Can anyone recommend a great tube preamp that also has a headphone out?

+1 on the Rogue RP-5.  I have the RP-1 and really like it and the support has been good as well.

I've had a Manley 300 for a few years.  If your budget can handle it, it's a fine preamp. I just made my first audio purchase since the Manley and I'm pairing the Manley with nat mono blocks.  Like them together very much.  I looked at linear tube audio also. Also a strong contender.

@soix 

I agree with the Don Sachs Preamp. I hope to get one soon as well. But HOW does one get "spousal approval"?. I'm not sure my wife has ever given approval....at least until after she hears it. I had to sneak a ScoutMaster turntable in the house. She didn't notice cause it looked similar to the one it reeplaced. But I messed up a month later when I brought her the credit card bill with it listed. I didn't mean to do that.. That was about 10 yrs ago. Shes still with me....43 yrs this yr.

Check into the Rogue Pharaoh,  it's probably got all you ask for and more. Has a great headphone out! IMO. it's right in your budget brand new.

“...But HOW does one get "spousal approval"

Sometimes its much better to ask for forgiveness later than ask for permission first.