I’ve haven’t read any Sherlock, but I thoroughly enjoyed both Robert Downey, Jr. movies, love the new BBC series, and Elementary is appointment viewing. So, I figure it’s time to dive into some of Sir Arthur’s original stories. There seem to be a lot of anthologies out there. Any recommendations or is there a stand alone novel I should start with?
Nearly all the Holmes material is short stories.
The Complete Sherlock Holmes: All 4 Novels and 56 Short Stories costs $10
I prefer the Novels and have read them dozens of times since childhood. This illustrated collection has the four novels.
Or just drop by any Library and check out the 4 novels individually.
Study in Scarlet
The Sign of the Four
The Hound of the Baskervilles
The Valley of Fear
Oh my, just noticed the Kindle version of the four Holmes novels is 99 cents. Buying that right now for myself. 
I haven’t read Holmes in at least 10 years.
You don’t really need to read them in any order. The novel A Study in Scarlett sets up the characters, but your almost certainly familiar with the basic back story from pop-culture, so if you want to start with some of the short stories instead of one of the novels, I doubt you’ll have any trouble following them.
Otherwise, the stories don’t require you to be familiar with any earlier works, and Doyle was famously unconcerned with continuity in any case. But there isn’t really any reason to read them out of the publishing order (unless, as I said, you want to start with some of the short stories before reading the longer novels). So I’d just do that.
It really does not matter very much where you start. Although Holmes gets older and has “retired” in a couple of later stories, and Watson originally lives with him, and later has got married and moved out, there is not otherwise much of an “arc” to the Holmes stories as a whole. All of them are more or less independent of one another, the only real exception being when Holmes dies (The Final Problem) and then comes back ("The Empty House).
An obvious place to start would be with the very first Holmes story, the novel A Study in Scarlet, where Holmes and Watson first meet. Just be warned, though, that it is not entirely typical, since about half the book is a flashback, set in America, that does not involve Holmes or Watson at all. (The Valley of Fear is like this too.) Really, though, it does not matter. Just plunge in wherever is convenient. It is all good. (Although that is not say every story is as good as every other: rather they vary between pretty good and brilliant.)
I hope you will not be disappointed, by the way, to find the real thing, and the character of the “real” Sherlock Holmes, are nothing like Sherlock. Sherlock is excellent both in its own right and as hommage, but it is, quite intentionally, very different in tone and content from Doyle’s stories. (I haven’t seen the Robert Downey jr. movies, but I suspect the same point applies.)
The Hound of the Baskervilles is my personal favorite. The mood that is struck up on the moors is so spooky. I love both the book and the old 1939 movie with Basil Rathbone. It’s currently on youtube. It’s so old that I think its in the public domain now.
BBC did a series with Jeremy Brett back in the 70s and 80s that is the definitive screen Holmes.
I started with that book. In fact, it was one of the first books I read when I got into reading about a year ago. The flashback threw me so much that I actually started a thread about it. I honestly though I was reading a different book. I truly thought I had downloaded two books bundled together. I asked here and did some Googling to make sure I was still in the same book (and found I wasn’t the only person asking that question). I was basically told that it’s so totally unrelated to the first half of the book you really don’t have to read it if you don’t want to.
Anyways, that’s where I started.
Study In Scarlet
The Sign Of Four
Hound of the Baskervilles
Then I went on the Adventures but I had to put that down for a while. It’s like trying to watch episodes of House one after another. They become a bit repetitive when they’re that short. But as others said, you really don’t need to read them in any particular order. You can read A Study In Scarlet if you want to learn about how him and Watson met and meet some of the local cops ahead of time, but you’ll put it together fast enough if you don’t.
Also @aceplace, I noticed you said they were 99¢. I know I got them for free from Amazon, you shouldn’t have to pay for them since they’re out of copyright. The ones that aren’t free at Amazon ARE free at Gutenberg.org and they’ll transfer right over to your Kindle (and show up on your Amazon.com account just as if you bought it there, they play nice together).
Free PDF facsimiles of some of the original publications (with notes) can be found here:
http://sherlockholmes.stanford.edu/archive.html
http://sherlockholmes.stanford.edu/readings.html
As others said, don’t worry about the order too much. Doyle wrote stories out of sequence on occasion.
I found the complete works available for my nook for about three or four bucks (can’t remember which) and that’s less than many dead tree versions of a single novel. So if you have an ereader, you might want to buy the collection.
I tend to read a few short stories, read another author, go back to Holmes, read another author, etc. Otherwise, I tend to get tired of the setting.
As someone who just recently read Sherlock Holmes for the first time, I’ll tell you the truth. A Study in Scarlet and The Sign of Four suck. They suck hard and they suck long.
The Hound of the Baskervilles is great. The stories are hit and miss. Proceed as you see fit.
Nitpick: It wasn’t actually the BBC, it was Granada, and the series was broadcast on ITV. Definitely the definitive canonical Holmes as far as I’m concerned.
This is truth.
The best place to start is with the Adventures, the first twelve short stories. About 95% of everything that is “Holmes” comes out of these stories. Then Hound, then you can fill in around them as you feel like.
If you’re serious enough to care, the various editions of the Annotated Holmes are worth using for your reading copy. Besides page annotations on the obscure points of the story and time, there are helpful notes that tie things together, and inter-story essays and references (which you can skip the first time through) that go into great, sometimes Britishly-silly, depth on fine points of the two men, their lives, and the milieu.
Good advice.
Though it’s pretty much a given that if you don’t like “The Hound of the Baskervilles” you won’t like much else in the repertoire.
Do not start out with the last of the short story collections, as most of them are inferior to the early ones (despite Holmes’ efforts to pump them up by telling Watson stuff like “Strangest case I ever had!”).
“The Sign of the Four” and “A Study In Scarlet” are enjoyable in my view, better than “The Valley of Fear” but not up to “The Hound of the Baskervilles”.
Persecute! Unbeliever! Persecute!
Yeah, my personal recommendation is to start by reading The Adventures of Sherlock Holmes, because it’s both the earliest and, arguably, the best of the several short story collections to be published. The short stories are more characteristic, but Hound of the Baskervilles is the best of the novels.
The short novel A Study In Scarlet is the first Holmes story to be written, and it does introduce Holmes to Watson and to us. But the second half of the novel is all backstory explaining the lead-up to the crime, and doesn’t involve Holmes at all, which of course isn’t what most readers expect/want from a Sherlock Holmes story. (See the thread Is this ever going to end (Middle of A Study In Scarlet)?
Almost all of Doyle’s Sherlock Holmes stories are old enough that they’re in the public domain (in the U.S.) (and the later ones that aren’t, aren’t nearly as good). That means you should be able to find e-book editions for free or nearly free, depending on what edition you want. You can, for example, get everything Arthur Conan Doyle ever wrote that’s currently in the public domain for $2.99—or just download the individual books for free from Project Gutenberg.
Most of us first saw Jeremy Brett as Holmes on PBS; at the time, we just assumed that everything British came from the BBC. I love those shows & they are currently streaming on Netflix…
I’d read The Adventures of Sherlock Holmes first, and also the short story “The Adventure of Silver Blaze”, which includes the famous line about “the curious incident of the dog in the night time.” It’s my favorite Holmes story.
Camden House has the (complete) Complete Sherlock Holmes online. You will see by the original illustrations that Jeremy Brett looks like the canon Holmes.