Entrepreneur and hospitality mogul Paul Prager once abhorred buying objects owned by other people— but you’d never know it touring the Tidewater Colonial home, three guest cottages and 13 other structures encompassed in Maiden Point Farm, the 250-acre Miles River estate he shares with his wife, Joanne. Or The Prager Building and 14 mostly food- and beverage-focused businesses that comprise his holdings in Easton—a charming Chesapeake hamlet, about half of whose downtown he rebuilt and owns.

“When I first met Paul, he was not a fan of ‘used furniture,’ as he called antiques,” remembers Shaun Jackson, design director of Prager’s Bluepoint Hospitality, who has worked with him on every project since transforming his Fifth Avenue maisonette in 2006. “Now, he’s a connoisseur.”

The Herter Brothers desk in his office at The Prager Building in the heart of historic Easton is evidence of that; Prager has the world’s largest private collection of the Gilded Age firm’s pieces. In addition to furniture, especially Swedish Expressionist, English and Biedermeier, he collects porcelain, paintings, crystal and silver. He also has a weakness for luxury cars, including Rolls-Royces, Ferraris, Bentleys and Aston Martins. “We like stuff,” avers this 66-year-old, Brooklyn-born renaissance man whose grandparents escaped Austria in the Holocaust.

The founder of multibillion-dollar infrastructure provider Beowulf Electricity & Data, Prager is a 1980 graduate of Annapolis’ Naval Academy, where his love for the Chesapeake region began. In the early 2000s, he started looking for a place away from Manhattan where he and Joanne could raise their four children, now grown. He saw dozens of properties before discovering Maiden Point. “It appealed to me because it was honest, of the place and a true peninsula. It opens up to the sun and sky,” says Prager. The couple bought the property in 2003 and now own more than 1,000 acres of Maryland farmland.

The 2008 recession triggered Prager’s makeover of downtown Easton. “Small towns were in crisis,” he recounts. “The theory was, we have a farm and want it to be a place that kids would enjoy and want to come back to as adults, where second-home owners would want to spend more time. We needed to buy enough to make a difference, to affect change.” And to lure his corporate staff from New York and Colorado. He purchased what is now The Prager Building in 2008; Beowulf and Bluepoint are both headquartered there.

Jackson explains the strategy. “Paul was making a romanticized version of a European town we’d all want to live in—but American, with brick sidewalks and Federal-era style.” Prager opened spots on Federal Street that he thought his family and corporate staff would enjoy: a salad-centric café, Sunflowers & Greens; the coffee shop Weather Gage; and Bas Rouge, an Austrian restaurant that earned a 2024 James Beard Award for Best Chef Mid-Atlantic for executive chef Harley Peet, who runs all of Prager’s food operations.

Other Bluepoint Hospitality eateries include a cold-press juice store, Bumble Bee Juice; a single malt Scotch and Champagne bar, The Stewart; a Chanel-inspired ice cream and pie shop, Bonheur; a Neapolitan pizzeria, Roma Alla Pala; a crêperie dubbed P. Bordier; and an epicurean food emporium, The Wardroom. A crystal-and-silver boutique and book and poster shops are also in the mix. The Prager Family Center for the Arts occupies an 1856 building that was once the Ebenezer Methodist Episcopal church and now houses the Ebenezer Theater and Zach Gallery.

New projects abound. The renovation of the Washington Street Pub (which will retain its name and Old World character) should be complete in June of 2025. A farm owned by Prager in Trappe, Maryland, makes European-style cheeses. At Prager Vineyards, a former farm, winemaker Helen Keplinger recently harvested the first grapes from vines planted five years ago. “We bottled a few cases and it’s brilliant,” enthuses Prager, who is looking for space to open a wine boutique. Not satisfied with building businesses, he longs to build homes on the Tred Avon River waterfront.

No detail along the way escapes him. “I have to touch every single item,” says the entrepreneur. “The grain of the wood, the cleft of the stone slab floor, the weight of the crystal—they make it all come together as a living organism.”