
| IDENTITY INC | Gaithersburg | G81 Diseases, Disorders & Medical Disciplines | $20.5M | 6 |
| THE AMERICAN OCCUPATIONAL THERAPY ASSOCIATION INC | North Bethesda | — | $20.3M | 10 |
