It might be easier to process the directory tree in two passes. I'm thinking something like the following might work:

#!/usr/bin/perl

use warnings;
use strict;
use File::Find;

my %targetdir;
my %visiteddir;

sub wanted_stage1 {
    return unless -f;
    $targetdir{$File::Find::dir}++ if /\.old$/;
}

sub postprocess {
    return unless $targetdir{$File::Find::dir};
    return if $visiteddir{$File::Find::dir}++;
    print "Changing files in $File::Find::dir\n";
}

# build list of directories containing *.old files:
find({wanted => \&wanted_stage1}, ".");

print "Directories to process: @{[sort keys %targetdir]}\n";

# process files in directory list:
find({wanted => sub{}, postprocess => \&postprocess}, sort keys %targe
+tdir);

__END__
.:
code.pl
code.txt
one
two

./one:
bar
foo
three

./one/three:
four
something.old

./one/three/four:
blah
something.old

./two:
bar
foo
something.old

Directories to process: ./one/three ./one/three/four ./two
Changing files in ./one/three/four
Changing files in ./one/three
Changing files in ./two
[download]