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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.
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Celebrating 25 years at the Washington Street Theatre. The Olean Theatre Workshop, Inc. is a not-for-profit corporation that performs and presents a variety of theatrical productions.
The district encompasses 17 contributing buildings in the central business district of Olean. The district developed between about 1866 and 1939, and includes buildings in a variety of architectural styles including Beaux-Arts, Queen Anne, and Art Deco. Located in the district are the separately listed Olean Post Office and Olean Public Library. Other notable buildings include the Former First National Bank, current Manufacturers Hanover Building by Mowbray and Uffinger (c. 1915, 1938, 1950), Original First National Bank of Olean (c. 1866-1869), Masonic Temple by Warner and Brocket (1893), Olean House (c. 1889, 1893), and W.T. Grant Building (c. 1873-1878, Façade Update c. 1935-1940).
US Post Office—Olean is a historic post office building. It was designed and built in 1910-12 and is one of a number of post offices in New York State designed by the Office of the Supervising Architect of the Treasury Department, James Knox Taylor. It is a two story masonry and steel frame building. Its Renaissance Revival design compliments the adjacent Olean Public Library. It is located in the Union and State Streets Historic District.
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.
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.