I Finally Went to My First Estate Sale and Discovered It Certainly Won't Be My Last

Vintage inspired living space.

Ashley Montgomery Design

Despite having a home filled with thrifted pieces and antiques, I'd never quite felt comfortable digging through someone else's belongings. Estate sales seemed off-limits to all but an elite group of regulars, those who scout out the best sales well in advance, take weekdays off to show up early, know just how to haggle for the best prices, and boast homes full of secondhand treasures from the rich and richer. And, I thought, wasn’t it kind of morbid to sift through someone’s belongings, knowing the sale was open likely because they’d recently passed away?

How wrong I was. It all changed with a last-minute invite from a friend. She was going to an estate sale in Bethesda, MD. The widow of the late author and Presidential speechwriter, William Safire, had recently decided to downsize, and the home was sure to be full of political finds, midcentury style, and Washington memorabilia. And, with a partner in crime by my side, I felt like this was exactly the right occasion to dive into the estate sale scene.

And, with a partner in crime by my side, I felt like this was exactly the right occasion to dive into the estate sale scene.

Formal sitting room with fireplace.

Britt Design Studio

I met my friend there at 11 a.m. on Sunday and a line had already formed outside. This is the first lesson I learned: lines are common at the estate sales of big-names, and they’ve become even more common if occupancy is limited inside the house. Be prepared to wait if you’re going to an estate sale that has the promise of incredible finds.

I asked my friend how she’d found out about the sale. She’d seen a sign while out running errands and decided to check it out. A quick stop on the first day led her to go back on Sunday, with me in tow. A roadside sign is always a good bet, but now that I’m hooked, you’ll find me perusing estatesales.net and making notes on the next big sale. 

When it comes to timing, if you want the first pick or if you have your eye on a particular high-value item, then you’ll want to go on the very first day. However, if you’re simply browsing, then going on the last day of an estate sale, often Sunday, can come with significant advantages. I walked up to the front door on that Sunday morning and saw a sign that spoke to my bargain-loving heart: 50% off. Yes, that meant 50% off the prices as marked.

The gorgeous $70 crystal decanter that I can imagine Mr. Safire sipping brandy from? Just $35. A stunning Hermès scarf marked at $60? $30. Seriously. The prices were unbelievable and, had I been a bit more experienced in the estate sale scene, I would have known to leave a bid on the pristine Wedgwood Florentine china set. The final day is when the real bargains–and haggling–can be found. 

Formal sitting room with luxe art.

Erin Williamson Design

Since I’m still an estate sale novice, I went straight to an expert to learn more about everything I have yet to learn. Rebecca Thistlewaite, the director of business development at Hunt & Peck Auctions and Estate Sales, shared with me three must-know tips for those looking to start filling their homes with vintage treasures—and you better believe I’m putting these into practice ASAP. 

“Estate sales aren’t just old and dusty homes full of secondhand goods," Thistlewaite says. "They can be treasure-troves of incredible design and taste and house amazing collections. A favorite of ours was when we orchestrated the estate sale of the late film lobbyist Jack Valenti. Inside was an unbelievably staged collection of folk art, design, early Americana, and film/Hollywood ephemera.”

These homes are just that—homes. So, as my first estate sale was filled with political photos and books, an artist's home might be filled with amazing art or the estate of an ambassador might have finds from around the world. Do your research on the people behind these sales to get an idea of what you might discover.

 And don’t get caught up in dated décor. You may have a minimalist or modern style, but that doesn’t mean you won’t come across a statement piece you absolutely need.

“Use your imagination to think about pieces outside of their current home and design uses," Thistlewaite adds. "Antiques can look absolutely incredible in modern and very minimal settings. Buying and designing with antiques or vintage brings an element of originality to a room. Antiques don’t always need the aesthetic of your grandmother‘s stuffy and museum-like sitting room. They are meant to be used and put into creative and different vignettes. Estate sales are great places to search for and buy antiques and unique pieces.”

Vintage inspired living space.

Ashley Montgomery Design

Antiques can look absolutely incredible in modern and very minimal settings.

 Lastly, she says, “Make sure to look for well-made pieces. Henkel Harris and old Baker and Kittinger were the top of the line at one point. Not only do they retain a lot of their value, but their construction, design, and materials are best-in-class.”

I walked away from my first estate sale with just three small items: the aforementioned crystal decanter and Hermès scarf, along with an Hermès tie—which, for the record, my husband wore to an interview a few weeks ago, and I like to think Mr. Safire’s success brought him good luck. While I didn’t go home with any heirloom antiques or fine art, I’m in deep now, and you can guarantee that I’ll never pass by an “Estate Sale This Way” sign again.