How to dynamically add a "CheckBox" or "List Box " property Item to a Property Grid

I have a requirement to add dynamically a list box or checkbox to a propertygrid at runtime. I do not know at compile time what type of property items to be added to property Grid.

I am able to achieve to add dynamically a simple property item like a text
by overriding the "PropertyDescriptor" Class in my customdescriptor class.

But how to add in similar way a checkbox or listbox to propertygrid dynamically ?
I was not successfull till now.

But I can achieve the same thing for example adding a checkbox property item at compile time(without overriding PropertyDescriptor) by using UiTypeEditor like:

public class CheckBoxTest : System.Drawing.Design.UITypeEditor
{
public override bool GetPaintValueSupported(ITypeDescriptorContext context)
{
return true;
}

public override void PaintValue(System.Drawing.Design.PaintValueEventArgs e)
{
System.Windows.Forms.ControlPaint.DrawCheckBox(e.Graphics, e.Bounds, ((CustomProperty)e.Context.Instance).checkValue ? ButtonState.Checked : ButtonState.Normal);
}
}

But If I try to achieve the above to be executed at runtime by overriding "PropertyDescriptor" These functions are not called.

Can anyone have any idea ?

Thanks,
Rajan