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By c. 1194, the Gloucester Jewry was extremely prosperous, almost certainly due to the military trade and ranked 5th out of a list of 21 Jewries in the Northampton Donum. A total of 22 members of the community were listed from the Gloucester community in the Donum. However, these good fortunes were not to last, as some of the military activities were shifted to Hereford. In 1216, military campaigns against Wales were transferred to Hereford. This permanently depressed the Gloucester Jewry and is evidenced in the 1223 tallage, where now Gloucester ranked fourteenth out of sixteen Jewries, with at Hereford fifth and Worcester fifteenth. The high placing of Hereford in the position previously enjoyed by Gloucester tells the story of Hereford's gain at Gloucester's loss.

However, while Gloucester was not to reach eminence again as a Jewry, the community was to continue in the city up to 1275. Members of the community continued in money lending and financial operations, though other members of the Jewish community would carry out a number of other limited trades and avocations as were available to them, and as such as were permitted to non-guild members. Much less is known from the records about these Jews, but we know that Jews traded in wine and cheese, and later in corn, wool and wood, or in unclaimed pledges from pawn-broking activities, worked as metal smiths, or even as mine specialists, or they would provide services for their own community, such as teachers, scholars, servants, bakers, slaughter-men, etc. there are other more exotic trades, for example at Norwich we encounter Diaia le Scalarius ('the ladder-maker').

The community, which only comprised a small number of households in the 13th century, lived in a small Jewish quarter right in the centre of city in the East Gate. The East Gate was originally called Jewry Street (at least up to 1314) due the presence of the Jewish community. There were in the 13th century about 12 principal dwellings (1239), with other minor dwellings for the poorest members of the community. Most houses of the Jews were clustered around this area, with the most important members of the community closest to the High Cross in the very centre of city, but away from the areas with the most unpleasant and smelly trades. There was a synagogue with a large attached Curia, or 'court', which contained all or most of the Jewish communal facilities, an arrangement similar to that in the German Jewish communities and parallel to Jew's Court in Lincoln.

The Jewish quarter was a residential area, with a concentration of Jewish residents, but as was the case in the rest of England, was not a ghetto and Jews often had Christian neighbours. The local Jewish population would live in a variety of housing suitable for their rank and income - the poorest would often live in virtual hovels, the middle-classes would live in stone and wood houses, while the richest members of the community would live in fine stone houses - medieval first floor halls with palatial features such as chimneys and glass in the windows. One of the leaders of the medieval community was Bonenfaunt ('Good-Child'), who lived in his 'great house' close to the Synagogue.