Start with why you're moving. Once you're sure the move makes sense, rent a dumpster. Decluttering 20 years of belongings is a project no matter how you time it, so get rid of what you don't need to bring to the next house before you list. Less clutter photographs and shows better, and a garage makes a good staging area to sort from. On structuring the two transactions, a common approach: 1. List your current home with a contingency that you find a suitable replacement property first. 2. Once you're actually in escrow on your own sale, make an offer on the new home contingent on that sale closing. Having your property already in escrow makes your offer far cleaner and more credible to the seller you're buying from, because your side of the deal is largely de-risked. The instinct for most people is to wait until they've found the perfect new home before listing, out of fear of ending up with no house at all. The contingency structure is what protects against that gap, and it only works if your home is listed and moving. A good agent on your side, and a lender who can model both payments, keeps the timing from getting away from you.