What’s your stuff worth? Let this Tampa Bay expert tell you.

Jeffrey Hess may have written the book on Rolex watches, those stately timepieces beloved by collectors, but he’s also an expert on downsizing. “I’ve been fortunate enough, and I say that with great reverence, to help thousands of people settle estates,” said Hess, the owner of Hess Fine Art, Hess Fine Auctions and Old Northeast Jewelers in St. Petersburg and Tampa. Hess has sold antiques and appraised household goods for two decades and is the author of the book, “The Best of Time: Rolex Wristwatches: An Unauthorized History.” He authors the weekly “What’s It Worth?” column in the Tampa Bay Times. He also helps customers navigate the challenge of decluttering their homes and moving into smaller spaces.

We asked Hess for advice on how to decide which items to toss and which to keep. “I have one major rule,” he said. “If it’s going to leave a hole in your psyche, if it’s going to leave a hole in your heart, don’t sell it.”

A few obvious non-starters are dishes, books and furniture. Of the estimated 10,000 china sets brought to his stores over the years, Hess has bought fewer than 100 complete sets. Most are made by Herend, a Hungarian company that produces luxury, hand-painted and gilded porcelain china worth about $15,000 a set.

Books, unless they were published before the 1860s, have little value. “Obviously, first editions are great, but what you are really looking for is historical books,” said Hess. “Colonial books from the 1760s to about 1810, if they were printed in America, typically have some value. Medicinal books prior to 1860 are collectible, especially (books about using) plants as medicine.”

Furniture “is a problem,” Hess allowed. “What’s really popular right now is mid-century modern,” he said. “That’s the stuff our parents threw away in the 1950s and 1960s.”

Hess recommends that his customers sell furniture on Facebook if they don’t want to donate the pieces. Some furniture consignment shops, such as Déjà Vu in St. Petersburg, offer to sell gently used furniture from smoke-free environments and split the proceeds.

Pianos also fall into the worthless category, said Hess. The internet is full of videos featuring people smashing pianos and stories about piano factories destroying merchandise they can’t sell. An exception would be Steinway pianos that have a history of being played by a famous pianist or on a prominent stage.

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On the flip side, people have a tendency to throw out things that have surprising value. Specifically, paper and military items. “Antique diaries, war photos and signed documents are valuable,” Hess said. “Ribbons and medals, especially from World War II and the (American) Indian Wars, are highly, highly collectible.” Confederate swords are always worth a few hundred dollars but could be worth thousands if they were carried by officers.

The sports memorabilia market has taken a dive in recent years because of fake merchandise or fabricated authenticity certificates. But, if it’s pre-1960s memorabilia that can be authenticated, Hess said, it’s still valuable.

Hess has a few rules for selling quality items. First, high-end antiques and fine art should likely go to public auction in New York City. “The transparency of an auction is really good because you can see it and you know the auctioneer is making the small percentage they agreed to make,” he said.

Second, some homeowners may benefit from whole-house sales. That’s when a representative comes in, identifies the expensive stuff and sells it along with the homeowner’s other items. “What you have to avoid is hiring a salesperson who is going to sell your expensive Monet for $1,000 because they can’t identify (it properly),” said Hess. Also, be aware, hiring an expert can be more costly because of the labor-intensive process.

“The next level is what we call the garage sale people,” said Hess. These are independent companies that do everything, including hauling out trash, donating items to charity, selling furniture and cleaning the homeowner’s property. “They come in and just buy everything for one check, or else they don’t charge you and they keep all the junk. That’s really, really helpful,” he said, especially if time is a factor.

When Hess’s experts buy everything in a house, they will discard junk and donate items that can be used but aren’t necessarily valuable. His preferred charity is CASA, a domestic violence support organization in Pinellas County that operates a thrift store near downtown St. Petersburg.

Where to donate

CASA’s thrift store accepts furniture, clothing, appliances, shoes, jewelry and household items. casapinellas.org.

Goodwill has numerous donation centers throughout Pinellas, Pasco and Hillsborough counties. goodwill.org.

College Hunks Hauling Junk & Moving will pick up truckloads of items for donation or dumping. They partner with a number of agencies, including Goodwill and Habitat for Humanity ReStores. collegehunkshaulingjunk.com.

Empath Suncoast Hospice Resale Shops accept donations of clothing, furniture, home goods, collectibles, small appliances and more at its three locations. ifyouthrift.org.

Salvation Army thrift stores are located throughout Pinellas and Hillsborough counties. They accept clothing, furniture, household items, appliances and cars. satruck.org.

Detox Designer Resale Boutique buys like-new clothing, including luxury purses, from customers by appointment. detoxstpete.com.