Recommendation for Headphones under $250

Sennheiser 580 via MassDrop (they’re identical to Senheiser branded models).

Drop has great deals on Senns. The 580 is very good (I’ve owned a pair for 20 years, and now own the 600 and 650 too).

Sennheiser 580
 

Look you dont have to go cheap to get great sound with the proper connection you want, I would recommend Grado Labs headphones.

Matt M

Is it important that other people can’t hear any sound coming from the headphones?

@mattmiller 

+1 good recommendation.

Grado

@soix No, I live alone so it doesn't matter if anyone hears the sound coming from the headphones.

@mattmiller ....Wow, I didn't know Grado made headphones so inexpensive!  I'll definitely take a look at those!

@patrickdowns ...Thanks for the recommendation!  I've heard of Sennheiser, but what is MassDrop?  The link appears to be a cross promotion from the two brands....Interesting....

the Philips SHP9500 cost around $75, sound very true-to-source and are very comfortable--highly rated by the headfi community

There’s a pair of Hifiman Sundaras on Amazon being sold in “Like New” condition from a very reputable seller for $240 (retail $299) and you can have them by this Tuesday with free shipping. Great headphones.  Check out this video review.  He also reviewed my Hifiman Arya Stealth ‘phones, my Singxer SA-1 headphone amp, and my Musician Pegasus DAC and in all cases his opinions closely mirror my own so I trust his ears and he knows his stuff.

https://soundnews.net/headphones/full-size/hifiman-sundara-rev.2021-review-my-favorite-headphone-under-400/

calgarian5355

Mass, or Massdrop, is an outfit that makes deals with manufacturers to make a lower-priced version of their product, iirc. So, the Mass6xx is identical to the Sennheiser-branded phones and I see they are branded Senn and Mass. I think I have that right.

This is the one I would get, their Senn 650 equivalent (I have Senn 600s and 650s):

"If you know audio gear, you know the Sennheiser HD 650. The company’s flagship from 2003 to 2009, this open-back headphone has shown serious staying power. Praised for its richly detailed, effortlessly enjoyable sound, it remains one of the most talked-about products on Head-Fi today—and is still widely considered among the best headphones under $1,000. So when we teamed up with Sennheiser on its first-ever community-driven design partnership, the HD 650 was a natural place to start. A new revision of the popular all-rounder, the Massdrop x Sennheiser HD 6XX has that same great sound plus a few updates, and a price that makes it even easier to love.

It's drop.com.  Get the HD6XX.  I have a dozen sets of headphones including some top of the line ones and the HD6XX are what I grab most often.  No, they don't sound better than the TOTL headphones, but they are super comfortable, easy to drive, and do a lot of things right in terms of sound quality.

Apos has Hifiman Sundara for $299 now on sale. 

I've owned a lot of these, so I'll give my personal opinions. I happen to love several.

The Grado sound is in-your-face, fun, detailed, and punchy. I think sound stage is small until you move into the 325's, which are my favorite (I have not heard the X version). They have a very focused and forward sound, in general, though, so it's a flavor that is divisive. It's easy to hear them and immediately think, "Yep, this is what I was looking for." I think my preference for music that is recorded poorly kept me from committing to the Grado brand. 

The Sennheiser 580 or 600 headphones have a much more laid back presentation. Great detail, but with less airiness. They're comfortable and easy to listen to for a long time. I used 580's for over 10 years and upgraded to the 600's and had them for another 5. They were my choice for a long time. They take a little of the intensity and energy away, but the trade off is warmth and listenability. Very forgiving of poor recordings or amplification, IMO. In fact, they never sound bad. Haha. I have never wanted to turn them down. 

I moved those along for the HiFiMan Sundara headphones. As my stereo got better and better, I wanted that kind of space, air, and detail in my headphones. Sundaras are, without question, the most like a pair of high fidelity speakers strapped to your head, but not without excellent room-like atmosphere. The soundstage is very articulate and instruments are easy to pinpoint. I have been living with these since the Sennheisers. They're a lot of fun, but I'm considering a change back to Sennheiser because I cannot help but feel like I spend more time listening to the headphones than the music. I have never been able to engage with my music like I did when I had either the 580's or the 600's. Having said that, I think if you're looking for the lowest price point that can bring you the highest fidelity and get a really good taste of what's up the stream, get Sundaras. I see them for $200 often, which is the best deal on hifi cans I've ever seen. 

Another vote for the HiFiMAN Sundara.

If you’re sensitive to timing anomalies you really need to give them a listen.

I don’t like overpriced, overhyped, so-called ’High End’ products that are simply masquerading as the Emperor’s New Clothes.

The Sundara’s are nothing like that. They must be the best ever headphones at that price.

If you can’t stretch to them you could try their more affordable brethren the HiFiMAN HE400se.

These might just be the best value for money product in all of audio.

They are that good.

Focal Elegia discontinued. I snagged an open box pair from Adorama at $279. They were brand new. Easy to drive. Sound a little harsh at first but break in fairly quickly. They were $1k headphones originally.

I have a pair of 1More Triple-Driver Over-Ears Headphones and listen to them in addition to far more expensive jobs like Kennerton Rognir Planar, JM Audio Editions XTC-Closed, and RAAL SR-1b phones.  No the 1Mores don't do speed, space, and detail like the TOTL phones but their bass is fun and they sound pretty good for the money.  I don't think they are produced anymore but are available online on eBay and other used equipment sites for less than their original $250 retail price.  There are numerous positive reviews as well including one reviewer who pronounced them the world's best phones.  Well, maybe not, but gives you an idea of how much they punch above their weight.  If you get a pair make sure you get the silver colored US version that uses a graphene-laminated mylar driver and not the champagne colored overseas version that uses a metal (beryllium?) driver.

BTW, forgot to mention above that the 1More Triple-Driver Over-Ears phones are easy to drive with their 32 ohm impedance and 106 dB/1MW sensitivity.  I can easily drive them from my laptop and phone.