After Simonds died in 1905, she turned the house into a luxury hotel. Two years later she was married to Barker Gummere, also a banker. Daisy moved with a young year old daughter to live with him in New Jersey on an estate named Rosedalewhich she had also designed. There she played host to prominent figures such as Woodrow Wilson. Barker died in 1914, and Daisy oversaw the conversion of the house into a girls' academy. She eventually moved to Washington, D.C. Her third husband, Clarence Crittenden Calhoun, was a wealthy lawyer from Kentucky. The couple were married in 1918. Daisy attended the 1920 Democratic National Convention, which inspired her to found a women's rights organization. Her husband funded the construction of Rossdhu Castle, a large home near Beach Drive in Washington, which Daisy Calhoun designed. It was very ornate, but the family was forced to move into the gatehouse upon the beginning of the Great Depression in 1929. She also founded the Women's National Foundation (which was dissolved after several years) and the Women's Universal Alliance (in February 1922), the later of which held a World Welfare Conference in 1923.