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Buyers and sellers tend to both be happy at the time of the transaction. There are exceptions, like forced sales due to foreclosure and what not but exclude those.
If you are buying something, you must be happy with it. Question is, do you remain happy with your purchase? There is a certain percentage of buyers remorse in the market. Perhaps due to poor math skills and realizing you can't afford the house, maybe you didn't notice the road noise in June but you really can hear it in November through May. There can be tons of reasons people fall out of love with something and they decide to sell the property. Making them happy sellers.
There is sellers remorse well. "If I had held that house I would have made..."
It depends on the way you look at it. Obviously if someone is selling they want out, and obviously if someone is buying they want it... which makes for a win-win situation. Buying has always been better for me. However, people buy and sell real estate for many different reasons and the real estate market entertains both buyers and sellers or else there wouldn't even be a market. For someone the seller can be winning if they have to sell fast due to a job transfer or death in the family etc. And for someone else the buyer can be winning because they finally found their dream home that they have been searching for the past 2 years. If it didn't benefit each side in a certain way then there wouldn't be a real estate transaction because often times selling and buying is a personal decision to make. Therefore, there really is no "which side is winning or better" as it just comes down to a matter of a real estate transaction. Ofcourse if you are in that position, each side may have their own personal prospective on it though.
In a good transaction, neither side "wins". They both benefit.
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