Sunnyledge

Built for a prosperous doctor, this house was designed by Longfellow and Harlow (soon to be Longfellow, Alden, and Harlow), and shows the restrained good taste that would be the hallmark of the firm’s work for decades. Although it is technically on the Squirrel Hill side of the street, socially this house forms part of the Shadyside millionaires’ row along Fifth Avenue.

The Admiral Apartments, Shadyside

A simple modernist brick box is given an Art Deco flair by distinctively patterned brickwork.

Negley-Gwinner-Harter House, Shadyside

This Second Empire mansion had a narrow escape: the third floor burned out in 1987, and the owner died the next year, leaving the house a derelict hulk. It was rescued from demolition at the last minute by serial restorationist Joedda Sampson, who painted it in her trademark polychrome style; it has since passed to other owners, whose pristine white also works well with the design. The house was built in 1871; Frederick Osterling worked on early-twentieth-century renovations and additions.

Art Nouveau Apartment Building in Shadyside

This would be a fairly ordinary building, in what we might perhaps call Renaissance style, except for its curious Art Nouveau ornamentation.

Third Presbyterian Church, Shadyside

The “chocolate church” at Fifth and Negley was designed by Theophilus P. Chandler Jr., whose name always sounds to old Pa Pitt like the villain in a Marx Brothers farce. Chandler worked mostly in Philadelphia, but he also designed First Presbyterian downtown and the Duncan mausoleum in the Union Dale Cemetery.