Who Gets the Dock? 

It simply does not come up — until it does. And when it does, it is rarely at a quiet moment. It tends to arrive in the wake of a health scare, a death in the family, or a disagreement between siblings that has been simmering for years beneath the surface of summer long weekends. That is the conversation I want to have with you today — not because it is comfortable, but because addressing it now, while the dock is quiet and the decisions are yours to make thoughtfully, is one of the most generous things you can do for the people who love this place as much as you do.

The cottage that holds your family together today can just as easily become the thing that pulls it apart — if the right conversations don't happen first.

A Muskoka waterfront property is not a simple asset. It carries value that is both financial and deeply emotional — and those two dimensions can work against each other in an estate situation. From a purely financial standpoint, the Canada Revenue Agency treats a cottage as a capital property. On the death of the last surviving owner, the property is deemed to have been disposed of at fair market value. If your family purchased that property decades ago, the resulting capital gain — and the tax owing on it — can be substantial. Without proper planning, surviving family members may face the prospect of selling a beloved property simply to cover the tax bill.

From an emotional standpoint, the challenges are just as real. Who gets to use the cottage and when? Who pays for the roof, the dock, the septic system? What happens if one sibling wants to sell and the others do not? These are not hypothetical questions. They are conversations I have watched fracture families who shared a generation of beautiful summers together.

What Proper Planning Actually Looks Like

I want to be clear: I am not a lawyer or a tax advisor, and nothing in this post constitutes legal or financial advice. What I can offer is what I have observed at the table — the approaches that protect families and the gaps that tend to cause harm.

The families who navigate cottage succession most gracefully tend to have addressed several things well in advance:
• A clear ownership structure. Whether the property is held personally, jointly, or through a family trust or corporation has significant implications for both tax treatment and decision-making authority. Each structure has trade-offs, and the right choice depends on your family's specific circumstances. A tax lawyer or estate planner familiar with Ontario cottage ownership is the right person to guide this.
• A documented family agreement. Some families formalize a Cottage Sharing Agreement — a document that outlines usage schedules, maintenance responsibilities and cost-sharing. It does not need to be a legal document to be effective, but having expectations in writing before conflict arises is invaluable.
• A current valuation. If the property forms part of your estate, an Opinion of Value from a qualified real estate professional gives your executor and your family a credible baseline. This is not the same as a formal appraisal, but it provides context and can assist with planning decisions. It is also something I can provide.
• A conversation — an actual one. This is the step that is most often skipped. Gathering the family, sharing your intentions and inviting questions is uncomfortable but irreplaceable. The families who have done it tell me, without exception, that they wished they had done it sooner.

The Capital Gains Reality in Ontario

Since the 2024 federal budget proposed increasing the capital gains inclusion rate from one-half to two-thirds for gains above $250,000 — a change that has ongoing legislative implications — the financial stakes of cottage succession have come into sharper focus for many Ontario families. While the specifics of these rules continue to evolve, the underlying reality is unchanged: a waterfront property that has appreciated significantly over decades will attract tax on deemed disposition. The question is not whether that tax exists, but whether your estate has the liquidity to manage it without forcing a sale.

Strategies such as a principal residence designation (subject to eligibility rules), life insurance to cover tax exposure, or transferring the property to a family trust during your lifetime are all tools that an estate planner can model for you. They require time to implement. That is precisely why this conversation is best had now.
The families who plan ahead get to choose. The families who don't often find that circumstances choose for them.

When the Property Does Come to Market

I have represented estates selling Muskoka waterfront properties, and I can tell you that an estate sale handled with proper planning — current valuations, clear ownership documentation, well-maintained property condition — proceeds far more smoothly and typically achieves a stronger result than one that arrives under time pressure with unresolved family dynamics in the background.

Buyers can sense uncertainty. A property that comes to market with clarity of title, accurate disclosures and well-maintained systems signals that it has been cared for and that the sellers are prepared. That confidence translates to price.

A Note on Timing

The Muskoka waterfront market, like any market, moves in cycles. The value of your property today reflects factors that will not remain static. Having a current understanding of what that asset is worth — in today's market, with today's buyer expectations — is part of sound estate planning regardless of whether you intend to sell. If you have not had a market conversation about your waterfront property in the past two or three years, that alone is worth revisiting.

Where to Start

If this blog has prompted you to think about conversations you have been postponing, here is a simple place to begin. I am not suggesting you call an estate lawyer today, though that would not be a bad idea. I am suggesting that you start with the people closest to you and simply ask: do we have a shared understanding of what happens to this place?

If the answer is no — or if it is unclear — that is the conversation worth having. Everything else flows from there.

I am always available to provide an Opinion of Value for planning purposes, to speak confidentially about what I am seeing in the market, or simply to have a grounded conversation about your property and what the future might look like. There is no obligation and no pressure — just the kind of honest counsel that I believe every waterfront family deserves.