You could set a style on the ListBox, which switches ItemTemplate based on the number of items.
<ListBox ItemsSource="{Binding Items}">
<ListBox.Resources>
<local:SizeConverter x:Key="SizeConverter"/>
<DataTemplate x:Key="SmallTemplate"></DataTemplate>
<DataTemplate x:Key="MediumTemplate"></DataTemplate>
<DataTemplate x:Key="LargeTemplate"></DataTemplate>
</ListBox.Resources>
<ListBox.Style>
<Style TargetType="ListBox">
<Style.Triggers>
<DataTrigger Binding="{Binding Path=Items.Count, Converter={StaticResource SizeConverter}}" Value="Small">
<Setter Property="ItemTemplate" Value="{StaticResource SmallTemplate}"/>
</DataTrigger>
<DataTrigger Binding="{Binding Path=Items.Count, Converter={StaticResource SizeConverter}}" Value="Medium">
<Setter Property="ItemTemplate" Value="{StaticResource MediumTemplate}"/>
</DataTrigger>
<DataTrigger Binding="{Binding Path=Items.Count, Converter={StaticResource SizeConverter}}" Value="Large">
<Setter Property="ItemTemplate" Value="{StaticResource LargeTemplate}"/>
</DataTrigger>
</Style.Triggers>
</Style>
</ListBox.Style>
</ListBox>
The SizeConverter would be an IValueConverter which returns a size category based on the incoming count, the convert method could be something like this:
public object Convert(object value, Type targetType, object parameter, CultureInfo culture)
{
int count = (int)value;
if (count < 4) return "Large";
if (count < 12) return "Medium";
return "Small";
}