[1][2] Eskenazi was born Sarah Skinazi to an impoverished Sephardic Jewish family in Istanbul,[3][4] in the Constantinople Vilayet of the Ottoman Empire.

Avram Skinazi found work in a cotton processing mill and took various odd jobs to improve his family's financial standing.

At the time, he entrusted young Sarah to a neighboring girl, who tutored several local children in basic reading and writing.

Realizing that she could not maintain her career as a performer while raising an infant, she brought him to the St. Taksiarchis nursery in the city of Xanthi.

His father's family agreed to support him there, and Paraschos Zardinidis eventually grew up to be a high-ranking officer in the Greek Air Force.

She quickly teamed up with two Armenian cabaret artists, Seramous and Zabel, who reportedly liked her because she could speak Turkish, and because she showed talent as a singer.

In 1929 Roza cut four sides for Columbia, three of which were amanedes (Tzivaeri, Minore, and Matzore) and one demotic (Emorfi Pou Ein I Leivadia).

Her music had a certain edginess to it, and one of her songs, Πρέζα όταν Πιείς ("When You Take Heroin"), was even censored by Greek dictator Ioannis Metaxas.

As a result of his decisions, many other traditional Rebetiko artists were marginalized, though a new trend in the genre, led by Vassilis Tsitsanis, was gaining ground.

Despite the repressive regime, she continued performing, and in 1942, she even opened up her own nightclub, Krystal, together with her son Paraschos, with whom she had since been reunited.

Although she was a Jew, she had managed to obtain a fake baptismal certificate, though her safety was also ensured by an affair she had with a German officer.

Throughout her long career, Roza developed good relations with Columbia Records Vassilis Toumbakaris and Minos Matsas, who had recently founded Odeon/Parlophone.

She gave a few concerts as well, but the real turning point in her life came when she met Christos Philipakopoulos, a young police officer almost thirty years her junior.

Eskenazi was now in her sixties, and the music scene in Greece had changed considerably since she launched her career over four decades earlier.

Smyrneiko (the music of İzmir) and Rebetiko had declined in popularity, and she, as well as other masters of the genre, were relegated to occasional appearances at village festivals and other small events.

RCA recorded two 45s containing four of her songs (including "Sabah Amanes") with violinist Dimitris Manisalis, but the release was limited.

Suddenly, the youth of the country developed a renewed interest in the urban songs of the past, and several important compilations were released.

In 1973, she was documented in the short film To Bouzouki (directed by Vassilis Maros) and in 1976 she did a TV special with Haris Alexiou, which included interviews and songs, as well as a couple more appearances.

As one of the few surviving Rebetiko singers who remained active at the time, artists and musicologists began studying her style, which was deemed "authentic".

While musicians and academics were intrigued by her abilities, as well as by her insights into a lost musical world, the general public was less enthusiastic, and considered her more of a curiosity.

In 2008, the village's cultural committee raised enough money to erect a simple tombstone, with the inscription, "Roza Eskenazi, Artist".

In 1982, two years after her death, Kostas Hatzidoulis published a brief memoir entitled Αυτά που Θυμάμαι ("The Things I Remember"), based on interviews Eskenazi gave later in life.