4. The Captain Joseph Roe House (1773-81)

If you discount Fraunces Tavern, the Captain Joseph Roe House is actually the third oldest building in Manhattan dating to 1773-81. We previously showcased this in our article about the “wicked” secrets of South Street Seaport, penned by William Roka, a historian at the South Street Seaport Museum. Roka writes that though Georgian townhouse was originally built in a fashionable district, nearly a century later it was Kit Burns’ Sportsman Hall, home to illegal boxing matches and even more infamously, rat pit killings: “Wharf rats packed 50 to cage were let loose into the area and then a weasel would be sent in. Howver it was only when the fighting dogs were let in that the crowds would really go wild! Some of Burns’s prize dogs could kill 100 rats within a few minutes.”

According to the Historic Districts Council, this building at 273 Water Street is the oldest building in South Street Seaport and was often occupied by merchant families, with Captain Roe often at sea. It was converted into luxury apartments in the late ’90s.