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Judge Judy Double Whammy: Buys Mansion and Lists Condo in Naples, Florida

SELLERS: Judy and Jerry Sheindlin
LOCATION: Naples, FL
PRICE: $11,000,000
SIZE: 8,550 square feet, 4 bedrooms, 4 full and 2 half bathrooms

YOUR MAMA’S NOTES: Quick on the heels of the purchase of a big mansion in Naples, FL, — more on that in a minute, butter beans — resolutely stern, immensely popular, and exceedingly well compensated television court show queen Judy Sheindlin, who reportedly rakes in an astonishing $47 million a year, slipped her mansion-sized penthouse in a full-service Gulf-front high-rise, also in Naples, up for sale on the open market with an $11 million asking price. Property records show the 8,550-square-foot penthouse, decoratively done up more like an anonymously luxurious Connecticut country house that a bare-footed South Florida beach condo, was purchased in July 2005 for $6.9 million by the eye-rolling and jet-owning syndicated television supernova and her husband, Jerry Sheindlin, also a real life judge before he landed for a couple of seasons in the late 1990s and early 2000s on the faux-bench of “The People’s Court” to adjudicate high-drama small claims cases.

A hexagonal or possibly octagonal foyer, where a Suburu-sized chandelier hangs over a gilt-trimmed and six-footed circular table, opens to an ample and rather primly furnished formal living room with vast picture windows that provide sweeping views up and down the sugar sand coastline and over the glimmering Gulf of Mexico. Glass sliders in an adjoining formal dining area lead to a roomy glass-enclosed loggia, one of the penthouse’s four terraces that combined, per listing details, offer 1,560-square-feet of indoor/outdoor living space. With flat-fronted walnut (or walnut-esque) cabinets and lustrous jet black granite counter tops, the angled, center island kitchen is a decidedly more sleek space than the adjoining family room that encompasses an informal dining area and includes thick crown moldings, floral and avian print sofas and chairs, and a gas fireplace with double stack mantelpiece set into an angled wall next to a bank of floor-to-ceiling bookshelves. Listing details show the penthouse’s four bedrooms and four full and two half bathrooms encompass a spacious master suite with dual bathrooms and dressing areas plus two additional guest bedrooms — one worked over in salmon and the other in butter yellow, a well as a staff suite with kitchenette. There is also an office/library with another gas fireplace and a petite fitness room that, much to this property gossip’s decorative chagrin, is fully carpeted and lined in a downright dizzying red and cream vertically striped wallpaper. The penthouse, which carries monthly homeowners association fees of $2,785 according to online marketing materials, transfers with parking for three cars in an air-conditioned garage as well as a private cabana/artist studio near the resort-style complex’s Gulf-front swimming pool.

Just a couple of weeks before Thanksgiving and, we assume, desirous of more space, a private pool, or some other creature comfort their penthouse didn’t afford them, the Sheindlins, who have a dozen grandchildren, splashed out $8.6 million for a 10,607-square-foot, extended family friendly manse in a guard-gated development that’s less than a mile from their penthouse. Listing details show the residence, which this property gossip can’t properly peg to any particular architectural style but will call a “Late 20th-Century Floridian Traditional,” was built in the early 1990s on not quite an acre and, along with half of a dozen other homes, backs up to a wee pond. There are six bedrooms and nine full and two half bathrooms including a main floor master suite plus a separate guest apartment. In addition to all the customary rooms one expects to find a “Late 20th-Century Floridian Traditional” of this size — i.e. double-height great room, formal dining room, paneled library/office, and super-size kitchen that adjoins a breakfast nook and opens to an also double-height family room — some of the property’s more memorable amenities include: an impress-the-guests-style double-volume foyer with black marble flooring and a staircase that splits about three-quarters of the way up; two air-conditioned three-car garages, one that will accommodate a limousine; and a brick gazebo wherein the ceiling is painted with billowing clouds on a baby blue sky. The back of the house does not open directly to the backyard but instead into a capacious, 3,200 square foot micro-screen enclosed courtyard that keeps the bugs out and shelters a double-height loggia, outdoor kitchen, a 74-foot lagoon-style swimming pool, three water falls, and an over-sized spa.

Not surprisingly for a couple with their immense income, Judges Judy and Jerry preside over a fat portfolio of multi-million dollar residences that extends from north to south and coast to coast. In addition to their Naples holdings, the couple keeps a nearly 12,000-square-foot, nine-bedroom manor house set on about 12.5 verdant and extensively landscaped acres in the almost outlandishly prosperous community of Greenwich, CT, that they picked up in September 2007 at a cost of $13.2 million. In 2013 the judges not only shelled out $10.7 million for a super-luxe five bedroom condo at the ultra-exclusive Montage in downtown Beverly Hills, they traded in their two-bedroom and 2.5-bathroom pied-a-terre on the 11th floor of the supremely posh Sherry Netherland building on New York City’s Fifth Avenue — listed for $9 million, sold for $8.5 million — for a graciously proportioned $8.5 million duplex penthouse atop a white glove pre-war co-operative in the Old School Sutton Place ‘hood with four bedrooms, 4.5 bathrooms, and a planted terrace that wraps around the entire lower floor.

Listing photos (penthouse): Premier Sotheby’s International Realty
Listing photos (mansion): Premier Sotheby’s International Realty

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