Billionaires, especially those ensconced in the gold-plated tech world, have long been magnets for public fascination when it comes to their outsized lifestyles and headline-worthy purchases. While Elon Musk famously opted to downsize into a modest pre-fab home — in stark contrast to Meta’s Mark Zuckerberg who expanded his footprint with a 1,400-acre Hawaiian ranch — one name a little closer to home continues to circle the limelight for his impressive real estate holdings: Mike Cannon-Brookes.
As the co-founder of Atlassian, one of Australia’s most successful software companies and definitely the most iconic, Cannon-Brookes has parlayed his formidable business acumen into a sprawling collection of high-profile properties across the country. Reports indicate that the total portfolio — shared at times with his estranged wife, Annie Cannon-Brookes — could be worth in excess of $350 million AUD. From harbourside mansions in Sydney’s most elite suburbs to farmland in the Southern Highlands, let’s take a closer look at Cannon-Brookes’ affinity for prime real estate.
Fairwater Estate, Point Piper (Sydney Harbour)
- Price: $100 million AUD
- Size: 1.12 hectares
- Date of Purchase: 2018
When it comes to Mike Cannon-Brookes’ holdings, his real estate top dog is without a doubt Fairwater, a sprawling harbourside estate in Point Piper. Acquired in 2018 for a historic $100 million AUD, Fairwater ended more than a century of Fairfax family ownership as well as setting an Australian house price record.
Boasting 1.12 hectares of land on Sydney Harbour, Fairwater is often described as the “jewel” of his collection. Beyond its historic significance — love them or hate them, the Farfaxes are about as iconic as Australian dynasties come — it offers private waterfrontage, beautifully manicured gardens, and a heritage-listed main residence that simply drips with classic architectural features.
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But wait, there’s more: Cannon-Brookes didn’t stop with Fairwater alone. He reportedly also purchased a $12 million AUD property next door, plus a $4.3 million AUD apartment in a nearby block. These acquisitions not only secure his privacy but also expand his footprint along some of the most coveted harbourfronts in the country.
Double Bay Heritage Houses (Sydney’s Eastern Suburbs)
- Prices & Dates of Purchase:
- $7 million AUD in 2016
- $9.1 million AUD in 2018
- $17 million AUD in 2018
Double Bay has also proven irresistible to Cannon-Brookes, in much the same way it does to anyone with a bit of cash behind them in Sydney. What began as a $7 million AUD purchase of a heritage home in 2016 quickly escalated into a multi-property spending spree just two years later. In 2018, two more high-end residences nearby were added: one for $9.1 million AUD and another for $17 million AUD.
Just down the road from Point Piper and the Fairwater estate, these acquisitions sit within Sydney’s elite harbour-hugging neighbourhood, known for grand estates on substantial blocks of land. Each home’s exact usage remains a private affair, but from the outside, it’s easy to imagine these properties serving as additional family spaces or possibly for entertaining his many lucrative business connections.
Woollahra Former German Consulate
- Price: $18 million AUD
- Date of Purchase: 2020
- Size: >2000 sqm
Only a few kilometres from Double Bay, Cannon-Brookes also acquired the former German consulate building in Woollahra for $18 million AUD in 2020. A stately, full-brick structure on a 2,000+ sqm block, it served for decades as an official diplomatic site before being snapped up by private buyers.
Zoned for mixed-use, the property has the potential for office and/or residential conversion, and media reports at the time of purchase indicated it might become a headquarters for Annie Cannon-Brookes’ design label. Its location in the rather well-to-do Woollahra, paired with an imposing and unique facade, means that this property remains an eye-catching piece in the portfolio.
Newport Mansions (Northern Beaches)
- Main Waterfront Home:
- Price: $24.5 million AUD
- Date of Purchase: 2020
- Block Behind:
- House Next Door (in Annie’s name):
- Price: $14.25 million AUD
- Date of Purchase: 2022–2023
Venturing north to Sydney’s Northern Beaches, Cannon-Brookes famously scooped up the $24.5 million AUD waterfront home that supermodel Jennifer Hawkins and her husband Jake Wall built some years earlier in Newport. Dubbed “Casa Paloma,” the architect-designed mansion features multiple levels of unobstructed water views, a home cinema, a boathouse, and a slipway — all in all, it represents a pretty quintessential Pittwater lifestyle.
In a move that’s fast becoming something of a signature, Cannon-Brookes later picked up a block behind the property for $1.4 million AUD, bolstering his personal domain. If that wasn’t enough, Annie Cannon-Brookes added to the local cluster by purchasing another house next door for $14.25 million AUD in 2022–2023, expanding their presence on one of Sydney’s most picturesque shorelines even further. No flies on this former couple.
Palm Beach & Pittwater’s Western Foreshores
- Palm Beach Home: Purchased in 2013, Price undisclosed
- Great Mackerel Beach: Two houses at $2.3 million AUD and $2.55 million AUD
- Coasters Retreat: $4.65 million AUD
- Scotland Island Estate: $8 million AUD
Going further up the peninsula, Cannon-Brookes has slowly but surely been amassing a cluster of properties along Pittwater’s western foreshores. Some of these spots — like Great Mackerel Beach — are only accessible by boat, offering unbeatable privacy on the fringes of a sprawling city as well as a laid-back environment that stands in stark contrast to the bustling central harbourside that defines their main residence.
He reportedly owns two houses on Great Mackerel Beach for $2.3 million AUD and $2.55 million AUD, each a typical mid-century beach cottage sitting on the sandy shoreline. There’s also a $4.65 million AUD Coasters Retreat holding and an $8 million AUD estate on Scotland Island. All these acquisitions demonstrate a fascination with waterfront living, each property providing one-of-a-kind vantage points across the water.
Mt Gibraltar / Mittagong (Southern Highlands)
- Greyladyes Farm:
- Price: $13 million AUD
- Purchased: 2022
- Size: 9.8 hectares (initially), now expanded
- Tintagel (Next Door):
- Three Additional Properties:
- Combined Price: $12.25 million AUD
- Size: Largest sits on 2.45 hectares
Nestled in the north-facing slopes of Mt Gibraltar at Mittagong, Cannon-Brookes snapped up several properties as part of a savvy real estate consolidation strategy. The anchor piece, Greyladyes Farm, was acquired for $13 million AUD in 2022. Soon after, he bought Tintagel next door for $9.1 million AUD, followed by three additional properties totalling $12.25 million AUD.
One of these three houses, perched on 2.45 hectares, is a retro 1970s structure bought for $6 million AUD. Another, on about 4,336 sqm, cost $2.25 million AUD. By bringing these parcels together, Cannon-Brookes effectively doubled his local footprint from 9.8 hectares to nearly 20 hectares, pouring close to $35 million AUD into this gorgeous corner of the Southern Highlands.
Other Southern Highlands Holdings
Beyond Mt Gibraltar, the articles suggest Cannon-Brookes boasts at least 11 more Southern Highlands properties from Joadja to Moss Vale and Kangaloon, bringing his total spend in the region to an eye-watering $114 million AUD… and that number may be conservative. Some of the key purchases include, but may not be limited to:
- Joadja Creek Farm (2016): $3.3 million AUD
- Widgee Waa, Kangaloon (2019): $15 million AUD
- Think Big Stud: $15.25 million AUD
- More farmland in Kangaloon: $8 million AUD
- Hathaway, Bowral: $3 million AUD
In 2019, Cannon-Brookes reportedly matched the district’s long-standing property price record by paying $15 million AUD for the Widgee Waa property, purchasing it from investment banker Mark Burrows. Just down the road, he also purchased the 120-hectare Think Big Stud for $15.25 million AUD, famously linked to the late racehorse owner Dato Tan Chin Nam. While Cannon-Brookes no longer runs it strictly as a stud, some reports indicate he focuses on regenerative agriculture there, aligned with his much-touted interests in sustainability and environmentalism.
Another purchase in Kangaloon —57 hectares for a punchy $8 million AUD — adds to an increasingly vast patchwork of farmland. His earliest buy in the region was Joadja Creek Farm in 2016 for $3.3 million AUD. The local holdings make clear a desire to invest not just in trophy homes but also in expansive rural tracts, offering some hard-to-find solitude and the option to pursue philanthropic or environmental projects.
Dunk Island (Far North Queensland)
- Price: $24.5 million AUD
- Size: 135 hectares
- Date of Purchase: 2022 (in Annie’s name)
Every self-respecting billionaire needs an island, and for Cannon-Brookes, that box is checked with Dunk Island. Although purchased in Annie Cannon-Brookes’ name, the island forms part of the broader family’s acquisitions. Located about four kilometres off Mission Beach on the Cassowary Coast, it was once a bustling tourist destination until Cyclone Yasi ravaged the resort in 2011.
Changing hands multiple times since Dunk Island’s future remains uncertain but full of potential. Reports suggest that Annie acquired the freehold portion for $24.5 million AUD, possibly with the aim to rejuvenate or preserve its natural beauty. In any event, the lush 135-hectare tropical isle stands out as one of the most unusual pieces in the Cannon-Brookes property puzzle.
A Portfolio in Flux
There’s an important new development in this story. That is: in mid-2023, news broke of Mike and Annie Cannon-Brookes’ separation after 13 years of marriage, prompting speculation over how their immense real estate holdings might be divided. Property watchers have wondered whether select estates — particularly those in the Highlands, or prized positions in Newport — might come to market. Since that announcement, Annie has also made independent property moves, indicating that some portion of this portfolio is or will be under her sole name.
Final Word
Mike Cannon-Brookes’ real estate holdings underscore a near-universal truth about ultra-wealthy property portfolios: the physical spaces people choose to own and develop can be as revealing as any public statement or philanthropic effort. The properties that line the harbour, farmland slopes, and island coasts are part sanctuary, part status symbol, and part statement of sustainable intentions. Together, they stand as one of Australia’s most intriguing and expansive private empires, one that appears certain to evolve further, and fast, in the coming years.
