In the heart of northern Sonoma wine country, where ancient oaks shade golden hillsides and vineyards stretch toward the horizon, Montage Residences Healdsburg has unveiled one of its most striking estate offerings to date. Priced at $9.85 million, The Estate Home at 165 Sycamore Court is a 7,899-square-foot architectural showpiece that channels the serenity of a treehouse with the polish of a contemporary luxury retreat.
Designed by BAR Architects in collaboration with Ohana Design & Build, the residence is anchored by a towering heritage oak, its sprawling canopy framing the home like a living sculpture. Three distinct wings are connected by glass-enclosed hallways, creating a fluid connection between interior spaces and the surrounding landscape.
Floor-to-ceiling windows draw the outdoors in, revealing views of oak groves, sculpted hillsides, and an infinity-edge pool that appears to merge with the natural contours of the land. Expansive terraces and covered patios extend the living experience beyond the walls, offering private vantage points from every bedroom.
Inside, five bedrooms and six and a half baths are distributed across two levels, allowing for privacy and separation between living, entertaining, and guest areas. The chef’s kitchen serves as a culinary centerpiece, complete with custom Henrybuilt cabinetry, integrated wine storage, and premium appliances — perfectly tailored for the wine country lifestyle.
The primary suites each feature private terraces, with one offering an outdoor shower for an immersive connection to the surrounding oak grove. Every bedroom opens to its own covered terrace, ensuring that the home’s connection to nature is felt in every corner.
The estate’s 1,430 square feet of outdoor living space is crafted for both quiet moments and spirited gatherings.
An infinity-edge pool with adjoining hot tub and outdoor shower
A private BBQ dining terrace
An outdoor living area with firepit for cool wine country evenings
Landscaped pathways that weave through the property’s 15,450-square-foot homesite
Ownership at Montage Residences Healdsburg grants exclusive access to The Residential Club, a private enclave offering a pool and cabanas, hot and cold plunges, bocce and pickleball courts, a fitness center, and indoor-outdoor lounges with fire pits.
The Residential Concierge team is on-site to coordinate everything from housekeeping and maintenance to private chef dinners, in-residence spa treatments, and transportation services. Owners also enjoy reciprocal privileges across the global portfolio of Montage Hotels & Resorts and Pendry Hotels & Resorts.
Situated on a quiet cul-de-sac, the estate enjoys a rare balance — secluded beneath an oak grove yet mere moments from the Forbes Five-Star Montage Healdsburg resort’s amenities. Residents can dine at signature restaurants, book curated wine tours, or arrange bespoke wellness experiences, all while retreating to the privacy of their own estate.
As a turnkey opportunity with meticulous design and unparalleled access, The Estate Home stands as a compelling proposition for buyers seeking a primary residence, vacation home, or investment property in one of California’s most desirable destinations.
Inspired by what you read?
Get more stories like this—plus exclusive guides and resident recommendations—delivered to your inbox. Subscribe to our exclusive newsletter