144 Piper Street

Unmatched Legal STR Opportunity in Downtown Healdsburg. More than just a charming home it's a licensed, income-producing vacation rental in the heart of Wine Country, just 2 blocks from Healdsburg Plaza. One of only a handful of properties with transferrable short-term rental zoning, this rare investment offers built-in demand & long-term upside. Originally built in the 1880s, the 2-bedroom, 1-bath cottage has been thoughtfully updated with designer finishes, including copper countertops, a cozy living room, and a bright sunroom ideal for morning coffee or evening wine. The covered front porch & private backyard offer inviting outdoor spaces. A standout feature is the oversized 1.5-car garage, with exciting potential to convert into seamless indoor-outdoor entertaining space envision doors opening to the backyard for the ultimate lounge or game room. With exceptional nightly rental income & a turnkey setup available (furnishings offered separately), it's ready to generate revenue or serve as a luxurious Healdsburg escape. Space to add a hot tub or cold plunge completes the vision. You won't find another legal STR like this, this close to the Plaza, at this price point.

Days on Market

161 days

Current Status

Contingent

Original Price

$1,575,000

List Price

$1,575,000

On Market Date

Mar 6, 2025

Contingent Date

Aug 7, 2025

Property Type

Single Family Residence

Area

Healdsburg

Zip Code

95448

MLS ID

325011482

APN

002-163-009-000

Year Built

1880

Stories in Building

Unavailable

Possession

Other

Data Source

BAREIS

Origin MLS System

Bed

2

Bath

1

Parking

0

Detached, See Remarks

SQ FT

1,812

SQ FT Source

Not Verified

Lot SQ FT

3,746.0

Lot Acres

0.086 Acres

Cooling

Central, Window Unit(s)

Heating

Central

Laundry

Hookups Only

Main Level

Bedroom(s), Family Room, Full Bath(s), Kitchen, Street Entrance

Possession

Other

Fee

$0

MLS and other Information regarding properties for sale as shown in Theo have been obtained from various sources such as sellers, public records, agents and other third parties. This information may relate to the condition of the property, permitted or unpermitted uses, zoning, square footage, lot size/acreage or other matters affecting value or desirability. Unless otherwise indicated in writing, neither brokers, agents nor Theo have verified, or will verify, such information. If any such information is important to buyer in determining whether to buy, the price to pay or intended use of the property, buyer is urged to conduct their own investigation with qualified professionals, satisfy themselves with respect to that information, and to rely solely on the results of that investigation.

School data provided by GreatSchools. School service boundaries are intended to be used as reference only. To verify enrollment eligibility for a property, contact the school directly.