Prestige Property: 7 Hillside Avenue, Vaucluse, NSW
A rare trophy home in Sydney’s east hits the market.
By Terry Christodoulou
Fri, May 28, 2021 4:13pm
2 min
2 min
Set in a truly enviable setting, this hillside pile in Sydney’s blue-ribbon suburb Vaucluse arrives with sweeping vistas of the eastern suburbs and harbour.
Designed by Howard Tanner of DKT architects in the early ’00s, the nearly 2000sqm site sees a 7-bedroom, 7-bathroom, 10-car parking mansion offering unadulterated luxury at every turn.
The home boasts natural stone flooring and timber underfoot, with soaring ceilings and extensive use of glass used to form its character.
Making the most of the home’s lofty location, the design maximises the views and embraces its many courtyards and manicured gardens designed by Paul Bangay.
A grand entry foyer welcomes one into the home, here the double0heigh ceiling is warped in glass while showcasing the grand two-way staircase.
All the living areas are found on the ground floor. Here, the formal dining is elegance exemplified with an ambient gas fireplace and French doors to the gardens.
Also on this level is the kitchen. Built for entertainers, it features a Corian benchtop, enormous island bench, an array of appliances including an eight burner Barazza cooktop. A butlers’ pantry is also found here.
Four spacious bedrooms alongside a family room comprise the upper level. The lavish master boasts a glamorous ensuite – replete with marble – and freestanding bath, ‘his’ and ‘hers’ walk-in-robes, the latter with more breathtaking views.
Downstairs, the basement sees a 10-car garage – perfect for the avid car collector – with an expansive cellar.
Elsewhere the home features a gym on the ground floor, well-appointed office and a separate guest house complete with its own kitchenette, living and bathroom.
Outside is where the home really shines, with a poolside terrace making it easy to lounge and enjoy the surrounds. Here, a powder room is accessible through the terrace and is adjoined by a Wisteria clad arbour.
The home is found in an exclusive cul-de-sac setting and is close to Kincoppal Rose Bay School, Hermitage Foreshore reserve and within walking distance of Rose Bay’s vibrant village centre.
The property is listed with Ken Jacobs (+61 407 190 152) of Christie’s International Real Estate. Price guide $38m; hillsideavenue.cve.io
MOST POPULAR
The Australian leather house has opened an immersive four-day pop-up in Manhattan, unveiling its Bloom Collection and redefining what a product launch can look like.
Following the successful launch of its Palais Collection, MAISON de SABRÉ has unveiled a new modular handbag system offering more than 720 styling combinations.
Related Stories
A five-bedroom Palo Alto home designed by Steven Ehrlich is listed for $44 million, making it the city’s most expensive listing. Built around a dramatic concrete spine, the home features four courtyards and a pool.
By E.B. Solomont
Thu, Sep 24, 2026 3 min
3 min
For years, tech entrepreneur Asher Waldfogel and his wife, Helyn MacLean, dreamed of building a modern house in Palo Alto, Calif.
The couple, however, worried about clashing with the Mediterranean-style architecture typically associated with their neighborhood of Old Palo Alto.
So they tapped architect Steven Ehrlich to create a design that paid homage to its surroundings with stucco, mahogany and titanium zinc cladding. They spent $20 million over several years building the house, completed in 2005.
Now looking to be closer to their adult daughter on the East Coast, they are putting the five-bedroom home on the market for $44 million—the most expensive listing in Palo Alto.
Waldfogel is an angel investor who co-founded Redback Networks, a telecommunications-equipment company. MacLean previously had a career in fundraising.
The couple purchased the roughly 0.4-acre site for $7.1 million in 2000 and demolished a circa-1930s Spanish Colonial home. The house they built pinwheels around a central staircase. It has 7,900 square feet of livable space, with four distinct courtyards and a pool.
A key feature of the home is a cast-in-place concrete wall, or spine, that is two stories high and about 80 feet long. “There’s a little bit of controlled chaos in what comes out of the form,” unlike a perfectly uniform surface, Waldfogel said. “If you want that, you do it in plastic.”
Waldfogel said he and his wife are thinking about the next phase of life now that their daughter is grown, although they have not decided where they will move. They also have a home in Sun Valley, Idaho.
“Right now we’re just trying to emotionally let go and decide what to do next,” he said.
Palo Alto, an epicenter of venture capital and tech startups in Silicon Valley, is home to some of the country’s biggest tech titans. Sales volume and prices are rising, with a median sale price of $3.5 million for the three months ending in August, up 5.8% year-over-year, according to real-estate brokerage Redfin.
Arthur Sharif of Sotheby’s International Realty—San Francisco Brokerage has the listing.
