Hoffman House Hotel, ca. 1905

Located in what was once an exclusive residential area, the Hoffman House Hotel was considered one of the first hotels/commercial ventures in the Madison Square area. Opened in 1864, the original hotel occupied the building one in from the corner (though this circa 1905 image depicts the original locale with a late 19th-century rooftop addition). In 1870 as Broadway and Fifth Avenue lined with newer and fancier hotels, the Hoffman opened a large annex at the corner The hotel was well known for its cuisine, artworks, and opulent decoration, and was a popular headquarters for Democratic politicians.

On January 22, 1870, the New York Herald announced that sisters Victoria C. Woodhull and Tennessee (Tennie) C. Claflin had rented Parlors No. 25 and 26. They established a stock brokerage firm, becoming the first female brokers, before decamping to a Broad Street office with the help of friend Cornelius Vanderbilt.

By the middle of the 1890s, the annex had been replaced with the grand Moorish-influenced building seen here at the corner. The original building gained an extra three stories around the same time, only to be completely demolished and replaced with a new gleaming white limestone structure in 1907. Alas, the loss of revenue during the reconstruction and the Panic of 1907 signaled the early death knell for the hotel. After entering bankruptcy in 1910, the hotel closed its doors (both of them) in 1915. Both of these buildings, and its hotel neighbor on the block, the Albermarle, were demolished for a 16-story loft building soon after.