I have a Grid as a root container with two columns defined (There\'s only one row).
The first column has flexible width and second column has 300px fixed width.
You can make the Content of every ListBoxItem stretch by setting HorizontalContentAlignment in the ItemContainerStyle
<ListBox ...>
<ListBox.ItemContainerStyle>
<Style TargetType="ListBoxItem">
<Setter Property="HorizontalContentAlignment" Value="Stretch"/>
</Style>
</ListBox.ItemContainerStyle>