Although I would decline to testify in court, I think these are the four oldest pubs in Sydney town. They all stand close to the waters'-edge: hence, the naval names.
These first two have been restored with panache. The Lord Nelson (1842) attracts the chrome-fittings and blonde-wood set whereas The Hero of Waterloo (1843) attracts the literary lions with leftish-leanings. They are only about 3oom apart, both down in Millers Point which is the suburb beside the southern pylon of the harbour bridge. Of course, with Sydney being settled in 1788 there were pubs established prior to this. However, they do not still exist. One of these earlier pubs was The Sailors' Arms (1831) which is the house with the veranda immediately down from The HoW in Windmill Street, but it was soon turned into a dwelling house. Pubs in Sydney prior to 1800 were mostly under canvas.
These last two are like my father's mythical axe wielded during my childhood: with six new handles and three new heads! The Orient and the FoW have had more face-lifts than Olivia Neutron-Bomb. The Orient (1844) and The Fortune of War (1828) are both in George Street, The Rocks which loops down under The Bridge. They both look a bit dodgy and my guess is they attract the brew'n'spew crowd.