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What to expect at Midwest estate sales

Katherine Langford
Editor-in-Chief · Tuesday, November 10, 2026 at 11:00 AM · 4 min read
What to expect at Midwest estate sales — Whitefish Bay Business news

For bargain shoppers, an estate sale presents a unique opportunity to look through what it took someone a lifetime to collect. But because these are the possessions of a recently deceased person — in homes that may be well kept, in disarray, or dilapidated — attendees are expected to show compassion and a certain decorum. “There is a layer of empathy for the person whose estate it was, for the family who is now having to say goodbye to this person. You’re in someone’s home and you’re looking at all their things,” Kate Davis said recently on Wisconsin Public Radio’s “The Lee Rayburn Show .” Understanding Wisconsin, Together. WPR’s “Wisconsin Today” newsletter keeps you connected to the state you love without feeling overwhelmed. No paywall. No agenda. No corporate filter. Facebook This field is for validation purposes and should be left unchanged. Email Subscribe Davis is the author of the new book “Bring Cash: A Guide to Estate Sales in the Midwest and Beyond ” and writes the weekly Substack newsletter “ Midwestern Estate Sailing. ” Estate sales in the region are particularly interesting for the stories they tell about the late homeowners and the treasures they reveal, she said. In the 1940s and ‘50s, “there was a ton of wealth in the Midwest,” Davis said. “And people still had that ethos left over from the Depression that when you acquired things, you held onto them. And (the Midwest) is a place where a lot of people live their whole lives. They had these beautiful homes full of things … and they never had to downsize.” When to go to an estate sale Everything is more expensive at an estate sale on weekdays, Davis says, “but they can also be much quieter then. If you can go on a Thursday or Friday, you’ll have more of the space to yourself and you’ll be able to shop a little bit more slowly. If you like a crowd and you want to stand in line and chat and get to know people, then Saturday is a more fun time to go.” Either way, you should do research in advance. Most estate sales will have ads and photos of available items posted on Estatesales.net or Estatesales.org . “Then if you know there’s something at the sale that you like and can’t live without, my recommendation is to get there as early as possible,” Davis said. That’s how she acquired for herself a pizzelle maker at an estate sale. A pizzelle maker is used to bake thin, decorative, Italian waffle cookies. Her other favorite estate sale purchase a couple years ago was a 1993 Mercury Tracer hatchback with only 60,000 miles on it. “I wish I could predict what will sell quickly, but the answer is always ‘it depends,’” Davis said. “It depends on who sees the ad, who shows up that day, and what it is you’re looking for. There are some things that almost always sell quickly. Vintage band T-shirts are a great example.” What to bring Whenever you show up at an estate sale, Davis said you should carry the following: Reusable bags: “Often, sales won’t have bags,” Davis said. “And you can bring like milk crates if you’re shopping for, say, dishware.” A tape measure: “This can be handy if you’re shopping for clothes and you can’t try something on. Or if you’re shopping for furniture, so you can check that it will fit in the space (you have at home) or in your car.” Disposable gloves, hand sanitizer, even a mask: Some estate sales are held in homes that haven’t been recently maintained “so things can be a little bit dirty,” she said. A set of basic tools , including a couple screwdrivers and a wrench “so if you do buy a big table or other furniture, you can take off the legs and it’ll fit in your car a little bit easier.” A flashlight: “I know a lot of us have one on our phone, but it can be a real power move when you’re in a garage to pull a flashlight out of your bag and use it to look around,” she said. Cash is king The top tip Davis has for people attending estate sales is the title of the book: “Bring cash.” “Cash just makes it easier for estate sales coordinators to keep track of what they’re making for themselves and for the beneficiaries of the estate,” she said. “And it is just easier to make a deal, right? You’re like, ‘Well, this is priced at $23, but I’ve got a $20 bill, and they’re like, “OK, that works for us.” Related Stories Trump administration promises $8B to help farmers cover high cost of harvest Squeezed by a tough economy, many farmers are relying on decades-old machinery

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