Answer: Unfortunately, I am not certain what kind of chestnut tree you have. Castanea dentata or the American chestnut should be fully winter hardy in your area so you would not need to worry about the cold weather. You would need two trees for pollination to occur. It theoretically is able to produce nuts at a fairly young age, however most of the trees succumb so quickly to the chesnut blight disease that they never produce nuts at all. If you have the Chinese chestnut (Castanea mollissima) or a hybrid which is tolerant of the blight, or if you have one of the horse chestnuts, winter cold is again not a problem.
Chinese chestnuts are more widely available, so I would guess this is probably what you have. You would need two different named varieties for nut production. In a commercial setting these are field grafted to put a good nut producing variety onto a seedling rootstock, and the nut production usually begins about three years after the grafting is done. If you planted seedlings or grafted trees, you might see nuts in about three to five years. How long it takes depends on how well the trees establish and mature -- so weather, site, and care would all contribute.
Although cold is not a problem, you may want to take steps to protect the young trees from deer and rodent damage during the winter. For voles and rabbits, you can use a wire mesh or hardware cloth cylinder at least two feet taller than expected snow levels to encircle the trunk, also stretch the wirecloth outward along the ground for about two feet all around the tree to prevent them tunneling under it. Cover it with gravel to keep it flat and in place. For deer, a taller cylinder of fencing with a diameter of six feet or so should keep them away. Or, you can use deer and rodent repellent sprays sold at garden centers. Read and follow the directions for application and reapply as indicated on the label.
In general you would also apply an organic mulch over the root area in a flat layer about three or four inches thick. Maintain this year round to help keep weeds down and to help feed the soil on an ongoing basis as it rots down.
Enjoy your trees!
Best of luck with your trees!
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