Addy-Spencer House

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).

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.

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.

Shadyside Presbyterian Church is a large congregation of the Presbyterian Church (U.S.A.) in an historic part of Pittsburgh, Pennsylvania, United States. Located at the corner of Amberson Avenue and Westminster Place in the Shadyside neighborhood, Shadyside Presbyterian Church was founded in 1866 as a congregation in the Presbyterian Church in the U.S.A. and has enjoyed a long history of local, national, and global recognition for its outreach and service. The Shadyside church building is listed on the National Register of Historic Places as a prime example of Richardsonian Romanesque architecture. It was completed in 1890 to designs of American architectural firm Shepley, Rutan & Coolidge, the successor firm to H.H. Richardson's own office.Throughout its long history, the church has been served by a succession of notable preachers, including Hugh Thomson Kerr Sr., Robert Cleveland Holland, Howard C. Scharfe, and F. Morgan Roberts. Between 2003 and 2012, the congregation had as its senior pastor M. Craig Barnes, noted author and speaker, and professor at Pittsburgh Theological Seminary, until his election as president of Princeton Theological Seminary. Conrad C. Sharps served as senior pastor 2014–2018. The Rev. Dr. John Allan Dalles, a well-known hymn writer, Pittsburgh native, and graduate of Pittsburgh Theological Seminary, was the church's Interim Senior Minister and Head of Staff, 2019–2021. The current pastor, the twelfth in the church's history, is the Reverend Austin Crenshaw Shelley. It was here, in 1933 that the now global practice of celebrating World Communion Sunday on the first Sunday in October was originated, under the leadership of The Rev. Dr. Hugh Thomson Kerr. It also was the first church anywhere to pioneer regular radio broadcasts of its worship, on KDKA, the first commercially licensed radio station in the United States, and was the first church to broadcast worship to both the North Pole and to the South Pole.

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 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.

Ellsworth Avenue is located in the Shadyside neighborhood of Pittsburgh, Pennsylvania. It is mostly a commercial street that has locally owned businesses, galleries, restaurants, and bars. It runs southwest-northeast, parallel to Walnut Street, another commercial street, and is bounded by Shady Avenue to the east and South Neville Street to the west. Ellsworth Avenue is one of Shadyside's three business districts, along with South Highland Avenue and Walnut Street.Several Pittsburgh Historic Landmarks line Ellsworth Avenue. At the corner of Neville and Ellsworth is the Church of the Ascension, an episcopalian church that was named a landmark in 1971. Colonial Place is a mansion designed by George S. Orth that became a landmark in 1898. Roslyn Place (a wood-paved street) and Ellsworth Terrace are also landmarks located here.

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.

Penn Avenue is a major arterial street in Pittsburgh and Wilkinsburg, in Pennsylvania. Its western terminus lies at Gateway Center in downtown Pittsburgh. For its westernmost ten blocks it serves as the core of the Cultural District with such attractions as Heinz Hall, the Benedum Center and the Byham Theater as well as the David L. Lawrence Convention Center and the Heinz History Center bordering it. Exiting downtown it is the major route through the city's Strip District, Lawrenceville, Bloomfield, Garfield and East Liberty neighborhoods. Its eastern portion exits the city at Wilkinsburg where it continues to exist as Penn Avenue with a numbering system that begins anew using small numbers as it approaches Interstate 376 the "Parkway East". Penn Avenue is about 8.7 miles (14.0 km) long.From downtown, Penn Avenue travels in the same general direction as the Allegheny River, thus it passes close by a number of the bridges of the city that cross that river. In the downtown area, Penn Avenue is the main bisecting street of the Three Sister Bridges that form the Roberto Clemente Bridge, Andy Warhol Bridge and Rachel Carson Bridge. It passes the 16th Street Bridge, and goes straight through the Strip District.

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.

UPMC Shadyside is a nationally ranked, 520-bed non-profit, tertiary, teaching hospital located in the Shadyside neighborhood of Pittsburgh, Pennsylvania. UPMC Shadyside is a part of the University of Pittsburgh Medical Center (UPMC), and grouped in with the flagship UPMC Presbyterian. The hospital is near UPMC's flagship campus which houses Presbyterian and Montefiore. As the hospital is a teaching hospital, it is affiliated with University of Pittsburgh School of Medicine. The hospital has an emergency room to handle emergencies, with a rooftop helipad to transport critical patients to and from the hospital. UPMC Shadyside houses the flagship campus of the UPMC Hillman Cancer Center, a nationally ranked cancer hospital.Founded in as the Homeopathic Medical and Surgical Hospital and Dispensary, it changed its name to that of the neighborhood of Shadyside on May 12, 1938. Shadyside agreed to be bought by UPMC on June 5, 1996.