The Question About Winter Comes Up Less Now

For years the first thing buyers asked me about the Lakes Region was what happens here in the winter. That question comes up a lot less since 2020. What changed was not Wolfeboro. What changed was how people feel about a town that refuses to rush.

Forty or fifty years ago, this town really did shut down after Columbus Day. The Lakes Region followed a classic New England seasonal rhythm. That version of Wolfeboro no longer exists. Most restaurants that once shuttered for winter are now open year-round. The infrastructure that supports year-round living has quietly expanded as more buyers stopped thinking of this place as a summer escape and started imagining it as somewhere they could actually live.

The pandemic accelerated something that was already building

When remote work made it possible to live where you had previously only played, interest in Lakes Region properties surged. Buyers who had visited for summers started asking different questions about year-round logistics, schools, winter activities, broadband. The adjustment from city or suburban life still involves trade-offs worth naming. The closest Walmart is about a half hour away. Dining options are fewer in January than in July. I tell buyers this not to discourage them but because the ones who are prepared for it thrive here.

The tax conversation nobody expects

New Hampshire has no income tax and no sales tax. Establishing residency by spending 183 days in the state turns a vacation property into a primary residence with real tax advantages. Many of my clients split time between New Hampshire and Florida, both states with favorable tax treatment, building a lifestyle that balances warm winters with New England summers.

Margot Skelley is a REALTOR at Compass Real Estate in Wolfeboro, NH, specializing in luxury lakefront and waterfront properties across Carroll County. She is the author of The Skelley Report, a monthly market letter published the first Friday of each month.