Hi Jesus,

Thank you for contacting Mearto with your appraisal inquiry.
As one of the most famous men of the 20th Century, Winston Churchill is certainly one of the ones whose ephemera and memorabilia collectors want in their collections. He was a prolific writer and there is not really a shortage of material on the market today; elements that increase the value in individual pieces depends most notably on who he is writing to (the more important the addressee the more valuable), as well as the content of the correspondence (topics directly relating to his service during his time as Britain's Prime Minister are the most highly sought after). It goes without saying that original documents and manuscripts are worth more than facsimile copies, of which you have some.
To give you a sense of the price range of what his documents command, a single letter signed by him to Queen Elizabeth II regarding her coronation brought $11,000 at auction in 2022, while a collection of 'thank you' letters, most hand-written, brought just $700 in March 2023.
Based on the photos and information provided, and subject to examination, this is:

CHURCHILL, Winston
(British, 1874-1965)
An archive of correspondence from Winston Churchill, many addressed to Mrs Taft or Mrs Pearman, his secretary. Some original, some typed, some newspaper clippings.
41 pieces
CONDITION: appears to be in generally good condition
PROVENANCE: acquired at a flea market
$400-600*
*represents a fair-market value for auction purposes; retail or asking price may vary.

Please let us know if you have additional items to appraise, or questions/concerns, and thank you again for using Mearto.
~ Delia