To reproduce:
- set the alignment like this:
radCheckedListBox1.CheckBoxesPosition = Telerik.WinControls.UI.CheckBoxesPosition.Top;
radCheckedListBox1.CheckBoxesAlignment = Telerik.WinControls.UI.CheckBoxesAlignment.Near;

Workaround:
void radListView1_VisualItemFormatting(object sender, ListViewVisualItemEventArgs e)
{
    DetailListViewVisualItem item = e.VisualItem as DetailListViewVisualItem;
    if (item != null)
    {
        var checkBox = item.Children[0] as ListViewItemCheckbox;
        checkBox.PositionOffset = new SizeF(0, - (radCheckedListBox1.ItemSize.Height /2 - checkBox.Size.Height/2));
    }
}