Gary Smedley, aged 19, crept into the woman’s three-bedroom semi-detached at Bawtry Road in Austerfield while she was asleep.
The victim went downstairs the following morning and found her door open with the lock and door handle broken.
Smedley stole seven rings, including her wedding and engagement rings, and five pairs of earrings, said Stephanie Hollis, prosecuting.
“The woman was very upset and had lived there for 47 years with nothing happening like this previously,” she added.
Smedley was arrested after his fingerprint was found on a bedside ornament.
Just a few days before this incident, Smedley had also broke into an unoccupied semi at Elmfield Road in Rossington.
The owner of the property was in the process of decorating the property to put it up for sale.
Smedley was spotted by a neighbour as he walked down the drive and then came out of the house five minutes later.
The neighbour found the patio door open and water dripping from the ceiling.
The owner was alerted and on attending the property discovered that floorboards upstairs had been taken up and five metres of copper piping from the boiler had been stolen.
Part of the ceiling had collapsed and each of the downstairs rooms was damaged to the value of £3,000.
When arrested Smedley claimed he had acted as a lookout for the Rossington break-in and another youth was present.
He initially denied burgling the pensioner’s home.
Sheffield Crown Court heard he first appeared in court at the age of 16 and has several convictions for dishonesty.
In May this year he was given a community order with supervision for stealing more copper piping and radiators from commercial premises.
Samina Rashid, defending, said he had moved to live with his mother who had a bi-polar condition and acted as her carer.
He then went to live with his father who had depression and ended up caring for him.
“He turned to drugs and found it difficult to cope,” she said.
Smedley, who ives at Frampton Terrace in Gainsborough, admitted the burglaries on May 2 and May 6.
Judge Simon Lawler told him: “You have been given a number of chances by the courts.
“Some of the stolen jewellery was of great sentimental value which has not been recovered.”
Smedley was given three years at a young offenders’ institution.