I think there are two types of this, only have experience with 1 so far. Within a single season, absolutely. In deep winter entering water temp (EWT) is around 30degF (this is a pretty accurate measure of bulk ground temp). Typical for where I live is 50degF.

Other type is permanent change that persists year over year. Haven't lived here long enough to measure this. But if you pull more heat from the ground in the winter than you put back into it into summer (we use a water to air compressor for AC in summer), then yes, it can happen and does happen. Don't know if we are in this bucket yet.