Last October, Dennis Miller sold his custom Cape Dutch-style Montecito compound for a whopping $49 million to Ellen DeGeneres and Portia de Rossi. But the “Saturday Night Live” alum turned podcaster and conservative political commentator isn’t straying far from staples like Lucky’s Steakhouse, the Stonehouse, or Montecito Country Mart — he won’t even have to hire a moving van. Records reveal Miller and longtime wife Slim Paley have plunked down $16.3 million for another Montecito property that not only lies on the same street, it’s almost directly across the road from the DeGeneres-de Rossi complex.
The estate consists of a nearly 6,400-square-foot Mediterranean compound built in 1986, with a four-bedroom main house, a three-bed guest structure, guard houses, and equestrian stables — all of it situated on five contiguous, usable acres. Nicknamed “Gloria,” the vast property was long owned by University of Phoenix billionaire Peter Sperling, who used the entire caboodle as the guest quarters, complementing his even larger main estate next door.
Sperling unloaded Gloria in November 2020 for $15.5 million, to a mystery buyer who only held onto the place for three months before flipping it — at an $800,000 profit before taxes and closing costs — to Miller and Paley.
Hidden behind massive 12-foot iron gates and some of the tallest eucalyptus trees in all of Montecito, the main house is accessed via an exceptionally long gravel driveway that leads through and under a forest-like canopy of evergreen foliage on its way to a substantial motorcourt. The guesthouse has a separate motorcourt of its own, too, one shaded by a towering oak tree.
Inside, the main mansion is luxuriously elegant, even if the wall-to-wall carpeting and some of the woodwork reveals the structure’s dated ’80s roots. Amenities include a many-columned living room with a fireplace and French doors opening to an al fresco terrace. The adjacent living room has its own fireplace and is open to the living area but can be made cozier, thanks to disappearing pocket divider doors that effectively separate the two spaces. Also on the property are a library and family room, both with their own fireplaces, and at least one of the guest bedrooms opens to a balcony overlooking the grounds.
And yes, the grounds are majestic and undoubtedly the property’s standout feature, with tropical touches that include groves of banana trees and mature date palms mixed with native California species like ancient oaks, sycamores, and more eucalyptus trees. From the main house, a stone walkway leads down flights of stairs to the swimming pool. There are two private wells on the property, per the listing, a big boon in drought-plagued Montecito.
When they’re not puttering around Montecito, Miller and Paley can likely be found up in the resort town of Ketchum, Idaho, where the couple owns a tennis court estate overlooking the trout-filled Big Wood River.
