I’ve never tried, but hardy souls with medium-sized telescopes have managed it. You need a 5-inch reflecting telescope (or larger), dark skies, and a little patience. Check out these charts for help in determining Pluto’s current position, and look here for a description of a recent occultation.
Pluto was at its recent brightest in 1989, at perihelion – its closest passage to the sun. It will grow dimmer until the year 2113, when it will reach aphelion.
Whatever it is, Pluto is a long, long way from here.