Middletown, N.Y., is home to the historic and stately former headquarters of the New York, Ontario & Western, now referred to as “an unofficial shelter for the homeless,” since a fire in 2004 gutted the privately owned building. Just a few years ago hopes were high that a local health center would transform the dilapidated building into something the community could be proud of, but that hope faded as the hospital’s financial problems and the failure of a key grant application torpedoed the plan. The building remained a blighted, magnet for transients as the structure continued to deteriorate. The city of Middletown repossessed the now fire-damaged building in June and pledged to seek a company to redevelop it, rather than demolish it immediately. Construction of the building began in 1892, designed by Bradford Lee Gilbert in the Richardsonian Romanesque style of the late Victorian era, with more modern elements following in 1904 and 1920 additions. The railroad went bankrupt and was abandoned in March 1957.

—Eric Berger