A prestigious waterfront mansion in Double Bay has finally found a new owner after a dramatic 15-month journey that saw the initial sale collapse, leaving the vendors $2 million out of pocket.
The historic sandstone residence at 21 Gladswood Gardens, originally the coach house of the renowned Gladswood Estate, has sold for $20 million after an earlier agreement for $22 million fell through last year.
The five-bedroom property, sitting on a substantial 978-square-metre waterfront block, had been home to the MacMahon family for more than four decades after they purchased it in 1983 for $782,000 – a sum that seems almost quaint by today’s standards.
The property’s winding path to sale reflects some of the challenges facing Sydney’s premium property market. The initial buyer, an expatriate, was unable to complete the purchase due to complications with selling their Hong Kong property, leaving the vendors back at square one despite having agreed terms over a year ago.
Cohen Handler buyer’s agent Tom Penfold stepped in to secure the property for his eastern suburbs client, capitalising on the reduced asking price. According to Penfold, his client was immediately taken with the property’s character and potential.
The new owner, described as appreciating both the building’s heritage charm and untapped possibilities, plans to undertake sympathetic renovations whilst preserving the property’s historic sandstone character. Sources close to the sale indicate she intends to move into the residence following careful restoration work.
This Double Bay transaction mirrors a similar situation in neighbouring Vaucluse, where another high-end property has experienced comparable setbacks. The residence at 31 Vaucluse Road, previously owned by investor William Wu, also saw an initial sale agreement collapse before eventually selling for approximately $3 million less than originally agreed.
Wu and his property developer mother Jing Wang assembled an impressive $100 million portfolio across the eastern suburbs in 2021, including the Vaucluse property which they acquired for $13.32 million. The six-bedroom mansion, featuring seven bathrooms and an eight-car garage on an 879-square-metre block with harbour views, initially carried a $23.8 million guide in 2023.
After exchanging at around $24 million, that deal also fell through, with the property eventually selling through Bradfield BadgerFox agents Alexander George and Peter Leipnik for approximately $21 million to a local buyer.
These cases highlight some volatility in Sydney’s luxury property market, where high-value transactions can be particularly susceptible to buyer financing issues and international market conditions. Recent analysis suggests Sydney’s eastern suburbs property market is experiencing low volume but rising demand in 2025, with the biggest uplifts concentrated in North Sydney, the eastern suburbs and the inner west.
Domain forecasts that house and unit prices will rise by 4-6% in Sydney in 2025, up from the 3.2% increase posted in 2024 but down from approximately 10% in 2023, suggesting the market may be entering a more stable phase.
For the MacMahon family, whilst the final sale price was $2 million below their initial agreement, the transaction still represents a remarkable return on their 1983 investment, reflecting the enduring appeal of Double Bay’s premier waterfront locations.
The sale reinforces Double Bay’s position as one of Sydney’s most sought-after addresses, where historic properties with harbour frontage continue to attract buyers willing to pay premium prices, even in challenging market conditions.
Published 28-July-2025
