Tivoli Avenue, Rose Bay home, shoots for $30 million

There is a particular kind of address in Sydney that needs no introduction — a street name that, spoken aloud in the right circles, conjures an immediate picture of sandstone, sail-white water and old harbourside money. Tivoli Avenue is one of them. And the house that has just come to market at number one is precisely the kind of trophy residence this pocket of Rose Bay was built to hold.

Brad Pillinger, who has sold some of Sydney’s most expensive homes and set many records over his career, has a $30 million guide for the renovated home that is selling for the first time in two decades. The late 1990s-built home, at the entry of Tivoli Avenue on the corner of New South Head Road, was bought for $7.2 million in 2006.

At $30 million, this is not simply a renovation — it is a reinvention. The entire interior has been stripped back and rebuilt with the kind of restraint that only comes from serious money spent well. Nothing here shouts. Instead, walls of glass do the talking, drawing the harbour and the city skyline into every principal room and letting Sydney’s most photographed view — the Bridge, framed by open water — become the home’s real decorative statement.

Across three considered levels, the house reads less like a single dwelling than a small, beautifully organised village: a huge main suite with its own dressing room, freestanding bath and balcony sits apart from a teenage retreat and two further bedrooms tucked privately into the lower level with their own terrace — the kind of separation that busy, multi-generational households have come to prize above almost anything else. A lift connects it all, quietly, for owners who intend to enjoy this address for decades rather than years.

Entertaining, unsurprisingly, has been treated as a discipline in its own right. There is a formal living and dining wing anchored by custom joinery and a library-like wall of bookshelves, a separate second lounge for quieter evenings, and a designer induction kitchen with its own scullery — the unglamorous but essential engine room that lets marble benchtops stay marble-clean. Outside, a pool with a water feature sits alongside a heated spa positioned, deliberately, to catch the harbour view at dusk. A Vergola-shaded terrace and covered barbecue patio complete an entertaining sequence that moves seamlessly from indoors to out, which is, after all, the whole promise of eastern suburbs living.

Practicality has not been sacrificed for polish. Triple garaging with dedicated motorcycle space, a cellar, and generous storage throughout speak to owners who collect — cars, wine, art — as much as they entertain. A sandstone security wall and discreet, secure entry give the home the low-key privacy that genuine trophy properties now require as standard, not luxury.

And then there is the setting itself. Few streets in Sydney offer a walk to this calibre of private schooling, the café culture of Rose Bay village, and the Hermitage Foreshore Walk to Watsons Bay — arguably the city’s most scenic stretch of harbourside path — all within a few unhurried minutes on foot.

The street seldom sees property transactions, but it did make headlines last year when a waterfront sold for $82.5 million. It was bought by Yianni Gourlas and John Angelis, the latter’s father being business Jim Angelis, who has owned next door since 2021 when he paid $45 million for Villa Florida, the landmark Spanish Mission-style home which was once owned by comedian Barry Humphries. Angelis rebuilt the home, spending just shy of $19 million.