Question: How old are Dean and Sam in season 9?
Answer: Dean is 33 and Sam is 29 around season 9.
Answer: Early 30's. The flashback shows them 22 years earlier when their dad says "Dean take your brother and go." Dean looks to be 5 and Sam is just a baby.
All Hell Breaks Loose: Part 1 - S2-E21
Continuity mistake: Before the Roadhouse fire, Ash and Dean are talking on the phone. Ash looks at his watch, on his left hand, it says 8:10, and has a black dial/face. As Dean and Bobby go through the rubble, Dean identifies Ash by his watch. Still on his left hand, it is now upside down, evident by the crown of the watch (used to move the hands of the watch) which previously facing his hand, is now facing his elbow. Also, the dial/face of the watch is now silver instead of black. This is a different watch, and was inadvertently put on the burnt arm upside down.
Sam Winchester: Why'd you let me fall asleep?
Dean Winchester: Because I am an awesome brother. What did you dream about?
Sam Winchester: Lollipops and candycanes.
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Answer: There are 4 years between Sam and Dean so Dean was 4 or 4 1/2 when he took Sam out of the house. Sam was 6 months.