Archives: Listings

Beautiful Mediterranean-style house just 2 blocks from the Downtown Healdsburg in Sonoma County. Open gourmet kitchen/dining/living room with French doors lead to 3 view decks. 3 bedrooms, 3 full baths and a pullout couch – perfect couples getaway to Wine Country. Gated entrance, private patio, and parking garage. EV charger on site! Studio & House…

Welcome to Clementine Cottage, your charming cozy wine country retreat, just two blocks off Healdsburg Plaza, and steps away from Sonoma County’s world class restaurants! This adorable 2 bedroom, 1 bath cottage w/sleeper sofa offers the perfect blend of comfort, class and convenience. The Cottage is located centrally in one of the best wine tasting…

Welcome to Bridle Path Bed and Breakfast in the charming town of Healdsburg! Our spacious and inviting suite with private bedroom, den/sitting room, bath, hot tub and private outdoor patio offers a perfect blend of comfort, luxury, and natural beauty, ensuring a memorable stay in the heart of wine country. The unique layout provides ample…

Enjoy the beauty of the Wine Country with a stay at 1083 Guest House in Healdsburg, your private haven in the Wine Country. Come and experience tranquility and luxury with a country feel just minutes from downtown Healdsburg, known for some of the best restaurants, wineries, antiques shops in Northern California. 1083 Guest House is…

Your own personal – HOME away from home! European charmer- Literally downtown Healdsburg- only STEPS away from the Historic Plaza.  Park just behind property – then walk to wineries and restaurants. Or tour the Hbg area, surrounded by Northern Ca. finest regional wine appellations, including Alexander Valley, Chalk Hill, Dry Creek & Russian River Valley. The…

Located inside a circa-1905 Victorian home at 134 North Street, Healdsburg, Cuvée House is behind and above the Healdsburg Bubble Bar tasting room and lounge. This very special spot is one of only two homes in the heart of downtown Healdsburg available for short-term vacation rental bookings.  [email protected], you will be treated to elegant furnishings…

Nestled on six peaceful acres, Casa Comunita offers a rare combination of tranquility, privacy, and charm. Five thoughtfully designed rooms sit at the top of a lush meadow, creating an idyllic setting that feels worlds away—yet remains just five minutes from vibrant downtown Healdsburg. Inside each cottage, king-sized beds, private patios, spacious walk-in showers, and…

Just 2 blocks from the Plaza, this 1880s cottage blends vintage charm with modern comfort. Walk to tasting rooms, shops & top dining, plus enjoy a complimentary Croix Estate wine tasting! Our 1880s cottage has been part of Healdsburg’s story for over a century—now it’s ready to be part of yours. Just two blocks from…

At the heart of downtown Healdsburg lies the lively Healdsburg Plaza—a vibrant town-square gathering spot where local culture, events, alfresco dining and casual strolls converge. Surrounded by historic storefronts, shaded trees and open-air seating, the plaza invites visitors to sip coffee, pop into wine-tasting rooms, listen to live music or simply linger in the atmosphere…

Escape into nature just minutes from downtown Healdsburg at the Healdsburg Ridge Open Space Preserve — a serene 155-acre natural sanctuary of oak woodlands, grasslands, wetlands, and serpentine chaparral. Wander the easy to moderate trails, keep an eye out for deer, bobcats, and over 40 bird species, and soak in sweeping views of the Russian…

Tucked just above the town of Healdsburg, Fitch Mountain serves as a dramatic natural backdrop and peaceful escape. The preserve spans roughly 173 acres and encompasses the 991-foot summit along with its surrounding slopes. Rich woodlands of oak, madrone and Douglas fir lead to panoramic views of the Russian River and Dry Creek and Alexander Valleys.…

Step into the heart of Healdsburg’s vibrant nightlife at Elephant in the Room—a 21+ pub where great music, craft beer, and fresh pub fare come together. Located on Healdsburg Avenue, this laid-back gathering spot features a spacious outdoor beer garden and live shows on Fridays, Saturdays (and often Sundays). Open every day from 1 pm…