Agree with everyone on butyl tape. Also I suggest countersinking the holes slightly to give a small shoulder area where the butyl can sit around the boat. Put the bolts through the base of the winch and wrap them with a small rolled snake of tape right where they come through. You can also put a layer of tape on the entire bottom but it probably isn't needed and as others have mentioned watch out for any drain holes.
With the butyl tape, you need to come back several times over at least a few days and tighten the bolts further as it relaxes and flows into place. Then trim the excess that comes out around the outside before putting the top of the winch on. Note, not all butyl tapes are created equal. As has been recommended by many on this list, bed-it butyl tape is what I have been the happiest with: https://bed-it.com/?gad_source=1&gclid=CjwKCAjw8diwBhAbEiwA7i_sJfsZj1Ga-q3dJepvUm9eG958mdXQ3BBk-yhNqhTZT0OAmtG8fOke1xoCytoQAvD_BwE Nathan Post S/V Wisper C&C 34 KCB Portland ME
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