So nice she bought (and sold) it twice! That’s how Ellen DeGeneres feels about this historic Montecito equestrian property, parts of which date to the late 1800s. DeGeneres and Portia de Rossi have owned numerous Santa Barbara County homes over the years, but this 6-acre estate seemed to have a particular tug on their heartstrings. The former talk show host first pulled the trigger on the place in 2017, paying $7.2 million, and flipped it less than a year later for $11 million to Tinder founder Sean Rad.
But in 2021, DeGeneres was back again. This time, she spent $14.7 million to buy the horsey spread back from Rad, only to flip it once more in 2023—this time for a whopping $21 million to Bumble founder Whitney Wolfe Herd, who promptly had the place featured in C Magazine.
Though it was never on the market, the Montecito house sold yet again this year, changing hands for an astonishing $22.8 million. (Yes, that’s more than triple what it fetched in 2017, yet the property remains essentially unchanged, albeit with upgraded interiors and stables.)
From the start, the new owner was widely rumored to be an unnamed A-list celebrity. Then, just weeks after the house closed, all-powerful celebrity gossip juggernaut Deuxmoi received an anonymous email claiming the new owners were highly-photographed Hollywood couple Kylie Jenner and Timothee Chalamet.
While Chalamet and Jenner are believed to have stayed at the house during this year’s recent Santa Barbara Film Festival, we did a deep dive into records and can tell you the house was most definitely not purchased by Chalamet. And though the property is now owned by a semi-mysterious LLC clearly connected to the Kardashian family, we also do not believe it was purchased by Kylie Jenner.
In reality, it seems certain the house was actually acquired by Kylie’s older sister Kendall, who—in addition to her multifaceted career as a reality television star, the world’s highest-paid fashion model, tequila entrepreneur and professional cucumber cutter—is also an avid equestrian and horse owner. And over the last few months, she has posted a slew of photos that were clearly taken at the Montecito property in question to her Instagram account.
Located in a discreet gated community and immediately next door to Oprah Winfrey’s 166-acre “Promised Land” mega-estate, Jenner’s new home is actually a compound consisting of two separate houses: there’s a Monterey-style residence built in 2006, plus a historic adobe ranch house that reportedly dates to 1845, making it one of the oldest homes in the county. Altogether, the two houses offer four bedrooms and five bathrooms in nearly 6,800 square feet of living space.
Known as Rancho San Leandro, the compound is accessed by a long driveway flanked by 130-year-old olive trees. Beyond the driveway is a fountain-equipped cobblestone courtyard tightly wrapped by the various houses and professional equestrian facility.
The historic adobe features a 50-foot great room anchored by two original fireplaces, one at each end of the vaguely gothic-like space. In addition to a single large bedroom suite, this structure also features heavily beamed wood ceilings, a renovated kitchen with premium appliances, a butler’s pantry, window seats and oversized windows with garden, ocean and Santa Ynez mountain views. And somewhere there’s access to a subterranean “pool room” and wine cellar.
As for the more modern building, it features three additional bedrooms, four more bathrooms, a library, family room and a second kitchen. There’s also a staircase with gorgeous tilework, a gym, and a three-car attached garage, plus a winding cobblestone path outside that leads to the four-stall horse barn. No doubt Jenner was impressed with those facilities and the additional corrals and regulation rubber/sand dressage area.
Elsewhere on the property are pastures framed by high hedges and more olive trees, a wee hidden garden or two, and more stunning mountain vistas and peek-a-boo ocean views.
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