if using Ancestor you have to bind to DataContext
<CheckBox IsEnabled="{Binding Path=DataContext.enabledVar,
RelativeSource={RelativeSource Mode=FindAncestor,
AncestorType=telerik:RadGridView}}"
Another aproach could be to use element binding set name
<telerik:RadGridView x:Name="myGrid" ...
And then in the celltemplate bind to it
<CheckBox IsEnabled="{Binding Path=DataContext.enabledVar, ElementName=myGrid}"
Hope this helps.