These are nice boats. They are slightly less beefy and slightly less commodious than their near sisters, the Pearson Vanguards which were also 32 foot Rhodes designs of the era. If I remember correctly the Chesapeakes were imported by Henry Walton of Annapolis, Maryland and were beautifully finished with mahogany trim and nice stainless steel and chrome plated cast brnze details. (Walton''s son still lives in Annapolis)
These boats sail well for a boat from that era and seem to be well behaved in a breeze. That said, by today''s standards these boats were painfully slow and quite wet. The have a short waterline by any objective standard and so (if they behave like the Vanguard which my family owned for quite a few years) they are not too great in a chop. They are also next to useless in light air.
I am not terribly fond of the sail plan on these CCA era rule beater boats. Boats of this era were designed with comparatively small and low aspect ratio mainsails and counted on the use of very large genoas in winds up to the high teens. As a result they are a lot of work to sail well. The wide single spreaders, the wide shroud base and longish keel keep them from pointing as well as more modern designs.
These boats were typically sailed with large heel angles at speed which made working below a little difficult and uncomfortable. It also made it pretty wet in the cockpit in a seaway. They do have a slower motion than the early fin keel spade rudder boats that followed them but they also roll through wider roll angles.
The longish keel (which is not really a full keel as classically defined) had a cut away forefoot and a raked rudder post that was pretty far forward in the boat. In their day, these were considered to be more like a long fin keel with an attached rudder than a full keel. The cutaways reduced wetted surface and increased speed a bit but it also meant that they do not really track like a full keel nor do they have the light helms of spade rudder boats. The general proportions of the rig
, the large heel angles and the rudder attached to the keel resulted in a lot of weather helm in a breeze which really wears you down on a long leg and causes the autopilot
to use a lot more amps than a boat with a lighter helm.
Of course then there is the usual old boat concerns. You need to have this boat throughly surveyed by a really competent certified Marine Surveyor. Boats of this era can have a mix of problems including standing and running rigging
that is well past its useful lifespan, deck rot and structural bulkhead separation, fiberglass fatique at high stress areas, rudders and rudder posts that well in excess of thier useful lifespan, tired sails, deck hardware that is underpowered and undersized (by modern standards) and imposible to find parts for, dangerous hardware like reel winches
and roller furling
booms, engines in need of rebuild or replacement, upholstery that has lost its give, instruments, plumbing, electrical systems that are obsolete and past their safe lifespans, aesthetic issues and so on. While none of these problems may be present on the specific boat that you are considering, even a combination of a few of these items can quickly add up to far more than these boats are worth in perfect condition.
To me boats like the Chesapeake 32 are wonderful to look at. Sailing them evokes an aesthetic of a different era. They were simple boats that offer a type of experience that that is different than more modern designs. If that "come with me now to yesteryear" character appeals to you then the Chesapeake 32 was one of the better boats of that length and time frame.