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  • Jay Brothers

Wayside: Brothers Wed Sisters & Live Adjacent

Updated: Dec 14, 2023

Built by Alexander Samuel Caldwell (1857-1905) and Margaret L. “Maggie” Winston Caldwell (1862-1933) in 1897, Wayside was a 2 story house located at 928 Caldwell Lane.

It was located behind and to the west of the Longview estate owned by his brother James and May Winston. Alexander’s nephew was Rogers Caldwell. Maggie was the sister of May. Her father was Dr. Charles K. Winston, a professor of obstetrics and a founder and president of the University of Nashvillle. Alexander was a brother of James E. Caldwell. A son and nephew was Rogers Caldwell of Brentwood Hall. After their marriage, Alexander and Maggie stayed at Longview for a while. Alexander was in the fire insurance business and then supervisor of the loan department of Northwestern Mutual Life Insurance. Maggie was very involved in the Daughters of the American Revolution (DAR). Their son Will became president of Nashville Buick Co. When her three sons served in World War I, Maggie served as manager of the car dealership - the only woman auto dealer in the United States. In 1918, she became president of the Tennessee Federation of Women’s Clubs.

Wayside burned down in 1932, and Maggie died the next year. The heirs likely developed much of the surrounding estate as the family name is remembered with Caldwell Lane, Caldwell Ct. and Winston Place. See also Brentwood Hall, Longview


Nashville Pikes Vol 1, pp. 132-137

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