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Healdsburg Sherman Street

Healdsburg, CA 95448, USA

CHECK AVAILABILITY (30 NIGHT MINIMUM)

All Inclusive Price

Opening Snapshot

Some homes are designed to impress. Others are designed to make you feel at home the moment you walk through the front door. Healdsburg Sherman Street does the latter beautifully. Located just a pleasant stroll from downtown Healdsburg, the home enjoys what we think is one of the best locations in town. It's close enough that you can walk to the Plaza for dinner, live music, or a glass of wine without worrying about driving home, yet far enough away that the neighborhood feels quiet, residential, and wonderfully relaxed. Originally built as a 1960s ranch home and thoughtfully renovated over the years, the house has a calm, welcoming personality. Soft grays, crisp whites, and coastal blues create an atmosphere that immediately puts you at ease, while generous windows and skylights fill the home with natural light. This is not a flashy house. It's a deeply comfortable one—and sometimes that's exactly what makes a property memorable.

GUESTS

BEDROOMS

BATHROOMS

PETS ALLOWED

POOL

HOT TUB

FIRE FEATURE

DEDICATED WORKING SPACE

WINERY ESTATE

EV CHARGING

HOME FOR SALE

Virtual Tour

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What we love

What stands out most about Healdsburg Sherman Street is how well it supports everyday living. The open kitchen, dining, and living spaces create a natural gathering place for family and friends. The kitchen itself is surprisingly generous, with a second oven and sink that almost make it feel like two kitchens in one. Whether you're hosting a dinner party or simply cooking with ingredients picked up at the Healdsburg Farmers' Market, it's a space designed to be used. The home offers three bedrooms and three bathrooms, along with a fourth room that has been thoughtfully converted into a dedicated office. For guests staying a month or longer, having a true workspace makes a tremendous difference and allows work and leisure to coexist comfortably. Outside is where this property becomes truly special. The owners are clearly passionate gardeners, and it shows. Every flower bed, pathway, and planting feels carefully considered, creating the sense that you're staying in someone's private garden retreat. Expansive decks extend the living space outdoors, offering multiple places to relax, dine, or simply enjoy the surroundings. One of our favorite details is the outdoor bathing experience. Instead of a traditional hot tub, the home features a large outdoor soaking tub nestled in the garden alongside an outdoor shower. Large enough for two, it provides many of the same pleasures while feeling perfectly suited to the character of the property. It's the kind of feature that encourages you to slow down after a day exploring wine country. The outdoor kitchen, barbecue area, large dining table, and generous seating make entertaining easy, whether it's an intimate dinner for two or a casual evening with friends. And then there's the garage. Technically, it's a two-car garage. In reality, it feels more like a beautifully finished flex space. Large sliding doors connect it to the home, and it could easily become a game room, a fitness area, a children's hangout, or the perfect place for a ping-pong table. Frankly, it's almost too nice to use as a garage.

Keep in mind

Part of this home's charm comes from its history. Although extensively remodeled, Healdsburg Sherman Street is still fundamentally a 1960s ranch house. The ceilings are lower than many newly built luxury homes, and the bedrooms are more modest in scale. Throughout the property, there are little reminders of its original character. Personally, we think those details give the house warmth and authenticity. The owners have done an exceptional job adding windows, skylights, and thoughtful updates that flood the interiors with light while respecting the home's original bones. Guests looking for a sleek, ultra-modern estate with soaring ceilings and vast open spaces may prefer a newer build. Guests looking for a beautifully updated home with personality and soul will likely feel right at home here.

Work Mode

Healdsburg Sherman Street is well suited for guests blending work with an extended stay. The home's fourth bedroom has been thoughtfully converted into a dedicated office, complete with a built-in desk and plenty of natural light. It's not a large workspace, but it provides welcome separation from the main living areas, making it easy to jump on a video call or focus for a few hours before heading into town or enjoying the gardens. For couples traveling together, it's an especially practical setup; one person can work comfortably while the other enjoys the house, the outdoor spaces, or a stroll to the Plaza. It's another example of how this home was designed for living, not just vacationing.

The brag

Joe B. lens:
After years in hospitality, I've found that the best homes are often the ones that feel genuinely lived in and loved. The gardens, the outdoor spaces, and the thoughtful renovation make this feel less like a rental and more like being welcomed into someone's exceptional home.
Joe R. lens:
I love houses that are versatile. You can work here, entertain here, relax here, or simply walk into town and enjoy Healdsburg without ever getting in your car. The office, flex-space garage, and outdoor living areas make it easy to settle in for a month.
Together we agree:
This is the kind of house that quietly grows on you until you realize you never want to leave.

Getting around

The location strikes a wonderful balance between convenience and tranquility. Downtown Healdsburg, its restaurants, tasting rooms, and community events are an easy walk away, while the surrounding wine country, cycling routes, and Russian River adventures are just a short drive from the front door.

Joe-Tested,
Joe-Approved

Perfect for a family, a couple working remotely, or anyone looking to experience Healdsburg like a local—with beautiful gardens, inviting outdoor spaces, and the rare luxury of being able to walk into town whenever the mood strikes.

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Additional Property Details

City & State:

Maximum Capacity:

Property Type:

Year Built: 

Renovation:

Property Size:

Bedroom Configuration:

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From the Owner:

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Amenities

House Rules

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More Information

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