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Sebastopol Montgomery Road

Sebastopol, CA

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Opening Snapshot

Perched on a wooded hillside above the vineyards at Freeman Vineyard & Winery, this charming three-bedroom cottage delivers one of the most atmospheric settings we’ve seen in the western reaches of the Russian River Valley. You’re right at the edge of where redwood forest meets farmland, in that magical overlap between Russian River and Sonoma Coast - cool evenings, warm days, and vines producing some of the region’s most celebrated Chardonney and Pinot Noir just steps away. While the wine caves aren’t directly beneath the house, they’re close enough to feel like part of the experience, which we find undeniably cool. The cottage itself is tucked into the trees, surrounded by privacy and quiet, with wooded views in every direction. It’s serene, soulful, and deeply connected to its place, exactly the kind of home that makes Wine Country feel special rather than performative.

GUESTS

BEDROOMS

BATHROOMS

PETS ALLOWED

POOL

HOT TUB

FIRE FEATURE

Virtual Tour

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What we love

This house has personality in spades. Painted a deep forest green (a color Joe B. has always loved), the exterior immediately feels grounded and appropriate for its setting. Inside, the home has been thoughtfully renovated with a generous, beautiful kitchen and a welcoming great room where the living, dining, and cooking spaces flow together seamlessly. Large doors open out to the deck, blurring the line between indoors and the surrounding redwood forest. There’s a wonderful cultural layer here as well. The winemaking family’s Japanese heritage subtly shows up throughout the home in art, in the clean aesthetic, and in thoughtful details like high-end Japanese toilets with built-in bidet features (once you have them, it’s hard to go back). The furnishings strike a lovely balance: classic antique pieces mixed with clean, modern lines that keep the home feeling fresh and unfussy. The bedrooms are bright and calming, the hot tub is perfectly positioned for long, wine-soaked evenings, and while the deck shows a little wear, it’s exactly where you’ll want to sit, glass in hand, soaking in the quiet.

Keep in mind

This is a cottage, not a sprawling estate, and that’s part of its charm. With three bedrooms and three baths, it’s ideal for couples, small families, or close friends rather than large groups. The deck, while wonderful, is a bit weathered, which reflects the home’s honest relationship with its forested environment. You’re also very much immersed in nature here: wooded views, quiet nights, and cool coastal air are part of the deal. If you’re looking for manicured lawns or resort buzz, this may feel too peaceful. But if privacy, personality, and a true sense of place matter to you, this home delivers in all the right ways.

The brag

Work Mode:
Joe B. lens:
The forest-green exterior, the antique furnishings, the Japanese details, this house feels curated, not styled. It’s warm, thoughtful, and deeply respectful of its setting. This is exactly the kind of personality-rich home we love bringing into The Joes.
Joe R. lens:
You’re literally next to vineyards producing world-class wines (I love their chardonnays!), with total privacy and quiet. The layout works beautifully for real living, and the hot tub plus great room combo makes it easy to settle in and stay awhile.
Together we agree:
This cottage is soulful, private, and unmistakably Wine Country in the most authentic way possible.

Getting around

Located just outside Sebastopol, you’re a short drive to Russian River Valley wineries, the Sonoma Coast, and the town’s restaurants and shops. A car is essential, but the reward is access to some of Sonoma County’s most beautiful, less-traveled roads. We especially love the nearby The Barlow market district in Sebastopol featuring local food, wine, beer, and shops. And a fun fact, this tiny hamlet of just 7000 locas boasts 7 wonderful grocery stores - an epicurean paradise!

Joe-Tested,
Joe-Approved

Freeman Winery Cottage is full of heart. It’s peaceful, personal, and deeply rooted in its landscape - exactly the kind of place you come for a month and leave feeling genuinely restored.

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Additional Property Details

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From the Owner:

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Amenities

House Rules

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