Healdsburg CA Real Estate & Homes for Sale

Downtown Healdsburg Opportunity This charming single-story Craftsman bungalow 1,663 sq ft home offers 3 bedrooms and 2 full baths . The sale also includes 438 Piper Street a contiguous 3,920 sq ft lot ideal for expanding the residence, adding an ADU, or creating your dream backyard with a pool. Classic features include a welcoming front porch, hardwood floors, a gas fireplace, and built-ins in the formal dining area. The spacious kitchen offers plenty of potential, and several outbuildings provide additional storage or creative space. Located just blocks from the Plaza, this rare in-town offering is full of possibilities.

Nestled in the heart of Alexander Valley, with commanding views of iconic Mt. St. Helena and undulating vineyards below, this is a rare opportunity to own a refined wine country estate on over 10 pristine acres. With approximately 7,088 square feet, this architectural gem exudes a timeless balance between old-world elegance and contemporary luxury. The main residence, thoughtfully laid out across two stories, offers four generous bedrooms and six bathrooms, designed with both grand entertaining and intimate living in mind. Additional features include a wine cellar, large fitness studio, outdoor dinning, garden shed/workshop, animal corrals, chicken coup, fenced in pastures and multiple entertainment zones that flow into the outdoor living areas. A sparkling pool and spa, bocce court, and panoramic lounging spaces invite year-round enjoyment amidst the peaceful heritage oaks and mature Japanese maples. The estate's thoughtful layout and scale offer the ultimate wine country lifestyle: private, polished, and effortlessly sophisticated. Whether a primary residence or weekend retreat, 4030 Old Barn Road delivers an unparalleled experience of Sonoma luxury living. (Interior design & furniture is by Vesta. All furniture is available for purchase directly with Vesta.)

Peaceful Creekside Retreat in Healdsburg - Welcome to 4011 Mill Creek Road - a serene and secluded escape nestled along the banks of year-round Mill Creek, just minutes from downtown Healdsburg and the heart of wine country. Set on a gated third of an acre, this charming compound offers a thoughtfully updated one-bedroom home with a modern kitchen, cozy living room, dining area, and a charming reading nook. Upstairs, you'll find flexible spaces perfect for an office, studio, or guest accommodations. A separate detached structure offers even more versatility, featuring a welcoming sitting room downstairs with a quiet nook, and an expansive upstairs space boasting gorgeous views across the lawn and out to the creek. Wraparound decking invites you to soak in the sights and sounds of nature - perfect for morning coffee, al fresco dining, or evenings spent with friends and family. The lush lawn, mature redwoods, and easy creek access create an ideal backdrop for relaxation, meditation, or recreation. This is more than a home - it's your ultimate Healdsburg getaway. Quiet, peaceful, and uniquely connected to the natural beauty of Sonoma County.

Welcome home to 1306 Pinon Drive within the coveted 55+ community in Healdsburg. This single-story gem is a 2-bedroom, 2.5 bathroom recently remodeled home. Step inside a contemporary floor plan with raised ceilings. The gourmet kitchen is a dream, featuring upscale appliances such as Subzero refrigerator, Thermador oven, and a unique outdoor bar pass-through. Bask in the elegance of oak floors, complemented by custom-built shelving, Fleetwood doors, and an expansive deck with motorized shades, ensuring a seamless indoor-outdoor living experience. This home is facing the open space and has direct access to the Russian River.

Located in the heart of Alexander Valley just minutes from Healdsburg & Geyserville, this 4.4 acre property offers a rare blend of Wine Country lifestyle and investment/development potential. The property features one large building with three updated residences totaling approx. 2,970 sqft. Two 3BD/2BA units each offer 1,104 sqft, while a 1BD/1BA unit spans 760 sqft. Each includes private entries, patios, laundry, hot tubs, outdoor dining & modern finishes ideal for multi-gen living or multi-unit rental income. A 2.9 acre producing Primitivo Zinfandel vineyard (with estate designation) adds agricultural value. The vineyard pays for itself and is professionally managed. Zoning is RR (Rural Residential), which also allows for vacation rental use. The property has been managed as a furnished 30 day+ fixed term rental and is now vacant and ready for your vision. If you are looking for a second home, income producing property, vacation rental or a building site this property checks all the boxes. Additionally, a barn is ready for creative repurposing, storage or a workshop. Enjoy sweeping vineyard & mountain views, mature redwoods for privacy, and proximity to top wineries, dining, and recreation. This is a unique opportunity in one of Sonoma County's most coveted locations.

8909 Mill Creek sits gracefully atop 10 acres, offering sweeping views of redwoods, vineyards, and Mount St. Helena. Striking architecture greets you on arrival: a floating composition of metal and glass anchored by board-formed concrete walls, hinting at the sophisticated interiors within. Rich materials and impeccable finishes define the two-bedroom modern home, where custom rift-sawn white oak cabinetry, Miele appliances, sleek lighting, and multi-zoned radiant floor heating create a luxurious, highly livable space. A private study offers an ideal retreat for work or reading, while expansive floor-to-ceiling windows blur the line between indoors and the stunning natural surroundings. The outdoor experience is equally refined, with a luxurious saltwater black-bottom pool framed by lavender and thyme, perfect for sunny days or starlit evenings in the spa. The expansive deck and patio make outdoor entertaining effortless. A generously sized pool house with a full designer bath offers a picturesque backdrop, ideal for guests or as a studio. Currently a successful vacation rental, 8909 Mill Creek provides income potential for future owners. Located just 20 minutes from downtown Healdsburg and 35 minutes from Sonoma County Airport, it offers both convenience and serene seclusion.

Charming Healdsburg property with two homes on one lot. This rare offering features a beautifully maintained 2 bedroom. 1.5 bath craftsman-style bungalow paired with a separate second unit is ideal for multi-generational living, rental income, or extended guest space. The main home features original details including crown molding, tall baseboards, vintage windows, and updated flooring. Spacious living and dining rooms, updated kitchen and renovated bathroom blend period charm with modern comfort. Detached garage/workshop with abundant storage and workspace. The detached second home offers private access and flexible living space. Outdoor living is a dream with mature fruit trees, a shaded entertainment patio, and multiple garden areas. Set on over a quarter acre, the property includes lush gardens and outdoor entertainment areas. Just minutes to Healdsburg Plaza, and proposed smart train station.

Discover the perfect blend of comfort and convenience in this Healdsburg property, featuring two separate homes on one lot. The main home offers 2 bedrooms, 2 baths, a gourmet kitchen with cherry cabinetry, granite countertops, stainless appliances, and Travertine tile floors. Oak floors grace the rest of the home, with French doors from both bedrooms opening to redwood decks, perfect for enjoying warm Healdsburg evenings. A charming 550+/- sq ft cottage in the back includes a full kitchen and bath, ideal for entertaining, overnight guests, extended family, or a home office. The address offers the possibility of fiber internet, so it is perfect for remote work! The gated paver driveway, flanked by 10 mature grape vines on the North side of the property, provides plenty of space for multiple vehicles or RV parking. Ideally located, you're just a short stroll or roll to the Healdsburg Plaza's year-round concerts, world-class restaurants, boutiques, tasting rooms, coffee shops, and artisan bakeries. To top it off, the property is also just half a mile from Healdsburg's Veterans Memorial Beach for summer days full of riverfront relaxation. Enjoy flexible living in the heart of wine country with this unique and versatile property!

Welcome to this peaceful and lush Healdsburg haven located on the north end of town. This east facing single level light and bright 4 bedroom, 2 bathroom home has been updated throughout! A new eat-in kitchen boasts quartz counters, new cabinets, a new oven, dishwasher and a bay window. The bathrooms have new tile, quartz counters, cabinets and lighting. There is new laminate flooring throughout. The west facing living room has a cozy wood-burning fireplace, a bay window and french doors that open to a shady backyard oasis. Dine al fresco and watch the sun set. A newer HVAC will keep you comfortable all year long. A natural pebble driveway with a refreshed landscape and new fencing leaves room for your own vision. Walk, bike, trot, scooter, one-wheel or drive to the heart of Healdsburg where art, music, live theatre, boutique shopping, fine dining and antique shops are sure to allure you, your family and your friends...including those that want to visit and outstay their welcome. Your own piece of Healdsburg under $950,000 can be YOURS!

Located just five minutes north of the historic Healdsburg Plaza, 103 Chiquita Road includes a 3 bedroom, 2.5 bath main residence and a fully equipped 1 bedroom, 1 bath attached ADU with a private entrance and mailing address (1604 Winding Creek Way). Thoughtfully updated and move-in ready, this home is ideal for multi-generational living, a guest retreat, or potential rental income. The 1,511 SQFT main home features an open-concept living, dining, and kitchen area with abundant natural light, hardwood flooring throughout, built-in closet organizers, and fresh interior paint. A convenient half bath is located on the main level. Upstairs, you'll find the primary suite with en suite bathroom and walk-in closet, two additional bedrooms, a full bath including soaking tub, and a laundry room. The 444 SQFT ADU offer's a kitchen, living area, private bedroom, washer/dryer and walk-in shower perfect for extended stays or passive income.

Nestled on 4.56 acres in Alexander Valley; The Glass & Vine a 3,965sqft modern retreat offers vineyard views and modernity, blending within the beauty of Cabernet vines. Expansive glass walls and industrial steel, frame vista views, while warm wood tones and a custom concrete-encased fireplace create an inviting oasis. The open living area flows to a gourmet kitchen with stainless counters, high-end appliances, and a pizza oven, opening to a vineyard-view deck, for al fresco dining under ancient oaks amidst the vineyards. A floating staircase ascends to the loft-style, primary suite; a haven with rustic beams, a spa-like, en-suite featuring dual sinks, a walk-in rain shower and a soaking tub facing the valley. Two bedrooms, a chic bathroom and a media room complete the main home. A guest home, adorned with rooftop solar, whispers privacy, its deck drinking in vineyard vistas. Three solar banks bloom in a garden, weaving sustainability into the land's embrace. Multi-level decking, a Jacuzzi, and fire pits cradle Zen-ful moments beneath starlit skies. With a current Airbnb license, this sanctuary, minutes from Healdsburg Plaza, the Russian River, and renown wineries, marries eco-conscious luxury with secluded grace, where each vineyard sunset hums a timeless ode.

New co-ownership opportunity: Own one-eighth of this turnkey home, professionally managed by Pacaso. Nestled on 3.3 acres in Sonoma's wine country, this 5-bedroom, 5-bath home embraces sustainable architecture. The idyllic setting is just 10 minutes from charming Healdsburg. The H-shaped, single-level floor plan is anchored by a great room positioned under a distinctive butterfly-shaped roof. The home's chic design integrates sustainable construction and design elements with functionality. Glass doors open to the beautifully landscaped front and rear terraced decks. Light pours into the great room, kitchen and bedrooms. The primary bedroom and bath have access to private outdoor spaces. The resort-style pool faces a two-suite guest casita, a pool house with a second full kitchen, a cabana and an outdoor kitchen with a pizza oven. Small vineyards grace the front and back yards. A private office, full bath and studio is located adjacent to the detached 2-car garage, and are accessed via a separate entrance. The property is on West Dry Creek Road, renowned for biking among vineyards and wineries.

First time on the market for this custom-built home on over half-acre lot. Fire sprinklers on cement tile roof. Cement stone and frame exterior. Assessor says two bedrooms, but there are also two offices and two dining rooms. Could easily be converted to four bedrooms. Plenty of space with flex rooms. Lots of storage. Large wrap-around stone patio with access to four rooms is perfect for entertaining. Quality custom home includes beam ceilings, inlaid wood floor, in addition to marble and granite flooring. Backs to Fitch Mountain Park. No showings until 5/25/25.

Presenting one of Healdsburg's most treasured architectural gems, The George Alexander House, an iconic Queen Anne residence built in 1905 and gracefully positioned on a large premium parcel just two blocks from the heart of the downtown Plaza. Located on prestigious Matheson Street, in the town's most distinguished historical district, this residence is surrounded by heritage homes and timeless charm. Rich in history and masterfully preserved, the home's enchanting architecture includes an octagonal tower, intricate frieze work, decorative finials, and a series of exquisite stained glass and quatrefoil windows. The abundance of ornamental detail distinguishes this property as one of the most iconic in all of Healdsburg. The estate also features a detached one-bedroom caretakers cottage perfect for hosting guests in privacy or serving as a serene retreat. Rarely does a home of such provenance, elegance, and location come to market. The George Alexander House offers the unique opportunity to own a piece of Healdsburg's storied past while enjoying the very best of Wine Country living.

Nestled in the heart of picturesque Healdsburg- Sonoma wine country's crown jewel, this charming 1950s 3BR/2BA single level home blends vintage character with modern turnkey conveniences adorned with flowers and a mature orange tree on a large lot walking distance to the Plaza and parks. Recently renovated and pride of ownership this home is cladded with stunning oak wood floors. While some portions of the home in the high traffic areas have been protected with tasteful fresh laminate flooring the gorgeous original wood flooring run throughout. The bright, functional kitchen flows nicely into the dining area and open living space with easy access to the attached two-car garage. Cozy up on cool evenings by the inviting gas fireplace, with dual wall furnaces providing efficient warmth throughout and for warmer days, a convenient wall-mounted A/C unit keeps the space comfortable. The shared bath features a tub and updated vanity, while the primary suite includes an ensuite shower and direct access to a spacious backyard (big enough for a pool) and ready for relaxing, gardening, or entertaining under the yard's open sky or beneath the wisteria wrapped covered patio. 790 Rose Lane will delight those seeking the World-class downtown Healdsburg access on a charming quiet street.

Impeccable, fully remodeled elegance meets modern luxury in this designer-finished home in Healdsburg's coveted Fitch Mountain Villas. No detail was overlooked in this top-to-bottom renovation. A new stone paver driveway, carriage-style garage door, and chic exterior lighting set the stage. Inside, natural light fills the open-concept layout featuring wide plank French oak floors, a gas fireplace, and a stunning kitchen with custom cabinetry, veined soapstone counters, brass fixtures, a farmhouse sink, and BlueStar gas range. The living space flows to a unique backyard with an outdoor kitchen, sun-drenched garden area, and direct access to a sprawling HOA-maintained greenbelt with a saltwater pool, spa, and sport courts. Upstairs, a bonus room with built-ins and shutters serves as an office, media room, or guest suite. Two guest bedrooms share a stylish bath with penny tile and subway surround. The primary suite offers dual walk-in closets, a serene balcony, and spa-like bath with marble floors, quartzite counters, walk-in shower, and private water closet. A rare blend of modern finishes and timeless design just minutes from downtown Healdsburg.

Discover the perfect blend of elegance and comfort in this beautifully updated 4-bedroom, 2.5 bathroom home. Designed for effortless living, the open-concept floor plan showcases a vaulted-ceiling living room with a striking custom built-in mantel and fireplace, creating a warm and inviting ambiance. The chef's kitchen is a culinary dream, featuring stunning granite countertops, premium stainless steel appliances, and a spacious island ideal for entertaining. Thoughtfully updated, this home boasts a newer roof and a central air conditioning system for year-round comfort. Located just minutes from downtown Healdsburg, the Montage, and the Healdsburg Community Center, this property offers both convenience and charm in a highly sought-after location.

Welcome to 9981 West Dry Creek, an exquisite estate and the final residence on this notable road. On the market for the first time in 26 years, this custom-built Santa Barbara-style home offers a unique mix of seclusion and stunning natural surroundings, with rose gardens, olive trees, and more encircling the property. Spanning over approximately 3,300 square feet on 49+/- acres, the residence includes three generously sized bedrooms and 2.5 baths, all thoughtfully designed for modern living. The home's interior is an ode to smart, elegant design, boasting an open-concept kitchen, a cozy breakfast nook, a sophisticated living room, and a formal dining roomideal for both intimate gatherings and grand entertaining. A serene hallway, mirroring a cloister-style covered porch, leads to a convenient half bath, a laundry room, and independent bedroom ensuites, ensuring both comfort and privacy. At the end of the exterior-covered walkway, you'll find a spacious two-car garage, approximately 428 square feet, with an unfinished second floor offering limitless possibilities for a gym, office, media room, or an ADU. With access to seasonal creeks, trails ideal for hiking and ATV rides, this property is ideal for those who value a connection with nature.

Every aspect of this residence exudes style and unsurpassed attention to luxury detail. Newly built and architect-designed by Elliot Sutro, this thoughtfully crafted single-level home blends comfort with meticulous attention to detail. The 1,834 sq ft main home with a 330 sq ft wall of glass, flows seamlessly to a spacious 500 sq ft entertainment terrace and a beautifully finished 414 sq ft ADU above the garage, offering flexibility for guests or work. A Standing Seam 24-gauge metal roof adds long-lasting protection. This spacious floorplan's amenities encompass a kitchen with Taj Mahal quartzite island, Caesarstone counters, Crystal Cabinet Works cabinetry, a 36 Wolf gas range, wine cooler, and Heath ceramic tile. Radiant heated floors and motorized window treatments. Outdoors, expansive gardens feature an Italian Bluestone tile patio, a 4-ft gas fire pit, and a graceful Girona fountain of Alpine Stone. Designed for low-maintenance living, energy efficiency and ideal as a full-time home or a lock-and-go getaway. 6 kwh Solar treatment, annual production is 4,072 kWh.

Welcome to 431-433 University Street in charming Healdsburg, CA! Just four blocks from the bustling downtown plaza, this centrally located duplex offers tranquility in a private setting. Positioned as the middle unit in a trio, it ensures a quieter living experience. Unit 431 impresses with its recent remodel, featuring elegant travertine stone flooring throughout the main areas and a custom kitchen adorned with high-end cabinetry and stunning countertops. Enjoy the cozy breakfast nook with garden views, ready to be landscaped to your taste. Unit 433 is tenant-occupied, offering two bedrooms and one bathroom, along with a quaint landscaped garden. While updates may be desired, maintaining the tenancy presents a great income opportunity. This property includes an attached garage, on-site parking, and a spacious backyard. With 3,078 square feet of living space on a 9,937 square foot lot, this duplex is perfect for both investors and those seeking a new home base.

Healdsburg River Gem! Welcome to this delightful 2-bedroom, 1-bath bungalow offers nearly 1,100 square feet of inviting living space. Located minutes from the river and Del Rio Woods park, perfectly timed for summer adventures, this sweet home is a must see! Featuring a 1 year old roof, dual-pane windows, central AC, and gorgeous hardwood floors. The open-concept layout includes a spacious kitchen with a large island, a cozy corner fireplace, and expansive double decksideal for entertaining or simply enjoying the outdoors year-round. The converted downstairs garage adds even more flexibility, offering the perfect space for a home gym, game room, or relaxed hangout area. Just a short drive from Healdsburg Plaza, you'll enjoy quick access to world-class dining, boutique shopping, and some of Sonoma County's finest wineries. Whether you're seeking a full-time residence or the ultimate weekend retreat, this charming river bungalow has so much to offer.

Step into the heart of Sonoma County. 1019 Westside Road is a prime opportunity to aquire a wine country classic. Kitchen features custom white oak cabinetry with loads of functional storage. Existing site plan and flat 1 acre parcel is ideal for a family compound. With room to expand, the property includes a separate building, a blank slate to develop a luxury ADU or entertainment-centric pool house. With space to add a pool this is screaming destination property. Property features include mature landscaping. Gardens are bursting with lemon, orange, lime, fig and apple trees. Strawberries, artichoke, blueberry, tomatoes, squash and herbs. Lovely views from inside and outside the home round out this park-like setting. A very clean, well-cared for property that is both move-in ready and a prime value-add with substantial upside. One of the best locations in Healdsburg. Located in sought after Madrona Knolls, just up the hill from The Madrona, this private collection of estate properties with no HOA is a rare find. If what you want is a country property close to town, this is about as close as you will get. Buyer to verify square footage, permits, zoning and all other details.

This exquisite French Country home offers sophisticated charm in a fantastic neighborhood of multi-million dollar estates. Featuring dramatic high ceilings with stunning windows that flood the interior with natural light, this residence combines luxury with comfortable living. The thoughtfully designed open floor plan seamlessly connects cooking, dining, and living spaces, perfect for both everyday enjoyment and entertaining. Enjoy the convenience of main-level living with the primary bedroom suite, garage, and all essential living spaces on the first floor. Upstairs offers two additional bedrooms, a private office, and a versatile bonus room ideal for a fitness area, playroom, or hobby space. The private yard provides a serene outdoor retreat with a dedicated BBQ area and ample space for a future pool. Located in one of Healdsburg's most coveted neighborhoods this home is not to be missed.

Private Healdsburg Haven with Expansive Landscaping and Timeless Charm - This peaceful and sunny haven feels a world away, yet it's just minutes from downtown Healdsburg. Set on 1.21 acres, the property offers privacy, beautifully curated outdoor spaces, and effortless indoor-outdoor flow. The home includes 2 spacious bedrooms - an upstairs primary with en suite and a downstairs bedroom with a murphy bed for flexibility - a formal living room, a family room with an open-concept kitchen, a dedicated office, a separate laundry room, and downstairs full bath - thoughtfully laid out for both daily living and work-from-home flexibility. French doors open from the family room to a large deck overlooking the landscaped yard, where crushed granite walkways wind through Sonoma fieldstone boulders, a graceful maple tree, and lush garden beds. It's a setting designed for peaceful mornings, al fresco dining, or evenings under the stars. A detached 3-car garage includes a flex space above - ideal for a studio, workspace, or creative retreat. This is the kind of property that balances calm and connection - nature, space, and town all within easy reach.

Perched on the scenic slopes of Fitch Mountain, this classic Healdsburg cabin offers rustic charm, modern flexibility, and breathtaking views of the Russian River and rolling countryside. With three inviting decks, two showcasing stunning vistas, this is a home designed for outdoor living and peaceful relaxation. The main living space is warm and cozy, complemented by a flex room below, ideal for extra storage, a hobby room, or other uses. Adding even more versatility, a detached room offers a private space that can be tailored to whatever the heart desires - yoga studio, art space, workshop, or quiet retreat. The property also includes rare and convenient 3-car parking, making hosting and daily life a breeze. Located near river access and scenic trails, and just minutes from downtown Healdsburg (1.5 miles from Healdsburg Plaza), only 100 feet outside city limits, this one-of-a-kind property is the perfect wine country getaway or full-time haven, blending nature, charm, and opportunity in one remarkable setting.