Incorporating headphones into my pc audio system

  I already have a good computer audio setup for playback through my speakers but would like the option of using a high quality headphone when I need to keep things quiet.

    My current system consists of a laptop running JRiver, a Synology 2 TB NAS and an Oppo 105 as a preamp and DAC.  Even though I managed to construct a fairly solid system for ripped CDs and downloaded 24/96 flac files recorded direct to digital, I still consider myself somewhat of a newcomer to computer audio that  still has a lot to learn. 
   My current need is to learn how to best incorporate a yet to be purchased pair of high quality headphones into my system.  My confusion centers around the way my system is currently setup;  my Synology storage device is hard wired into my Comcast wi-fi router. My laptop running JRiver and my Oppo 105 serving as my DAC are both connected to my wi-fi and operating wirelessly.  The Synology, router and Oppo are all located between my speakers in my rack along the 14' short wall of my 23' x14' room.  My listening chair is along the opposite short wall where I also have my laptop.
     I know I could plug headphones into the 1/4" headphone jack of the Oppo but the chord would need to run the entire length of the room.  I was hoping someone had a better solution.  I also know wired is generally considered better than wireless for sound quality but I'm open to a wireless solution since I haven't noticed any sound degragation using wireless connectivity in other areas of my system.
     Just curious what solutions others here use and  would also appreciate any good over-ear headphone  recommendations in the $200-600 range.  
Thanks,
 Tim