A 1939 Vincent-HRD 998cc Series-A Rapide is set to lead Bonhams' Spring Stafford motorbikes sale on April 26, with a valuation of £220,000-260,000 ($328,317-388,011).
Vincent began production of the Series-A in 1936, but was forced to cease at the outset of the second world war in 1939.
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Only 78 were produced, of which very few are known to have survived to the present day.
The bike has remained in the same family collection since 1959.
Bonhams comments: "One of the most exciting motorcycles to be offered on the open market in recent years, this wonderful Vincent-HRD Series-A twin represents a possibly once-in-a-lifetime opportunity for discerning collectors."
Another specimen in similar condition sold for £225,000 ($335,712) in 2012.
A 1926 Coventry Eagle 980cc Flying Eight is estimated at £80,000-120,000 ($119,316-178,954).
Coventry was among the finest British motorcycle manufacturers of the inter-war era, but was slowly forced out of business by the Depression and closed in 1939.
An article on the bike in a 1925 edition of Motor Cycle magazine reads: "There is an undeniable fascination in owning a machine capable of seemingly illimitable speed."
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