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Healdsburg Matheson Street

Healdsburg, CA

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Opening Snapshot

There are homes that feel like a retreat… and then there are homes that feel like you’ve somehow hacked the system. Healdsburg Matheson Street is firmly the latter. Set on one of the most coveted streets in town where the “who’s who” quietly coexist behind perfectly manicured facades, this modern farmhouse delivers something almost impossible to find: space, style, and privacy in town. Originally a modest bungalow, the home was completely reimagined in 2019 into a bright, expansive, design-forward residence that lives like a country estate but with the heartbeat of downtown Healdsburg just a short stroll away. With a three-bedroom main house, a fully equipped guest house, and multiple indoor-outdoor living zones, this is the kind of place where mornings start slow, afternoons spill into the pool, and evenings end on the Plaza without ever needing a car. It’s polished, it’s easy, and it’s quietly exceptional.

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 magic here is the balance and it shows up everywhere. First, the kitchen. Vaulted ceilings, walls of glass, and light pouring in from every angle. It’s the kind of space that makes you want to cook even if you had no plans to. Coffee lingers longer, dinners stretch out, and somehow everyone ends up gathering here without trying. Then there’s the layout. The main home flows beautifully, with thoughtful separation between social spaces and private retreats. Upstairs, the TV/recreation room is a standout and is perfect for movie nights, kids disappearing for a few hours, or just a quiet escape from the main living area. Step outside and the backyard punches well above its weight. Pool, hot tub, fire pit,outdoor kitchen, lawn, garden beds - it’s all there, dialed in and ready. And the guest house? A game changer. Two additional bedrooms and its own living space make this ideal for two families, in-laws, or that one friend who always says they’ll “just pop by” and then stays a week. And then the real kicker: you’re on Matheson Street. You can walk to dinner, wine tastings, coffee, the Plaza - everything that makes Healdsburg what it is - without sacrificing the comfort of a fully dialed home base.

Keep in mind

This is in-town living, and that’s both the appeal and the tradeoff. Homes are closer together, and while the backyard is beautifully designed, it’s not sprawling vineyard acreage. You won’t get that wide-open, middle-of-nowhere wine country feel here. Instead, you’re trading space for access and in this case, it’s a trade we’d make every time. Also worth noting: with the guest house and multiple living areas, the home can comfortably accommodate larger groups, which is a huge plus but it does mean a bit more shared energy if you’re filling all the rooms. That said, the layout does a great job of giving people space when needed. Bottom line: if you’re coming for walkability, design, and ease, this hits. If you’re chasing total seclusion, you’ll find better fits elsewhere.

Work Mode

Dedicated office space in the main house makes this an easy yes for longer stays. Strong natural light, separation from living areas, and the option to convert additional rooms into workspace means you can actually get things done—then walk to lunch when you’re done.

The brag

Joe B. lens:
This is one of those homes I walk into and immediately think, “yeah, I could live here.” The kitchen alone sells it but the combination of design, location, and livability is what makes it special. It’s effortless in all the right ways.
Joe R. lens:
You’ve got a pool, a rec room, and a legit setup for multiple families and all walking distance to town. That’s rare. I’m already picturing mornings on the lawn, afternoons in the pool, and nights out without touching the car.
Together we agree:
A true unicorn: five-bedroom flexibility, modern design, and downtown walkability all wrapped into one beautifully executed Healdsburg home.

Getting around

You’re right in the heart of it. The Healdsburg Plaza, top restaurants, tasting rooms, and morning coffee spots are all an easy walk or bike ride away. No need to plan your day around driving, just step out the front door and go.

Joe-Tested,
Joe-Approved

This is one of those rare finds that checks almost every box. Stylish, spacious, and steps from everything. Healdsburg Matheson Street isn’t just a great stay, it’s a smart one.

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Additional Property Details

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From the Owner:

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Amenities

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