| 1 | Luminis Health Anne Arundel Medical Center INC | Health Care | $686.9M | $1.1B |
| 2 | Luminis Health Doctors Community Medical Center INC | Health Care | $254.6M | $214.4M |
| 3 | Physician Enterprise LLC | Health Care | $251.8M | $43.1M |
| 4 | United Association of Journeymen & Apprentices of the Plumbing & Pipe | Employment | $204.6M | $492.2M |
| 5 | United States Naval Academy Foundation INC | Education | $204.1M | $369.1M |
| 6 | Luminis Health INC | Health Care | $150.9M | $810.6M |
| 7 | St. Johns College | Education | $138.5M | $494.3M |
| 8 | Chesapeake Bay Foundation INC | Environment | $61.4M | $129.3M |
| 9 | United States Naval Academy Alumni Assoc | Education | $59.2M | $155.3M |
| 10 | Arundel Community Development Services INC | Housing & Shelter | $39.9M | $32.1M |
| 11 | International Training Fund | Community Improvement & Capacity Building | $36.9M | $56.9M |
| 12 | Public Library Association of Annapolis and a a Co INC | Unclassified | $35.9M | $30.5M |
| 13 | Luminis Health Imaging INC | Health Care | $33.6M | $126.2M |
| 14 | Anne Arundel County Mental Health Agency INC | Mental Health & Crisis Intervention | $30.6M | $12.0M |
| 15 | Community Foundation of Anne Arundel County INC | Philanthropy, Voluntarism & Grantmaking | $28.9M | $41.8M |
| 16 | Philip E and Carole R Ratcliffe Foundation INC | Philanthropy, Voluntarism & Grantmaking | $28.2M | $62.5M |
| 17 | Maryland State Education Association | Employment | $27.4M | $56.0M |
| 18 | Annapolis Life Care INC | Human Services | $27.0M | $114.1M |
| 19 | Innovative Learning INC | Education | $23.8M | $22.7M |
| 20 | Key School INC | Education | $23.2M | $69.6M |
| 21 | Langton Green INC | Human Services | $22.3M | $23.9M |
| 22 | Annapolis Yacht Club INC | Unclassified | $20.3M | $65.9M |
| 23 | Alliance for the Chesapeake Bay INC | Environment | $16.1M | $10.6M |
| 24 | Homes for America INC | Housing & Shelter | $15.7M | $50.0M |
| 25 | Chesapeake Conservancy INC | Environment | $15.3M | $20.6M |
| 26 | Plasma Protein Therapeutics Association | Unclassified | $15.0M | $12.8M |
| 27 | Naval Academy Sailing Foundation INC | Public & Societal Benefit | $13.8M | $33.2M |
| 28 | Luminis Health Real Estate Holding Company INC | Unclassified | $13.7M | $71.6M |
| 29 | National Investment Center for Seniors Housing & Care INC | Human Services | $13.3M | $38.9M |
| 30 | Bay Community Support Services INC | Human Services | $13.3M | $13.6M |
| 31 | United States Naval Institute | Unclassified | $12.8M | $7.8M |
| 32 | Luminis Health Anne Arundel Medical Center Foundation INC | Health Care | $11.6M | $38.1M |
| 33 | Entomological Society of America | Science & Technology | $11.1M | $6.8M |
| 34 | Maryland Rural Development Corporation | Community Improvement & Capacity Building | $10.1M | $5.5M |
| 35 | Harbour School Foundation INC | Education | $9.9M | $26.9M |
| 36 | Oyster Recovery Partnership INC | Unclassified | $9.6M | $2.7M |
| 37 | Maryland Association of Realtors INC | Unclassified | $9.3M | $30.4M |
| 38 | St. Annes School of Annapolis Incorporated | Unclassified | $8.4M | $4.9M |
| 39 | Historic Annapolis INC | Arts, Culture & Humanities | $7.6M | $21.8M |
| 40 | Trace International INC | Community Improvement & Capacity Building | $7.5M | $8.8M |
| 41 | Luminis Health J Kent McNew Family Medical Center INC | Mental Health & Crisis Intervention | $7.3M | $25.7M |
| 42 | Aviation Information Sharing and Analysis Center INC | Community Improvement & Capacity Building | $6.9M | $6.3M |
| 43 | The Naval Institute Foundation Incorporated | Unclassified | $6.1M | $14.7M |
| 44 | The Light House INC | Housing & Shelter | $6.1M | $14.4M |
| 45 | Qm Quality Matters | Education | $6.0M | $6.7M |
| 46 | Visit Annapolis & Anne Arundel County INC | Unclassified | $5.6M | $6.5M |
| 47 | Flexible Packaging Association | Unclassified | $5.2M | $3.5M |
| 48 | Stover Foundation 09-19-96 | Philanthropy, Voluntarism & Grantmaking | $5.1M | $25.5M |
| 49 | Maryland Hall for the Creative Arts INC | Arts, Culture & Humanities | $5.0M | $16.5M |
| 50 | Americans United for Democracy INC | Public & Societal Benefit | $4.8M | $129K |
| 51 | The Joseph E & Marjorie B Jones Foundation | Unclassified | $4.8M | $24.0M |
| 52 | Maryland Network Against Domestic Violence INC | Unclassified | $4.8M | $1.6M |
| 53 | Anne Arundel County Community Action Agency INC | Community Improvement & Capacity Building | $4.8M | $3.1M |
| 54 | Anne Arundel Economic Development Corporation | Community Improvement & Capacity Building | $4.4M | $10.2M |
| 55 | Luminis Health Pathways INC | Mental Health & Crisis Intervention | $4.3M | $8.3M |
| 56 | Washington International Horseshow Association Ltd | Recreation & Sports | $4.3M | $776K |
| 57 | Annapolis Symphony Orchestra Association INC | Arts, Culture & Humanities | $4.3M | $5.8M |
| 58 | Eastport Yacht Club Ltd | Unclassified | $4.1M | $10.8M |
| 59 | Bywater Mutual Homes INC | Unclassified | $4.1M | $12.3M |
| 60 | Chase Home INC | Unclassified | $3.9M | $8.0M |
| 61 | Teachers Association of Anne Arundel County Incorporated | Unclassified | $3.9M | $7.9M |
| 62 | Parents for Montessori Education INC | Education | $3.9M | $9.0M |
| 63 | Naval Academy Primary School Association Incorporated | Education | $3.8M | $1.3M |
| 64 | Bomi International 457 B Plan | Unclassified | $3.8M | $3.4M |
| 65 | Race for Life INC | Animal-Related | $3.8M | $5.7M |
| 66 | American Boat and Yacht Council INC | Unclassified | $3.7M | $1.9M |
| 67 | Maryland United Fc | Recreation & Sports | $3.6M | $1.7M |
| 68 | Annapolis Maritime Museum INC | Unclassified | $3.4M | $9.6M |
| 69 | Boys & Girls Clubs of Annapolis & Anne Arundel County INC | Youth Development | $3.3M | $4.5M |
| 70 | Milton J Dance Jr Endowment INC | Unclassified | $3.2M | $51.7M |
| 71 | Kathy Jerry Wood Foundation INC | Philanthropy, Voluntarism & Grantmaking | $3.2M | $19.0M |
| 72 | Constitution Foundation | Philanthropy, Voluntarism & Grantmaking | $3.1M | $17.3M |
| 73 | Chaney Foundation Ltd | Unclassified | $3.0M | $5.4M |
| 74 | Dea Code Family Foundation INC | Philanthropy, Voluntarism & Grantmaking | $2.9M | $17.9M |
| 75 | Society for the Prevention of Cruelty to Animals of a a Co Md in | Animal-Related | $2.9M | $18.0M |
| 76 | Chesapeake Montessori Foundation INC | Education | $2.9M | $3.6M |
| 77 | Harbour House INC | Mental Health & Crisis Intervention | $2.8M | $1.4M |
| 78 | Pepsi-cola Bottlers Association | Unclassified | $2.8M | $2.3M |
| 79 | T O U C H Therapy INC | Diseases, Disorders & Medical Disciplines | $2.6M | $1.6M |
| 80 | Fleet Reserve Club of Annapolis INC | Unclassified | $2.5M | $2.9M |
| 81 | Maryland Chamber of Commerce INC | Unclassified | $2.5M | $1.9M |
| 82 | Tose Foundation INC | Philanthropy, Voluntarism & Grantmaking | $2.5M | $4.2M |
| 83 | Wrage Foundation | Philanthropy, Voluntarism & Grantmaking | $2.2M | $5.1M |
| 84 | Alvin & Louise Myerberg Family Foundation INC | Philanthropy, Voluntarism & Grantmaking | $2.1M | $8.1M |
| 85 | Upstream Alliance INC | Environment | $2.0M | $3.4M |
| 86 | Norman J Fisher and Doris Fisher Foundation | Philanthropy, Voluntarism & Grantmaking | $2.0M | $7.0M |
| 87 | Journey to Lead INC | Science & Technology | $1.9M | $2.2M |
| 88 | Associated Builders & Contractors INC | Unclassified | $1.9M | $481K |
| 89 | Maryland Forestry Boards Foundation INC | Environment | $1.7M | $119K |
| 90 | Fordi Family Foundation INC | Philanthropy, Voluntarism & Grantmaking | $1.7M | $4.5M |
| 91 | Maryland Independent College and University Assoc INC | Unclassified | $1.6M | $2.6M |
| 92 | Arts Council of Anne Arundel County INC | Philanthropy, Voluntarism & Grantmaking | $1.6M | $1.3M |
| 93 | Teachers Council INC | Education | $1.6M | $402K |
| 94 | Samaritan Houses INC | Mental Health & Crisis Intervention | $1.6M | $5.1M |
| 95 | Maryland League of Conservation Voters Education Fund | Environment | $1.5M | $1.4M |
| 96 | Chesapeake Legal Alliance INC | Environment | $1.5M | $1.6M |
| 97 | American Legion | Unclassified | $1.5M | $207K |
| 98 | Associated Builders & Contractors INC | Community Improvement & Capacity Building | $1.5M | $1.6M |
| 99 | Navy-marine Corps Regional Training Center | Unclassified | $1.4M | $2.8M |
| 100 | The Ballet Theatre of Maryland Incorporated | Arts, Culture & Humanities | $1.4M | $621K |