The 41-year-old enjoyed an incredible career at the top of the game, winning two Champions League trophies - with Ajax and United - four Eredivisie titles, four Premier League titles, and being named Europe's best keeper on three occasions, as well as winning a record 130 caps for Holland's national team.
And, as he prepares to settle down to watch the Red Devils in their Premier League showdown with Chelsea at Stamford Bridge on Sunday, Van der Sar can't help but feel an element of regret that he's no longer involved, particularly when he sees the evergreen Ryan Giggs and Paul Scholes in action at Old Trafford.
Inevitably, the question that haunts the Dutchman the most, is whether or not he called-time on his career too early. But that will forever remain unanswered, so there's no point prolonging the debate.
"Playing is the biggest thing there is. You want to experience it for as long as possible and when you see people like Paul Scholes playing you think 'maybe'," Van der Sar explained. "It is such a great life. I would urge anyone to cherish every moment.
"Life is better now, but in a different way. I have more time with my family. There is not as much travelling.
"But nothing can replicate the thrill of making a great save at an away ground, or hearing your own fans cheering you, or the atmosphere when you score a goal or win a big game."
One of Van der Sar's career highlights during his time with Manchester United, was the dramatic penalty shoot-out save to deny Nicolas Anelka and Chelsea in Moscow, to help clinch the Champions League trophy for Sir Alex Ferguson's side in 2008.
It was one of few success stories that he experienced against the Blues, and for that reason alone, he is anticipating a difficult task for United this weekend.
"We didn't win at Chelsea too many times when I was at United and it won't be any easier this weekend," he added. "They have changed their formation. They are more lively now and have more go-forward in their team.
"They certainly look to have great attacking options in midfield, which is the area United seem to have struggled a little bit.
"So far United have not had many tests, just Tottenham, and unfortunately they lost that. But this will be a big one."