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By America, am I safe in assuming that you mean the United States of America?

If so, then the five oldest European occupied cities (there were Native American cities dating back to before European colonization) are:

San Juan, Puerto Rico (1521)

Pensicola, Florida (1559 destroyed, then refounded 1698)

St Augustine, Florida (1565)

Jamestown, Virginia (1607)

Santa Fe, New Mexico (1607)

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14y ago

What else can I help you with?