https://en.m.wikipedia.org/wiki/Diffraction-limited_system
Practically to go really big you need to use interferometry. There are radio experiments that can do this at Earth scale - the Event Horizon Telescope can image very small objects (black holes) by making simultaneous observations from all over the world. The telescopes point at the same place and use very very good timestamping. At the South Pole we have a hydrogen maser for that. Then all the data gets sent somewhere for correlation and a lot of processing. The analogy I like most is imagining you have a big mirror (Earth) but you've blacked out almost the entire surface except a few points where the telescopes are.
Radio is particularly amenable to this because you can build big dishes more easily than for visible light, and the diffraction limit is lower because it's proportional to wavelength/aperture. So in addition to big dishes, you're observation wavelength is much much longer (mm vs nm).
There's a log-log plot on that wiki page which is quite difficult to read, but the important point is that radio is all the way at the top and the best we have is the VLBA.
Visible interferometry is much harder...!
https://en.wikipedia.org/wiki/Extremely_Large_Telescope
Typically for non-adaptive optics telescope the atmosphere will limit you to the scale of about an arcsecond. Meaning objects which take up less than an arcsecond of the sky will appear as points. Adaptive optics telescopes however have much better resolving power.