Black Squirrel Cottage was built on the site of an earlier house that was demolished in the late 1870s. In 1880, Electra Eddy purchased the lot from Lucy Cottrell, the landowner. In 1885, Charles and Margaret Eddy mortgaged the property for $9,000, then sold it the following year to John Egmont Schermerhorn for $25,000.

John Egmont was a 7th-generation descendant of Johannes Schermerhorn (1716-1768), Commander and owner of shipping vessels that traded between New York City and Charleston, S.C. The Schermerhorns (and other families like the Van Cortlandts) were associated with New York Society and "old money" circles, accumulating wealth through early mercantile ventures and real estate. Mr. Schermerhorn named the house “The Lanai”, perhaps referring to its original porches.

The house has worn many hats in the intervening years: single-family residence, photography shop, and, for the past 35 years, a bed and breakfast.

The current proprietor purchased the property in 2022 and dove into a three-year historic restoration to help the house realize its newest iteration as Black Squirrel Cottage.