Written in German and signed "Freud," both letters are dated 1923.
The first letter is adressed to his ailing former student Elis Revesz, a few days before her death. The other was sent to her husband, Hungarian psychoanalyst Sandor Rado, shortly after she passed.
When Revesz got sick, Freud was informed by his friend and colleague Sandor Ferenczi.
Revesz died a couple of days after Freud's letter arrived, according to US-based RR Auction.
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Freud then sent a moving letter to the widower, single father, and prominent Hungarian psychoanalyst Rado.
"I am totally devastated over that outcome. Please do accept the expressions of my most sincere sympathy. While a student of mine, your wife had been particularly dear to me," Freud wrote in the letter dated February 2, 1923.
The letters are accompanied by both original mailing envelopes, both addressed in Freud's hand.
The bidding for the letters closes on March 7.