Sawyer Hemsley is at it again. Barely six weeks ago, everyone’s favorite cookie mogul dropped $12 million on a Hollywood Hills mansion, tucked away in L.A.’s coveted Bird Streets neighborhood. Since then, the entrepreneurial and frequently sassy cofounder and chief marketer of the Crumbl chain has embarked on an all-out shopping spree—he’s bought not one but two more multimillion-dollar homes in quick succession, one located in prime New York City and the other unexpectedly hidden on the outskirts of Portland, Oregon.

Hemsley, 33, is now also much more famous than he was even six weeks ago. In August, the sweet treat savant and dance music aficionado went majorly viral on TikTok, with videos about him racking up tens of millions of views; he subsequently came out as gay and now sports more than 400,000 followers across various social media platforms.

Somehow, between all of that online drama, Hemsley has found time to jet-set around the country, collecting luxury homes like they’re so many infinity stones. He’s also created dozens of LLCs to hold his properties and other investments, nearly all of them with sugary sweet names: “Nutty Buddy LLC,” “Caramel Popcorn LLC,” “Brownie Batter LLC,” and many more.

While L.A. and New York are obvious and typical destinations for rich folks seeking a part-time second home, Oregon is much more of a residential wild card. We aren’t entirely sure what drew Hemsley to this $5.2 million Portland-adjacent property, located on the scenic shores of Lake Oswego, as he doesn’t appear to have any personal connection to the area, but he’s certainly rich enough to make an impulsive financial decision or two.

It’s no secret that Crumbl, despite having been started by Hemsley and his cousin Jason McGowan less than 10 years ago, has already achieved a widely publicized $2 billion valuation on the back of its giant, ultra-sweet cookies, which retail for $5 a pop. And Hemsley and McGowan have cashed in on that success; over the summer, the pair sold a minority stake in the business to TSG Consumer Partners. Even more notably, however, they’ve also taken out a whopping $500 million loan from Blackstone to fund future expansion.

Built in the early 1960s and offering six bedrooms and four bathrooms in a spacious 4,600 square feet of living space, the two-story Oregon house is traditional outside and cleanly contemporary within. And it offers all the amenities you’d also expect to find at a modern beach home down south in California: there’s a open floor plan, porcelain tile floors that mimic hardwood, an updated kitchen and separate wet bar, and gallons of white paint.

But the real value in this property, of course, are the location and water views. Perched on the tip of a peninsula, the house offers a hefty 230 feet of lake frontage from a newly constructed deck, plus a brand-new separate boathouse with its own rooftop deck. And though the property is relatively secluded, it remains just a short jaunt from hiking and biking trails, Whole Foods, and the quaint shops that line downtown Lake Oswego.

The realtors for the Lake Oswego property noted the house closed in record time, just two weeks after the buyers—Hemsley and his L.A. realtor boyfriend, we presume—flew into town to spend one weekend at Lake Oswego and immediately decided they needed a vacation home there. It was clearly love-at-first-sight for Hemsley, who wrote about it on his Instagram account, saying the Lake Oswego “feels like if Lake Como and Finland had a baby.”

Located in the graffiti-adorned Spears building in Manhattan’s Chelsea neighborhood, Hemsley’s new condo is one of about 30 lofts in the red-brick structure. At one point operated as a furniture warehouse, the six-story building dates to the 1880s and was originally a cigarette packing facility; following 100+ years of industrial usage, it was converted to condominium residences in the late 1990s.

Although many of the Spears building’s luxury lofts have renovated out the details of the building’s industrial past, certain units retain the original wooden support beams and plank ceilings used in the former factory. Hemsley’s new home appears to be one of those units, though the place has clearly undergone a meticulous renovation in recent years.

Hemsley paid $7.2 million for the N.Y.C. pied-à-terre, which has three bedrooms and three baths in 3,000 square feet of living space. And it doesn’t appear he was concerned with getting a deal here; last sold in 2024 for $6.4 million, the condo was offloaded to him by tech entrepreneur Elia Zaitsev, who doesn’t appear to have made any significant changes to the place during his brief ownership.

Highlights of the second-floor unit include soaring ceilings, abundant natural light, and ample wall space for a major-league art collection. There’s also a very contemporary kitchen with black walnut cabinetry, an open-plan living area that spills out to a terrace with views of High Line Park, and red-brick walls that provide the otherwise austere spaces with some much appreciated warmth.

Privately tucked away in its own wing and secluded from the remainder of the loft by pocket doors, the primary bedroom suite features large windows, a walk-in closet, and a separate dressing room. The other two bedrooms share a bathroom and are best suited for guests.

This is also a full-service luxury building in Manhattan, of course, so conveniences include a full-time doorman, a building superintendent, onsite storage units, and a lushly landscaped communal rooftop terrace with High Line Park views. For those amenities, Hemsley will fork out just under $3,000 per month in common charges.

As you can see, Hemsley’s cookie domination has allowed him to become a bonafide real estate mogul. And in addition to his new homes in California, New York, and Oregon, he also maintains a Las Vegas condo and an Idaho ranch, and he still holds ownership interests in a handful of Utah properties, mot of them co-owned with his mother.

But for now, the main Sawyer Hemsley residence still remains a very custom mansion in the Salt Lake City suburb of Orem. Blindingly maximalist inside, that 9,000-square-foot, architectural vague fusion was officially unveiled to the public in this year’s Utah Valley Parade of Homes.