In yesterday's post, I mentioned one of the first books in which I read about the Greenleaf cottage in Lenox, Jackson and Gilder's Houses of the Berkshires, 1870-1930.  The book has a nice chapter on Windyside, which among other things, contains the following tidbit:
"Windyside was one of three neighboring houses constructed along the newly created Yokun Avenue in 1874-75. A gentlemen's agreement between the three new owners--Greenleaf, Danish consul Henri Braem, and New York lawyer John E. Parsons--accounts for the positioning of these houses at staggered intervals, allowing each an unobstructed southern view"--p. 40.Not long ago, Ancestry.com release the U.S., Indexed County Land Ownership Maps, 1860-1918.  An 1894 map illustrates nicely the three properties -- Parsons, Braem, and Greenleaf -- and shows the staggering of the houses.
Judging from the positioning of the properties, I'd guess that south is to the left. I rotated the orientation of the map to make the wording more readable, and in the original image, what is now the left side was at the bottom, though there was no key indicating direction on the original image.
 Jackson, Richard S, Jr., and Cornelia Brooke Gilder. Houses of the Berkshires, 1870-1930. New York: Acanthus Press, 2006.
 Ancestry.com. U.S., Indexed County Land Ownership Maps, 1860-1918 [database on-line]. Provo, UT, USA: Ancestry.com Operations, Inc., 2010. Original data: Various publishers of County Land Ownership Atlases. Microfilmed by the Library of Congress, Washington, D.C.