Glasgow's former Lord Provost was one of 91 people honoured when the Queen presented him with his OBE at Buckingham Palace, Mr Winter having met the monarch only once during his five years in office.
But in the past six weeks, Mr Winter has met Her Majesty twice - each time at the palace.
Mr Winter's wife Sheena and 28-year-old daughter Sara went with him to collect the award.
He said: "I met the Queen in Buckingham Palace six weeks before at an event to do with her Diamond Jubilee.
"She invited people who had made some contribution to her special year, and I suppose I was invited in my former capacity as Lord Lieutenant of the City of Glasgow.
"When I went to receive my OBE she knew exactly who I was. She is amazing.
"There were 91 people receiving awards and the ceremony lasted an hour and 20 minutes but she stood on her feet all the time and managed to have a conversation with every one of us."
Mr Winter said he was not nervous about meeting the Queen but was in awe of Buckingham Palace. He said: "It is breathtaking in its beauty, its paintings, wall papers and wonderful chandeliers. It is like the City Chambers on a grander scale and there is much more of it."
The first time Mr Winter met the Queen was when Pope Benedict XVI travelled to Glasgow two years ago to conduct a Mass in Bella-houston Park in front of around 65,000 worshippers.
Mr Winter started work at the age of 17 in 1954 as a trainee welfare officer in local government and retired 42 years later as director of social work for Strathclyde Regional Council - one of the biggest departments of its kind in Europe.
In 1999 he was elected to the city council and stepped down in May as the longest serving Lord Provost since 1606.