Surprisingly, this question has been studied somewhat extensively in academia.
Chapman and Morrison in 1994 did a comprehensive survey of the impact hazard for differently sized comets and meteors on Earth. They have this to say about an impact winter in discussing what constitutes a global catastrophic impact:
A global impact winter will commence when sufficient submicrometre dust is injected into the stratosphere to produce optical depth $> 2$ worldwide for a few months ... This optical depth corresponds to $10^{16}$ g of stratospheric aerosol. ...
Scaling from nuclear weapons tests and the K/T event, Toon and his colleagues find that an optical depth $\approx 2$ would result from a groundburst with a yield of $10^{5}$ - $10^{6}$ MT corresponding to a diameter of 1.2 km for a stony object striking at 20 km per second.
The K/T event here refers to the meteor that killed the dinosaurs.
It should be made clear that it appears the bare minimum size for an impact winter defined this way is the figure above - the authors do cite a range for globally catastrophic meteor sizes in the paper, but they are considering hazards arising from meteors other than just impact winter in providing that range.
1.2 km diameter (or 0.7 miles) would appear to be your best bet as a threshold for impact winter. It should be noted that the authors don't consider an impact winter for a time period longer than a few months, although they do state that:
... a $>5$ km object would create a global firestorm and so much darkness ... that vision would cease.
providing some measure of how bad things can get beyond that threshold.
Long-term impact winters don't seem to be something discussed in the literature despite my best efforts.