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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.
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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.
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.
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.
Temple B'Nai Israel is a historic synagogue. It was built in 1929, and is a three- to four-story-tall, light brown brick structure with terra cotta decorative details. It measures 85 feet long, 42 feet wide, and 50 feet tall. The front facade features a massive arched terra cotta portal encircling a large, round stained glass window. The congregation was established in the 1880s.
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.
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).