You would not guess it from the office towers, but Underwood Street is wet ground pretending to be a city lane. This was the mouth of the Tank Stream — the creek that decided where Sydney sat — and in 1798 emancipist shipwright James Underwood laid down what Dictionary of Sydney calls the colony’s first commercial shipyard here. Keels went into the estuary; the shoreline has since been filled, bridged and built over until the original waterfront feels like a rumour. That is the point of the street: the water moved, the name stayed.
Underwoods grant ran from George Street through to the stream. Before 1807 he had already reclaimed extra yard space into the estuary, then raised a flat-roofed Regency house with a roof walk looking back to Sydney Cove, plus stores. From this pocket came the sloops Contest and Diana, the brig Governor King, and the near-200-ton King George — Kable & Underwoods sealing and coastal fleet, launched where commuters now cut through to Pitt Street. The Royal Australian Historical Society marked the yard as Green Plaque 68 in the mid-1980s Bicentennial series; look for it rather than expecting timber slips.
The red-brick building at the bend is a later joke the street tells on itself — a 1930s–40s residential-style block dropped into a commercial canyon. Treat it as an observation, not as Underwood fabric. Pair the lane with the Tank Stream posts and with Circular Quay west: same harbour, different century of fill.
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