Can headphones ever be as good as high end stereo?

For me, it's not either/or but both/and.

I enjoy listening to my Spendor speakers, and I also enjoy music through my Sennheiser HD800 headphones.

The HD800s were game-changers for me. Like you, I had mainly owned modest headphones before, some basic Grados, and a more expensive pair of AKG 702 (the 65th Anniversary edition). The AKGs made me realize that headphones can be better than I had thought. And now that I have the HD800s, I thoroughly enjoy listening through headphones.

The HD800s have an actual sense of soundstage, unlike headphones that put everything between your ears. They are comfortable, at least on my head. And they sound superb driven by OTL tubes amps, including a modest little Bottlehead Crack and a Woo WA2.

I mainly listen to classical and jazz, and I do like to turn it up when the music demands. The HD800s remain clean at high volumes. (Not ear-damaging levels, of course.) And I don't find them to be bright, at least not when driven by the tube amps I use.

One caveat -- I don't do vinyl. So, I can't say whether record surface noise or turntable mechanical noise would be exacerbated through headphones.

I haven't tried Stax electrostatics--and am in no rush to do so, given how much I like the HD800s.

I might sound like a salesman for Sennheiser but I have no affiliation -- just an audiophile and music lover happy with a purchase.

My solution to the wife volume problem was to buy a ranch-style house. She goes to the bedroom at one end of the house, my listening room is all the way at the other end.

Sometimes the best way to keep it together is to keep yourselves apart!

My first pair of good headphones were Sennheiser HD424s back in the early 1980's. My most recent pair is the larger Sennheiser Momentum. I've listened to them all over the years. The Sennheiser line always place consistently strongly, at most any price point. Audio Technica as well. I have always wanted to like AKGs, and they can be very good, but I have had many poor auditions of those over the years. My sampling of STAX phones is much smaller, but that is the other long time gold standard line I know of, though marketing of these to US has changed considerably over the years. Hard to find in the US to audition these days.

I've listened to a lot of phones in last few years and have heard most of the leading contenders. Lots of useful headphone reviews availble to sort through. You'll find many well liked ones and little agreement on what is best. There are some nice newer lines out there as well, but I have not heard anything there that clearly knocks out the long term leaders. Just more good stuff to sort through and choose from.

I am NOT a Beats fan. Stay away from trendy new lines for the most part, but some are still quite nice.

A rancher is a good solution.

I had my downstairs office insulated when our curent home was built so I can go in there and play as loud as I want anytime in our 3 story modern Victorian style home, but I have given thooght about what to do when the time comes to downsize. A nice rancher just might be the ticket for this and other reasons in retirement.

This component is designed to be used with headphones. When properly calibrated the soundstage will be in front of you as if you were listening to music through speakers. I had the experience of hearing it myself a few years ago and came away quite impressed. At the time I believe the cost was about $3500. They also sell the component in combination with Stax kits. If you are willing to pay $4500 for a set of headphones plus an appropriate amp to drive them which could run you at least a couple thousand more, then this may be an interesting alternative:

http://www.smyth-research.com/products.html