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Healdsburg Maybee Lane

Healdsburg, CA

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Opening Snapshot

Arrive through an unassuming gate past a caretaker’s cottage, and you might think you’ve taken a wrong turn. The driveway doesn’t exactly set the stage for what’s ahead. But step beyond it and everything changes: a bright, airy farmhouse, seamless indoor–outdoor flow, and views that stretch across the eastern hills of Sonoma. This is a soulful retreat hiding in plain sight.

GUESTS

BEDROOMS

BATHROOMS

PETS ALLOWED

POOL

HOT TUB

FIRE FEATURE

Virtual Tour

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What we love

The main house offers three bedrooms and three baths, thoughtfully designed so every square foot counts. Just beyond the pool sits the guest house — with a rec room downstairs, a shared pool bath, and a charming upstairs bedroom reached by a quirky spiral staircase. It’s utterly memorable and gives the property extra versatility. Outdoors, the fun keeps multiplying: a basketball hoop and play area, a small fitness studio on the hill, a fire-pit lounge right off the living room, and a pool with loungers that feel like their own little resort. The dining pavilion — complete with outdoor kitchen — makes throwing a big dinner party almost too easy. The best part? Everything is close together, so you’ll actually use it all.

Keep in mind

There’s no garage, and parking is limited — bigger groups may need to juggle cars. The home isn’t walkable to town, but that’s part of its country charm. The furnishings are beautiful, expensive, and thoughtfully chosen — just not as bold or quirky as you might expect in a second home. That said, they’re perfectly appropriate and let the sweeping views do the heavy lifting, creating interiors that complement rather than compete.

The brag

Joe B. lens:
The flow from kitchen to dining to outdoor pavilion is entertainer heaven. You can go from cooking to cocktails to dinner under the lights without missing a beat.
Joe R. lens:
The guest house by the pool is my kind of quirky — rec room below that doubles as an office, spiral staircase up to a tucked-away bedroom, plus a little studio on the hill for fitness.
Together we agree:
Maybee Lane delivers a perfect blend of charm, quality, and playful outdoor living.

Getting around

This isn’t a walk-to-town property — you’ll need the car to get to downtown Healdsburg’s cafés, restaurants, and tasting rooms. But that’s part of the wine-country rhythm: drives through vineyards to get to the good stuff.

Joe-Tested,
Joe-Approved

Modest arrival, magical stay. Maybee Lane is a beautifully built, view-filled retreat that proves charm and quality can come in small, surprising packages.

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Additional Property Details

City & State:

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From the Owner:

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Amenities

House Rules

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