Frequently second homeowners contact me during the winter months expressing the desire to list their homes in the spring or if they're already listed, to withdraw their house from sale for the winter. This is not always the optimal strategy, depending on the type of property and the market conditions.
Lake houses are a good example of a property type that benefits from "early" listing. If you're a buyer, you want to be in and ready to enjoy the spring and summer at your new waterfront (or even water access) pad. If it takes about 60 days to close a deal with financing, then you're looking at having an accepted offer by the end of March to be in for Memorial Day. Therefore it makes sense to be listed, I would argue, even before the holidays, if possible, to maximize the showing period.
And that holds true for most second homes that are geared particularly toward summertime enjoyment. (Ski houses will have a different cycle.) Buyers will want to take full advantage of their first summer season, which means the sale process starts in winter or early spring.
Another important factor is inventory levels. This winter a lot of agents find themselves with fewer properties to show, following a very active end of summer and fall. I'm still closing a number of properties that have had agreements since the very busy autumn period, and will find myself with what I consider a low level of inventory for the next few months. That means that properties that have the most appeal, and that are priced right, will receive a lot of attention, in spite of the reduced number of buyers coming Upstate in winter.
I happen to have purchased my cottage in winter, and closed in early April, just in time for spring. The thing about buyers who see property in wintertime, is that they are clearly motivated. Braving colder weather and sometimes inhospitable driving conditions, those who make their way up, clearly want to buy. So while the number of buyers in the marketplace drops, the "quality" in terms of their likelihood of purchasing increases.
And of course there is a glut of properties that come on the market in spring, so it stands to reason that there is greater competition. If a home is properly prepared for sale and priced correctly. If decent photographs can convey the property well, and especially if it is a lake house, then wintertime can be a great time to list your second home for sale.