It's hard to really tell. It most likely means that he does have some sort of feelings for you that's for sure. Whether he actually likes you back or not is a bit difficult to know.
Some people can have this superiority complex where they want you to be under their control. Walking you home and asking you about liking him keeps you thinking about him and it kinda keeps that crush you had on him alive. And when you have a crush on someone, it's very easy to be manipulated by that person you're crushing on. So if your close friend is a control freak with a superiority complex, he'll do whatever it takes for you to continue to have that crush on him maybe without him actually realizing it. Plus it does make you feel pretty superior when you know that you are wanted.
But on the other hand, it could mean that he is interested in you. I find that it's rather interesting he's asking whether you regret liking him. It's as if he doesn't want you to regret anymore since he now likes you but it could also mean that he's just trying to keep your crush alive as I've said before.
If you really want to know for sure, then talk to him. You said he was a close friend so this shouldn't be much of a problem. When talking to him about this, be sure that you're nowhere near people who could possibly influence his response. You want him to be honest with you. Also don't make it too serious when you ask him either so try to take it rather lightly. Even though the matter isn't something you would typically take lightly, the lightly attitude toward it would keep a lot of pressure off from your friend. The less pressure he's under, the more likely he is to be able to converse with you about this freely.
Anyway, best of luck to you!