How many horses can you have in one homestead? Is it possible to have your hearthfire steward buy a horse for the homestead, buy a horse yourself at a stables, take Frost and earn Shadowmere. This will make a grand total of four horses in your homestead... is this possible?

You have three horses you mentioned, the one at the stables, and horse the carriage driver has.

So up to 5.

Is that including your wife? LOL

You're horse will walk away to it's natural post if you get up and Ride a different Horse.

For example if you brought your Horse that was bought from the Whiterun Stables to your Homestead, then went to get the Solitude Horse, your Whiterun horse would walk all the way back to the Whiterun Stables

But do Frost and Shadowmere have a natural post to walk away to? I heard Shadowmere just walks back to Falkreath Sanctuary if you get on another horse.

The horse will be in the place where you ride another horse.

Say you have Shadowmere, you buy a horse from the stable master, once you get on that new horse, Shadowmere will now be at those stables.

I was able to get that generic horse, Shadowmere, and Frost all in the Whiterun Stables.

Meh, All of my Horses just walk away to the Stables I bought them from.

That's why I bought that horse from the stables in Whiterun. It was also my home base.

How can I make ALL the horses stay at my homestead?

You have to bring them there manually.

Also a good idea to have Arvak. He will make the process alot easier.