Siteline | One of the Most Magnificent Estates in Montecito

At over 18,000 square feet, the Italianate estate Sotto Il Monte at 2845 Sycamore Canyon Road is as grand as Montecito gets. (It’s definitely the largest house I’ve ever visited, not counting those turned into museums.) Designed in 1927 by George Washington Smith, it was owned by Frank J. Caufield, a founder of the Kleiner Perkins venture capital firm, for the past two decades. He died last year, and now Sotto Il Monte is on the market for $39.75 million, offering us mere mortals a rare chance to see inside.

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Bedrooms: Eight in the main house.
Bathrooms: Nine full and three half in the main house.
Size/Acreage: 18,302 square feet / 11.9 acres.
Price: $39.75 million.
Last sold: Around 2000 for an unknown amount.
Listing agent: Dusty Baker of Sotheby’s.

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The first thing you notice is the massive motor court, through a decidedly narrow set of gates (one of four leading to the property) and dotted with spectacular specimen trees.

Dusty Baker of Sotheby’s, the listing agent, sent over some historical background:

Three years after purchasing Rancho Tajiguas on the Gaviota Coast in 1923, Kirk B. Johnson, a founder and the president of First National Bank of Beverly Hills, and his wife, an heiress to the Gillette fortune, decided to move to the Santa Barbara area permanently. They purchased what was then called Mt. St. George Estate in Montecito, renamed it La Toscana, and commissioned architect George Washington Smith to design a world-class villa. […] Along the way, the estate has had several owners who fastidiously maintained the villa, its ancillary structures, and the incredible gardens. Owners have included philanthropist Sir Daniel Donohue, who first bestowed the name Sotto Il Monte; entrepreneur Manseur Ojjeh (who has also owned the Johnsons’ Rancho Tajiguas); and auto racing entrepreneur Andy Granatelli.

The public rooms on the ground floor certainly have the proportions of a different era. And just look at those floors and ceilings.

As is often the case at any price point, the kitchen is disappointing—likely because the various owners through the years rarely, if ever, set foot inside. There’s enough space in adjacent rooms to create something amazing.

The primary bedroom is on the ground floor, and it includes a sitting room, office, and solarium with indoor pool. The bathroom faces onto the courtyard, which could get a little awkward if you don’t train the staff never to look that direction.

After my visit, I chatted with a broker who had also seen the property, and he wondered how livable it was. That struck me as somewhat beside the point—the appeal is more about provenance and prestige. Then again, my brain kept registering it as a hotel rather than a home, since that’s the only time I’ve ever been anywhere similar. Obviously, people who can afford $40 million houses have more experience with this kind of thing.

Upstairs, the bedrooms are lovely, if not as dramatic.

And then there are the 12 acres of grounds, including the best dragon tree ever. If your first thought is that it’d make a fabulous location for a big party, you’re not alone: Kim Kardashian married Kris Humphries at Sotto Il Monte in 2011, to neighbors’ annoyance.

There are more photos of the estate online, but they can’t begin to capture everything—the pool house with a sunken bar, the gym, the catering kitchen, the staff quarters that could pass for a small town, the climate-controlled 24-car garage, the greenhouse above a 60,000-gallon reservoir, the dog run….