Shadyside Presbyterian Church

Negley–Gwinner–Harter House (also known as Gwinner–Harter House, and William B. Negley House) located at 5061 Fifth Avenue in the Shadyside neighborhood of Pittsburgh, Pennsylvania, was built from 1870 to 1871 for William B. Negley (June 5, 1828 – January 16, 1894, a lawyer who attended Princeton University, served as a Major in the American Civil War under General James S. Negley, and was the son of Jacob Negley and the nephew of Sarah Negley and Thomas Mellon). After Joanna Wilmerding (Bruce) Negley, the widow of William B. Negley, died in 1910, Edward Gwinner, a stone and railroad contractor, purchased the property in 1911. Gwinner had it remodeled and expanded. The original architect is unknown, but Frederick J. Osterling remodeled the house and was responsible for additions between 1912 and 1923. Gwinner died in 1949, and his widow, Adele, owned it until 1963, when the house was sold to Dr. Leo Harter. In 1987, a fire caused by a paint-stripping gun during renovation burned much of the third floor and damaged the roof. Harter died in 1988, and the house sat vacant for eight years, was boarded up, and had even been considered for demolition. Then in 1995, restoration contractor Joedda Sampson and her husband Ben, a builder and developer, purchased the property and restored it. The restoration took nine months. In 2002, the house was purchased by Kenneth Lehn and Marina Persic Lehn. According to the Allegheny County Pennsylvania Real Estate Assessment Page, the house's estimated previous year market value for 2010 was $1,110,800. This Second Empire style house was added to the List of Pittsburgh History and Landmarks Foundation Historic Landmarks in 2000.

The McCook Family Estate (also known as the Willis McCook House) is a historic mansion located at 5105 Fifth Avenue in the Shadyside neighborhood of Pittsburgh, Pennsylvania, USA. It was built during 1906 and 1907 for Willis McCook and his family. McCook was a prominent businessman and lawyer who represented Henry Clay Frick.

The Moreland-Hoffstot House in the Shadyside neighborhood of Pittsburgh, Pennsylvania is a building from 1914. It was listed on the National Register of Historic Places in 1978.

Sunnyledge (former McClelland House) at 5124 Fifth Avenue in the Shadyside neighborhood of Pittsburgh, Pennsylvania, was built in 1886. It was designed by architects Longfellow & Harlow, and was originally the home and office of Dr. James H. McClelland. McClelland was the founder of nearby Shadyside Hospital, now part of the University of Pittsburgh. Members of the McClelland family remained residents of the home until the 1980s. It is now the Sunnyledge Boutique Hotel and Tea Room. It was added to the List of City of Pittsburgh historic designations on April 12, 1995.

Fifth Avenue (sometimes spelled 5th Avenue) is one of the longest streets in Pittsburgh, Pennsylvania, United States. It begins downtown and moves eastward for over five miles (9 km). Fifth Avenue passes by the Carlow University, the Cathedral of Learning and other buildings of the University of Pittsburgh, then forms the borders between Shadyside on the north and Squirrel Hill and Point Breeze to the south. Finally, after passing Chatham University, The Ellis School, and Mellon Park, it turns north and forms the border between Larimer on the west and North Point Breeze and Homewood (Pittsburgh) on the east. At the intersection with Frankstown Avenue its name becomes Washington Boulevard (PA 8) and descends a branch of Negley Run to meet Allegheny River Boulevard (PA 130) near the Highland Park Bridge. At least 30 streets either cross or intersect with Fifth Avenue, including Penn Avenue, which intersects it twice (once in Downtown and again near Point Breeze). Forbes Avenue parallels it from Downtown through Uptown and Oakland before diverging at the University of Pittsburgh; they form a one-way pair through Uptown and Oakland (Forbes from Downtown toward Oakland, Fifth from Oakland toward Downtown).

Addy-Spencer House located at 919–20 St. James Street in the Shadyside neighborhood of Pittsburgh, Pennsylvania, was built in 1869. It was added to the List of Pittsburgh History and Landmarks Foundation Historic Landmarks in 2000.

Winchester Thurston School is an independent, coeducational preparatory school located in the Shadyside neighborhood of Pittsburgh, Pennsylvania. Established in 1887, Winchester Thurston offers PK–12 education in Lower, Middle, and Upper School. The school is a member of the Pittsburgh Consortium of Independent Schools.

Rodef Shalom Congregation is a National Register of Historic Places landmark in Pittsburgh, Pennsylvania, designed by architect Henry Hornbostel.Located on Fifth Avenue on the border of the Oakland and Shadyside neighborhoods, it houses Congregation Rodef Shalom, the oldest Jewish congregation in Western Pennsylvania and the largest Reform congregation in the area. Across the street from the temple is the headquarters of Pittsburgh's PBS station WQED. On the grounds of the building is the Rodef Shalom Biblical Botanical Garden.

The Bindley Hardware Company Building in the Shadyside neighborhood of Pittsburgh, Pennsylvania was built in 1903 alongside of the Pennsylvania Railroad main line, next to the Shadyside Station. The building was constructed for John Bindley by his brother Albion. John had been the president of the Pittsburgh Chamber of Commerce and of the National Hardware Association. He tried to organize the industry into a "National Combine" or trust, but this attempt failed due to opposition from the government. Instead, he organized a dominant regional hardware wholesaler in Pittsburgh, a major center of hardware manufacture, with this building serving as its main warehouse.The building was listed on the National Register of Historic Places in 1985.

The Rodef Shalom Biblical Botanical Garden (0.3 acres) in Pittsburgh, Pennsylvania's Shadyside section is a Biblical botanical garden.Opened and free to the public since 1987 from June 1 through September 15. It was founded by Rabbi Walter Jacob and his wife horticulturalist Irene Jacob. It now displays more than 100 plants once grown in ancient Israel, including cedars, dates, figs, olives, and pomegranates. All are labeled with biblical verses, or their biblical name. The garden also includes a waterfall, desert, and a representation of the Jordan River from the Sea of Galilee to the Dead Sea. It produces a new show on ancient Near Eastern horticulture each summer.The garden is on the grounds of the Rodef Shalom Congregation, which houses Western Pennsylvania's oldest Jewish congregation, dating back to the 1840s.

Roslyn Place is a small wooden-paved cul-de-sac located in the Shadyside neighborhood of Pittsburgh, Pennsylvania. The street was built in 1914 in the Nicolson Pavement style and is home to the historic Roslyn Place district.

Roslyn Place is a collection of houses located at 506-523 & 525 Roslyn Place in the Shadyside neighborhood of Pittsburgh, Pennsylvania. Built between 1914 and 1917 in the Colonial Revival and Georgian Revival architectural styles, the houses currently serve residential functions.