Credit Karma President Joe Kaufman purchased the Woodside estate of Paul “Red” Fay Jr., a former undersecretary of the Navy and a close friend of President John F. Kennedy, for $16 million, according to public records.

Nearly 4 acres of property has not been traded in over 65 years, It includes a 1920s “vintage ranch home,” a “caretaker’s cottage,” swimming pool, tennis courts and sports fields, according to listing records for Compass Broker Scott Dancer, who represents the buyer and seller. Dancer declined to comment on the deal.

According to the obituary, Fay purchased 205 Winding Way with his wife Anita in the 1950s and lived there until his death in 2009 at the age of 91. He served with Kennedy in the South Pacific during World War II and became his lifelong friend, even serving as usher at the future president’s wedding in 1953. He served as Undersecretary of the Navy under President Kennedy, a post he held until January 1965. He wrote a best-selling book about their friendship in 1967, entitled “The Joys of His Company.” Anita Fay died in January 2022 at the age of 97, also around the time of their long — according to her obituary — homecoming.

Their three children inherited the family estate, which was listed for $22 million in August, according to property records. It went into contract about 10 months later, on April 17, and sold three days later for $6 million below the asking price. Fast closings are a strong sign of an all-cash deal.

Kaufman bought the home with his wife, Angelica, and already owns a similar-sized Woodside estate about a mile from their new property, according to deed records.

He lived in China for over a decade before coming to the Bay Area in 2015 to become Credit Karma’s first CFO. Kaufman became president of the bank’s website, known for its free credit checks, in 2021 when the company was acquired by Intuit for $7.1 billion.

Woodside has seen several ultra-high-end sales this year, including the $44.5 million sale in February of the 11-acre estate of former JetBlue chairman Joel Peterson. That same month, Warriors owner Joe Lacob paid $40 million for a newly built home on more than three acres across from Larry Ellison’s longtime estate. The property was at one point one of the most expensive homes on the market in the Bay Area, with an asking price of $110 million.

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