12111 Chalk Hill Rd, Healdsburg

A Chalk Hill estate that redefines wine country living.

Tucked into the prestigious Chalk Hill AVA, this extraordinary 268± acre estate is more than just a property—it’s a rare opportunity to build a generational legacy in one of Sonoma County’s most coveted wine country settings.

Offering unparalleled scale, privacy, and potential, this estate is one of the few remaining properties of its size and zoning in the region. With two legal parcels, it presents the flexibility to hold the full acreage as a private compound—or thoughtfully subdivide, sell one, and retain the other.

The estate features a beautiful main residence (approx. 5,549 sq ft), an attached guest house / exercise room and wine cellar (approx. 2,000 sq ft), a charming pool house, and a large barn with an attached caretaker’s unit, offering ample space for multi-generational living, entertaining, or creative reimagining.

With 13± acres of established vineyard, vast open pastures, and ideal pathways for equestrian or ATV use, the land offers an unmatched combination of utility and beauty. Two gated entrances provide easy access and a sense of arrival, while long view corridors and the natural topography enhance both privacy and potential.

And for those seeking flexibility, the property is zoned for vacation rental use—an incredibly rare designation in Sonoma County, especially in premium AVA locations like Chalk Hill.

Whether your vision leans toward winemaking, hospitality, equestrian living, or a private retreat to gather for generations, this is a blank canvas in a location where few remain.

Property Highlights:
• 268± acres in the renowned Chalk Hill AVA
• Two legal parcels – create a compound or divide and sell one
• Vacation rental zoning – a rare entitlement in a premium vineyard region
• Main residence, guest house, pool house, and large barn with caretaker’s quarters
• 13± acres of established vineyard
• Gently rolling terrain with open pastures and riding/ATV trails throughout
• Two gated entrances for flexible access and privacy
• Panoramic views and premier wine country surroundings
• Minutes to Healdsburg, Windsor, and acclaimed wineries and restaurants

Exclusively Offered at $5,975,000

Private Showings by Appointment Only

Contact us for the full offering package or to schedule a private tour.

Ryan Anderton 707.244.7181

David Hunt 707.244.7863