Mark,
I had the fortune to play at Winchester last year, and I think it definately falls into the same category as Salem and TCC. The are all quite similar, with mature trees lining most fairways (but no claustrophobia) and some interesting elevation changes. Salem is a bit more benign in terrain, but has a wonderful set of greens. Winchester's elevation changes are slightly more drastic, so the greens are flatter as much of the site's movement happens off the greens. TCC (and I have not played the composite layout) has several all-world holes (3!!) but for me was more amazing for its place in golf history.
Winchester's front nine is not as interesting as the back, except for the pretty drop shot par-3 ninth. The back nine has several very good holes like 10, a long par four with a two tiered green played into a breathtaking open area, 13, a short par five with a dual fairway choice off the tee around a central fairway bunker and parallel ridge, and 16, a 405-yd par four that plays over a ravine to a severely left-to-right sloping green.
When playing these Ross (and Flynn) classics, it always amazes me how much good golf there is in such close proximity to Boston. Add these three tracks to Brae Burn, Charles River, Myopia, Woodland, Essex, Plymouth, Wellesley, and Oakley on the private side, and (the ever-improving)George Wright, Franklin Park, and Sandy Burr (fun Ross in Wayland, MA) and you have a collection of courses that may secure Beantown as the #3 classic golf course architecture city in the country behind Philly and greater NYC.
--Brad