After two decades of walking alongside clients through life’s most difficult and defining moments, we’ve learnt that the decision to sell a home is rarely about property – it’s about people and the circumstances they find themselves in. While market movements, interest rates, and investment strategy sometimes influence timing, the most common reason people sell their properties is generally far more personal. We refer to them as the Five Ds: death, divorce, disease, downsizing, and departure.
These events often thrust families into unfamiliar territory where financial decisions must be made under pressure. The sale of a property, while sometimes necessary, can become a source of additional stress if it isn’t approached with clarity, structure, and professional guidance. In this article, we take a closer look at each of the Five Ds, along with the lessons we’ve learned helping clients navigate them.
1. Death
The loss of a loved one is emotionally devastating and can often trigger a series of urgent, untimely financial decisions. In many cases, the primary residence is the most valuable asset in the deceased estate, and the property needs to be sold to create liquidity needed for estate duty, capital gains tax, executor’s fees, or to distribute inheritances fairly among beneficiaries. One of the most common mistakes we encounter is families attempting to sell the property before the executor has been officially appointed by the Master, bearing in mind that the issuing of Letters of Executorship can take months, which, in turn, can delay everything from bond cancellation to transfer.
Where multiple heirs stand to inherit a property, there are often competing emotional and financial interests, such as where one sibling wants to keep the house for sentimental reasons while the other urgently needs their share of the proceeds. Without clear communication and legal structure, conflict is almost inevitable.
Financial insight: Ensure your will clearly outlines your wishes regarding property and that there is sufficient liquidity in your estate to prevent a forced sale. Appointing an executor with property expertise can also streamline the sale process and reduce unnecessary delays.
2. Divorce
We’ve sat across the table from many clients in the midst of divorce—and the one constant is complexity. The marital home is not just a financial asset – it represents stability, memory, and is often the emotional heart of the family. However, from a financial perspective, it’s also one of the first assets to come under scrutiny.
If you’re married in community of property or own the house jointly, keep in mind that both parties must agree to sell and sign the offer to purchase. But, when communication breaks down – as is often the case in divorce – this can delay the transaction or even lead to costly legal intervention. From our experience, even in amicable divorces, financial pressures can force couples to accept offers below market value just to finalise the settlement agreement.
It’s important not to underestimate the associated costs of selling a property: bond cancellation fees, municipal clearance certificates, agent commission, and capital gains tax—especially on a secondary property—can significantly erode the proceeds. And if there are children involved, considerations around proximity to schools and maintaining a stable home environment further complicate the equation.
Financial insight: Before making any decisions, consult with both a financial planner and a divorce attorney. These experts can help you understand affordability, simulate future cash flows, and determine whether it makes financial sense to sell or to retain the property.
3. Disease (ill-health or disability)
Few events can alter a client’s financial landscape as profoundly as the onset of a serious illness or disability. When disease or injury strikes, it often triggers a reassessment of living arrangements – whether due to the physical demands of upkeep, the need to be closer to medical facilities, or the opportunity to release equity to fund treatment or ongoing care.
One of the most common pitfalls we encounter is poor timing. Medical urgency can force rushed property sales, leading to below-market offers, missed legal requirements, or insufficient time to secure a suitable alternative home. In cases of cognitive decline, the stakes are often higher in that a court-appointed curator bonis or administrator may delay the process of realising the property.
While downscaling is often a sensible step following a diagnosis, it often comes with costs that clients don’t always anticipate, such as transfer duties, estate agent commissions, the expense of modifying a new property for medical accessibility, and potential capital gains tax on the sale. Without careful planning, these costs can erode the very capital the sale was intended to free up.
Financial insight: Keep your estate planning up to date and ensure that decisions about your property are made while you still have full mental capacity. Review your insurance portfolio to ensure it includes adequate disability and dread disease cover, so that property decisions are made from a position of choice rather than financial or medical crisis.
4. Downsizing
As clients enter their late fifties and early sixties, downsizing becomes a common conversation. Sometimes it’s a planned move, such as when children have left home and the house is simply too large. However, it is often financially driven – rising municipal costs, unmanageable home maintenance, or reduced retirement income that makes the family home unaffordable. From experience, we know that this is one of those transitions that requires a deep emotional shift. We’ve had clients who clung to an unrealistic asking price for years, convinced that one more buyer would come through – while their retirement income was being depleted unnecessarily. Others underestimated the real costs of moving and have found themselves worse off after downsizing. There’s also the decision between freehold property, sectional title, and life rights = each with vastly different legal and financial implications. Life rights, in particular, are poorly understood and should ideally be evaluated with the guidance of a financial advisor and property lawyer.
Financial insight: Don’t make assumptions about what ‘freeing up capital’ will look like. Have your financial advisor run a cash flow projection that factors in all expenses associated with downsizing—including levies, maintenance, and medical provision. Timing is key, and it’s best not to wait until your financial position forces the move.
5. Departure (emigration or semi-gration)
Whether driven by political uncertainty, lifestyle changes, or retirement planning, many South Africans choose to relocate—either abroad or to another province. These transitions often involve selling a primary residence, which can trigger a range of financial and tax considerations.
For those emigrating, the sale of South African property introduces layers of complexity around tax, timing, and compliance. If you are no longer a tax resident, proceeds from the sale may need to be transferred abroad using your Foreign Investment Allowance, which requires clearance from both SARS and the South African Reserve Bank – a process that involves obtaining a valid Tax Compliance Status (TCS), amongst other documentation. Capital Gains Tax (CGT) is another important factor. If the property was rented out at any stage or not used continuously as your primary residence, only a portion of the gain may qualify for the primary residence exclusion, resulting in partial CGT liability.
Managing a property sale from overseas can be challenging—especially if tenants are involved or if you’re relying on third-party agents. Within South Africa, semi-gration—particularly from Gauteng to the Western Cape—presents its own set of realities. While many assume they’ll get more value for money, the reality is that coastal regions often come with higher property prices and ongoing costs, which can catch buyers off guard.
Financial insight: Plan your exit strategy with a cross-border financial planner before you leave. Understand how tax residency, exit taxes, and property sales intersect—and how poor sequencing can result in lost proceeds or unnecessary tax leakage.
Selling a property during a time of upheaval isn’t just about market value—it’s about timing, liquidity, legal capacity, and emotional readiness. As financial planners, our role is to help clients make calm, informed decisions when circumstances are anything but calm. That means anticipating risk, building flexibility into the plan, and ensuring that estate, tax, and investment strategies are aligned. If you’re navigating one of these transitions, don’t try to do it alone. With the right team around you—and a plan tailored to your circumstances—you can turn a challenging event into a financially sound outcome.
Have a wonderful day.
Sue
