In 1912 Madison newspapers began to carry ads by the Frank B. Wynne Company for a deluxe countryside subdivision, Highlands, in an area between Old Sauk Road and Old Middleton Road. The project was designed by Ossian Cole Simonds, 1855-1931, a landscape architect who was popular with Madison clients. His work in Madison included such sites as Tenney Park, the Yahara River Parkway, and the Vilas Park lagoons. In 1915, he helped design Nakoma.
Lots in Highlands were originally two to five acres.
From the beginning Highlands attracted doctors and university professors who were able to afford automobiles for the five mile drive to downtown Madison.Text from Part VII of The Origins of Some Madison, Wisconsin, Street Names. (Historic Madison, Inc. of Wisconsin)
Today, the majority of the housing stock looks to have been built much later than the development's 1912 genesis.
(text added red arrows show route taken in video)
UPDATE. Madison's "Levittown" at 66. (12/2/2017)