Priced at $22.5 million in 2015 and then reduced to $16.5 million last year, the massive East Bay estate at 10 Winding Lane in Orinda has just traded hands with a $12.25 million contract price.

Previously owned by the CEO of McKesson, the buildings on the gated 8.6-acre estate total over 23,000 square feet of finished space, including a 14,200-square-foot main home (with a 2,100-square-foot master suite and 855-square-foot closet); a 5,600-square-foot sports center (with a gym, multiple sports courts, his and hers locker rooms, a “bocce center,” indoor and outdoor kitchens, living rooms and spas); and a 3,100-square-foot carriage house with a banquet hall over its five car garage.

Comments from Plugged-In Readers

  1. Posted by cleverpunhere

    I could never tolerate such a tiny master closet.

  2. Posted by frozentoast

    I can’t figure out why the CEO of Mckesson would live in the East Bay when the office is in San Francisco. Bridge traffic is a nightmare and helicopters are not allowed (aka Trump).
    Could he have taken – gasp- Bart?? Or maybe this was just a weekend house?

    Moral of the story – 20M buyers are hard to find in the east bay.

    • Posted by Oaklandlover

      Gasp. I’m sure you’ll choke in shock to learn many CEO’s live in the east bay, and also many famous athletes, as we have seen here in SS in many articles.

      Clearly they don’t think like you.

    • Posted by nexttheory

      You’re assuming he a) contributes work to collect his salary and b) would execute that by being present at an office.

    • Posted by Occupied in Oakland

      High level earners have always been fleeing SF for the East Bay, since 1849. The Ghiradellis, the Schillings and, like all of their peers, while they had homes in SF – they mostly lived in Oakland, Piedmont, Berkeley or Kensington. Read up on it. The wealthy considered SF “unhealthy and uncivilized”.

      Post WWII they headed to for Lamorinda. In the late 80’s further East to Danville and Blackhawk. Back in the early 90’s SF was a sinking ship as Fortune 500 companies fled to the Tri Valley.

      Traffic is so hellish between the FiDi and the Bay Bridge because all those high level earners want an estate to drive home to… in the East Bay.

    • Posted by Brahma (incensed renter)

      Walkscore: 0. This is just the place for the suburban-loving corporate titan who wants to drive his Land Rover everywhere, because they have to.

      As far as helicopters, sure, you won’t be able to land on the lawn like in The Wolf of Wall Street, but an owner of this place could have their private chauffeur drive them to Buchanan Field, which is about a half an hour drive away in light traffic, and then have their private helicopter take them into SFO, then drive into the office from there.

      I agree that a self-driven auto commute into SF from Orinda would be rough 5 days a week, especially if the CEO had to be there by 9am.

    • Posted by 4th Generation SF

      He prob owned a place in SF as well, that was his weekend place most likely.

  3. Posted by Notcom

    Maybe he worked at night.

    Honestly, people: yes, $20M buyers are hard to find in the east bay, just as they are in the west bay (did the latter ever get a buyer?), and yes this might logically seem to be the home for someone who doesn’t need to drive – or chopper – thru three counties: IIRC, the Leshers (remember them ?) of newspaperdom (remember those ?) used to live nearby.

    But everyone is missing the entertainment value of settlement vs. (initial) asking for these ridiculously overpriced high-end properties…and giggling from afar, after-all, is the only connection most of us will ever have with them.

  4. Posted by citicritter

    That aerial view perfectly illustrates the lame tacked-on nature of the fake roof, as the largest of the many ‘faux historicist’ features adorning this McMansion…

  5. Posted by credible1

    Are you kidding. The CEO has a place in New Hampshire and spent most of the time there or out of state so he didn’t pay tax on his income. Most CEOs have tax advisors that track the number of days in each state to minimize tax liabilities. Also, when he wasn’t on the corporate jet, he had a driver and security guard drive him to the office in SF, which was probably only a few times at most a month.

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