Omega and Breitling have pieces which fit squarely inside your price range. You might find a pre-owned Rolex, but then you're limited by what's available on the used market. Right now, Rolex AD's aren't getting a lot of stock, and they're inflating the prices of the pieces they do have. About a month ago I found a Rolex GMT II (with the "Batman" bezel). I think the list price is around $11,000, which is painful in its own right, but the dealer was asking just over $15,000, with no apologies (and no discounts!).
I have numerous pieces of many different brands, and the three I wear most often are my Breitling Colt 43, my Oris Williams F1 and my Omega Seamaster 300 Co-Ax.
Just remember, once you get into the Swiss watch market, it's hard to go wrong...