That’s not an easy price point to hit with all the features you’re after, but I’ll offer my recommendation, which is the relatively new and surprisingly brilliant Kanto Ora. I think they come in at about $100 over your budget. I would consider them well worth saving for.
They’re tiny, active bookshelf-style speakers with USB & Bluetooth connectivity that sound fantastic and have the option of adding a subwoofer down the road if you decide you want some extra low-end heft.
You can kind of go one of two ways with this: look for a consumer appliance type speaker, like Sonos, Bose, etc. Or you can aim at entry-level hi-fi, which is where the Kanto Ora and other good alternatives like the Audioengine A2+ sit.
Sonos is the default recommendation, and a good one, but if you’re going to grab used Sonos speakers I’d caution against any that run on their older S1 software platform. A pair of old Play:1s can be updated to run on the S2 platform and would give you an overall good experience. They have hardware versions with no smart assistant. I’ve seen them on used marketplaces within your budget. However, the older Sonos speakers do not have Bluetooth.
Sonos is also a great choice if you expect to add more speakers in the future that you want to be able to chain together. If you’re interested in easily playing the same music in your office, your living room, your kitchen, etc. then Sonos is a good bet. Other whole-home consumer audio platforms exist and trade advantages/disadvantages against Sonos, but this is one of those cases where if you don’t particularly care about audio and just want something that’s ubiquitous, simple, and (mostly) does what it says on the tin: Sonos is safe.
One potential gotcha to be aware of with Sonos standalone speakers: they don’t make good computer or TV speakers. There’s no way of connecting them permanently to a Mac that won’t have significant latency unless you have a Sonos soundbar in the mix. Even a physical connection via the line-in port. This is because the signal has to run through Sonos’ DSP first. Their soundbars are designed to be the “heart” of a zero-latency A/V system. For the standalone speakers, the Bluetooth and AirPlay connections are fine—but obviously that connection has to be re-established periodically.
If it were me, and I was buying purely to have a great audio experience at my desk without breaking the bank (or the desk), I’d buy the Ora every time. If I didn’t care about computer connectivity and just wanted a whole-home audio system, Sonos is great. I own a pair of Era 100s and a Move 2 and I love them for what they are and accept them for what they aren’t.