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The James Simmons House is a late 18th century house at 37 Meeting Street, Charleston, South Carolina which was, at one time, the most expensive house sold in Charleston. It was likely built for James Simmons, a lawyer. By 1782, it was home to Robert Gibbes, a planter. Louisa Cheves (later McCord), a prominent antebellum writer, was born at the house on December 3, 1810. In 1840, Otis Mills, the owner of the Mills House Hotel, bought the house for $9,000. In October 1862, during the Civil War, the house was loaned to Gen. Pierre Beauregard, who used the house as his headquarters until August 1863. In 1876, Michael P. O'Connor, later a member of Congress, bought the house.
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.
It was the most expensive house sold in Charleston when it sold for $7.37 million in May 2009. It remained the most expensive house sold in Charleston until August 2015 when the Col. John Ashe House at 32 South Battery sold for about $7.72 million. 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.