Whether you own a cottage, a family home, or any other high-value asset, working with an experienced estate lawyer to craft clear, specific, and regularly updated instructions is not just good practice — it is essential.
Curated Content Property Pitfalls

Why Cottage Estates Are a Breeding Ground for Family Conflict

Kamloops Moving & Storage
By Thomas Brodie 
March 22nd, 2026

Vacation properties carry both deep sentimental value and considerable financial worth, making them one of the most common sources of conflict in estate settlements.

Beyond their sentimental significance, cottages bring a host of practical complications including ongoing maintenance costs, property taxes, insurance obligations, and the challenges of shared decision-making among multiple owners. In many families, one sibling may have a stronger emotional bond with the property, have invested more time maintaining it, or be in a better financial position to take it on — all of which can foster resentment and division among heirs.

A recent case before the Ontario Superior Court of Justice powerfully illustrates how vague language in a will — combined with a dramatic rise in property value — can tear families apart and lead to lengthy, costly legal battles.

In Haddock v. Haddock, the absence of any clear provision addressing what would occur if the cottage’s value exceeded one beneficiary’s entitlement was the single most critical factor in triggering the dispute. This case serves as a powerful cautionary tale for any Canadian family that owns a vacation property and has not recently reviewed their estate documents.

A will drafted more than a decade ago may no longer reflect the current value of assets or the circumstances of beneficiaries — and the consequences of that gap can be both financially devastating and emotionally destructive. Taking the time to plan properly today can spare your loved ones from years of conflict, legal expense, and heartbreak tomorrow.

Legal and estate planning professionals strongly advise property owners to address these scenarios explicitly in their wills.

Key considerations should include whether the cottage is to be shared among heirs, transferred to a single beneficiary with appropriate financial compensation to others, or sold with proceeds divided equally. Tax planning is equally important, as capital gains and other obligations can significantly affect the estate’s overall value.

Whether you own a cottage, a family home, or any other high-value asset, working with an experienced estate lawyer to craft clear, specific, and regularly updated instructions is not just good practice— it is essential.