Isaac Singer was 60 years old and one of the richest men in America when he came to Devon. He had not invented the sewing machine - he had invented the version that worked well enough to sell - and the Singer Sewing Machine Company had made him a tycoon. He was also, by the standards of his time and any other, an extraordinarily complicated man: at least 24 children by several women, a string of scandals, a personality that finally made New York society uncomfortable enough that he sailed for Europe. He bought the Fernham estate in Paignton around 1871, demolished the existing buildings, and commissioned a local architect named George Soudon Bridgman to build him a new mansion. Singer wanted a theatre inside the house. Bridgman happened to be working with a young apprentice newly returned from London - Frank Matcham, who would go on to design the great Edwardian music halls and theatres of London. It is entirely possible that the Oldway theatre was Matcham's first commission. Singer died on 23 July 1875 with the house still being finished.

Isaac's son Paris Singer inherited his share of the sewing-machine fortune and a taste for grand European architecture that exceeded even his father's. Between 1904 and 1907 he rebuilt Oldway as a version of the Palace of Versailles. The grand staircase was carved from marble with bronze balusters and lit by an enormous reproduction of David's painting of Napoleon crowning Josephine. The first-floor gallery was a one-third-scale Hall of Mirrors. The grounds were laid out with formal French parterres. Paris Singer also had a famous affair with the American dancer Isadora Duncan, who lived at Oldway for stretches and danced barefoot in its mirrored gallery. The relationship ended badly in 1917. Singer became an American citizen for tax reasons and moved permanently to the United States the following year. The mansion he had built to be French in spirit was never really lived in again.

During the First World War, Oldway was given over to the wounded. The Rotunda was filled with rows of beds and the building became the American Women's War Relief Hospital, treating soldiers brought back from the trenches of France and Belgium. King George V visited in 1915. After the war the house bounced through uses that increasingly mismatched its grandeur. It became the Torbay Country Club in 1929 with tennis courts and a bowling green laid over what had been formal gardens. The Torbay Golf & Country Club opened in 1933 with Oldway as its clubhouse. During the Second World War the house held RAF cadets training to be aircrew. In 1943 it was damaged in an air raid - Paignton was attacked repeatedly by Luftwaffe fighter-bombers - and parts of the roof and east wing took fire and shrapnel. The Singer family finally sold the mansion to Paignton Urban District Council in 1946 for £46,000. The original construction cost is estimated to have been around £200,000.

For decades Oldway served as council offices. Couples were married in the rotunda where wounded soldiers had once lain. In 1993 it was Grade II*-listed for its architectural importance. In 2012 Torbay Council approved a £12 million scheme to convert the mansion into a luxury hotel and sheltered retirement flats. It was a plausible saviour for an ageing building. It did not happen. The developer, Akkeron, claimed Torbay Council had caused delays through lease disputes and demanded £8 million in damages. The agreement was terminated in August 2016 and the legal dispute killed the project. Oldway has been closed since 2013. The bowling green still operates. The tennis courts are gone. In 2018 the Victorian Society named Oldway in its top ten buildings 'crying out' to be saved. In 2023 it was added to Historic England's Heritage at Risk register. A National Lottery Heritage Fund bid for around £10 million is in play. The Hall of Mirrors still waits behind locked doors, parquet dulled by years of disuse, watching itself in its own gilded reflections.