Kirsten Craze
Updated 22 Apr 2026, 5:09pm
First published 22 Apr 2026, 5:06pm
Watsons Bay was once a world away from the rest of Sydney, but today the one-time fishing village’s peninsula position is a coveted spot for homebuyers wanting a waterside address away from the hustle and bustle.
With a permanent population of about 850 people, the once sleepy suburb is now home to multi-millionaires — and a handful of billionaires — paying up to $35m for their slices of paradise. More than 40 years ago, the Anderson family bought theirs for just $285,000.
Fast forward to 2026 and their harbourside sanctuary — which was thoroughly reimagined in the early 2000s — has come to market with a $15m auction price guide with David Maloufof Highland Double Bay Malouf.
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304 Old South Head Rd, Watsons Bay
Harbour views.
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“This offering has been part of the same family for over 40 years,” Malouf says.
Designed by the late architect Furio Valich, this tightly held residence has a contemporary three-level layout and harbour views stretching towards Middle Head and the city skyline.
Elevated to make the most of its enviable setting, the five-bedroom home is a spacious private retreat with multiple entertaining zones inside and out.
At ground floor level, beyond the welcoming foyer, the floorplan opens to a combined kitchen and casual dining zone to one side, with an adjoining formal lounge and dining area with statement fireplace. Both spaces spill out to a covered balcony that places the harbour at centre stage.
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Pool side.
An aerial view of the home.
It has been in the same family for over 40 years.
$15 price guide.
The modern kitchen houses hidden appliances, including Sub-Zero refrigeration, and a central island cooktop allows the chef to look out at the picturesque backdrop.
On the same floor there is a separate study, a media room or guest quarters with an ensuite, an additional bedroom and walk-in wardrobe, plus a powder room.
Up on the first floor the main bedroom has water views, a balcony, a dressing room and an ensuite. Two more bedrooms on the same level each have walk-in wardrobes and share a full family-friendly bathroom.
Plenty of living space.
And plenty of light.
A great part of the world.
It’s just minutes to all Watsons Bay has to offer.
For more entertaining options, the lower ground level is home to a grand rumpus room with cocktail bar and a neighbouring wellness space with a bathroom and sauna. A covered patio is the ideal barbecue zone and flows out to the pool and spa with surrounding landscaped gardens and a level lawn by Karen Prichard.
Additional features of the property include a double lock-up garage with workshop cupboard and internal access, a large internal laundry and vast under-house storage. The Old South Head Rd home is about 130m from Watsons Bay Baths, 270m to the ferry wharf, 300m from Doyles, and 350m to Gibsons Beach, with the local pub, cafes, coastal walk and buses nearby.
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