Former Frank Sinatra Penthouse Has Illustrious Past

SELLER: Penny Hart (formerly owned by Frank Sinatra)
LOCATION: New York City, NY
PRICE: $7,700,000
SIZE: 3,200 square feet, 4 bedrooms, 4 full and 2 half bathrooms

YOUR MAMAS NOTES: After much anticipation and chattering by property gossips around the globe the last week or so, a glammy New York City triplex penthouse long ago owned by Rat Pack crooner Frank Sinatra has finally popped up on the open market with an asking price of $7,700,000.

Mister Sinatra, who went to meet The Great Sound Mixer in the Sky in 1998, owned the glassy aerie atop the so-called Edgewater building at the eastern terminus of East 72nd Street from 1961 until 1972. Over the decade he owned the place he reportedly and not surprisingly entertained a cavalcade of famous friends including Dean Martin, Peter Lawford, Marilyn Monroe, President John. F. Kennedy, and Sammy Davis Jr., who (allegedly) used to toss champagne glasses off the terrace.

As much celebrity sheen as Mister Sinatra's ownership gives the completely over-hauled triplex, the penthouse's post-Sinatra years are no less fascinating. In 1972 Mister Sinatra sold the penthouse to Dr. Denton Sayer Cox, an Upper East Side internist who famously treated a high profile clientele that included Mister Sinatra himself, Pulitzer and Nobel Prize winning writer John Steinbeck, troubled singer Judy Garland, and pop artist Andy Warhol who, according to current listing information, once called the penthouse "a glittering grotto in the sky."

In 2007 the good Dr. Cox, then 79 years old, was badly beaten and hospitalized with severe and mysterious chemical burns that covered more than 40% of his body. He claimed he'd been attacked on the street near his penthouse by a trio of thugs who doused him with an unknown substance. However, the general consensus by the police and media was that the septuagenarian physician was actually horrifically brutalized inside his East 72nd Street penthouse during some sort of sexual encounter gone horribly wrong with an unidentified male companion.

Dr. Cox died from his injuries in March 2007 and the penthouse was sold by the executors of his estate to Penny Fern Hart, a Long Island-based car insurance mogul. Property records we peeped show the penthouse was purchased by Miz Hart in July 2010 for $2,300,000 while an earlier report in the New York Post pegged the purchase at "$4.5 million in 2008."

Like the penthouse's previous owners, Miz Hart has a somewhat inneresting and illustrious life, too. In 2002, after a chance meeting in what was described as "a Midtown Manhattan pick up bar," Miz Hart (reportedly) became romantically entangled with a mobbed-up gentleman named Tommy Cappa who had just days before been released after six years in the pokey for his role in a failed murder conspiracy. We don't know if Miz Hart and Mister Cappa continue to be coupled but at one point she described him in court papers as her "'soul mate,' fiancée, best friend, and partner" as well as a "'devoted, sensitive, and affectionate' role model for her three children." Oh, what a tangled web we weave...

Anyhoo, presumably it's Miz Hart who's responsible for the recent renovation of the three-story penthouse that has, according to current listing information, (approx.) 3,200 square feet of interior space and another (approx.) 2,200 square feet of terraces on two levels. The penthouse has 4 bedrooms and 4 full and 2 half bathrooms including a (melo)dramatic, two-story master suite connected with a floating glass and steel staircase that more than resembles the sort of thing one might expect to find installed in an Apple Store.

A wrap around terrace encircles the 22nd floor living space that includes a living room with monolithic marble-faced fireplace and inlaid hardwood floors that extend into a wee dining area open to a clean-lined kitchen finished with dark marble floors, a white porcelain farmhouse sink and Euro-style stainless steel appliances.

Each of the three guest/family bedrooms on the lower floor has a private bathroom and direct access to the terrace that rings the apartment's lowest level and hangs over busy, loud and dirty FDR Drive with sweeping views up and down the East River and directly across to the dour apartment blocks lined up on Roosevelt Island.

A winding staircase climbs to a second floor landing where there's a second powder pooper—the first is not so ideally situated in the kitchen—and access to the lower level of the sexed-up, two-floor master suite.

The lower level—formerly Mister Sinatra's party room—has a voluminous 18-foot ceiling; convenient wet bar for those like Your Mama who enjoy a pre-bed and/or early a.m. nipper of something boozy; a 20-foot long fitted dressing room with—ahem—a convenient back door entrance; and three, angled, prow-like walls of glass filled with decidedly urban, bird's eye vistas of the mixed residential and industrial neighborhoods up and down both side of the cold, grey and powerful East River. Double glass doors open to an expansive terrace outfitted with, according to listing information, a putting green and solar panel.

The aforementioned floating glass and steel staircase in the master bedrooms makes a harrowing and, let's hope, meticulously engineered climb up to the mezzanine where the floor plan included with current listing information indicates there's a sitting/sleeping area, an itty-bitty study and oddly-shaped but reasonably sized bathroom.

Listen children, The Dr. Cooter can be awfully clumsy and Your Mama is straight-up lazy like a hog in the wet blanket humidity of an Alabama summer—not to mention more often than not drunk as a skunk—so that staircase is simply out of the question. We could never navigate that practically see-through thing in the middle of a dark night. And, besides, who wants guests and other people traipsing through their boo-dwar in order to get to the putting green on the roof terrace? Not Your Mama, that's who.

Of course, we ain't in the market for a suped-up seven and some million dollar penthouse on the edge of the Upper East Side of Manhattan so our opinion is entirely irrelevant. None-the-less we can certainly understand why a young and rich Wall Street bachelor or a profligate professional athlete might find this overtly-sexy, superhero-style duplex bedroom to be hella sick or da bomb or whatever silly colloquialism the kids say nowadays to describe a bedroom that Your Mama's boozy b.f.f. Fiona Trambeau colorfully called a "a God damn panty dropper."

listing photos and floor plan: Rubicon Property