City | Rank | County | 2024 Pop. |
|---|---|---|---|
| California | 1 | St. Mary's County | 13,931 |
| Lexington Park | 2 | St. Mary's County | 13,856 |
| Chesapeake Ranch Estates | 3 | Calvert County | 9,931 |
| Wildewood | 4 | St. Mary's County | 8,675 |
| Leonardtown | 5 | St. Mary's County | 5,102 |
| Golden Beach | 6 | Charles County | 3,956 |
| Drum Point | 7 | Calvert County | 3,020 |
| Lusby | 8 | Calvert County | 2,436 |
| Solomons | 9 | Calvert County | 2,221 |
| Mechanicsville | 10 | St. Mary's County | 1,829 |
| Long Beach | 11 | Calvert County | 1,751 |
| Callaway | 12 | St. Mary's County | 1,419 |
| Charlotte Hall | 13 | St. Mary's County | 1,408 |
| Cobb Island | 14 | Charles County | 1,320 |
| Calvert Beach | 15 | Calvert County | 1,062 |
| Piney Point | 16 | St. Mary's County | 1,061 |
| St. Leonard | 17 | Calvert County | 582 |
| Broomes Island | 18 | Calvert County | 544 |
| Tall Timbers | 19 | St. Mary's County | 483 |
| St. George Island | 20 | St. Mary's County | 200 |
| Benedict | 21 | Charles County | 128 |
| Taylors Island | 22 | Dorchester County | 98 |
| Rock Point | 23 | Charles County | 80 |
| Port Tobacco Village | 24 | Charles County | 25 |