| HEALTHPORT INC | Salisbury | F32 Mental Health & Crisis Intervention | $29.2M | 8 |
| THE BOYS AND GIRLS CLUBS OF METROPOLITAN BALTIMORE | Baltimore | O23 Youth Development | $29.1M | 5 |
| PENN-MAR ORGANIZATION INC (MD) | Freeland | F33Z Mental Health & Crisis Intervention | $29M | 5 |
| AMERICAN COLLEGE OF GASTROENTEROLOGY | North Bethesda | H700 Medical Research | $29M | 26 |
| MECHANICAL CONTRACTORS ASSOCIATION OF AMERICA INC | Rockville | — | $28.9M | 20 |
| BALTIMORE COUNTRY CLUB | Baltimore | — | $28.6M | 10 |
| WOODMONT COUNTRY CLUB | Rockville | — | $28.6M | 5 |
| DISABLED VETERANS NATIONAL FOUNDATION | Lanham | W30 Public & Societal Benefit | $28.6M | 4 |
| PLUMBERS AND PIPEFITTERS MEDICAL FUND C/O CARDAY ASSOCIATES | Columbia | — | $28.5M | 2 |
| BROOK LANE HEALTH SERVICES INC | Hagerstown | F31Z Mental Health & Crisis Intervention | $28.5M | 13 |
| CHESAPEAKE BAY TRUST | Annapolis | — | $28.4M | 5 |
| HUMANIM INC | Columbia | E50Z Health Care | $28.4M | 7 |
| KIPP BALTIMORE INC | Baltimore | B29 Education | $28.4M | 5 |
| HOMEWOOD LIVING MARTINSBURG INC | Williamsport | E91 Health Care | $28.3M | 6 |
| GLENELG COUNTRY SCHOOL INC | Ellicott City | B200 Education | $28.3M | 7 |
| MARYLAND ZOOLOGICAL SOCIETY INC | Baltimore | D500 Animal-Related | $28.2M | 7 |
| Easter Seals Serving DCMDVA Inc | Silver Spring | G20B Diseases, Disorders & Medical Disciplines | $28M | 8 |
| THE HUMANE LEAGUE | Rockville | D20 Animal-Related | $27.9M | 8 |
| RYUJI UENO FOUNDATION INC | Bethesda | T50 Philanthropy, Voluntarism & Grantmaking Foundations | $27.8M | 0 |
| BOARD OF TRUSTEES OF THE MID-ATLANTIC REGIONAL COUNCIL OF CARPENTERS HEALTH FU | Oxon Hill | Y43 Mutual & Membership Benefit | $27.8M | 0 |
| ST VINCENT DE PAUL OF BALTIMORE INC | Baltimore | P200 Human Services | $27.8M | 6 |
| Georgetown Hill Child Care Center Inc | Montgomery Village | P33Z Human Services | $27.7M | 9 |
| LUTHERAN VILLAGE AT MILLER'S GRANT | Westminster | L22 Housing & Shelter | $27.6M | 8 |
| THE ARC NORTHERN CHESAPEAKE REGION INC | Aberdeen | — | $27.4M | 7 |
| Coordinating Center for Home and Community Care Inc | Millersville | P44Z Human Services | $27.4M | 8 |
| MARYLAND STATE EDUCATION ASSOCIATION | Annapolis | J40 Employment | $27.4M | 14 |
| THE VENETOULIS INSTITUTE FOR LOCAL JOURNALISM | Baltimore | A33 Arts, Culture & Humanities | $27.3M | 14 |
| MORGAN STATE UNIVERSITY FOUNDATION INC | Baltimore | B43I Education | $27.3M | 0 |
| FAHRNEY-KEEDY MEMORIAL HOME INC AKA FAHRNEY-KEEDY HOME AND VILLAGE | Boonsboro | P750 Human Services | $27.2M | 7 |
| AMERICAN ASSOCIATION FOR LABORATORY ACCREDITATION | Frederick | U99D Science & Technology | $27.2M | 9 |
| COLUMBIA COUNTRY CLUB | Chevy Chase | — | $27.1M | 7 |
| COURTLAND GARDENS NURSING AND REHABILITATION CENTER INC | Baltimore | E91Z Health Care | $26.9M | 4 |
| ANNAPOLIS LIFE CARE INC | Annapolis | P750 Human Services | $26.9M | 8 |
| Inteleos | Rockville | — | $26.9M | 12 |
| NATIONAL CHILDREN'S CENTER INC | Silver Spring | P8XZ Human Services | $26.8M | 4 |
| ALLIANCE INC | Baltimore | J300 Employment | $26.8M | 4 |
| ROLAND PARK COUNTRY SCHOOL INC | Baltimore | B200 Education | $26.6M | 7 |
| BALTIMORE MUSEUM OF ART | Baltimore | A510 Arts, Culture & Humanities | $26.5M | 7 |
| Ourcare Inc | Lanham | E11 Health Care | $26.5M | 0 |
| PLUMBERS AND STEAMFITTERS LOCAL 486 MEDICAL FUND BOARD OF TRUSTEES | Columbia | — | $26.5M | 4 |
| THE SEED SCHOOL OF MARYLAND | Baltimore | B25 Education | $26.3M | 8 |
| Baltimore Washington Emergency Physicians Inc | Glen Burnie | E63Z Health Care | $26.1M | 14 |
| CREATIVE OPTIONS INC | Rosedale | P700 Human Services | $26M | 2 |
| PRIMARY CARE COALITION OF MONTGOMERY COUNTY MARYLAND INC | Silver Spring | E70 Health Care | $26M | 6 |
| ADVENTIST HOME HEALTH SERVICES INC | Gaithersburg | — | $25.8M | 16 |
| THE HEIGHTS INC | Potomac | — | $25.8M | 8 |
| MARYLAND MASONIC HOMES LTD | Cockeysville | L22 Housing & Shelter | $25.7M | 6 |
| MONTGOMERY COUNTY GREEN BANK CORPORATION | Rockville | C35 Environment | $25.5M | 3 |
| JOHNS HOPKINS HOME HEALTH SERVICES INC | Baltimore | E20Z Health Care | $25.5M | 10 |
| YOUNG MENS CHRISTIAN ASSOCIATION INC | Frederick | P270 Human Services | $25.3M | 5 |
