Any morning that starts with a tour of a $23.5M triplex—rather, quadruplex—with 360-degree views of NYC is unfailingly, indubitably, unquestionably, and most certainly going to be a mighty good morning. Thankfully, such a morning recently happened when the Hearst Magazines powers-that-be granted us a sneak peek of this year’s Ultimate Bachelor Pad, Esquire’s annual balls-to-the-wall version of a masculine showhouse. The setting? The penthouse of 1 Main Street (the Clocktower Building) in Brooklyn’s DUMBO neighborhood, which first hit the market for $25M in 2009, pulled a disappearing act in summer 2010, and was re-listed for its current ask of $23.5M in April, at which time Curbed NY founding (and former) editor Joey Arak deemed it an “epic party pad.” Prescience of a future Esquire takeover or stone-cold common sense? Who cares! Let’s talk about that 3,000-square-foot great room!

The tour guide? Stephen Jacoby, the magazine’s associate publisher and the very guy who spearheaded the Ultimate Bachelor Pad program in 2003. It’s done very well, he tells us, talking up the charitable angle—this year, proceeds from various events will benefit the Fresh Air Fund, the Natural Resources Defense Council, the International Medical Corps, and City of Hope. (In non-philanthropic news—fun fact!—Greek shipping heir Paris Latsis bought the 2004 Esquire apartment fully furnished for then-fiancé Paris Hilton.) Luck that listing agent Michele Kleier (of HGTV“s Selling New York fame) hopes will repeat this year. “Just like we all look better going to a black tie event than going to the supermarket, any apartment, no matter how good the bones looks better ‘dressed,’” she says. “Also we’re getting top celebrities, movers and shakers, and tastemakers from all over the world coming to these charity events—we’re hoping one of them is going to want to stay for the night and move in.”

The elevator opens directly into the space—as if this echelon of real estate would have it any other way—which is a combo-platter living room, dining room, kitchen, breakfast room, and bar area, all decorated by L.A.-based designer Shelley Starr with sponsorship by/inspiration from Hugo Boss. Think: a masculine, neutral palette, modernist furnishings, and a custom Swarovski light fixture that makes full use of the 50-foot-high ceiling. Four 14-foot windowed clock faces—for which this building gets it name—frame the square and afford unrivaled views of the city. Which brings us to our first of many philosophical impressions: unlike Ultimate Bachelor Pads of years past, this one seems decidedly less “decorated”—and it’s a good thing. Why compete with the architecture when nearly every floor has windows that begin at knee level?

Up the three-story glass elevator and on to the second floor, a curvaceous galvanized-steel sculpture by Brooklyn-based artist Brooks Atwood of POD Design+Media fills up a full wall and a bar area, and—as promised!—the digital “ghost” of Pan Am actress Margot Robbie is hanging out, dancing around, and moving from one surface to the next. Also delivered the goods is the “Office of the Future,” actually a blank white room containing a fabric-covered touch-screen box in the middle of it. (Apparently actual computers are passé in the ultimate bachelor’s world!)

After spending approximately 47 minutes enraptured by the infrared sensors—they make cool sounds and shine brightly with pretty colors—we decamped, if you will, to Campion Platt’s master suite down the hall. It was here where we learned that the ultimate bachelor also shuns normal sleeping furniture; instead of a traditional bed, Platt juiced up a daybed with some luxe linens, pillows, and a throw made from the silk lining of a suit by Ermenegildo Zegna, who sponsored the space. “The room layout didn’t not lend itself to a typical bed setup,” Platt says. “I felt the architecture was so strong that I had to respond with a powerful, sexy den-like bed scene, an entertaining, come-hither-for-more setup—low, sensual, and treated like a stage, not a bed.” Good call, good sir. Off this production is a walk-in closet (filled to the nines with Zegna clothes) and a 30-foot-long master bathroom with a transparent glass shower wall and full-on views overlooking the East River, Governor’s Island, and the Statue of Liberty.

The “Digital Loft” on floor three combines creative direction from marketing media agency Luxurious Animals, furnishings from Italian firm Poltrona Frau, and travel themes from Lufthansa. Up there we find the so-called “Fifth Clock,” an image of a clock face rendered onto a screen against rotating background photos depicting various city skylines. There’s a fancy social-media board hanging above some low-slung, angular furniture: it broadcasts how the hashtag #Esquireapt is faring on Twitter, among other things—who has checked in at the Esquire Apartment on Foursquare, for example.

Finally, ascending the final flight of stairs lands us on the rooftop terrace, an indoor/outdoor space with sponsorship from Conrad Hotels & Resorts, interior design by SFA and 360-degree crow’s nest views of all five boroughs. The sight is so spectacular that our trusty photographer felt inspired to whip out some panoramic wizardry. Feast:

- Sarah Firshein