New York Co-Founder Sells ‘Medieval’ West 67th Street Duplex for $4.1 M.

Milton Glaser, the grandfather of New York graphic design, has sold his grandfatherly third-floor duplex at 27 West 67th Street for $4.1 million. The buyer, according to city deeds, is New Jersey real-estate magnate Jeffrey Greenberg, his neighbor from across the hall.

“It had arched brick ceilings! You came in and thought you were in some sort of French-medieval-countryside architectural thing,” the 78-year-old Mr. Glaser said.

He and his wife Shirley lived in the co-op for 30 years. So why move? “We said, ‘You know, we have to get this place painted, and the cabinets aren’t closing.’” But that would’ve taken eight months.

“Then we looked at the extraordinary steel spiral staircase that goes from our living area to our sleeping area …. We said, ‘One day soon, that staircase is going to become the most important thing in our life.’”

Aging hurts, in other words. But Mr. Glaser, who co-founded New York magazine in 1968, redesigned The Village Voice and created the “I NY” emblem, couldn’t move to Florida. He bought a three-bedroom Chelsea condo instead, reportedly paying $2.875 million.

According to Prudential Douglas Elliman broker Harry DiOrio, who is listing Mr. Greenberg’s old apartment across the hall for $1.85 million, the Jersey real-estate man had been pining for the Glaser duplex, where the ceilings are 10 feet higher.

“I think the buyer is planning to gut-renovate the apartment,” Mr. DiOrio said of Mr. Greenberg. He described the finishes in the Glasers’ apartment as “cool and all, but weathered and tired.”

The couple moved to the arty co-op from St. Marks Place, where they’d lived for 18 years. “Auden lived on the street—you could see him walking in his slippers,” Mr. Glaser said of the late poet. “And Ginsberg lived around the corner.”

But one day his wife was stabbed in their lobby, so George Lang (who owns West 67th Street’s iconic Café Des Artistes) suggested that the couple move uptown.

“And he was quite right,” Mr. Glaser said.

Hal Prince Directs $8.8 M. Townhouse Sale With Daughter

Over half a century after debuting on Broadway with The Pajama Game, the mega-legendary musical man Hal Prince has been dealing big-time real estate like a virile young Manhattanite.

According to city records, the director/producer and his daughter Daisy Chaplin Prince have sold their five-story townhouse at 124 East 64th Street for $8.8 million. The buyer is listed as a trust, with Margot and Benjamin London as trustees: Luckily for them, their purchase is a $2.1 million discount from the original January 2006 price tag.

The mint-condition house stretches 6,400 square feet—plus there’s a 950-square-foot terrace off the “huge chef’s country eat-in kitchen.” Bucolically, there’s also a fireplace there, according to the listing with Barbara Fox.

The living room and library on the 51-foot-long parlor floor also have wood-burning fireplaces, plus “huge arched windows” and 14-foot ceilings—which means there’s ample space for Mr. Prince’s 21 Tonys.

But did his daughter, a theater director, live in the townhouse without Mr. Prince? Either way, the two reportedly bought another Manhattan place together last year, paying just under $3 million.

It’s good to be a Prince kid! Last month, city records also show that Mr. Prince and son Charles paid $1.795 million for a five-room apartment in the Pythian Condo on 135 West 70th Street.

The building, which was designed by the theater architect Thomas Lamb, was once a Knights of Pythias Temple. So, according to the listing with Halstead senior vice president Chester Gelband, there’s a south-facing terrace with “your own 15-foot Pharaoh at your side.”

Pharaohs are hot right now.

The apartment only has 1,450 square feet, so it’s probably for the son alone. After all, the elder Mr. Prince is likely unimpressed by “original terrazzo floor and Venetian plaster walls”: The Pythian was built in 1927, and Mr. Prince was born one year later.

N.F.L. Commish, Fox News Anchor, Hike Their Seven-Room Co-Op for $2.72 M.

Heartbreakingly, the Upper East Side has lost one of its all-American families: Roger Goodell, the new commissioner of the National Football League, and wife Jane Skinner, a brunette Fox News daytime anchoress (plus their twin daughters). The pedigree family sold its seven-room co-op at 180 East End Avenue late last month for $2.725 million.

According to city deeds, the buyer is Douglas Millowitz.

Those deeds list the Goodells’ address in Bronxville—where the commissioner went to high school, starring in three sports, including football.

Tentative 2007 tax records value that Bronxville house at $5,158,400.

The family’s old city apartment has sporty touches like in-wall audio, plus conservative flairs: custom millwork, “fitted closets” and a 19-foot-long formal dining room. The master bedroom and living room are even longer, and the latter has a 109-square-foot terrace.

According to the Corcoran Group listing, the place is drenched in sunny vistas: There’s the East River and Gracie Mansion to ogle, plus westward open city views.

Sadly, though, the maid’s room is smaller than the balcony—but at least the maid is given her own in-suite bathroom. Fox News anchors can be bighearted like the rest of us! (According to Ms. Skinner’s online bio, viewers can catch her from 2 to 3 p.m.)

Mr. Goodell, who wrote 40 letters to get a post-college job in the N.F.L., took over the chief league spot last August. Weirdly, Corcoran’s online tour of the apartment shows zero football paraphernalia there. Maybe everything has already been moved to Bronxville?

No Contract for $59 M. Guccione Mansion, but ‘the Conservative American Loves It’

The brashest mansion in Manhattan, a nearly 20,000-square-foot Beaux-Arts townhouse that belonged to porn magnate Bob Guccione before his money woes, has entered its 13th month on the market.

But back in February, the New York Post reported that the mansion—which modestly gets the address 14-16 East 67th Street—had an accepted offer. Last month, the Post ran another item reporting that the deal would be signed in “the next few days.”

Was that true? “Absolutely, unequivocally, we do not have a signed contract,” said Leighton Candler, a Corcoran Group senior vice president, speaking to The Observer last week. “There’s a lot of activity, and frankly, to me, the more the merrier! We are very much on the market.

“And we’ve certainly had discussions—ongoing discussions—and that has been at a number we can easily say is around the record price that was set last year.” (The Harkness mansion on East 75th Street sold for a New York City single-residence record of $53 million in October.)

Why the confusion? “When you see the same people coming in and out with architects,” Ms. Chandler said, “people get the wrong idea.” And a house like Mr. Guccione’s, which first went on the market in February 2006 for $99.99 million, understandably shakes people up: The current tag is $59 million, though the 25-room palace reportedly cost Mr. Guccione $5 million a year to maintain.

So who’s interested? “It’s been celebrities, royalties, huge tycoons—everyone’s been through the house,” said Corcoran vice president Lisa Simonsen, who shares the listing.

“The conservative American loves it, oddly, as much as people from other continents love it,” Ms. Candler said later. Sadly, the conservative Penthouse mogul lost the place to creditor Laurus Funds after defaulting last year on loans against the mansion.

In June, there was an unsuccessful auction for the house, with a reported $45 million minimum bid. “That is the English way,” Ms. Candler explained. “What we have [now] is a normal, U.S., New York City way of marketing the house.” New York Co-Founder Sells ‘Medieval’ West 67th Street Duplex for $4.1 M.