James Simmons House

Louisa Cheves (later McCord), a prominent antebellum writer, was born at the house on December 3, 1810.

[3] In 1876, Michael P. O'Connor, later a member of Congress, bought the house.

[4] The house is a traditional Charleston double house (i.e., four rooms per a floor at the corners with a central hall and staircase) but, unlike most, has matching two-story bay windows on the front façade, perhaps an early 19th-century alteration to an originally flat-faced building.

[4] It was the most expensive house sold in Charleston when it sold for $7.37 million in May 2009, overtaking the previous record holder, the Patrick O'Donnell House.

[5] The house was bought by William and Nancy Longfellow from the founder of Blackbaud and majority owner of the Charleston Battery soccer team Anthony and Linda Bakker.