Images and floorplans are provided for illustrative purposes and remain the property of their respective copyright owners.

Chamberlain Avenue, Rose Bay NSW 2029

Sold

Search Band Search Visibility Band

$10M - $15M Medium Confidence Calculated based on our search observations.

House 6 Beds 5 Baths 2 Cars 1258 m²

Listed: 24th Jul 2026

Updated: 16 hours ago

Overview

Set against the breathtaking backdrop of Sydney Harbour and the city's dazzling skyline, this grand family estate sprawls across an impressive 1,258 square metre dual frontage block in the prestigious Rose Bay area. Known as ‘Chequers’, this residence artfully balances luxury, expansive indoor-outdoor living, and flexible design tailored to grand-scale entertaining and multigenerational family needs.

The estate's commanding harbour views create a captivating atmosphere and enhance daily living, promising a refined lifestyle for those who appreciate elegance and space. A sweeping driveway leads to an impressive entry foyer that sets a tone of grandeur and offers immediate vistas over the water.

The home cleverly integrates multiple formal and informal living areas including a formal living and dining room with high ceilings and polished parquet floors, providing distinguished settings for hosting. The gourmet granite kitchen flows seamlessly to family living zones and a large courtyard, embracing both intimacy and entertaining ease.

The accommodation is generous, featuring six bedrooms with built-ins, including a master retreat complete with his and hers walk-in robes and a private terrace overlooking the harbour, appealing to families valuing private sanctuary spaces. Additional dedicated areas such as a deluxe home office/library enhance the home's versatility.

The outdoor environment is a true entertainer's haven, boasting a sunny pool with landscaped low-maintenance gardens and a championship tennis court complete with pavilion. Recreation and leisure are further supported by a billiards room, a brand new 1,000-bottle wine cellar, and workshop facilities, catering to both hobbyists and social gatherings.

Practicality meets glamour with a double garage alongside six tandem off-street parking spaces, accommodating numerous vehicles with ease. Self-contained quarters with private entry and internal access provide independent living arrangements suitable for extended family or guests.

Located just a short stroll from Rose Bay village hubs, the harbour front, prestigious schools, and both surf and harbour beaches, this exclusive pocket offers a private resort lifestyle within reach of key amenities, thereby meeting the needs of discerning families seeking a blend of luxury, convenience, and lifestyle.

Local Market Insights

In Rose Bay, Quiet Listings observed 4 new houses entering the market over the last 30 days, unchanged from 4 in the prior period, with an average advertised asking price of $16,792,595. The property type mix of listed properties is predominantly Apartments at 43%, followed by houses (24%), and commercial properties (19%). The most active agency for houses in the Rose Bay area is currently Sotheby's International Realty, representing 50% of new listings, followed by Laing + Simmons with 25%. These insights are based on agencies currently monitored by Quiet Listings and are updated as the local market changes.

While every effort is made to ensure the accuracy and completeness of the property information provided, no guarantee is given. Buyers should independently verify all details, inclusions, availability, pricing, and other relevant information directly with the listing agent before relying on this information.