Ellen DeGeneres and Portia de Rossi have made headlines again with their recent real estate moves in Montecito. The celebrity duo has reacquired 319 San Ysidro Road, an elegantly rebuilt 1919 estate on eight acres, which they had initially sold earlier this year. After purchasing the property in June 2023 for $22.5 million, they gave it a glamorous makeover and sold it to mining magnate Robert Friedland and his wife, Darlene, in February for $32 million.

In addition to this, DeGeneres and de Rossi recently purchased 289 San Ysidro Road, a 3.15-acre vacant lot adjacent to 319, giving the property a second entrance from San Ysidro Road.
This purchase is part of a larger transaction involving the sale of their estate at 2781/2801 Padaro Lane, which they bought in December 2022 for $69.947 million—the highest residential sale in South County history. Reports indicate the Friedlands are the new owners of this estate as well. There is also speculation that 3165 Padaro Lane, bought by the Friedlands in September 2023 for $46.9 million, was included in the deal, though this has yet to be confirmed by official records.
The reasons behind these transactions remain speculative, but it’s possible the Friedlands required DeGeneres and de Rossi to reacquire the San Ysidro property as part of the agreement. According to title reports, the price of 319 San Ysidro Road was $32 million, while 2781/2801 Padaro Lane sold for $96 million.

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