What 25 Years on Lake of Bays Has Taught Me About Cottages, Clients & Moments That Last
By Jay Richardson, Broker | The Richardson Team — Refined Real Estate
Royal LePage Lakes of Muskoka | lakeofbayscottages.ca
Royal LePage Lakes of Muskoka | lakeofbayscottages.ca
I want to tell you about a couple I met at the Cottage Life Show almost 25 years ago.
They were exactly the kind of people this work is made for — warm, clear about what they wanted, and utterly certain that somewhere on a north Muskoka lake there was a cottage with their name on it. They just had not found it yet.
Every weekend for the better part of a season, they would drive up from the city, check into Deerhurst Resort and spend their days on the water with me, moving from property to property on Lake of Bays. We looked at everything that came close. Nothing was quite right. The lot was too narrow. The exposure was wrong. The neighbours were too near. The drive was too long. You know how it goes — when someone is searching for something they have been dreaming about for years, close is never close enough. And then one afternoon we turned down a laneway on Rabbit Bay.
I cannot tell you exactly what it was about that lot. The light, maybe. The way the shoreline curved. The quiet. But the moment we stepped out of the car, I watched something happen that I have seen only a handful of times in this career — two people look at each other and simply know. No discussion. No negotiation. No second visit. They bought the lot that day and built the cottage they had been trying to find on every other property we had visited together.
When someone finds the right place, they do not need to be convinced. You can see it in them the moment they arrive. I remember the day the offer was submitted and accepted. We climbed to the top of the Dorset Tower together and looked out over the lake that had become theirs. That evening we took a boat to Bartlett Lodge for dinner — a christening of sorts, a quiet celebration of something that had taken time to find and would last a lifetime.
That couple became friends. As so many clients do, over time. That is the thing about this work that no one quite prepares you for when you start out — you are not just helping people buy and sell property. You are present for some of the most significant decisions of their lives. And if you do it right, the relationship does not end at the closing table.
What the Years Actually Teach You
I have been selling waterfront property on Lake of Bays and across North Muskoka for more than two decades. I have worked through market booms and sharp corrections. I have helped families buy their first cottage and sell the one that belonged to their parents. I have navigated estate situations, dissolved partnerships, complicated titles and deals that fell apart the day before closing and somehow came back together.
If I am honest, the market has taught me less than the people have.
The market goes up and it goes down. Inventory tightens and then loosens. Interest rates move in directions that surprise everyone, including the economists. These cycles are real and they matter — but they are not the thing that stays with you.
What stays with you is the seller who cried quietly at the kitchen table when we accepted an offer on the cottage her family had owned for forty years. That is not a transaction. That is a privilege. The property is rarely just the property. Behind every transaction is a chapter of someone's life being written.
The Lesson I Would Give My Younger Self
If I could sit down with the version of myself who was just starting out in this market, I would tell her one thing above everything else.
Trust takes years to build and seconds to lose.In a market like ours — where properties are singular, buyers are sophisticated and sellers are emotionally invested — your reputation is everything. It precedes you into every conversation and follows you out of every closing. The moment you prioritise a commission over a client's best interest, or tell someone what they want to hear instead of what they need to know, you have started a process that is very difficult to reverse.
I have never sold a client a property I did not believe in. I have never told a seller their home was worth more than the market would bear simply to win the listing. I have turned away business I did not feel right about. And I have lost deals by being too honest — by telling a buyer that the property they loved had a problem worth understanding before they committed.
Every one of those decisions was the right one. Not because it was comfortable, but because it compounded. The clients who trusted me trusted me again. They sent their friends. They called me a decade later when circumstances changed. They became part of the community of people I am proud to have served.
That is what trust looks like when it is tended carefully over a long period of time. It does not look like a transaction. It looks like a relationship.
What Lake of Bays Has Given Me
I am not just a broker who works in this region. I live here. I know the roads and the laneways, the bays that catch the afternoon light and the families who have held their waterfront properties for generations. That kind of knowledge does not come from a database.This place has given me a career I love and a community I am proud to be part of. I sit on the board of Muskoka Women's Shelters. I support the Muskoka SPCA and Hospice Huntsville. These are not obligations — they are an expression of what it means to belong somewhere, to feel the weight of that belonging and want to give something back.
Buddy, my shelter rescue sidekick, comes to the office with me every day. He is not a professional credential but he might be the best thing about walking through the door in the morning. This lake has given me more than a market to work in. It has given me a life I would not trade.
The couple from Rabbit Bay still have their cottage — or rather, he does now, with his family around him. Kathy passed away some years ago, and I think of her often as I drive around the lake. The laneway, the lot, the moment they looked at each other and knew. That cottage holds all of it — the dream they built together, the summers that followed and the people who still gather there because of a decision made on an ordinary afternoon that turned out to be anything but.
That is what waterfront property really is, when it is the right one. Not an asset. A place that keeps the people you love close, even when life changes around it. That is what I am here to help you find.
Jay Richardson is a Broker and owner of The Richardson Team — Refined Real Estate, a boutique Royal LePage Lakes of Muskoka office specializing in luxury waterfront, cottage and rural residential properties in Lake of Bays and North Muskoka. She holds the CLHMS, RENE and RSPS designations and is a Lifetime Award of Excellence recipient. Reach her at lakeofbayscottages.ca.