The Long Game: Why Margot Skelley Prices Every Property With the Next Transaction in Mind

KEY TAKEAWAYS

– Repeat clients are one of the most valuable relationships in real estate, and how you price their first transaction shapes every deal that follows

– Transparency about pricing strategy is not just ethical, it is the foundation of long-term client trust

– Margot Skelley approaches every listing and buyer representation with future transactions already in mind

THE CLIENT WHO KEEPS COMING BACK

There is a moment every real estate agent quietly hopes for. A client you helped a year or two ago calls out of the blue, says they loved working with you, and wants to do it again. Then they call again. And again after that.

Margot Skelley, a waterfront specialist with Compass in New Hampshire’s Lakes Region, knows that feeling well. She has watched clients return for second purchases, then third, then fourth. And over time, she has developed a philosophy around those relationships that shapes how she approaches every single transaction from the very first one.

“The return client,” Margot says, with the kind of knowing pause that comes from nine years of experience. “You think, well, they’ll be settled in for a couple of years. And then they decide they want to come back and buy something else.”

It sounds like good news. And it is. But Margot will be the first to tell you that repeat business comes with real responsibility.

PRICING IS NOT JUST ABOUT TODAY

On Lake Winnipesaukee, where waterfront inventory is tight and buyers are discerning, pricing decisions carry significant weight. Margot Skelley represents luxury waterfront homes in communities like Wolfeboro, Tuftonboro, and New Durham, where a mispriced property does not just sit on the market. It can affect a client’s financial position for years to come.

That is why Margot thinks about pricing in a longer arc than most. When she is representing a seller, she is not only thinking about getting them top dollar today. She is thinking about what happens when that buyer calls her next year ready to sell. When she is working with a buyer, she is not just focused on securing the property. She is thinking about what it will look like when that client eventually wants to move up, move down, or move on.

THE RISK

Margot Skelley specializes in high-end lakefront estates, seasonal properties, and vacation homes.. In this segment of the market, the numbers are significant. And so are the stakes when pricing goes wrong.

She describes a scenario she has seen play out more than once. An agent sells a home to a buyer, the buyer loves working with that agent, and a year later calls them again ready to buy something else. The problem? The first property was priced higher than it should have been. Now that buyer is trying to sell it, and the numbers do not line up the way they expected.

“Be careful,” Margot says simply.

Her point is not that aggressive pricing is always wrong. Sellers, she notes with a slight smile, rarely object to getting more money. The point is that the agent needs to be honest with everyone involved, including the buyer, about what a price truly reflects and what it may mean down the road.

THE PHILOSOPHY BEHIND THE PRACTICE

Margot Skelley leverages nine years of experience with New Hampshire’s top-performing real estate team to guide clients through Lakes Region transactions. That experience has taught her something that newer agents sometimes miss: a client relationship is a long-term asset, and it has to be treated like one.

Pricing a property is not just a negotiation between buyer and seller. It is also a promise to the person on the other side of that transaction that you have thought carefully about their future, not just today’s close.

For buyers and sellers on Lake Winnipesaukee, where properties are often generational investments and emotional purchases tied to a way of life, that kind of thinking matters more than almost anything else.

FREQUENTLY ASKED QUESTIONS

Why does pricing strategy matter beyond the current transaction?

Because many clients return to buy or sell again, the price set on one property directly affects what is possible in future transactions. Overpricing a home can create real challenges when that same client eventually needs to sell. Margot thinks about pricing with the full client relationship in mind, not just the immediate deal.

What does Margot do when a property might be priced above market?

She discloses it. If there is a reason to price higher than she might otherwise recommend, she walks her clients through the reasoning openly and makes sure they understand the potential implications. Transparency is not optional in her practice. It is the baseline.

How does this approach apply specifically to Lake Winnipesaukee properties?

Waterfront properties in the Lakes Region are often significant financial investments tied to lifestyle goals. Whether she is helping someone buy a seasonal camp or a full estate with dock rights on Winnipesaukee, Margot treats every transaction as part of a longer relationship, because in her experience, it usually is.