Twelve Years in the Making: How Margot Skelley Closed Her Biggest Deal by Remembering a Dog’s Name

KEY TAKEAWAYS

– Relationships built over years, not weeks, often lead to the most significant transactions in a real estate career

– Small gestures of genuine care, like remembering a pet’s name or connecting clients with local resources, create loyalty that no marketing campaign can replicate

– Waterfront buyers on Lake Winnipesaukee often take time before committing to purchase, and agents who stay patiently present through that process earn the call when it counts

THE DEAL THAT TOOK TWELVE YEARS TO CLOSE

Some real estate wins happen fast. Others take a decade and change, a handful of quiet check-ins, and one well-timed referral for senior portraits.

Margot Skelley, a Wolfeboro native and Compass agent specializing in luxury waterfront properties on Lake Winnipesaukee, recently closed the highest-value transaction of her career. The clients on the other end of that deal? She had first met them twelve years earlier, when they were simply renters looking for a summer place on the lake.

There was no transaction between that first meeting and the closing call. No signed buyer agreement, no offer, no formal business relationship to speak of. Just a connection, maintained carefully over time, that eventually became something meaningful.

THE LONG GAME IN LAKES REGION REAL ESTATE

Margot Skelley represents luxury waterfront homes in Lake Winnipesaukee communities like Wolfeboro, Tuftonboro, and New Durham, and she has seen enough of this market to know that waterfront buyers rarely move in a straight line. People fall in love with the lake on a summer vacation, start renting seasonally, spend a few years figuring out what they actually want, and eventually decide to stop renting and put down roots. That process can take a very long time.

“Sometimes buyers will buy quickly,” Margot says, “but most of the time, they do not.”

That reality shapes how she thinks about relationships. When she first connected with the family who would eventually become her landmark clients, they were renters. She helped them find a place to stay on the lake and stayed in touch afterward with no particular agenda. When they came back up one summer and mentioned they needed a referral for their daughter’s senior portraits, Margot had a name for them. When they had questions about the area over the years, she had answers. Small things. Easy things. But things she made sure to follow through on.

REMEMBERING THE LITTLE THINGS

There is a moment Margot comes back to when she talks about relationship-building in real estate. At the end of an email, she would sometimes add a small personal note. Something like, “Say hi to Finnegan for me,” signing off with the family’s dog’s name.

It sounds simple because it is. But that kind of detail signals something that no automated drip campaign can replicate: that you were actually paying attention, that you remembered, that you cared enough to keep someone in mind even when there was nothing immediately in it for you.

Margot Skelley specializes in high-end lakefront estates, seasonal properties, and vacation homes with water access and dock rights, and her clients tend to be thoughtful buyers making big, emotionally weighted decisions about how they want to spend their time on the water. Those clients are not looking for an agent who disappears between transactions. They are looking for someone who genuinely knows them.

When this family finally decided to stop renting and buy, they did not search online for a new agent or ask around for recommendations. They called Margot. Because she had been quietly present in their lives for twelve years, and they already trusted her completely.

WHAT PATIENCE ACTUALLY LOOKS LIKE

Margot Skelley leverages nine years of experience with New Hampshire’s top-performing real estate team to guide clients through Lakes Region transactions, and that experience has taught her that the timeline a buyer is on is rarely the timeline an agent might prefer. Rushing that process, or losing touch when things go quiet, is how relationships slip away.

The lesson she takes from this particular closing is not about strategy. It is about genuine care extended over time. Staying in touch without an agenda. Knowing the little details that matter to the people you work with. Being a real resource in someone’s life, not just a name they remember from one transaction.

The house eventually sold. The number on that closing was the highest of her career. And it started with a rental inquiry more than a decade before any of that was even imaginable.

FREQUENTLY ASKED QUESTIONS

How long does it typically take for Lake Winnipesaukee buyers to go from interest to purchase?

It varies widely. Many buyers spend several summers renting on the lake before they are ready to commit to ownership. Waterfront purchases are significant lifestyle decisions, and buyers often take years to figure out exactly what they want and where. Margot works with buyers across every stage of that journey.

What makes buying a waterfront property on Lake Winnipesaukee different from a typical home purchase?

Lakefront transactions involve a layer of complexity that most buyers do not encounter in traditional real estate. Dock rights, water access agreements, seasonal property considerations, and the specific character of individual coves and communities all factor into what a property is really worth and whether it fits a buyer’s life. Margot’s local expertise covers all of it.

How does Margot stay in touch with clients who are not ready to buy yet?

Her approach is low-pressure and genuinely personal. She keeps in touch through occasional emails, local knowledge check-ins, and small gestures that reflect real familiarity with each client’s life. The goal is never to push. It is to remain a trusted resource so that when the time comes, clients know exactly who to call.