Construction for Roundwood Manor began in 1923 as a country home for the Van Sweringen brothers, Oris Paxton and Mantis James. The home was the second largest in Ohio after Stan Hywet Hall and at 90,000+ sq. ft., it remains the largest home in Hunting Valley. The Van Sweringen brothers built the home as a place to entertain guests and business associates, including, John D. Rockefeller and Charles Lindbergh. Daisy Hill was built around Roundwood Manor and the home acted as an anchor for the neighborhood. Daisy Hill was named after Louise Jenks or "Daisy", the hostess of Roundwood Manor. 

The vision for Roundwood Manor rose from the barn that existed on the land. Oris Paxton Van Sweringen saw the "T-shape barn" and its potential to become a beautiful home and business retreat. It is estimated that at the time, the brothers spent approximately $2 million on the home. The structure of the barn made up different parts of the manor, most notably seen in the Ship Room, which still has the original beams and meat hooks. 

Source: "The Cows Lose Their Home", The Plain Dealer 1966