Special Counsel Briely Trollope advises families on complex, high-value residential property transactions, where legal strategy must often sit alongside legacy planning and sensitive intergenerational dynamics. In this piece, she reflects on the past year of high-profile deals and considers what they reveal about evolving attitudes to home, wealth and ageing.
Over the last 12 months, property pages in Australia’s major newspapers have brimmed with stories of landmark high end property transactions. Sydney’s Dunara, the oldest home in one of the country’s most expensive postcodes, has come to market with a guide of $35 million, drawing attention not only for its price but for the heritage and history embedded in its walls.
In Melbourne, hospitality icon Vince Sofo and his wife Elisa sold their $30 million + home, described at the time by the AFR’s luxury property reporter as one of South Yarra’s “most beloved home.”
The confluence of many different drivers – demographic, economic and general zeitgeist – have resulted in an unprecedented number of notable property decisions being made. And it’s not only the volume that’s interesting. These transactions reflect important shifts in the way wealthy Australians think about home, legacy and ageing – shifts that reflect the kinds of issues being considered by people across the wealth spectrum about how they want to live at different life stages.
Home as the emotional and financial anchor
For wealthy families, the principal residence has always been a significant asset. What feels different now is the concentration of both wealth and sentiment in that single home.
Businesses are often divested or restructured long before a family contemplates letting go of the house that has served as the backdrop to decades of memories. Because people are living far longer, many homes remain occupied well into their owners’ 80s and 90s. The next generation only steps into stewardship later in life, often in their 60s, at a stage when the property carries enormous emotional and financial weight.
Property law and advice can veer rapidly into family counselling, as the sale process is rarely just about price. Family history, legacy decisions, tax implications, competing priorities among siblings (and grandchildren), and the deeply human anxiety of “letting go” all converge.
The human dimension has never mattered more.
Across this landscape, three trends have stood out this year.
Trend 1: The creation of private residential estates
One of the most visible new trends is the acquisition of adjoining houses to create private residential estates. Fashion industry couple Daniel Contos and Georgia Moore, who bought their fifth property in Vaucluse this year, and Melbourne brothers Tony and Steven Sass, who’ve acquired three adjoining clifftop mansions in Sorrento to create a seaside complex for their extended family, are both good examples.
The motivations for this increasingly popular wealth/lifestyle strategy are consistent: scarcity of prime land, a desire for privacy and security, and an understanding that no new parcels will be created in blue-chip suburbs. Lifestyle plays a major role. Many explicitly say they do not want to move into care; they want to remain in the home and garden they love, expanding the footprint to make ageing in place easier. These larger estates also allow space for adult children, visiting family, carers and support staff to live nearby without disturbing the rhythm of the main household.
Lesson for the less wealthy? While most Australians won’t be assembling a compound, the underlying question is universal: with the costs to sell and buy elsewhere becoming a bigger barrier, how can my home change with me over time? For some, that may mean adapting bathrooms for accessibility, converting under-used spaces into flexible accommodation for family or carers, or even exploring “next-door living” arrangements with friends or relatives.
The principle is future-proofing rather than short-term problem-solving.
Trend 2: “Downsizing” as an upgrade, not a retreat
Against the backdrop of families expanding their estates, another trend runs in parallel: the downsizing boom. But this is not downsizing in the traditional sense. Many long-held family homes are now being sold, but their owners are not trading down so much as trading differently.
Concierge services, wellness amenities, and curated dining and retail precinct, have redefined what premium apartment living looks like. Melbourne’s high-end, hotel-branded penthouse offerings take this even further, offering residents the ability to “live like a five-star hotel guest” year-round, with access to the hotel’s services and facilities.
Crucially, the perception of buying off-the-plan has changed. It is no longer synonymous with “cookie-cutter living.” Developers working at the top end now redesign floorplates – adding a second master suite, removing bedrooms, or creating bespoke workspaces – to meet the lifestyle needs of discerning downsizers.
Equally important is the social dimension. Many of these developments function as micro-communities. Residents form informal networks, rotate hosting duties for social gatherings, and enjoy the ease of locking up and travelling without worrying about gardens, gutters or security.
For anyone ready to start the conversation about downsizing, the lesson from the ultra-wealthy is to do it with purpose. Focus less on square metreage and more on liveability, proximity to healthcare, low maintenance, good insulation, walkable amenities and a sense of social connection. Even outside the luxury bracket, “downsizing with intent” can dramatically improve quality of life.
Trend 3: The rise of the transactional adviser
As the home can end up as the most contested and emotionally charged asset, more families are appointing what is known in the trade as a “transactional adviser” to oversee the whole process. These advisers are responsible for coordinating agents, managing inter-generational communication, preparing for disputes, and ensuring alignment on legacy decisions.
For homes where history, value and emotion converge, people increasingly want an independent consultant who can manage the entire transaction from strategy to settlement. This model mirrors high-stakes, complex, emotionally fraught corporate dealmaking, which is often better managed with a steady, external hand on the wheel.
And this kind of independent advice is not just for ultra-wealthy families. Whether upgrading, downsizing or selling a long-held home, an impartial party can provide structure, calm and future-focused strategy or navigate difficult discussions with the next generation. The value lies not only in risk management, but in having someone who can be pragmatic when you are, understandably, emotional.
Beyond the price tags
For most Australians, the stories featured in the luxury wealth section are read with a sense of “outsider looking in”. But the underlying themes are widely applicable.
The home has become the emotional and financial anchor of wealth, not just another asset.
Ageing in place is a near-universal preference, whether you own one dwelling or several.
Downsizing has become aspirational, centred on lifestyle rather than reduction.
The families buying and selling Australia’s most iconic homes are asking themselves far reaching questions: How do we want to live? How do we want to age? What legacy do we want this property to hold?
These questions are relevant to all property owners.
