This is a 1970s fiberglass sailboat made by Chrysler Corp. Yes, the same company that made the cars (but a separate division, I think).
It is in fair condition for a boat of this age. Yes, it floats and sails. It is a fun boat and can hold up to four people, I believe roughly 750 lb payload. Dry displacement is about 450 lb so it is easy to move around in the water even just with one person. I have sailed it solo mostly. Can also sail it with two people. It is a standard Bermuda rig with a mainsail and a jib on a cable. You can add a Spinnaker, but I don't have that. I do have both sails.
It comes with the trailer pictured. I fixed the lights on the trailer and they should work fine. It is not the kind of trailer you would want to take on the freeway but it is fine for getting the boat back and forth to a pond or Bay. I have even towed it behind my Prius, it is not a heavy setup.
The boat takes about 20 to 30 minutes to get ready for sailing once you have it at the launch. It is a pretty convenient little setup. It is a fun boat but I do not have time for this hobby anymore.
In terms of condition the boat does need some work, but it can be used as is. The engine runs and everything works. There is some fiberglass work and some wood repair that ought to be undertaken to get it into ideal condition. I think that is to be expected for a boat of this age. Those aspects are too hard to show in pictures but I can show you if you come to take a look.