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John Winstead House(s)/ Pleasant Hill: A Trio of Preserved Homes

Updated: Apr 29


Photo by Skye Marthaler


In 1827, John Matthews Winstead (1807-1896) married Nancy S. Whitfield (1811-1885). The couple settled on land he received from his father John M. Winstead, Sr. The Winstead family was among the earliest pioneers in the area in 1799. John Sr. had accumulated a sizable estate by his death. Two smaller log cabins had been built by Winstead Sr as his family and farm grew. The property is on Concord Rd. east of Edmondson Pike. The home was built to face south toward the Nolensville-Franklin road. When that road was discontinued, the entrance was changed to face Concord Road. The Winsteads built a 2 story brick home between 1855-58 on about 450 acres of land on a hill near the cabins.


By 1850, they had increased the farm even more, and 10 years later, in 1860, the Winstead family was among the richest in the state. John was justice of the peace from 1854-1882. Post Civil War, the family farm was about 500 acres and remained in family ownership through Edmondson relatives although descendants moved away.


Their son, William E. Winstead, purchased Winstead House from the Perkins family. In 1988, the owners were Winstead descendants Hugh and Anne Mary Edmondson with 10.5 acres. Hugh’s grandfather was John Winstead’s first cousin.


Pleasant Hill is now part of the exclusive 600 acre The Governor’s Club residential community and has an address of 9681 Concord Rd. The family sold Pleasant Hill in the late 1990s, and the historic homes are a centerpiece of the exclusive community. NRHP 88 See Winstead House


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