They capture key moments in his life, from his early years as a soldier to his leadership during the Second World War.
Each stamp features photographs of Churchill at pivotal times, accompanied by some of his most famous quotes from articles, books, letters, and speeches.
Churchill first appeared on a British stamp in July 1965 as the first contemporary individual to be featured.
Since then, he has been included in stamp issues such as the Churchill Centenary in 1974, National Portrait Gallery in 2006, Britain Alone in 2010, and Prime Ministers in 2014.
David Gold, Director of External Affairs and Policy at Royal Mail, said: “One hundred and fifty years after his birth, this stamp issue celebrates the enduring legacy of a leader who shaped the course of history and left an indelible mark on the hearts of the British people.”
Royal Mail collaborated with Allen Packwood, Director of the Churchill Archives Centre at Churchill College, University of Cambridge, to develop the stamps.
Packwood commented: “I think Winston Churchill would have been rather pleased to be the subject of these stamps, one hundred and fifty years after his birth.
“His archive certainly contains no shortage of letters.”
Winston Leonard Spencer Churchill was born at Blenheim Palace, Oxfordshire, on November 30, 1874.
After an early career in the army in the 1890s, he made his first foray into politics but was not elected as a Member of Parliament in 1899.
Instead, he travelled to South Africa as a war correspondent to cover the conflict between the British Empire and the Boer Republics.
His capture and daring escape made his name, and he was elected the following year.
He became a Cabinet Minister in 1908 at the age of 33 and married Clementine Hozier in the same year, entering a lifelong union.
His political career saw ups and downs, including losing office during the First World War over his advocacy for the unsuccessful Dardanelles campaign.
However, his warnings about Nazi Germany brought him back into the limelight.
He became Prime Minister in May 1940, promising ‘victory’ in his inaugural speech to the House of Commons.
Though he was defeated in the 1945 general election, he returned as Prime Minister in 1951.
Churchill retired in April 1955 due to failing health and passed away at the age of 90 on January 24, 1965, receiving a state funeral.
The stamps and a range of collectible products are available to pre-order from November 20.