The settlement of Caldmore grew up around an important road junction, the shape of which defined an open space of roughly triangular shape called Caldmore Green and, in the course of the 19th century, this became the principal focus for the development of a social and commercial area.

Later, the area surrounding Caldmore Green underwent considerable redevelopment in the 1950s with the removal of Victorian slums and their replacement by new flats.

Jerome K. Jerome, late Victorian novelist, essayist, humourist and playwright, best known for his classic comic novel Three Men in a Boat, was born at Belsize House on the corner of Bradford Street and Caldmore Road.

When one of the first tower blocks was demolished, the body of a man was discovered in one flat; he had not been seen for six years and was believed to have died of natural causes shortly after his last reported sighting, but the council had not served an eviction order because the flats had already been earmarked for demolition.

Between 1950 and 1970, hundreds of immigrant families from the Commonwealth settled in Caldmore, and today it has a strong Asian community.