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Up in the Air

Published May 15, 2013, 4:00 a.m. ET

If great hotels make Michael Holtz happy, a window seat in the second row of first class is sheer ecstasy. So when the founder and CEO of SmartFlyer, the Midtown-based luxury travel agency, designed his latest apartment, he wanted it to look like a hotel room and work as well as one of the state-of-the-art, front-cabin pod seats on Cathay Pacific, his favorite airline. His wanderlust is evident on his open kitchen’s counter: There’s a stack of hotel-brand baseball hats, an upper-class amenities bag from British Airways, a Delta pen and a Cathay-style touch-screen that lets him control his home’s sound, light, temperature and window shades with a swipe of a finger. He’s also able to adjust the settings remotely. “I can do it from Paris if I want to,” he boasts.

Holtz, 47, has bought and sold 11 condos in 15 years. But don’t think for a moment that he has no sense of place. His hotel-like apartment is one of four he owns at 165 Charles St. He’s president of the condo board there, and his pride in the Richard Meier-designed West Village building is evident as he gives a tour of its amenity spaces: its screening room (currently being improved after it was knocked offline by Hurricane Sandy), swimming pool and gym. “We have to be a five-star hotel,” he says. “That’s what people want.”

Holtz first took to the skies as a student, flying back and forth from college in St. Louis to his Long Island home. “I got fascinated with airlines, points and upgrades,” he says, and went into the travel business in college and again after his first post-collegiate job — on Wall Street — imploded in the 1987 market crash. At the time, he was renting on Mulberry Street in SoHo. He moved into a girlfriend’s apartment near Lincoln Square and liked the neighborhood enough that he bought his first condo there in 1998, a 41st-floor unit at the Park Millennium, on Broadway at 67th Street. He snapped up an adjoining unit a year later. “Rule No. 1,” Holtz says, “is that your next-door neighbor’s apartment is more valuable to you than to anyone else.” Though he planned to combine them, in 2003 he sold them separately for just more than $2 million — a $725,000 profit. “Not a bad return back then,” he says. “In 2007, you’d have thought it was bad.”

Holtz’s sights shifted downtown 11 blocks, though he was moving up in terms of real estate when he bought a $3.04 million, 66th-floor three-bedroom in the Park Imperial on West 56th Street, then under construction, in 2003. He was planning ahead, thinking he might marry and have a child, but even before the building was finished, he knew he’d never live there. “At the Millennium, I could roller-blade down 67th Street into Central Park,” he says. Broadway and 57th Street were impediments to that, so he rented out the unit, instead. A source says his tenant was fashion scion Alex von Furstenberg. In 2005, Holtz sold that apartment to Sean “Diddy” Combs for a $780,000 profit.

165 CHARLES ST.</p> <div id=

BOUGHT .4 million in 2005
NOW LISTED FOR .5 million This two-bedroom is one of four units Holtz has in the Richard Meier building.” />

165 CHARLES ST.
BOUGHT .4 million in 2005
NOW LISTED FOR .5 million This two-bedroom is one of four units Holtz has in the Richard Meier building. (Michael Sofronski)

PARK IMPERIAL BOUGHT .04 million in 2003 SOLD .82 milion in in 2005

PARK IMPERIAL
BOUGHT .04 million in 2003
SOLD .82 milion in in 2005 (
)

15 CENTRAL PARK WEST BOUGHT .775 million in 2005 SOLD .5 million in 2008

15 CENTRAL PARK WEST
BOUGHT .775 million in 2005
SOLD .5 million in 2008 (
)

Holtz was also lured further downtown in 2003, when he bought a second-floor unit in the first of the Meier-designed glass towers on Perry Street and the West Side Highway, paying just more than $2 million. “Downtown wasn’t as cool then as it is now,” Holtz says. The apartment was finished “but the area wasn’t.” Then he heard about 165 Charles and snapped up two units there, buying off plans after learning that a managing director of Corcoran Sunshine, the condo marketers, had already purchased, sight unseen. “So I figured it had to be a good buy,” he says.

With hardly a pause, the next year Holtz joined a pal on a visit to the just-opened sales office for 15 Central Park West. On impulse, Holtz bought a $4.775 million three-bedroom facing Broadway — “by far, the best deal I’ve done,” he says. When his friend decided to flip his unit right after closing in 2008, Holtz did, too, selling for $8.5 million to Spanx founder Sara Blakely and Marquis Jet co-founder Jesse Itzler, who lived there while renovating a bigger apartment on a higher floor in the Robert A.M. Stern colossus.

With the proceeds, along with a $750,000 profit from the 2009 sale of his Perry Street apartment, he put down a deposit for a full-floor unit in an East 22nd Street building by Rem Koolhaas, but got it back when the project was canceled. “It was super cool,” he says. “I could have lived there for a long time.” Instead, he doubled down with two more apartments at 165 Charles, and bought a 39th-floor unit at Extell’s still unenclosed One57. But not necessarily for keeps. “I’m a buyer and a seller,” says the champion flipper, “if the opportunity is right.” All four Charles Streets units are on the market. And it’s likely he won’t miss them if a buyer turns up.

“Sometimes, I wake up in the morning and reach for my seat belt,” says Holtz, sitting in his sparsely furnished living room. He’s exit-row qualified. “I can move pretty quickly.”