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.
Pending
$1,575,000
144 Piper Street, Healdsburg, CA 95448
2beds
1,812sqft
Est.:
Single Family Residence
Built in 1880
3,746.16 Square Feet Lot
$1,481,200 Zestimate®
$869/sqft
$-- HOA
What's special
Bright sunroomDesigner finishesCopper countertopsInviting outdoor spaces
- 174 days
- on Zillow |
- 323 |
- 11 |
Zillow last checked: 7 hours ago
Listing updated: August 26, 2025 at 08:04am
Listed by:
Ryan Anderton DRE #01946037,
Sonoma Realty Group 707-244-7181
Source: BAREIS,MLS#: 325011482
Originating MLS: Sonoma

Travel times
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 2
- Bathrooms: 1
- Full bathrooms: 1
Bedroom
- Level: Main
Bathroom
- Level: Main
Family room
- Level: Main
Kitchen
- Level: Main
Heating
- Central
Cooling
- Central Air, Window Unit(s)
Appliances
- Laundry: Hookups Only
Features
- Has basement: No
- Has fireplace: No
Interior area
- Total structure area: 1,812
- Total interior livable area: 1,812 sqft
Property
Parking
- Total spaces: 2
- Parking features: Detached, See Remarks
- Garage spaces: 2
Features
- Levels: Two
- Stories: 2
- Fencing: Full
Lot
- Size: 3,746.16 Square Feet
- Features: Landscaped, Landscape Front
Details
- Parcel number: 002163009000
- Special conditions: Offer As Is
Construction
Type & style
- Home type: SingleFamily
- Property subtype: Single Family Residence
Condition
- Year built: 1880
Utilities & green energy
- Sewer: Public Sewer
- Water: Public
- Utilities for property: Public
Community & HOA
HOA
- Has HOA: No
Location
- Region: Healdsburg
Financial & listing details
- Price per square foot: $869/sqft
- Tax assessed value: $1,042,241
- Annual tax amount: $12,086
- Date on market: 3/6/2025
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