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Performing arts.
Beardsley-Oliver House is a 2½-story, wood-frame dwelling built in about 1890. It exhibits a late Victorian blending of Shingle Style and Queen Anne styles.
Conklin Mountain House is a Second Empire style wood frame dwelling built in 1886. The front facade features a three story tower with mansard roof and a wraparound porch. The interior features elaborate and extensive woodwork. It was constructed by the owners of Conklin Wagon Works, one of Olean's most important industries in the late 19th century. It was subsequently owned by the Mountain family, who operated the Mountain Clinic Infirmary.
The 32.5-acre (132,000-m²) district encompasses 89 properties including 82 residences, two churches, one school (the Olean High School), and a landscape design. There are 76 contributing buildings. The structures reflect a variety of mid-late 19th-century and early 20th-century architectural styles including Queen Anne, Italianate, and Gothic Revival styles. The structures were constructed between about 1849 and 1937.
Olean Armory is a historic armory building. It was designed by State architects Isaac G. Perry (1890 structure) and Lewis Pilcher (1919 structure). It consists of a two-story, Tudor inspired administration building constructed in 1919, with an attached Romanesque drill shed constructed in 1890. The building features a number of castellated style features such as turrets and buttresses.
Olean School No. 10, now known as Ivers J. Norton School, is a historic school building. It was designed and built in 1908-1909, in the Prairie School style.
St. Stephen's Episcopal Church is a Gothic Revival style church building designed by upstate New York architect Robert W. Gibson (1854–1927) and constructed 1889-1890. The complex also includes the Ashton Parish House, constructed 1922-1923, and the rectory, known as the Watson Wing, built about 1885. It is home to Olean's oldest continuously operating congregation, established in 1830.