If both properties are in relatively the same area then I would suggest ultimately hiring one agent. Interview a couple of agents together with your fiance' and decide who you are most comfortable with and who is the most qualified. You are hiring an adviser and it should be someone you trust. However, I would recommend making a decision as to whether you want to sell one or both before you sell either. If you need help figuring out what to do then consult with an agent to determine which home holds the greater value. It is an out of pocket expense for listing agents to properly market your home for sale, so you want to be respectful of that persons time and consider that they will lose money if you decide not to sell, besides getting a home ready for sale, keeping your home in show condition and making it available for showings is an effort on your part. If your homes are in different areas then decide where you really want to live and maybe liquidating both properties and consider buying a place together to get a fresh start. Congratulations and good luck to you!