| SHOCK TRAUMA ASSOCIATES PA | Baltimore | E63Z Health Care | $34.8M | 12 |
| J Willard and Alice S Marriott Foundation | Bethesda | T20 Philanthropy, Voluntarism & Grantmaking Foundations | $34.3M | 2 |
| SO WHAT ELSE INC | Bethesda | T40 Philanthropy, Voluntarism & Grantmaking Foundations | $33.8M | 1 |
| THE MONARCH ACADEMY PUBLIC CHARTER SCHOOL INC | Baltimore | B29 Education | $33.6M | 2 |
| LUMINIS HEALTH IMAGING INC | Annapolis | E30Z Health Care | $33.6M | 14 |
| CALVERT IMPACT CAPITAL INC | Bethesda | S300 Community Improvement & Capacity Building | $33.4M | 8 |
| THE JUBILEE ASSOCIATION OF MARYLAND INC | Kensington | P700 Human Services | $33.4M | 8 |
| MONTGOMERY HOSPICE INC | Rockville | P740 Human Services | $33.2M | 14 |
| WASHINGTON ADVENTIST UNIVERSITY | Takoma Park | B42Z Education | $33M | 7 |
| ROLAND PARK PLACE INC | Baltimore | P750 Human Services | $33M | 8 |
| Oxford House Inc | Silver Spring | — | $32.9M | 2 |
| AMERICAN YOUTH HOSTELS INC | Silver Spring | L40C Housing & Shelter | $32.7M | 14 |
| Mercy Ridge Inc | Timonium | L220 Housing & Shelter | $32.5M | 5 |
| Center for Social Change Inc | Elkridge | Q30 International, Foreign Affairs & National Security | $32.5M | 9 |
| NORTH EAST REGIONAL BOARD OF DENTAL EXAMINERS INC | Linthicum | — | $32.5M | 28 |
| CALVERT SCHOOL INCORPORATED | Baltimore | B200 Education | $32.5M | 7 |
| THE BENEDICTINE SCHOOL FOR EXCEPTIONAL CHILDREN INC | Ridgely | B28 Education | $32.3M | 8 |
| SECOND FAMILY INC | Lanham | P700 Human Services | $32.3M | 11 |
| THE ARC OF SOUTHERN MARYLAND INC | Prince Frederick | — | $32.1M | 7 |
| Dimensions Healthcare Associates Inc | Upper Marlboro | E99Z Health Care | $32M | 13 |
| CORNERSTONE MONTGOMERY | Rockville | — | $31.9M | 9 |
| THE VILLAGE AT ORCHARD RIDGE INC | Frederick | L22 Housing & Shelter | $31.9M | 7 |
| SOMERSET COMMUNITY SERVICES INC | Marion Station | B82Z Education | $31.8M | 3 |
| JEWISH FOUNDATION FOR GROUP HOMES INC | Rockville | P700 Human Services | $31.6M | 8 |
| THE UNITED WAY OF CENTRAL MARYLAND INC | Baltimore | T700 Philanthropy, Voluntarism & Grantmaking Foundations | $31.6M | 33 |
| COLLINGTON EPISCOPAL LIFE CARE COMMUNITY INC | Mitchellville | P750 Human Services | $31.5M | 8 |
| UNIVERSITY OF MARYLAND ANESTHESIOLOGY ASSOCIATES PA | Baltimore | — | $31.5M | 15 |
| THE LIEBER INSTITUTE INC | Baltimore | H48 Medical Research | $31.3M | 10 |
| UNIVERSITY OF MARYLAND EMERGENCY MEDICINE ASSOCIATES PA | Baltimore | E63Z Health Care | $30.7M | 14 |
| SEVERN SCHOOL INC | Severna Park | B25Z Education | $30.7M | 7 |
| HEALTH CARE FOR THE HOMELESS INC | Baltimore | — | $30.7M | 11 |
| INTERNATIONAL UNION OF ELEVATOR CONSTRUCTORS | Columbia | — | $30.7M | 28 |
| ANNE ARUNDEL COUNTY MENTAL HEALTH AGENCY INC | Annapolis | F99Z Mental Health & Crisis Intervention | $30.6M | 7 |
| ADVENTIST PHYSICIAN SERVICES INC | Gaithersburg | — | $30.6M | 11 |
| WESTMINSTER PRESBYTERIAN RETIREMENT COMMUNITY INC | Rockville | P750 Human Services | $30.6M | 11 |
| THE MCLEAN SCHOOL OF MARYLAND INC | Potomac | B200 Education | $30.4M | 10 |
| AMERICAN GASTROENTEROLOGICAL ASSOCIATION INSTITUTE | Bethesda | G70Z Diseases, Disorders & Medical Disciplines | $30.3M | 23 |
| GARRISON FOREST SCHOOL INC | Owings Mills | B200 Education | $30.3M | 7 |
| THE BOYS' LATIN SCHOOL OF MARYLAND INC | Baltimore | B200 Education | $30.2M | 8 |
| IBEW LOCAL UNION NO 26 | Lanham | — | $30.2M | 18 |
| RAST FOUNDATION | Bethesda | T22 Philanthropy, Voluntarism & Grantmaking Foundations | $30.1M | 0 |
| BAKERY AND CONFECTIONERY UNION AND INDUSTRY INTERNATIONAL HEALTH BENEFITS FUND | Kensington | — | $30.1M | 12 |
| AUTO CARE ASSOCIATION | Bethesda | S41 Community Improvement & Capacity Building | $29.9M | 12 |
| UNIFIED COMMUNITY CONNECTIONS INC | Sparks | G23Z Diseases, Disorders & Medical Disciplines | $29.9M | 9 |
| JOHNS HOPKINS PEDIATRICS AT HOME INC | Baltimore | E60Z Health Care | $29.7M | 20 |
| PICKERSGILL INC | Towson | P750 Human Services | $29.7M | 6 |
| Calvert Health System Inc | Prince Frederick | E11 Health Care | $29.5M | 20 |
| JEWISH COMMUNITY SERVICES INC | Baltimore | P40 Human Services | $29.3M | 8 |
| PEOPLE ENCOURAGING PEOPLE INC | Baltimore | F80Z Mental Health & Crisis Intervention | $29.2M | 13 |
| 88 PLAN TRUST | Baltimore | Y43 Mutual & Membership Benefit | $29.2M | 0 |
