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In the 1840s and 1850s,Gramercy Park was filled with brick and brownstone rowhouses and mansions. Houses surrounding the private park were the most prestigious places of residence in pre-Civil War New York.
Quite a few homes still exist on East 18th and East 19th streets between Irving Place and Third Avenue, East 17th Street, East 15th and East 16th Streets.
129 East 17th Street (1878),is thought to be the oldest apartment house in the city. The Gramercy at 34 Gramercy Park East (George da Cunha, 1883) is one of the earliest cooperatives in New York, and 155 East 22nd Street is designed in 1889 by DeLemos Cordes.
Sass Smallheiser's Beaux-Arts building at 144 East 22nd Street (1901) and Bernstein Bernstein's unusual building at 152-156 East 22nd Street (1907) with five stepped gables and extensive terra-cotta detail were erected. In 1912, a multiple dwelling planned specifically for bachelors appeared at 52 Irving Place.
During the 1920s, tall luxury apartment houses and a hotel were built. The first apartment house along the park's northern face was 1 Lexington Avenue, begun in 1910. Between 1926 and 1929, three additional large-scale apartment houses were begun on Gramercy Park North, and in 1924 work began on the Gramercy Park Hotel. The hotel was extended in 1929-30. 81 Irving Place is designed by George Pelham and ornamented with terra-cotta detail.
By the early 20th century, loft buildings were being erected on Fourth Avenue (now Park Avenue South) and on many of the adjacent side streets, appearing as far east as Irving Place.
There were many buildings built for important institutions, such as - the United Charities Building, the Association for the Prevention of Cruelty to Children Building, the Church Missions House (a designated individual landmark), all build in 1892-93, and the Russell Sage Foundation Building, built initially in 1912-1915 and extended in 1929-31. The Manhattan Trade School for Girls (1915-19), the Children's Court (1912-1916), and the Domestic Relations Court Building (1937-39) and Washington Irving High School at17th Street/Irving Place.