James Benjamin Homestead is a historic home located at Flanders in Suffolk County, New York. It consists of a main section, built about 1785, which is a two-story, center-entrance residence, and one- and two-story rear additions, built about 1900. Also on the property is a small, late 19th-century barn. The house is hidden behind trees along New York State Route 24 and is a waterfront property along Reeves Bay, a segment of Flanders Bay, which is located between the Peconic River and the Great Peconic Bay. It was added to the National Register of Historic Places in 1986.