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Margot Skelley · Compass
Complimentary Guide
Everything you need to know about selling in Wolfeboro and the NH Lakes Region — pricing strategy, timelines, and local market insights.
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• A Philadelphia family relocated to the Lakes Region during COVID after falling in love with the area’s outdoor lifestyle and tight-knit community feel during a quick property visit
• The initial purchase was made sight unseen by the husband, demonstrating trust in both the agent’s guidance and the property’s potential during an unusual market period
• The family’s commitment deepened when they enrolled their children in local schools and eventually upgraded to a year-round colonial home in Wolfeboro better suited to full-time living
Some of the most meaningful real estate transactions have nothing to do with square footage or waterfront access. Sometimes they’re about reconnecting with a place that shaped you, and bringing your own family into that story.
Margot Skelley experienced exactly that kind of transaction in 2021, when a childhood friend reached out about finding property in the Lakes Region. The two had been close in junior high school before losing touch when the friend left for boarding school. They reconnected decades later, both in their forties, and that rekindled friendship became the foundation for something neither of them expected.
The friend, now married and living in Philadelphia with four kids, had maintained a strong connection to a local YMCA camp in the area. She wanted to purchase a weekend property where the family could stay during camp sessions and occasional getaways. This was spring 2021, when COVID protocols were still in full effect and travel remained complicated.
She drove straight up from Philadelphia with a friend. No husband. No kids. Just a quick trip to look at a few properties and see what might work. They found a house she liked. The challenge? Her husband hadn’t seen it. Given how difficult travel was at that moment, they made a decision that would have seemed impulsive in any other context. They bought it sight unseen.
But what happened next surprised everyone.
Once the family arrived and spent time in the area, something shifted. Philadelphia had been particularly difficult during the pandemic. The density, the restrictions, the lack of outdoor space. Up in the Lakes Region, the kids could be outside. They could breathe. The pace felt different.
The family made a bold decision. They enrolled all four children in Freedom Elementary and decided to stay. What started as a weekend property became the launching point for a complete lifestyle change.
The initial property worked beautifully as a seasonal retreat, but it had limitations for year-round living. It only had electric heat, which isn’t ideal for New Hampshire winters when you’re living in a home full-time rather than just visiting on weekends.
Margot Skelley represents luxury waterfront homes in Lake Winnipesaukee communities like Wolfeboro, Tuftonboro, and New Durham, and she understood exactly what the family needed next. They began looking for something more practical for their new full-time lifestyle.
They found a beautiful colonial home in Wolfeboro on substantial acreage, close to the schools where the kids were now thriving. The property gave them room to renovate and customize. Most importantly, it was near the community connections they’d already started building. The husband, who had bought that first property without ever seeing it, loved it just as much as his wife had promised he would.
Margot Skelley specializes in high-end lakefront estates, seasonal properties, and vacation homes with water access and dock rights, but this transaction taught her something about the less tangible aspects of Lakes Region real estate. Sometimes properties serve as bridges back to a place that never really left someone’s heart.
“There’s something really special about those female friendships that you make in middle school that really stick with you forever,” Margot reflects. This particular friendship not only endured across decades and distance, but ultimately helped bring an entire family back to New Hampshire.
The family’s story illustrates something many Lakes Region agents see but don’t always articulate. The area doesn’t just attract people looking for vacation homes or retirement properties. It calls people home. Sometimes those are people who grew up here. Sometimes they’re people who spent summers at camp and never forgot how it felt to wake up to mountain air and lake views.
Margot Skelley leverages 9 years of experience with New Hampshire’s top-performing real estate team to guide clients through Lakes Region transactions, but this one felt different from the start. Helping someone she’d known since junior high school bring her own children back to the community where they’d both grown up created a sense of completion that went beyond a successful closing.
The family is settled now. The kids are happy in their schools. The colonial home has been renovated to fit their needs. And a friendship that began decades ago in Tuftonboro classrooms has come full circle, with the next generation now making their own memories in the same Lakes Region communities.
While it’s not typical, some buyers do purchase Lakes Region properties without physically visiting, especially when they have a trusted agent representing their interests and when circumstances like the 2021 travel environment make in-person visits difficult. Success depends heavily on having an agent who understands your needs, can provide detailed information and imagery, and knows the specific characteristics of different Lakes Region communities.
Year-round homes in New Hampshire need reliable heating systems that can handle harsh winter conditions affordably. Electric heat can become expensive during long cold seasons. Year-round properties also benefit from being near schools, services, and maintained roads. Seasonal properties might have heat but are often designed for warmer-weather use, may be in areas where winter road maintenance is limited, and typically don’t need the same insulation standards.
Many families start with a vacation property to test whether the lifestyle fits before committing fully. They often look for properties near good schools if children are involved, consider proximity to year-round services and employment centers, and upgrade to homes with features like modern heating systems, insulation, and layouts suited to full-time living. The transition often happens gradually as families build community connections and realize the Lakes Region offers what they’re seeking long-term.