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Healdsburg Woodlands Drive

Healdsburg, CA

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Opening Snapshot

Perched high on a knoll inside the residential enclave of Montage Healdsburg, Healdsburg Woodlands Drive delivers one of the most jaw-dropping views we’ve seen from any home in the community. And that’s saying something. Among the Harvest Homes built here, the architecture and finishes are consistently beautiful. But this particular home sits at the very top of the hillside, giving it what we believe is the best view in the entire Harvest Home collection. From nearly every room, the landscape opens up to sweeping panoramas of vineyards, hills, and the wide horizon of Wine Country. Step through the front door and the home makes its first statement immediately: a dramatic glass wine wall ready to showcase bottles collected from your explorations across Sonoma. Beyond that, a modern open kitchen, living room, and dining area stretch toward floor-to-ceiling glass and that spectacular view. But the real story here isn’t just the home, it’s the lifestyle. Staying here feels like having four Montage suites for the month, with the entire resort as your extended living room.

GUESTS

BEDROOMS

BATHROOMS

PETS ALLOWED

POOL

HOT TUB

FIRE FEATURE

DEDICATED WORKING SPACE

HOME FOR SALE

WINERY ESTATE

Virtual Tour

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What we love

The view is the headline here. While several homes share this hillside, none capture the unobstructed panorama quite like this one. From sunrise coffee to sunset wine, the landscape feels like it’s constantly performing. The home itself is pristine and beautifully modern. The open living space flows effortlessly between the kitchen, dining, and lounge areas, all oriented toward the horizon. Everything feels clean, sophisticated, and thoughtfully designed, The main-level covered deck is enormous and essentially doubles the living space. It connects directly to the living area, making indoor-outdoor living seamless. Our favorite feature is the oversized hanging sofa swing, an irresistible spot for reading, sipping wine, or drifting into an afternoon nap while looking out over the vineyards. The primary suite on the main floor is spacious and serene, with a beautiful bathroom and an outdoor shower and deck access. Downstairs there is a second primary bedroom and two additional large ensuite bedrooms, all opening to another expansive covered deck. Both primary bedrooms feel like they were lifted straight out of a luxury hotel, with matching proportions, layout, and finishes that deliver a true guest room experience inside a private home. Down on the lower terrace, a plunge pool that doubles as a hot tub makes clever use of the hillside and is just about perfect for cooling off after a warm Sonoma afternoon. And of course, there’s the resort itself. Guests enjoy access not only to the Harvest Homes’ private clubhouse, pool, and fitness center, but also to the full amenities like restaurants, bar, spa, and trails - all within walking distance.

Keep in mind

The aesthetic here is very modern and intentionally hotel-like. The home interiors feel polished, contemporary, and curated. While the property is privately owned, you won’t find many personal artifacts or family touches, it’s meant to feel like a luxury resort residence. Another thing to note is that the Harvest Homes sit relatively close to one another. When you first approach the home, the arrival doesn’t feel like a grand private estate with a long drive or dramatic gates. That said, the home is very smartly designed. Once inside, the architecture and orientation of the house focus entirely on the sweeping hillside views. Nearly every room faces outward toward the vineyards and horizon, so your attention naturally moves to the landscape rather than neighboring homes. In practice, once you settle in, you have very little awareness of the homes around you, just the expansive Wine Country views.

Work Mode

Each of the four bedrooms includes a desk, making it easy to spread out and create dedicated work zones. The downstairs suite stands out with a screen wall separating the desk from the bed, offering a more private setup. Just note: a full-time workspace may take one bedroom offline.

The brag

Joe B. lens:
What makes this place so special is the blend of private home living with the hospitality ecosystem at Montage Healdsburg. You can spend the morning at the spa, grab dinner at the resort, and still retreat to your own spectacular home overlooking Wine Country.
Joe R. lens:
This is one of those houses where the view pulls you from room to room. Every window frames the hills differently. And that giant hanging deck swing? That’s where I’d be parked every evening watching the sun set with a glass of Aperture Cabernet Sauvignon.
Together we agree:
This home captures the rare combination of resort access, modern design, and one of the best viewpoints in Wine Country. It’s a pretty unbeatable setup.

Getting around

Although the home feels tucked into the hills, you’re just minutes from the restaurants, tasting rooms, and shops of downtown Healdsburg. Even better, many amenities of Montage Healdsburg and the newly opened Appellation resort across the street - dining, spa, trails, and bars - are within easy walking distance.

Joe-Tested,
Joe-Approved

Healdsburg Woodlands Drive delivers the rare combination of a luxury private home and full resort lifestyle. Add arguably the best view on the lovely hillside, and you’ve got a Wine Country stay that’s hard to beat.

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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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