One of my favourite experiences during Cup Match week is visiting my in-laws’ family cottage in Cape Breton Island, Nova Scotia, Canada. The cottage offers glimpses of Bras d'Or Lake, plenty of land, and a prime location in the town that provides easy access to Baddeck, Mabou, and the Cabot Trail. For my husband, it means getting up early every morning to go fly fishing.

This visit was slightly different because only my husband and I went to the cottage. My in-laws, who are now in their early 80s, are finding the drive from their home increasingly difficult, especially as it takes about 5½ hours. My brother-in-law and his children chose to go to Prince Edward Island instead this year.

The cottage itself is a multigenerational property that has been passed down through the family. It was originally purchased because it was large enough to accommodate multiple families and offered plenty of land for grandchildren to play on. Today, however, it faces what might be called a generational pause.

The current owners, my mother-in-law, her sister, and her brother are all well into their 80s and are finding the drive increasingly burdensome. As a result, discussions are now under way about whether it may be time to sell the cottage, especially as the next generation is choosing other vacation options more often and the property sits vacant for longer periods than it once did.

That is the emotional complexity at the heart of many multigenerational properties. What begins as a place of gathering can, over time, become a question of practicality, affordability, distance, and shared responsibility.

The issue is rarely only whether a property has financial value. More often, families are weighing memory against maintenance, legacy against liquidity, and tradition against the changing realities of the next generation.

While this situation above is specific to my in-laws, many families face similar challenges with multigenerational property ownership. For centuries, land and property have served as cornerstones of family wealth passed down as both financial assets and tangible links to family history.

Generational property ownership, the practice of transferring real estate within families over multiple generations, remains one of the most enduring strategies for building and preserving wealth.

Real estate holds a special place among assets families choose to pass down. Unlike stocks or cash, property offers a physical, lasting presence whether that’s a family home, a cottage, or even a commercial building that carries both sentimental and financial value.

This dual nature makes property especially resistant to being sold during difficult times; families often go to great lengths to keep land within the family, even when liquidating it might be the more financially straightforward option.

Moreover, property tends to appreciate over long periods, especially in desirable locations. A home purchased decades ago can represent substantial unrealised value by the time it’s inherited by grandchildren or great-grandchildren.

This appreciation, coupled with tax advantages available in many jurisdictions for inherited property, makes real estate an efficient vehicle for transferring wealth without triggering the same tax burdens as other assets.

However, despite its advantages, multigenerational property ownership is becoming more complex. Rising property values mean that heirs may face significant inheritance tax obligations, even if they do not reside in the country in which the property is located.

In some cases, families are forced to sell inherited assets simply to pay these taxes — an outcome that undermines the purpose of intergenerational transfer.

Family dynamics add another layer of complexity. When multiple heirs inherit a single property, disagreements over whether to keep, sell, rent, or renovate can strain relationships and sometimes lead to costly legal battles. This is particularly true when heirs live far from the property or have differing financial needs and priorities.

Co-ownership among siblings or cousins, once a source of shared family identity, can become a source of tension without clear governance agreements.

Additionally, younger generations are increasingly moving away for education and career opportunities, weakening the practical ties that once connected families to ancestral homes.

A homestead or cottage that made sense for a family rooted in a single place for generations may now feel like a burden rather than a blessing to heirs spread across different countries.

Families that successfully navigate multigenerational property ownership tend to share certain habits. They start planning early often decades before a transfer is expected allowing ample time to structure the transfer efficiently and address tax implications.

They involve heirs in decision-making well before the transfer, ensuring expectations are clear and that those inheriting the property want the responsibility it entails.

Many also work with estate-planning lawyers and tax professionals familiar with their jurisdiction. Establishing clear governance documents and rules for managing, maintaining, and potentially selling shared property can help prevent conflicts that threaten both family harmony and financial stability.

Ultimately, as housing markets shift and family structures become increasingly diverse, the tools, strategies, and traditions of multigenerational property ownership will continue to adapt and evolve.

Economic conditions, technological advancements, and changing societal values all influence how families approach the transfer and management of their generational properties.

Despite these changes, the core motivation remains constant: the desire to provide the next generation with a solid foundation whether that’s a place to call home, a reliable source of income, or a tangible link to family history that surpasses what a mere bank account or financial asset can offer.

In this sense, property is far more than just an asset; it embodies a legacy, a tangible expression of family continuity, identity, and values that can be passed down through generations.

It represents not only financial security but also emotional bonds, memories, and a sense of belonging that enriches family heritage long after the physical structure has endured.

• Carla Seely is the chief operating officer at Freisenbruch Insurance Services Ltd. With 26 years of experience in international financial services, wealth management, and insurance, she has obtained several investment licences through the Canadian Securities Institute. She holds the ACSI qualification from the Chartered Institute for Securities and Investments (UK), the Qualified Associate Financial Planner (QAFP) designation through FP Canada, and the Associate in Insurance (AINS) designation from The Institutes. She also completed a Master’s Degree in Business and Management through the University of Essex.

• For further inquiries or topics, contact her at justaskcarla@outlook.com