Collectors of Sherwood Anderson should certainly do their research on him before venturing into the world of collectibles. At first glance, it might seem that there are quite a few first edition collectibles to choose from, but the educated collector will know that almost half of the Sherwood Anderson books published were done posthumously. Granted, first editions of those books are certainly worth having, and will round out a collection nicely or offer a good starting point for a collector on a budget, but those are not likely to become investment pieces.

Anderson's most popular work is Winesburg, Ohio, a collection of short stories first published in 1919, so this is also one of the most expensive collectibles under certain conditions. First printing, first editions with a signature can easily cross the $10,000 mark.

Collectors on a budget have plenty to choose from with Anderson collectibles, from first editions of the aforementioned posthumously published works, to even signed copies that have been known to go at auction for around $100. Signed copies of both Dark Laughter and Many Marriages have sold at auction for $100 in recent years.

Sherwood Anderson was fond of signing books to specific people, often family members or in-laws (of which he had plenty, given his four marriages). He would also sometimes include a note or photo in the book. Books from personal collections that retain these personal touches are worth more than others from the same printing, even with signatures, though of course as always these prices may fluctuate based on the book's condition.