In order of age:
1951 hand-crank Singer for use at car shows,
1950's electric Singer "portable" that weighs a ton (in storage, for now),
1980's era Pfaff Hobby that I leave in work for the quilting class I teach,
1990's era basic Baby Lock (gave that one away recently),
late 1990's era Baby Lock 8800 (I use this for piecing), and
2007 Husaqvarna/Viking Sapphire (long throat space) for quilting.
I think that's five total. Easy to accumulate machines; as skills grow, so does the need for a fancier machine. Trading in old ones isn't always cost effective.