| OPERATIVE PLASTERERS AND CEMENT MASONS' INT'L ASSOC OF THE US & CANADA | Columbia | — | $25.2M | 18 |
| CHARTER SCHOOLS DEVELOPMENT CORPORATION | Hanover | B99 Education | $25M | 20 |
| THE EDUCATIONAL FOUNDATION OF AMERICA C/O INTENTIONAL PHILANTHROPY | Bethesda | T20 Philanthropy, Voluntarism & Grantmaking Foundations | $24.9M | 1 |
| THE FOUNDATION SCHOOLS | Largo | B24Z Education | $24.8M | 8 |
| ARDMORE ENTERPRISES INC | Lanham | J30Z Employment | $24.7M | 2 |
| COMMUNITY ACTION COUNCIL OF HOWARD COUNTY INC | Columbia | — | $24.7M | 7 |
| PROVIDENCE OF MARYLAND INC | Glen Burnie | J300 Employment | $24.5M | 5 |
| SEAFARERS INTERNATIONAL UNION OF NORTH A | Camp Springs | — | $24.5M | 21 |
| BRIDGINGLIFE INC | Westminster | — | $24.3M | 12 |
| INTERNATIONAL MASONRY TRAINING AND EDUCATION FOUNDATION | Bowie | B40 Education | $24.3M | 6 |
| CATHOLIC LEGAL IMMIGRATION NETWORK INC | Silver Spring | R20 Civil Rights, Social Action & Advocacy | $24.2M | 7 |
| BALTIMORE CIVIC FUND INC | Baltimore | T11 Philanthropy, Voluntarism & Grantmaking Foundations | $24.2M | 3 |
| JENKINS MEMORIAL NURSING HOME INC | Timonium | — | $24M | 3 |
| MEDSTAR AMBULATORY SERVICES INC | Columbia | — | $23.7M | 10 |
| PROJECT REDIRECT-DC | Silver Spring | P44 Human Services | $23.5M | 1 |
| ASSOCIATION FOR FINANCIAL PROFESSIONALS | Rockville | — | $23.4M | 12 |
| YOUNG MENS CHRISTIAN ASSOCIATION OF THE CHESAPEAKE INC | Easton | — | $23.3M | 3 |
| CASA INC | Hyattsville | — | $23.3M | 7 |
| NORWOOD SCHOOL INC | Bethesda | B240 Education | $23.3M | 7 |
| THE ARC OF HOWARD COUNTY INC | Ellicott City | P820 Human Services | $23.2M | 3 |
| THE JEMICY SCHOOL INC | Owings Mills | B280 Education | $23.1M | 8 |
| THE KEY SCHOOL INC | Annapolis | B200 Education | $23.1M | 7 |
| HOMEWOOD LIVING WILLIAMSPORT INC | Williamsport | L22Z Housing & Shelter | $23.1M | 9 |
| GEICO PHILANTHROPIC FOUNDATION | Chevy Chase | T20 Philanthropy, Voluntarism & Grantmaking Foundations | $22.9M | 0 |
| THE KAHLERT FOUNDATION INC | Sykesville | T20 Philanthropy, Voluntarism & Grantmaking Foundations | $22.9M | 3 |
| SEAFARERS HARRY LUNDEBERG SCHOOL OF SEAMANSHIP | Camp Springs | — | $22.7M | 0 |
| ACHIEVING THE DREAM INC | Silver Spring | B90 Education | $22.7M | 11 |
| SHORE UP INC P O BOX 430 | Salisbury | — | $22.5M | 1 |
| ASBURY COMMUNITIES INC | Frederick | E19 Health Care | $22.4M | 20 |
| FRONTLINE COMMUNITY SERVICES INC | Beltsville | L20 Housing & Shelter | $22.4M | 1 |
| VNA INC | Calverton | E020 Health Care | $22.4M | 11 |
| UNIVERSITY OF MARYLAND OBSTETRICAL AND GYNECOLOGICAL ASSOCIATES PA | Baltimore | — | $22.3M | 7 |
| Tuerk House Inc | Baltimore | F220 Mental Health & Crisis Intervention | $22.2M | 8 |
| 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 |
| THE AMERICAN OCCUPATIONAL THERAPY ASSOCIATION INC | Bethesda | — | $22M | 11 |
| 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 | $21.9M | 5 |
| FAMILY LEAGUE OF BALTIMORE CITY INC | Baltimore | P400 Human Services | $21.8M | 3 |
| US LACROSSE INC | Sparks | N70 Recreation & Sports | $21.8M | 10 |
| COLLEGEBOUND FOUNDATION | Baltimore | — | $21.7M | 4 |
| AMERICAN ASSOCIATION OF COLLEGES OF OSTEOPATHIC MEDICINE | Bethesda | B54C Education | $21.7M | 11 |
| KABOOM INC | Bethesda | N320 Recreation & Sports | $21.5M | 7 |
| PENN-MAR ORGANIZATION INC (PA) | Freeland | P82Z Human Services | $21.5M | 5 |
| THE NATIONAL FEDERATION OF THE BLIND | Baltimore | G41Z Diseases, Disorders & Medical Disciplines | $21.5M | 5 |
| VESTA INC | Lanham | F33Z Mental Health & Crisis Intervention | $21.4M | 7 |
| MELVIN J BERMAN HEBREW ACADEMY | Rockville | X30P Religion-Related | $21.3M | 9 |
| FUND FOR EDUCATIONAL EXCELLENCE INC | Baltimore | B20 Education | $21.3M | 8 |
| COLUMBIA VANTAGE HOUSE CORPORATION | Columbia | P750 Human Services | $21.2M | 6 |
| PLANNED PARENTHOOD OF MARYLAND INC | Baltimore | E420 Health Care | $21.1M | 8 |
