Jack Road is probably my second favorite new, used, and antique watch shop to shop in Tokyo. It's hard to go here and not want to leave without purchasing one of the beautiful watches they have in stock.
All watches are either brand new or used and certified. Used watches are immaculate and are typically just open box items or are in perfect condition.
They carry all the major players, IWC, Cartier, Breitling, AP, Hublot, Omega, Zenith, etc. With such a wide selection of watches you are bound to find what you are looking for and even get some very unique watches as well. Check out their website. It's in Japanese, but should be easy enough to navigate if you cannot read Japanese.
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Location Information:Address: Nakano 5-52-15 Broadway 3F
Closest Station: Nakano