Date unknown, but some Sears swing sets sold for around $40 in 1969, so this could be a little before that, given $30 was a common price point in the '50s-60s. These were very common in backyards throughout North America by the '50s. Some models had appointments like ponies to ride, tires, or even jungle-gym type attachments.
The '50s sets got safety improvements in the '70s, and by the '80-90s changes to safety laws saw the metal tube sets phasing out in favor of updated designs. It was possible for children swinging in unison to tip the structure over if not cemented down, not to mention opportunities for cuts and pinches. About 1 in 25 owners in 1971 reported an injury requiring medical attention.
Here's a photo of a metal tube swing similar to the Sears ad model, without the slide option.
Swings have been around a while. Here's a small model of one circa 1400BC from Crete, specific year unknown.
Nice. I made a post about a month ago about those Sears catalog houses. They aren't as well known these days.
I currently live in a kit house, not sears and modified, but built by my dad.
I'm amazed he managed to build a house and work. I was one and a half when he started in '81. We are actually in the middle of a new project now so... not quite done (never will be).
We also had one of these swing sets.