The Great Fire of 1866 destroyed nearly 1,800 buildings and left 10,000 people homeless, prompting a rebuilding of the city that gave Portland its characteristic architecture.

Built in 1857, this grand home opposite the Victoria Mansion was demolished in 1988. The outcry against the demolition led to the passage of a stronger demolition delay ordinance in the city.

Like Union Station, Grand Trunk Station was abandoned with the end of rail service to Montreal. The 1903 Queen Anne building was demolished in 1966. The office building adjacent to the station survives.

Built in 1800, this handsome Federal style structure was demolished in 1955 to accommodate the expansion of a local business.

The imposing Greek Revival style building was built in 1868, following the Great Fire. It was destroyed for the planned widening of Middle Street part of a larger transportation plan during the city’s urban renewal.

A mostly residential street of homes of varying styles was demolished for the construction of the arterial. The work was part of a larger transportation plan during the city’s urban renewal.

Built in 1897 to accommodate a growing congregation on Munjoy Hill, the St. Lawrence Church was listed on the National Register of Historic Places in 1979. In 1986 the congregation dissolved and sold the building to private developers. Suffering from years of insufficient maintenance and repairs, the church was demolished in 2008. The Parish House was restored and renovated as a performing arts venue.

Built in 1888, this iconic building was doomed when Maine Central Railroad ceased passenger service to Portland in 1960 and began selling off its properties. The station was demolished in 1961 to make way for a shopping center. The demolition led to the organization of Greater Portland Landmarks and rallied public support for preserving Portland’s historic character.

Several historic buildings at the corner of High and Free Streets were removed for the expansion of the Portland Museum of Art in 1980. The most prominent building was the original Young Men’s Christian Association Building (1897), a mixed use building of shops, offices and apartments. It was later owned by Harold and Ralph Libby and known as the Libby Building.