144 Piper St, Healdsburg

Unmatched Legal STR Opportunity in Downtown Healdsburg

This is more than just a charming home — it's a licensed, income-producing vacation rental in the heart of Wine Country, just two blocks from Healdsburg Plaza. One of only a handful of properties in town with transferrable short-term rental zoning, this is a rare investment opportunity with built-in demand and long-term upside.

Originally built in the 1880s, the 2-bedroom, 1-bath cottage has been thoughtfully updated with designer finishes throughout, including copper countertops in the kitchen, a cozy living room, and a bright sunroom ideal for morning coffee or evening wine. The covered front porch and private backyard create inviting outdoor spaces for guests or personal enjoyment.

A standout feature is the oversized 1.5-car garage, offering exciting potential to be transformed into a seamless indoor-outdoor entertainment space — envision doors opening to the backyard to create the ultimate game room, tasting lounge, or rec room.

With over $87,000 in gross rental income in the past year and a turnkey setup available (most furnishings and decor offered separately), the home is ready to generate revenue from Day One — or serve as a luxurious Healdsburg getaway. There's even space to add a hot tub or cold plunge for the full wine country experience.

You won’t find another legal STR like this, this close to the Plaza, at this price point. Don’t miss the chance to own one of Healdsburg’s most exclusive and versatile downtown properties.