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Sherwood just sounds wimpy and at the same time posh to me, just like Sheridan (which then reminds me of the British TV show "Keeping Up Appearances"). It's a good thing that you see this name as a middle name only, because I can't imagine the teasing a child would endure if it had to put up with Sherwood as a first name.

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With that said, I think a name like Sherwood will need to be paired with a masculine, no-nonsense first name. The only combination that I can think of is Marcus Sherwood, though the downside of that one is that Marcus ends with -s and that Sherwood starts with S-.