James Ockenden also kept an archive of ephemera relating to his wartime heroics which is also part of the auction lot.
The soldier from Portsmouth, Hants, received his VC – the highest award for gallantry – just weeks after being awarded the Military Medal in October 1917.
He single-handedly took out a German machine-gun nest - killing the crew - then forced the surrender of an entire garrison at a farm, having killed a further four enemy combatants.
On December 5th he was presented with his Victoria Cross by King George V and was later given the Belgian Croix de Guerre medal.
The lot will go under the hammer at Nesbits saleroom in Portsmouth – yards from where Ockenden lived.
It will be offered on May 21st with an estimate of £220-260,000.
The sale comes shortly after the Imperial War Museum in London announced it was to close Lord Ashcroft’s display of VCs – the biggest in the world.
Also included in the auction is a reunion menu signed by 30 other VC recipients, a letter from Portsmouth City Engineers Departments regarding the naming of a new street called ‘Ockenden Close’ – which still exists – and dog tags, photographs, invitations and other items.
Auctioneer John Cameron said: “We received instructions in 2021 to value the medals and associated collection for probate purposes and, as a keen military historian, it was a career high point.
“I was astounded at all of the paperwork and associated items and felt very privileged just to hold the medals in my hands.
“The following year I visited the Ypres battlefields with some friends including Alan Lashley, WW1 historian and author of a book on ‘The Portsmouth Pals’.
“Al knows the battlefields like the back of his hands and took us to the farm where James Ockenden earned his VC.
“Sergeant Ockenden was one of those heroes who let his actions do the talking.
“He was one of nine children and was born in 1890 to Alfred and Mary Ockenden. In 1909, having worked as a draper’s assistant, he went to his local recruiting office and was sent to join the Royal Dublin Fusiliers.
“He served in India and then after the First World War began he found himself as part of the disastrous Dardanelles campaign at Gallipoli in Turkey.
“In April 1915 he landed on ‘V’ beach at Cape Helles which turned into a bloodbath during which he was shot in the head.
“After recuperating he served in Egypt and while on leave married his sweetheart Caroline – or Carrie as he called her.
They had met at a bus stop and went on to have three daughters and a son.
“Shortly after his wedding he was on the Western Front and on September 28 1917 carried out an astonishing action during the opening salvos of the Third Battle of Ypres for which he was awarded the Military Medal.
“He led his men into a trench to relieve another company who had become trapped and disconnected from their officers.
Despite being spotted and the enemy putting up a huge barrage, Ockenden succeeded in the daring rescue.
“And it was just six weeks later – aged 26 - when he carried out his extraordinary action that led to his VC.
“He was acting company sergeant-major on October 4 when he rushed a machine-gun nest, killed its crew and captured it.
Not content with that he then rushed to a farm where a German garrison was embedded.
“Under heavy fire he was able to kill four of them, upon which the sixteen remaining soldiers surrendered.
“After the war he was honourably discharged on medical grounds and went on to work as a crane operator at Portsmouth dockyard and then as a school caretaker.
“Ockenden attended reunions and was always pleased to meet old comrades.
“When World War Two began he volunteered again and served in the Home Guard, qualifying for the WWII Defence Medal. In 1960 ‘Ockenden Close’ in Portsmouth was named after him.
“It is incredible that his medals and other ephemera have stayed together over so many years.
“The family have decided that now is the right time to sell. It has been an agonising decision for them and they are doing so to help out their daughter and granddaughter – Ockenden’s great-granddaughter and great-great granddaughter.
“They know some might have negative views but believe James Ockenden would approve, as a man who always put others before himself.”
Company Sergeant Major James Ockenden VC MM died in 1966 aged 75.
His medals are: The Victoria Cross, Military Medal, 1914-15 Star, British War Medal 1914-1920, Victory Medal, WWII Defence Medal, George VI Coronation Medal, Queen Elizabeth II Coronation Medal and Belgium Croix de Guerre Medal. They are all mounted for wearing.
Other items include a silver badge which is ‘Sir Alfred Butt’s Invitation to VCs’ and Ockenden’s name is on the back.
There are two VC and GC Association membership cards and rule book, cuttings, and a Princess Mary 1914 Christmas tin.
There are signed photos, discharge certificate, a military field map dated 26th August 1917 showing trench positions and a telegram of congratulations on his VC, amongst much else.
The citation: For most conspicuous bravery in attack. When acting as Company Serjeant-Major and seeing the platoon on the right held up by an enemy machine gun he immediately rushed the machine gun, regardless of his personal safety, and captured it. He killed the crew with the exception of one man, who made his escape. Sjt. Ockenden however, followed him, and when well in front of the whole line killed him and returned to his company. He then led a section to the attack on a farm. Under very heavy fire he rushed forward and called upon the garrison to surrender. As the enemy continued to fire on him, he opened fire killing four, whereupon the remaining sixteen surrendered.
Ends