Healdsburg CA Real Estate & Homes for Sale

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 over $87,000 in gross rental income last year & 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.

Welcome to your dream retreat in the heart of Sonoma County wine country! This spacious two-bedroom home offers the perfect blend of convenience, comfort, and luxury living. Located just a leisurely stroll away from Healdsburg's celebrated plaza, you'll have easy access to world-class restaurants and lodging, ensuring that every culinary desire is fulfilled and every stay is nothing short of extraordinary. Step inside to discover an inviting open-concept layout, seamlessly integrating the living, dining, and kitchen areas. The kitchen boasts sleek stainless steel appliances and an inviting eating bar, perfect for entertaining guests or enjoying casual meals. Upgrades abound throughout, including stunning real wood flooring, plush new carpeting, and stylish built-in cabinets, adding both elegance and functionality to the space. A private porch/deck can make outdoor dining a delightful ritual amidst the serene surroundings. Whether you're seeking a full-time residence or a second home retreat, this home is perfectly suited to both lifestyles. All furnishings included in listing price.

Stunning classic Craftsman in the heart of Healdsburg. An extraordinary opportunity to own a piece of Healdsburg's architectural history, this 1935 Craftsman offers timeless charm and versatility along with it's ORM multi-use zoning. Step inside and be greeted by exquisite craftsmanship, from high coffered ceilings and crown moldings to built-in cabinetry and stunning mahogany inlaid oak flooring. The grand living room, anchored by a beautiful fireplace, exudes character and warmth. The formal dining room, also featuring a fireplace, creates an inviting space ideal for entertaining. The updated kitchen boasts stainless steel appliances and a charming dining area, perfect for both everyday meals and hosting. There is also a separate one-bedroom/bath apartment on the upper level with a private entrance for privacy. The building effortlessly blends historic elegance with modern comforts. With plenty of off-street parking and endless possibilities, it's a rare find that offers a true sense of Healdsburg's past, present and future. It also has high-speed internet connectivity, walk-in basement and plenty of storage space. Just blocks to the plaza to enjoy restaurants, cafes and shopping.

270 awe-inspiring acres surrounded by Pritchett Peaks Wilderness Refuge, Lake Sonoma Recreation Area & Healdsburg Wineries, Falcon Highlands Ranch(FHR) offers the serenity of rural life & the charm of the Wine Country. FHR is bordered to the West by private vineyards, to the North & East by Army Core of Engineers lands(COE). Most of the FHR's property borders open land. Enjoy over 1-mile of Lake Sonoma frontage. The first 100 yards from Lake Sonoma is owned by COE. However, FHR does have direct access to the lake. This property offers gentle rolling land with oak studded meadows & redwood forests. It includes 3 legal parcels with a large 3,600 sq ft barn with an additional 2,160 sq ft main living area above, 2nd 912 sq ft ADU/guest house, 1,300 sq ft yoga studio, 3-tractor equipment garage, pond & miles of interior all weather roads. FHR is off the grid. Electricity is supplied by solar, lithium batteries with inverters & generators. The system is state-of-the-art, robust & dependable. This is truly a gentleman's ranch that offers top tier amenities, aesthetics & a location with perfect privacy, a refuge from the rest of the world yet providing convenient proximity to adventure, Healdsburg's world class wineries, restaurants & shopping. Here you will find the best of everything.

Healdsburg-an exquisite 1938c home effortlessly blending vintage charm w modern elegance. Nestled in a premier locale. this meticulously remodeled residence offers 2,681 +/-sqft of refined living space. Step inside to discover an inviting open-concept layout, ideal for both intimate gatherings or grand entertaining. The main residence boasts 3 spacious ensuite-bedrooms + office + 3.5 beautifully appointed bathrooms. Thoughtful design touches harmonize period details w contemporary conveniences, showcasing high-end finishes & designer elements throughout. The heart of the home features expansive living areas bathed in natural light, seamlessly connecting to a chef's kitchen w contemporary appliances, custom cabinetry & bespoke countertops - a perfect blend of functionality & style. This private entertainers' yard is a true sanctuary hosting a 826+/-sqft guest house providing another full BR & BA serving as a luxurious retreat for visitors while also a glamorous repose poolside. A fabulous resort-style outdoor space creates a haven of relaxation & entertainment, featuring a stunning recreational pool w spa & waterfall, flaming gas fire pit + outdoor BBQ center, multiple zones for al-fresco dining & lounging. Mature 50+ yr old olive trees along w interlinking patio & lawn areas

Modern Sanctuary with Sweeping Views. Nestled on a serene ridge above Healdsburg, this one-acre property is a rare retreat offering panoramic views of the town and beyond. A beautifully remodeled 3-bedroom, 2.5-bath home blends contemporary design with tranquil outdoor living. Meticulously upgraded in 2022, the single-level residence features custom finishes throughout, from the elegant hardwood floors to the new electrical, plumbing and windows. The heart of the home is a sun-drenched gourmet kitchen designed by Hommeboys Interiors, with top-tier appliances including a Bertazzoni gas range and Caesarstone countertops. Adjacent to the main house is a detached guest house that provides versatile space for guests, an office, or a fitness studio. The expansive grounds include a swimming pool, complemented by an outdoor fireplace and generous patio perfect for al fresco dining. Immerse yourself in the beauty of tiered gardens & artistic landscaping, while the glass botanical conservatory offers a peaceful space to enjoy the surrounding flora. Set against the backdrop of Fitch Mountain Preserve & just moments from the Russian River, this private oasis is also within easy reach of Healdsburg's vibrant downtown Plaza, renowned for its exceptional dining, shopping, and cultural scene.

Final remaining studio at Canopy, previously listed at $950,000, now offered at a $100,000 price reduction. Nestled in the heart of Healdsburg's vibrant Mill District, residence A103 masterfully blends architecture and interior design, creating a home that reflects the authentic charm and intimate allure of Healdsburg' s small-town spirit. Interior features include Italian-made MandiCasa cabinetry, temperature-controlled wine storage, Waterworks fixtures, natural stone countertops and wide-plank hardwood throughout. Mill District will soon feature a high-end boutique hotel, and private amenities complete with a fitness center and pool. With just a limited number of residences, this is a rare opportunity to own a home that blends rustic sophistication, urban vibrancy, and nature's beauty in one of the world's most coveted wine regions. If you're searching for the perfect wine country retreat, Mill District's Residence A103 offers the ultimate pied--terre. As our last remaining studio, now is the ideal time to discover this Canopy home. Images are conceptual renderings.

Now is the time to seize this unique opportunity to live, work, and create your future micro-winery, tasting room, and outdoor event space. With over a million dollars in renovation to the outdoor living space, electrical, and new foundation, this 1.75 acre parcel illuminates with possibilities. Breath life into these two large structures for the ideal posh country home, short term rental, or vacation destination amongst the neighboring wineries. The large 3 bedroom, 3 full bath currently offers respite to guests who frequent the property. Designed to make the large pool, spa, and outdoor kitchen the centerstage for large events and all-inclusive gatherings, this property awaits new land stewardship to expand on its professional renderings of a proposed winery, tasting room, and wine cave. Over 300 pinot vines planted just 5 years ago, let the new root stalks and your future business mature and grow into its full potential here in the heart of Sonoma's wine country.

A serene retreat nestled on 12 acres in Dry Creek Valley, a short 10-min drive to charming Downtown Healdsburg. This exceptional property offers the perfect blend of tranquility & convenience, making it an ideal getaway or a self-sustaining homestead. The spacious home features an updated kitchen and primary bed/bath. An additional ensuite bedroom spans the entire second level, while a sunroom stretches across the south side of the home. Hardwood floors, high cathedral ceilings, and incredible views offer modern comforts amidst nature's beauty. The property boasts groves of majestic, mature redwoods & oak woodlands, graced by the year-round, spring-fed Mill Creek, which hosts spawning steelhead each spring. This picturesque creek provides a refreshing spot to cool off on warm summer days. Near the creek, a well-maintained barn and office provide versatile spaces, often used by the current owners for special entertaining occasions & wine tastings. For outdoor lovers, the property offers ample walking or backcountry hiking right from your doorstep. A kitchen garden w/ raised beds is conveniently located near the home, complemented by over 4,000 SF of a fenced garden area, complete with a private water supply throughout. This is a rare offering in Sonoma County's wine country.

Perched in the heart of Healdsburg's scenic Eastside Road wine region, this stunning vineyard estate spans over 16 acres of picturesque countryside. The charming main residence boasts generous living space, featuring four bedrooms and four bathrooms (two full and two half), offering an exquisite blend of elegance and comfort. Set above the sweeping vineyards, a detached three-car garage includes a beautifully appointed one-bedroom, one-bath considered OFFICE/storage space, providing breathtaking views of the surrounding landscape. An additional two bedroom, 1 bathroom home at the base of the ridge and serves as the caretaker's residence, ensuring seamless estate management. The vineyard is currently operated by Ketcham Winery, and the seller prefers a lease-back arrangement to maintain continuity in wine production for its established brand. This is a rare opportunity to own a legacy vineyard estate in one of Healdsburg's most desirable locations, offering an unparalleled lifestyle in the heart of Sonoma County wine country.

Welcome to 366 Piper St, a beautifully updated condo nestled in the heart of Healdsburg, CA, just a few blocks from the square. This charming home offers a perfect blend of modern amenities and cozy living, making it an ideal choice for those seeking comfort and style. Spanning 1,188 +/- sq ft, this home features two spacious bedrooms and one and a half bathrooms, providing ample space for relaxation and privacy. The recently renovated kitchen is a chef's delight, boasting a breakfast bar, cooktop, dishwasher, gas oven, gas stove, and sleek stainless steel appliances. The living area is adorned with a warm and inviting fireplace, perfect for cozy evenings. The combination of tile and carpet floors throughout the home adds a touch of elegance and comfort. The bathrooms are thoughtfully upgraded, offering convenience and style. Interior has been just freshly painted. And don't forget the custom wine cellar. Enjoy the comfort of air conditioning and central heating, ensuring a pleasant atmosphere year-round. The convenience of having a washer and dryer in the unit adds to the ease of living in this delightful condo. Located in the vibrant community of Healdsburg, this home offers a wonderful opportunity to experience the best of California living.

Just blocks away from the Healdsburg Plaza, this property is a rare gem. Fully restored in 2024, this legacy property was once owned by Coronel Roderick Matheson's family (for whom the broad, cherry tree-lined street in Healdsburg is named after in the 1900's). In 2024, the home & grounds underwent a complete structural & interior restoration, elevating it to current luxury & custom construction standards. Modern amenities and high-end appliances have been thoughtfully integrated throughout the property while preserving it's original character. Set on 0.68 acres, the property offers remarkable privacy, thanks to its deep and wide lot, expansive street frontage & commanding u-shaped driveway. Parcels of this size are rarely found within walking distance to the Healdsburg Plaza. Currently, the property features a large pool, a fruit orchard, olive orchard, raised garden beds, & various heritage trees, including redwoods and California oaks all complemented by its timeless & modern home that has endured the test of time for over a century. There's ample space for a potential lot split under SB9 or expansions such as a garage, ADU, or gym. Come experience the splendor, the privacy & unparalleled quality of this remarkable downtown Historic Estate. (Fire Sprinklers on all floors)

Contemporary elegance and unparalleled convenience with this stylish 2 bed, 2 bath condominium located in the heart of Downtown Healdsburg. Enjoy the resort life by the pool or a leisurely walk on the Foss Creek Pathway. There is ample space for relaxation and entertaining as well as a private balcony to enjoy the summer evenings. If you don't want to entertain at home, you're just steps away from world-class dining, boutique shopping, art galleries and more!

Opportunity in Healdsburg. This 1.43 acre property spans from Sanns street to Badger street and offers Fitch Mountain Views. The 3 bedroom 1 bath home exudes charm, has pocket doors, molding and built ins throughout. Bring your ideas and contractor and check out the potential to split it or build a family compound. The City of Healdsburg states this area has a 6000 sf minimum lot size and you can check with them about other possibilities or restrictions.

Properties like this are often kept for generations. This peaceful, private sanctuary is nestled in a beautiful natural setting and is a magical palette for a creative lifestyle. Main home is about 3,075 sf (3/2)include a full 'daylight' basement. guest home is 840 sf (2/1)and studio-loft is about 600 sf. 30 magical acres of privacy yet only five minutes to the Healdsburg Plaza. There is over 2,000 feet of Felta Creek frontage and a natural plunge pool in Felta Creek at the waterfall. The enchanting property offers a main residence centrally located on the property and surrounded by scenic vistas. Enjoy stunning views of Fitch Mountain and Mount Saint Helena, and an elevated pond, which comes complete with state permits. The property also boasts an alternate homesite with elevated views, offering endless possibilities. Wander through the majestic redwood grove by the creek, an ideal spot for barbecues and picnics. The historic 1,100 red barn. From the kitchen window, enjoy sweeping views of a serene 3-4 acre meadow. Just a short 600-foot walk leads to West Side School, one of the top-rated rural schools in Sonoma County, making this a family-friendly gem. The charming 1910 home has good bones offering potential for renovation and personalization.

832 Brown, a charming single-level +-1,729 square foot three-bedroom, two-bathroom fixer, awaits your loving touch in the heart of downtown Healdsburg. Nestled on a spacious corner lot just a few blocks from the square, this property offers incredible upside potential for you to create your own unique vision. With plans already drawn and permits in hand, this remodel is ready to be transformed into a dream home. Don't miss out on this extraordinary opportunity!

Exquisite 4 bedroom residence with separate 1 bedroom/1 bath ADU situated on approx .3 acres. Recently completed in 2021, this home is an oasis close to the Healdsburg Plaza. The main residence features soaring ceilings, a dramatic centerpiece fireplace, architectural suspended staircase, walls of windows, a sleek modern kitchen with grey tone cabinetry and Miele appliances. The floor plan is ideal comprising 4 bedrooms and 3.5 baths, spacious executive office, chef's kitchen with adjacent breakfast room, large butler's pantry, elegant dining room and living room ideal for entertaining. Strong design elements with soft imbued colors and textures throughout. French doors open to the patio and pergola - an ideal place to put a pool, if desired. The Guest Studio/ADU is great for extended family, guests or caregiver as it includes a spacious bedroom and bathroom, full kitchen, laundry, living and dining area. The shared upper deck adjoins the main residence with the ADU. This home is a showcase of designer style and state-of-the-art construction. The elegant facade and landscaped grounds with the private gated rear driveway, make this a perfect fit for those attracted to sophisticated contemporary style with the convenience of an in-town walkable location.

Looking for the perfect project with privacy, views and room for all your country property dreams? Not far from downtown Healdsburg near Dry Creek Valley is this amazing opportunity with a single story home in Madrona Knolls. This is a small community of homes on large parcels just behind The Madrona. Ideal location where you can live in the country and still be just minutes to downtown Healdsburg. The tree lined driveway leads you to a mid-century style 3-bedroom home with two additional rooms and a 2-car garage. Sitting on 2.6 acres, with privacy, sunshine and views, the property has a pool and plenty of options for your country property dreams. Pastures for animals or just a buffer from neighbors, enclaves of gardening plots where you can grow vegetables and herbs or flowers. An orchard of fruit trees towards the front of the property and a wall of olive trees. All of this and a large metal barn that would make a perfect workshop, entertaining space or place for all your hobbies. Remodel the home or bring your new ideas and start fresh. Endless possibilities.

A blank canvas awaits for your own design elements in the highly sought after Healdsburg neighborhood of Fitch Mountain Villas. All the exterior of this home has been updated; new cement siding, new roof and new windows - which allows for the next owner to enjoy all the beautification pleasures of updating the original yet clean interior. Situated on a quiet street only a few steps away from the neighborhood pool, hot tub, tennis/pickleball/bocce courts, private walking paths and lawned open spaces. The spacious private backyard backs up to 148 acres of beautiful open space where you'll find families of deer roaming in the grassy rolling hills. The primary bedroom has high vaulted ceilings and private deck that overlooks the gorgeous natural serenity of the open meadows. Come see why so many new neighbors are calling Fitch Mountain Villas their Healdsburg neighborhood and build significant equity in the joys of a straight forward aesthetic remodel project. 575 Fieldcrest awaits your enjoyment.

Welcome to your dream oasis perched atop a picturesque hill, where luxury meets tranquility! This stunning home boasts breathtaking views and is just a stone's throw from the vibrant Healdsburg plaza. Enter through a gated entry to discover a harmonious blend of sophistication and comfort. Step inside to find an expansive main-level primary suite that feels like a personal retreat, complete w/a spa-like bathroom featuring a soaking tub, a grand shower adorned with custom tile, and an oversized walk-in closet. The family room, adorned with wood-beamed ceilings, opens seamlessly to the gourmet kitchen, showcasing high-end appliances, a farmhouse sink, and abundant storage perfect for culinary adventures. Exquisite wood work throughout adds a bespoke touch, while the cozy living room, complete with its own fireplace, invites relaxation. Enjoy the tranquility of the nearby 155-acre nature preserve and the proximity to world-renowned wineries all while savoring amazing private outdoor spaces ideal for entertaining. plenty of room for a pool. Be sure not to miss the lower level tepmerature controlled wine cellar complete with tasting area. Adjacent lot available, possible ADU/compound? With a 3-car garage and ample parking, this home is not just a residence; it's a lifestyle.

New construction and ready to move in. Owner financing available. Custom 3,000-square-foot elegant home located in the heart of Healdsburg's Wine Country. This beautiful four-bedroom, 3.5-bathroom home features a modern and spacious floor plan with dramatic open two story vaulted ceilings in dining and family areas, white quartz countertops, Bettazzoni appliances, an island breakfast bar, pantry closet, White Oak hardwood floors, two luxurious primary bedrooms, walk-in closets in every room, laundry room, and EV and Solar ready and installed. This open and airy home is perfect for entertaining guests.

The Studio at Mill District offers a rare opportunity to own a stunning one-of-a-kind furnished residence in the heart of Healdsburg, the premiere wine country destination of Northern California. This professionally designed pied-a-terre features an expansive great room, exquisite interior design and luxury furnishings which are included in the sale. The Studio boasts handsome custom cabinetry that elevates the room's aesthetic and masterfully integrates a murphy bed, closet storage and illuminated display area. A full gourmet kitchen, featuring premium Miele appliances, makes entertaining seamless when hosting an intimate dinner party or cocktails on the patio. The spa-like bathroom, private terrace, built in laundry, custom storage, secured interior access, deeded underground parking and assigned storage room add to the convenience and luxury of this residence. An extensive list of pre-and post-construction, investment-level upgrades set it apart and provide lasting value. The quiet Northeast-facing location offers bright morning light. Discerning buyers will appreciate the superb design, attention to detail, and the convenience of downtown urban living in this beautifully furnished and luxuriously spacious studio that's ready now.

Prime Development Opportunity in Healdsburg! Be part of Healdsburg's future while honoring its past with this rare development opportunity in Sonoma County's renowned wine country. Available for the first time in 50 years, this local family whose blue-collar legacy helped shape Healdsburg, spans over 3.17 acres across three contiguous APNs. Ideally positioned at the beginning of Bailhache Avenue on the outskirts of Healdsburg, this land carries the spirit of the community's roots, blending tradition with growth potential. Nestled next to a former quarry slated for future development, this property is strategically zoned with both industrial and rural residential designations, allow for a range of transformative uses. Existing on the land are four workshops/warehouses and nine residential dwellings of varied sizes, creating endless potential for a mix of multifamily residential or boutique hospitality projects. This is more than just a parcel of landit's a chance to contribute to Healdsburg's evolving story while honoring the hardworking families who built it. Don't miss the opportunity to create a vibrant future on this historic foundation. Secure your legacy in Healdsburg today.

Presenting an extraordinary opportunity at Canopy, where luxury, design, and nature converge. Nestled in the heart of Healdsburg's vibrant Mill District, Penthouse C401 offers a rare, full-floor residence designed by world-renowned AD100 firm Olson Kundig. With sweeping views of downtown Healdsburg and Fitch Mountain, this penthouse represents the pinnacle of refined wine country living. Spanning over 3600 sqft with 11'6 ceilings, C401 features floor-to-ceiling windows and sliding glass walls that create a seamless connection between the sophisticated interior and the expansive 2,006 sq. ft. terrace. Equipped with a full outdoor kitchen and generous dining and lounge areas, this penthouse is designed for unparalleled indoor-outdoor living and entertaining. Interior features include Italian-made MandiCasa cabinetry, Miele appliances, temperature-controlled wine storage, Waterworks fixtures, natural stone countertops and wide-plank hardwood throughout. Mill District will soon feature a high-end boutique hotel and private amenities complete with a fitness center and pool. With just a limited number of residences, this is a rare opportunity to own a home that blends rustic sophistication, urban vibrancy, and nature's beauty in one of the world's most coveted wine regions.

Discover this custom home designed and built using a locally renowned architect and interior designer, just one block away from the vibrant Healdsburg Plaza. This exquisite 3400 sqft, 5-bed, 4-bath residence offers flexible space to accommodate family and guests. A fusion of modern elegance and classic sophistication, ideal for those seeking both tranquility and convenience. Bask in the spaciousness of the great room where flowing rooms seamlessly connect and enjoy the sleek design and extensive use of marble, reclaimed wood, stained concrete, and iron. Two sets of French doors open onto an outdoor oasis, recently upgraded landscape with mature trees, climbing vines, outdoor lighting, a cozy fire pit and two picturesque arbors, perfect for intimate gatherings or quiet reflection. The primary bedroom, with its own French doors leading to a generous veranda, is a sanctuary complete with a spa-like bathroom featuring a soaking tub and large walk-in closet. Ascend to the 2nd primary suite with separate entrance. The home also offers an executive office, perfect for working remotely. Just one block from the heart of Healdsburg Plaza, experience the convenience of being steps away from world-class dining, boutiques, and cultural experiences.