The movie starts out with a boy and his father as shepherds.

They see a dragon, go after the eggs for profit and the dad dies.

The dad dies and the son is sent off to a lord who owes his father a debt. The boy is supposed to be trained as a vassel or knight or something.

The lord has a daughter who tries to help teach the boy when her father doesn't.

The dragon returns and the lord and the daughter's prospective husband go hunt it. The boy goes out separately to hunt.

The boy kills the dragon

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    When did you see this? Was it live action or a cartoon? What language was it in? Any famous actors or actresses? Any specifically memorable scenes or lines of dialog? – Stefan May 13 '13 at 11:32
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    Welcome to SFF. If you could answer any of @Stefan 's questions, that would be very helpful. Also, did you see it in a theater, on TV (station), or video. It seems strange, but even the smallest detail can help. – Donald.McLean May 13 '13 at 11:34

it looks like Dawn of the Dragonslayer (2011), A movie that don't currently have a Wikipedia page. Quote from the IMDb summary :

When Will's father is killed by a dragon, he embarks on an epic journey filled by vengeance that leads him to an ancestral home which he stays at and works for the tyrannical Sterling in order to learn how to slay the beast. While he is training, he befriends Sterling's daughter Kate, and Sterling becomes increasingly suspicious of and threatened by Will. He orders his men to kill him but Will escapes. Now Will must evade Sterling's men whilst trying to avenge his father

You could see the trailer here :

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