==> I assume this implies I saw the same deer four time not four deer.
I don't think it implies either one. The sentence claims that on four separate occasions, you saw a deer. There is nothing about identifying the deer itself. It may have been the same deer seen four different times; it may have been four different deer, each seen once; it may have been two deer, each seen twice; or a three and one combination. Who knows?
==> "On my way to work there were four times I saw [a] deer"?
Without the article 'a', there is no indication of how many deer you saw in each instance. The article 'a' clears that to one deer per sighting. But again, that provides no indication of whether it is the same deer or not.
If you want to be clear that you saw the same deer four times, then you could say, "I saw the same deer four separate times on the way to work". If you want to be clear that you have four sightings, with each sighting being a different deer, then perhaps you could say, "I had four deer sightings, each one a different deer, on may way to work".
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