WPF - How to implement two-way data binding with the dynamically created control?

I'm writing a program that dynamically creates Control based on the data type of the properties extracted using reflection. Here is the view in subject for examination.

    <ListView ItemsSource="{Binding PropertyControls}">
        <ListView.ItemTemplate>
            <DataTemplate>
                <StackPanel Orientation="Horizontal" Margin="8">
                    <TextBlock Text="{Binding PropertyName}" FontSize="14" Width="400"></TextBlock>
                    <UserControl FontSize="14" Content="{Binding Path=PropertyValue, Converter={StaticResource PropertyValueConverter}}"></UserControl>
            </DataTemplate>
        </ListView.ItemTemplate>
    </ListView>

I created an item template for the items in ListView. Each row consists of two elements; the label and the dynamically created control.

For instance, if the PropertyValue is a boolean, then the dynamically created control will be a checkbox. If the PropertyValue is a string, then the dynamically created control will be a TextBox. If the PropertyValue is a list of FileInfo, then a separate window will be created with another ListView and browse button with OpenFileDialog.

I was able to accomplish the dynamically created control by creating a class that implements IValueConverter and which is utilized as specified in the XAML. The PropertyValueConverter converts the PropertyValue into a dynamically created control by inspecting its data type.

My problem is when the CheckBox is checked, there was no event raised and the ViewModel is not modified by its changes. I suspect because the binding in the XAML was made to the UserControl and not to its child control which happens to be a CheckBox. Although it is possible to bind the IsChecked programmatically in the PropertyValueConverter, is there a better way to solve this?