Credit Karma president Joe Kauffman buys $16M Woodside estate 

Estate was longtime residence of “Red” Fay Jr., close friend of JFK

Credit Karma President Joe Kauffman and 205 Winding Way in Woodside
Credit Karma President Joe Kauffman and 205 Winding Way in Woodside (Zippia, Google Maps)

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

The nearly 4-acre property has not traded in more than 65 years and includes a “vintage ranch home” from the 1920s, a “caretaker cottage,” pool, tennis court and sports court, according to listing notes from Compass agent Scott Dancer, who represented both the buyer and seller. Dancer declined to comment on the deal. 

Fay bought 205 Winding Way with his wife Anita in the 1950s and lived there until his death at 91 in 2009, according to obituaries. He served in the South Pacific during World War II with JFK and became his lifelong friend, even serving as an usher in the future president’s 1953 wedding. He was the undersecretary of the Navy during Kennedy’s presidency and held the post until January 1965. He wrote a bestseller about their friendship called “The Pleasure of His Company” in 1967. Anita Fay died in January 2022 at 97, also in their long-time home, according to her obituary. 

Their three children inherited the family estate, according to property records, and listed it for $22 million the August after their mother’s death. It went into contract about 10 months later on April 17 and sold three days later for $6 million off that ask. The quick close is a strong indication of an all-cash deal.

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Kauffman bought the home with his wife Angelica and already owned a similarly sized Woodside estate about a mile from their new property, according to deed records. 

He lived in China for over a decade before he came to the Bay Area to be Credit Karma’s first CFO in 2015. Kauffman became president of the banking site, known for its free credit checks, in 2021, shortly after it was purchased by Intuit for $7.1 billion.

Woodside has seen several ultra-high-end sales this year, including the sale of former JetBlue Chairman Joel Peterson’s 11-acre estate for $44.5 million in February. That same month, Warriors owner Joe Lacob bought a new-build home on more than 3 acres across the street from Larry Ellison’s long-time estate for $40 million. That 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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