I have read more books than I can remember, ever since 6th grade I used to read novels in my free time and even in class, instead of listening to the teacher and even now as a university student my passion for reading hasn't died. I have always felt that the single most important feature of a good writing re-readability. Reading a book once is easy, but if you enjoy it reading again (and again), despite knowing book's main content, that's the real hallmark of good writing.
There can be a number of factors that make re-reading enjoyable. Author's wit, intelligence, plot subtleties, character developments, story arc, richness of details, emotional complexity, forethought- and many others.
Based on this criteria of re-readability following are few of the works that I read more than twice:
Hitchhikerk's Guide to Galaxy
First four volumes of Harry Potter
the Catcher in the Rye
Catch 22
Hobbit and Lord of the Rings
Sherlock Holmes canon
Anna Karenina
Foundation Series
For Whom the Bell Tolls
Cryptonomicon
Continuing the list, there are also books that I liked immensely (and they are on my all time fav. list) but I couldn't go through them second time despite trying it more than once. Some of those are:
The Da Vinci Code
One Hundred Years of Solitude
My Name is Red
The Name of the Rose
A Song of Ice and Fire
Lord of the Flies
Ender's Game
Disgrace
The Curious Incident of the Dog in the Night Time
Middlesex
How do you feel about your favorite works?