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$829,000
5 Beds ⋅ 5 Baths ⋅ 326064237 MLS
New co-ownership opportunity: Own one-eighth of this turnkey home, professionally managed by Pacaso. The Hollow occupies 3.3 acres on West Dry Creek Road in Healdsburg, where the H-shaped single-level floor plan and distinctive butterfly roof give the property an architectural identity that stands apart in Dry Creek Valley. The sustainable design integrates natural materials and passive light throughout, with glass doors on both sides of the structure connecting every room to the terraced decks and gardens beyond. The great room has vaulted beamed ceilings, light tile floors and a statement chandelier, with the open plan living and dining areas flowing naturally toward the outdoors. The kitchen has dark hardwood floors, a wall chimney hood, stainless steel appliances and a large island with bar seating. Five bedrooms each have their own private outdoor access and en suite baths, with the primary suite opening directly to the rear terrace. The pool, hot tub, outdoor kitchen and pergola anchor the rear terraced deck, with the surrounding acreage giving the property a quiet, private quality that is rare this close to Healdsburg's town square. Downtown Healdsburg's restaurant row on the plaza, the Saturday Healdsburg Farmers Market and the tasting rooms of Dry Creek Valley are all within easy reach. The Hollow is fully designed, furnished and managed by Pacaso. Owners arrive to find the home exactly as it should be, every time.

2252 W Dry Creek Rd, Healdsburg
$2,995,000
4 Beds ⋅ 4 Baths ⋅ 326063620 MLS
Experience a modern Wine Country retreat designed for effortless weekends, extended stays, and entertaining in Healdsburg. This exceptional custom-built home offers the rare opportunity to own new construction in one of Northern California's most desirable destinations, pairing contemporary design with a relaxed setting just minutes from downtown. Offering 4 bedrooms, 3.5 bathrooms, and 2,843 square feet, the home provides the space and flexibility to gather with friends, host family, work remotely, or simply escape the pace of the city. The dramatic great room features soaring cathedral ceilings, a sleek fireplace, and expansive windows framing peaceful hillside views. French oak flooring, contemporary lighting, and curated designer details create a warm, sophisticated aesthetic throughout. At the heart of the home, the kitchen features a 48-inch double-oven gas range, two additional wall ovens, a butler's pantry, custom cabinetry, and a waterfall island with bar seating. The adjoining dining and living areas open to a spacious view balcony, creating a seamless connection to the outdoors. A climate-controlled wine alcove offers an elegant display for your collection, with additional lower-level space providing room for expanded wine storage. The flexible floor plan includes a spacious en suite bedroom on the main level, ideal for guests, multigenerational living, or a private office. Upstairs, the primary suite is a peaceful retreat with a large private balcony, soaking tub, oversized shower, and walk-in closet. Two additional bedrooms provide comfortable accommodations for family and guests. Outside, the natural landscape offers a serene backdrop and the opportunity to make the property your own, whether that means a pool, expanded patios, or terraced gardens. Additional highlights include owned solar, several fruit trees, and a three-car garage. With new construction, modern systems, generous entertaining spaces, and the flexibility to lock up and leave when life calls you back to the city, the home is particularly well suited to a Wine Country lifestyle without the upkeep and renovation demands of an older property. Downtown Healdsburg's celebrated restaurants, tasting rooms, boutiques, and vibrant energy are just minutes away, making it easy to arrive for the weekend and immediately settle into everything that makes Northern Sonoma County such a compelling place to be.

1580 Clear Ridge Dr, Healdsburg
$895,000
3 Beds ⋅ 3 Baths ⋅ 326062731 MLS
Discover effortless Wine Country living in the highly sought after Fitch Mountain Villas. This beautifully maintained 3 bedroom, 2.5 bath townhome offers approximately 1,724 square feet of thoughtfully updated living space just minutes from the Healdsburg Plaza, renowned wineries, exceptional dining, and boutique shopping. Thoughtfully refreshed with today's buyer in mind, the home features new exterior paint, a new driveway, newer luxury vinyl plank flooring, fresh interior paint, freshly painted kitchen and wet bar cabinetry, new quartz countertops in both the kitchen and wet bar, a new stainless steel sink, stainless steel appliances, updated interior light fixtures, new exterior light fixtures, and accent landscape lighting. Together, these improvements create a move in ready home with timeless appeal. Designed for both everyday living and entertaining, the spacious floor plan offers generous living and dining areas complemented by a convenient wet bar. Upstairs, the vaulted primary suite provides a bright and inviting retreat with a walk in closet and abundant natural light. Step outside to your own private, fully fenced backyard retreat featuring a large wood deck with built in bench seating, mature trees, and exceptional privacy, an ideal setting for morning coffee, outdoor dining, entertaining, or relaxing with a glass of local wine. In years past, the deck has also provided a memorable vantage point for Healdsburg's Fourth of July fireworks. Residents of Fitch Mountain Villas enjoy the ease of low maintenance living, with front yard landscaping maintained by the HOA, along with resort style amenities including a swimming pool, spa, tennis and pickleball courts, bocce ball, scenic walking trails, and beautifully maintained grounds, all with one of Healdsburg's most affordable HOA dues. Whether you're searching for a full time residence, a weekend Wine Country getaway, or an investment opportunity, this is a rare opportunity to own a thoughtfully updated home in one of Healdsburg's most desirable communities, offering the perfect blend of move in ready comfort, low maintenance living, and Wine Country charm.

566 March Ave, Healdsburg
$4,650,000
3 Beds ⋅ 4 Baths ⋅ 326063402 MLS
Residence A102 boasts exquisite Italian-made MandiCasa cabinetry, premium Miele appliances, temperature-controlled wine storage, Waterworks fixtures, natural stone countertops, and wide-plank hardwood flooring. The home features an impressive 18-foot vaulted ceiling and expansive floor-to-ceiling windows. Sliding glass walls open to reveal a generous 645 sq. ft. terrace, complete with a fully equipped outdoor kitchen and cozy firepit, perfect for gatherings with friends and family. The 10-acre Mill District community will also include a boutique hotel, a swimming pool, and a fitness center, elevating the overall living experience. Residence A102 is ready for immediate move-in, and model homes are now open for tours. Nestled in the heart of Healdsburg, the newly developed Mill District enclave offers a perfect blend of charm and sophistication. Just a short stroll from the picturesque central square bustling with Michelin-starred restaurants, tasting rooms, and vibrant art galleries, Canopy at Mill District presents a curated selection of spacious homes that seamlessly combine rustic elegance with modern urban flair. Enjoy luxurious finishes and resort-style amenities while immersing yourself in the beauty of the outdoors. Photos shown may be of the actual unit, a model home, or a similar residence within the building.

151 Sawmill Cir Unit #105, Healdsburg
$2,750,000
2 Beds ⋅ 3 Baths ⋅ 326059316 MLS
Canopy at Mill District offers a serene sanctuary designed by world-renowned AD100 architect Olson Kundig. Representing the last two-bedroom residence available for sale at Canopy, Residence A202 is a brand-new home offered fully furnished with curated Restoration Hardware pieces. Perfectly perched on the second floor, this residence features two bedrooms, two-and-a-half bathrooms, and a versatile den. The heart of the home is an open floor plan, with a gourmet kitchen flowing seamlessly into the living and dining areas. Large floor-to-ceiling sliding doors lead to the private balcony equipped with a built-in BBQ, making it the perfect place for morning sunrises and effortless indoor-outdoor living. The interior is defined by rustic sophistication and luxurious finishes, including Italian-made cabinetry, Miele appliances, stone countertops, and temperature-controlled wine storage. The primary suite serves as a true retreat, featuring a large walk-in closet, a spa-like bathroom with a soaking tub, and a dedicated desk area. The second bedroom also offers a walk-in closet and an ensuite bathroom with a walk-in shower. For added flexibility, the den is perfect for a home office, a fitness space, or a cozy second seating area, while a pantry and laundry room off the kitchen provide additional functionality. Designed for the exclusive use of Mill District residents, The Poolhouse brings luxury health and social amenities just steps from Canopy. Unwind along the expansive pool deck surrounding the private lap pool, or host guests in the magnificent Residents' Lounge featuring a fireplace, full kitchen, catering kitchen, and generous spaces built for entertaining. Complete with a state-of-the-art Fitness Center showcasing progressive strength, functional, and cardio equipment, this premier sanctuary redefines modern luxury living. Canopy at Mill District represents a rare opportunity to enjoy a meticulously designed home in the most desirable location in wine country.The 10- acre Mill District community will also include a boutique hotel, a swimming pool, and a fitness center. Located in the heart of Healdsburg, this home blends urban vibrancy with resort-like amenities. You are just a short walk from the charming plaza, Michelin-starred restaurants, and world-class tasting rooms. Photos shown may be of the actual unit, a model home, or a similar residence within the building.

171 Sawmilll Cir Unit #202, Healdsburg
$795,000
3 Beds ⋅ 1 Baths ⋅ 326062859 MLS
Beautifully updated 3 bedroom single level home within walking distance to Big John's Market, coffee, restaurants and wineries. The private back yard has room for a pool and possibly an ADU. Enjoy the generous garden area, multiple fruit trees (plum, apple, orange, fig, pear, loquat and olive). Tucked away on a private low use street, this peaceful setting is great for entertaining your family and friends.

232 Twin Oaks Way, Healdsburg
$1,150,000
1 Beds ⋅ 1 Baths ⋅ 326062255 MLS
Escape to your own private mountain retreat on 240 breathtaking acres designed for self-sufficient living, recreation, and unmatched privacy. This exceptional off-grid property is a rare opportunity for survivalists, outdoor enthusiasts, hunters, or anyone seeking a peaceful escape from the everyday. The property features a rustic 1-bedroom cabin with a loft, freshly painted inside and out, offering a comfortable base camp with spectacular mountain views. Powered by a solar energy system with battery storage, the property is designed for sustainable, independent living. A reliable spring-fed water system supplies multiple storage tanks, providing a reliable water source. A lookout tower offers sweeping views of the surrounding landscape, making it ideal for wildlife observation, security, or simply taking in the quiet. Whether you're looking to establish a working ranch, build a legacy retreat, enjoy outdoor adventures, or create the ultimate off-grid homestead, this remarkable property offers endless possibilities. Experience the freedom, privacy, and beauty that only a property of this scale can provide. Schedule your private tour today and discover this one-of-a-kind mountain sanctuary.

8890 Mill Creek Rd, Healdsburg
$1,250,000
1 Beds ⋅ 2 Baths ⋅ 326062589 MLS
A truly one-of-a-kind offering in Healdsburg, this striking commercial condominium combines sophisticated design, exceptional functionality, and a versatile loft-style layout unlike anything else currently on the market. A full-size garage door and separate pedestrian entrance open to an expansive ground-level space equipped with a commercial-grade car lift rated for up to 9,000 pounds, ideal for an automotive enthusiast, contractor, collector, creative studio, showroom, or private workspace. Upstairs, the beautifully designed loft features an ultra-modern interior finished with European oak flooring, custom lighting, and an impressive collection of brand-new appliances, including a Fisher & Paykel range and Miele dishwasher. The sleek kitchen also includes a reverse-osmosis water filtration faucet, while the shower is finished with distinctive brick-red McIntyre Tile sourced locally in Healdsburg. Thoughtful upgrades continue throughout with central HVAC, Lutron dimmable LED lighting, and an integrated high-end security and automation system installed by Healdsburg-based Lavish Automation. Through the Nice app, the owner can conveniently manage lighting, climate control, video surveillance, and additional smart-home features. Bold, refined, and exceptionally versatile, this rare Healdsburg property presents an extraordinary opportunity for a buyer seeking a highly customized commercial space with elevated loft-style amenities.

1229 Grove St Unit #2, Healdsburg
$1,875,500
3 Beds ⋅ 2 Baths ⋅ 326060892 MLS
Experience the timeless beauty of Sonoma County at this idyllic ranch-style farmhouse, gracefully set on approximately 1.47 acres just beyond the Healdsburg city limits. Surrounded by neighboring vineyards and a picturesque pond, this beautifully maintained property offers the perfect blend of country living, privacy, and close proximity to Downtown Healdsburg. The single-level residence features 3 bedrooms, 2 bathrooms, and 1,742+/- square feet of thoughtfully designed living space. The spacious living room is anchored by a fireplace and uniquely flows into the glass greenhouse that brings the outdoors in throughout every season. The generous kitchen and dining room are filled with natural light and overlook the lush grounds, creating an inviting space for everyday living and entertaining. The primary suite enjoys an en suite bathroom and access to the backyard and pool. Several outbuildings provide additional spaces that can be used in a variety of ways. Outside, every corner of the property has been thoughtfully cultivated. Towering redwoods provide a dramatic backdrop to the sparkling pool and expansive patio, while beautifully landscaped gardens, raised planting beds, and winding pathways invite exploration. Enjoy evenings beneath the pergola with the outdoor barbecue and dining area, or enjoy a cup of coffee under the redwoods. The fenced pasture, charming chicken enclosure, and mature gardens create an authentic Sonoma County lifestyle rarely found this close to town. Located just minutes from the renowned Healdsburg Plaza, world-class wineries, acclaimed restaurants, and boutique shopping, this exceptional property offers the tranquility of country living with the convenience of one of Wine Country's most sought-after destinations.

961 Chiquita Rd, Healdsburg
$1,495,000
4 Beds ⋅ 3 Baths ⋅ 326060906 MLS
Elevated above the neighborhood, this ridge top home offers views of vineyards, Mount Saint Helena, and Geyser Peak. Here is an opportunity to own a single level, 4 bedroom, 3 bath, 2,432 square-foot home on over 1/3 of an acre in the Parkland Farms area of Healdsburg. Beautifully updated kitchen with new cabinets, Quartz counters and stainless appliances. The primary suite is privately positioned featuring a soaking tub, separate shower, and generous walk-in closet. A small Cabernet hobby vineyard on the property completes the wine country experience.

290 Appaloosa Trl, Healdsburg
$2,925,000
2 Beds ⋅ 2 Baths ⋅ 326058591 MLS
Experience the pinnacle of Wine Country living in the heart of downtown Healdsburg with this exclusive condo hotel offering at The Residences at Alyvia. This limited collection of 12 luxury residential condominiums is seamlessly integrated within a full-service 53-room hotel within the emerging Mill District community. Each residence is legally mapped as a condominium, governed by a condominium association, and managed by the esteemed Mayacama Hospitality. Owners enjoy a highly personalized lifestyle, including a custom arrival experience in which the team pre-stocks their favorite refreshments, arranges their personal amenities prior to entry, and provides a licensed storage unit for personal belongings. The Alyvia advantage provides a rare connection to the prestigious Mayacama Golf Club. Ownership includes the opportunity to establish a membership with Charter-level access, providing preferred golf privileges for owners, their families, and guests. While in residence, owners enjoy priority spa and restaurant reservations, private cabana opportunities, and full access to the wellness center, including fitness and pool. Designed for both personal enjoyment and effortless ownership, this property under City entitlements utilizes a professional Rental Management Agreement. Revenue is shared through a transparent 50/50 split of net rental income. Monthly HOA dues of $1,386.25 conveniently cover all essential utilities, including water, electricity, gas, and internet. This is a legacy opportunity to own a piece of Healdsburg's finest hospitality. Views are representative of the building's offerings; actual views vary based on unit location.

180 Sawmill Cir Unit #405, Healdsburg
$995,000
4 Beds ⋅ 3 Baths ⋅ 326056672 MLS
Discover one of Healdsburg's best-kept secrets. Tucked away on the sunny side of South Fitch Mountain, just across from the Russian River and county beach, this remarkable property offers a rare combination of year-round sunshine, exceptional privacy, and timeless character just ten minutes from Healdsburg Plaza. Lovingly shaped by the same artist for more than 45 years, the home showcases handcrafted details including custom tile, stained glass, warm wood accents, and abundant natural light. Three distinct living spaces provide flexibility for extended family, guests, creative pursuits, or income potential. Terraced gardens, stone pathways, and inviting outdoor living spaces create a setting designed for both entertaining and quiet reflection. With immediate access to swimming and kayaking on the Russian River, this is more than a home, this is a place where privacy, nature, and creativity come together in one of Healdsburg's most unique settings.

2693 S Fitch Mountain Rd, Healdsburg
$450,000
2 Beds ⋅ 1 Baths ⋅ 326056715 MLS
This 80-acre estate borders 6,000 acres of state park, providing access to miles of trails for hiking, equestrian activities, and mountain biking. The property features a charming 1940s stucco cabin with a durable metal roof, situated in an amazingly quiet setting with sweeping views of Gray Creek Valley. The land includes access to East Austin Creek and is home to abundant wildlife. Designed for a low-impact, self-sufficient lifestyle, the property utilizes solar power, a composting toilet, gray water absorption gravel boxes, and gravity-fed spring water. It is an idyllic setting for relaxation and a rejuvenating retreat.

8868 Mill Creek Rd, Healdsburg
$4,495,000
4 Beds ⋅ 4 Baths ⋅ 326056166 MLS
On a small private drive, surrounded by the natural beauty of Dry Creek Valley, Tre Torrente estate invites a slower pace and a deeper connection to Wine Country living. Thoughtfully remodeled, the approximately 3,896-square-foot main residence exemplifies exceptional craftsmanship and high-end finishes. The heart of the home unfolds through curated living spaces, offering four bedrooms, four baths, and a dedicated office designed for both inspiration and productivity. Sunlight pours through expansive windows, framing serene peek-a-boo views and creating a seamless connection between indoors and out. Imagine standing at the kitchen sink while overlooking rows of vines and stately oaks. Beyond the main residence, the expansive agricultural barn offers a charming, and well-appointed guest cottage on one end and a substantial office space on the other; ideal for remote work, creative pursuits, or managing a vineyard lifestyle. Outside, the enchanting property reveals its true magic. Meandering walking trails wind through the grounds, inviting morning strolls along one of the three seasonal streams and evening walks as the sun sets over the valley. Abundant water resources nurture lush landscaping, flourishing lawns, and raised planting beds ready for bountiful harvests. At the center of it all, a sparkling pool provides the perfect setting for warm afternoons, where golden light lingers a little longer and vineyard breezes drift through the trees. Loved ones gather around the firepit and lasting memories are made.

5519 Dry Creek Rd, Healdsburg
$7,295,000
3 Beds ⋅ 4 Baths ⋅ 326056014 MLS
B402 is the final opportunity to acquire a penthouse within Mill District's luxury residential community. Masterfully envisioned by Olson Kundig, the architecture prioritizes elevated design, privacy, and a seamless indoor-outdoor cadence, beautifully capturing dual East and West exposures that bathe the interiors in natural light from sunrise to sunset. The centerpiece of the expansive living space is a professional-grade chef's kitchen, anchored by an oversized kitchen island that comfortably accommodates seating for six stools. This culinary hub is equipped with integrated Miele appliances and complemented by a dedicated connoisseur's wine room. Adjacent to the kitchen, a grand living room centers around a striking contemporary fireplace, where floor-to-ceiling glass transitions effortlessly to an expansive private terrace featuring a premium outdoor kitchen tailored for sophisticated al fresco entertaining. Meticulously composed for both grand hosting and daily retreats, the residence offers three generous en-suite bedrooms, a refined private study, and a separate laundry room with a side-by-side washer and dryer. As owners at Mill District, residents have access to The Poolhouse, a private social, health, and wellness facility located just steps from Canopy. Centered around a private lap pool and expansive pool deck, it features a state-of-the-art gym and a Residents' Lounge complete with a demonstration kitchen, a catering kitchen, a fireplace, and generous spaces for socializing, entertaining, and hosting events. The lounge seamlessly opens onto a large terrace with an outdoor barbecue and dining areas overlooking the pool, perfectly integrating the indoors and outdoors to best enjoy the temperate wine country climate. Located just a short stroll from Healdsburg's iconic central square, this home offers immediate access to Michelin-starred dining and world-class tasting rooms.

151 Sawmill Cir Unit #402, Healdsburg
$925,000
4 Beds ⋅ 3 Baths ⋅ 326055787 MLS
Step outside, and the story unfolds in soft morning light filtering through the trees, carrying the fragrant breath of nearby vineyards. Welcome to charming Parkland Farms in coveted Healdsburg, where rolling hills embrace surrounding vineyards and Barbieri Park adds a serene touch of neighborhood beauty. Imagine coming home to this enchanting two-story residencenearly 2,000 square feet of warmth and possibility. A graceful 4-bedroom, 2.5-bath haven with wood-look flooring and soft carpeting, thoughtful original touches, and a inviting fireplace glowing in the great room. Natural light pours generously through the windows, while a versatile landing at the top of the stairs awaits your vision as flex-space. A spacious cement patio with open beams overlooks a blank-slate yard, ready for you to craft your personal Sonoma County oasis. Nestled mid-block and just minutes from the historic plaza, this home offers the perfect blend of comfort and connection. Whether you seek a cherished starter home, a wise investment, or a peaceful second residence, its move-in ready, brimming with immediate potential. Beyond your door, Dry Creek and Alexander Valley beckon with world-renowned wineries and intimate tasting rooms. The plaza pulses gently with farmers' markets, acclaimed Michelin-starred dining, and the unhurried cadence of wine country days. Russian River adventures, boutique shops, and farm-to-table experiences lie within easy reach. Conveniently located north of the San Francisco Bay Area, Healdsburg provides swift access to Sonoma County Airport (STS) and a scenic drive to San Francisco International (SFO). Here, refreshed possibility meets the timeless romance of Sonoma's vineyards, trails, and heartfelt community rhythman invitation to breathe deeper, create lasting memories, and let this special place write the next beautiful chapter of your story.

1715 Spur Ridge Ln, Healdsburg
$1,995,000
4 Beds ⋅ 3 Baths ⋅ 326054444 MLS
Under 15 minutes from the Healdsburg Plaza yet a world away in feel, this 6-acre retreat sits on West Dry Creek Road, one of the region's most coveted stretches. Turn off the road and the quiet settles in your chest. Taken down to the studs and rebuilt, it lives like new construction inside a true Wine Country setting. Inside, open-plan living looks out to the valley yet still feels warm and intimate the kind of space that gathers everyone in one place and never feels cavernous. The custom kitchen is built for real cooking and entertaining, with a Thermador suite, a 100-bottle wine fridge, and storage everywhere you look, from the deep drawers to the generous walk-in pantry and a mud room that keeps daily life tidy. The primary suite is a quiet escape with its own spa-like bath and heated floors, while three additional bedrooms give family and guests room to spread out. Dog lovers will appreciate the dedicated dog-wash room one of many thoughtful touches. Outside, 6 acres give rare room to roam with genuine privacy and an outdoor entertaining area framed by valley views. A turnkey blend of total renovation, real acreage, and true privacy, all just minutes from the Healdsburg Plaza!

3229 W Dry Creek Rd, Healdsburg
$7,995,000
6 Beds ⋅ 4 Baths ⋅ 326054898 MLS
Falcon Highlands Ranch is a remarkable 270-acre legacy estate overlooking Lake Sonoma, where extraordinary privacy, protected landscapes, and decades of thoughtful stewardship create an offering rarely found in Northern California. Bordering thousands of acres of protected public lands, the ranch enjoys an exceptional sense of open space and seclusion while remaining within easy reach of Healdsburg's celebrated wineries, restaurants, and amenities. This property includes 3 legal parcels offering flexibility to add to what is already here and create your own compound or retreat. This ranch offers over a mile of Lake Sonoma frontage with direct lake access, gentle oak-studded meadows, redwood forests, panoramic views, a permitted pond, miles of all-weather ranch roads, and extensive infrastructure developed over generations. Improvements include a barn with spacious living quarters, a guest house, yoga studio, equipment barn, horse facilities, productive wells, and a sophisticated off-grid power system utilizing solar energy, battery storage, generators, and wind-powered water systems. Falcon Highlands Ranch was intentionally designed for privacy, independence, and long-term land stewardship. More than 40,000 redwood trees have been planted as part of an ongoing forest management plan created by the owner, reflecting a decades-long commitment to caring for the land while creating a truly self-sufficient mountain estate. Whether envisioned as a private family compound, nature retreat, recreational ranch, or exceptional long-term land investment, Falcon Highlands Ranch offers an opportunity to for you carry the legacy forward with one of Sonoma County's most remarkable private estates.

13451 Rockpile Rd, Healdsburg
$4,800,000
4 Beds ⋅ 4 Baths ⋅ 326054301 MLS
Set atop a private ridge overlooking Alexander Valley, this gated 44.08 acre estate captures sweeping views of Mount St. Helena, vineyards, and rolling hillsides from nearly every room. The 4,630 sq ft residence is designed to embrace its surroundings with floor-to-ceiling windows, expansive living spaces, and seamless indoor-outdoor flow. The chef's kitchen features custom walnut cabinetry and granite countertops, while the main-level primary suite offers a private retreat with soaring ceilings, separate entrance, soaking tub, and travertine shower. Upstairs are three additional bedrooms, two full baths, and a flexible media room. Outdoor amenities include expansive entertaining decks, a built-in cook station, open-air fireplace, and custom saltwater pool. The property features approximately 8 acres of vineyard, an olive orchard, two private wells, solar power with battery backup, fire-safe water storage, and a detached garage/workshop. Offering privacy, sustainability, and breathtaking scenery just minutes from Healdsburg, this exceptional Alexander Valley estate embodies the best of Sonoma County wine country living.

5232 Maacama Ridge Rd, Healdsburg
$499,000
2 Beds ⋅ 1 Baths ⋅ 326054152 MLS
Welcome to this beautifully updated, light-filled end-unit condominium nestled in one of Healdsburg's most desirable communities. Offering the perfect blend of comfort, style, and convenience, this exceptional residence is just moments from the vibrant Healdsburg Plaza. Featuring two spacious bedrooms and one bathroom, the home is designed for easy living and effortless entertaining. Natural light pours through the windows, enhancing the inviting open floor plan, beautiful wood-look laminate flooring, new carpet, and thoughtfully updated kitchen with contemporary finishes. Step outside to your private deck just off the kitchen, where peaceful, park-like views create the perfect setting to enjoy your morning coffee or unwind with a glass of local wine in the evening. As a desirable end unit, the home offers additional privacy and an abundance of natural light throughout. Additional amenities include covered parking for one vehicle, a second assigned parking space, and convenient access to the community laundry facility. Ideally located within walking distance of the acclaimed Healdsburg Plaza, you'll enjoy easy access to award-winning restaurants, boutique shopping, renowned wineries and tasting rooms, seasonal farmers markets, and year-round community events. Low monthly HOA dues include sewer and garbage service, making this an outstanding opportunity to experience the relaxed luxury and charm of Healdsburg living.

426 North St Unit #14, Healdsburg
$769,000
2 Beds ⋅ 2 Baths ⋅ 326019417 MLS
A completely reimagined single-story home in Healdsburg's most sought-after 55+ community, and one of the best options in the market for Wine Country living. Positioned to face open space, every detail has been thoughtfully updated high-end flooring, crown molding, custom fireplace, remodeled kitchen with new appliances, wine bar with built-in refrigerator, and remodeled bathrooms. New windows, shutters, and an eight-foot sliding glass door open to the back patio. Fresh paint inside and out, new irrigation systems, and a true lock-and-leave lifestyle. With a recent price improvement and a per-square-foot cost well below the Healdsburg average, this turnkey home offers exceptional value in a community with a newly resurfaced pool, clubhouse, and direct Russian River access..all just minutes from the Healdsburg Plaza.

333 Orangewood Dr, Healdsburg
$8,495,000
4 Beds ⋅ 6 Baths ⋅ 326026293 MLS
Perched above the celebrated Dry Creek Valley, this extraordinary 55-acre estate commands sweeping panoramic views of Mount St. Helena, Fitch Mountain, and Geyser Peak. The elegant 6,300+ sq ft residence offers 4 bedrooms, 4 full bathrooms, 2 powder rooms thoughtfully designed to capture the breathtaking surroundings at every turn. The main residence also features a private first-floor one-bedroom, one-bathroom ADU complete with its own kitchen, dining room, and living room ideal for guests, a property manager, or extended family. A dedicated wine cellar rounds out this self-contained retreat, offering the perfect marriage of comfort and wine country living. Resort-style amenities include a sparkling pool, tennis and bocce court, with 9 acres of certified organic and biodynamically farmed vines and 800 olive trees speak to a true agrarian lifestyle. A 5,000 sq ft winery building with a 5,000-case permit completes this rare wine country offering all powered by solar energy. Freshly updated with a new roof and newly painted interior and exterior, this is Sonoma County wine country living at its finest. Sale includes home, attached ADU, 5K Sq foot Winery Production Building, Winery Equipment Seller's would like to lease back some of the vineyards for their wine brand.

2355 W Dry Creek Rd, Healdsburg
$859,950
3 Beds ⋅ 2 Baths ⋅ 325014268 MLS
Less than 2 miles north of Downtown Healdsburg. Single story 3 Bedroom/2 Bath lots of light and open floor plan. Back yard ideal for entertaining with access off dining room/kitchen. Large garage with shop area and stairs to upstairs storage in garage.

111 Philip Dr, Healdsburg
$4,250,000
4 Beds ⋅ 6 Baths ⋅ 326046452 MLS
Set amidst approximately 25 picturesque acres in the heart of Healdsburg wine country, this exceptional gated estate offers an unparalleled blend of luxury, recreation, and agricultural beauty. Designed for those who appreciate the Sonoma County lifestyle, the property combines vineyard living, resort-inspired amenities, and thoughtfully curated outdoor spaces into one remarkable offering. The single-story residence features five bedrooms and 3.5 bathrooms providing comfortable living and effortless indoor-outdoor flow. Numerous windows frame views of the surrounding vineyards, gardens, and rolling countryside, creating a sense of tranquility and connection to the land. Outdoor amenities abound. A stunning pool and spa create a private retreat for relaxation, while the brand-new pickleball/sport court invites friendly competition and active living. Gather with friends for a game of ptanque, stroll through the rose garden, or enjoy the fragrance and beauty of more than 200 newly planted lavender plants that enhance the property's charm. For those with agricultural interests, the estate offers approximately three acres of Zinfandel vines, a productive garden, greenhouse, and an innovative rainwater capture system designed to support sustainable farming and landscape irrigation. The grounds present an ideal setting for cultivating a boutique wine country lifestyle while enjoying the benefits of rural living. Additional improvements include a barn, temperature-controlled wine tasting room, and a detached two-car garage topped by a private one-bedroom ADU, perfect for guests, extended family, a caretaker, or a home office. The gated entrance provides privacy and security while creating a grand arrival experience. Whether hosting memorable gatherings, enjoying peaceful mornings overlooking the vines, or embracing the recreational amenities that make this property truly unique, this estate offers a rare opportunity to experience the very best of Healdsburg living. Surrounded by the natural beauty of Sonoma County and conveniently located near world-class wineries, restaurants, and the vibrant Healdsburg Plaza, this is more than a homeit is a lifestyle destination. A rare offering where luxury, sustainability, agriculture, and recreation come together on one extraordinary wine country estate.

22200 Puccioni Rd, Healdsburg
$4,500,000
7 Beds ⋅ 7 Baths ⋅ 326047173 MLS
In the heart of Alexander Valley, just past Jim town Store, we are pleased to present an exceptional compound offering endless possibilities. Whether envisioned as a full-time residence, a weekend retreat, or an income-producing property with space for guest accommodations or on-site management, this estate delivers both flexibility and charm. The main residence showcases a contemporary open floor plan with soaring ceilings and abundant natural light. The expansive primary suite, located on the main level, offers ultimate privacy and opens seamlessly to sweeping valley views, complete with its own serene fountain garden. Above, an open mezzanine with a full bath connects to a striking tower element, overlooking the grounds and the stunning 75-foot pool--truly the architectural centerpiece of the property. A spacious motor court anchors the compound, accompanied by a detached carport with a guest suite above, perfectly positioned to capture the surrounding views. Nearby, a charming Tutu's Cottage, a favorite among visiting grandchildren, offers a private, ground-level retreat. At the front of the property sits a fully independent, recently remodeled two-bedroom, one-bath cottage, currently tenant-occupied and ideal for rental income or extended guest use. On the other side of the main driveway, a grand vintage redwood barn on foundation is complemented by a separate tool shed, offering incredible potential for a car collection, workshop, storage, or game room. Across from the barn, a picturesque 1930s shingle cottage reminiscent of coastal homes in Mendocino features a formal garden and an inviting summer dining area. Just beyond, a charming standalone office provides a peaceful setting for work or creative pursuits. Completing the property are thoughtfully designed outdoor amenities, including a greenhouse, fenced vegetable garden, and an expansive steel pergola ideal for hosting gatherings, complete with a summer kitchen. Toward the rear, a partially shaded petanque court invites leisurely afternoons and abundant entertaining. Set across two parcels totaling just under 1.5 acres, this remarkable property offers a rare blend of character, versatility, and manageable scale in one of Wine Country's most desirable locations.

6017 Red Winery Rd, Healdsburg
$700,000
2 Beds ⋅ 3 Baths ⋅ 326046418 MLS
Discover an unparalleled sanctuary on 160 acres of pristine natural beauty along Austin Creek. Dating back to 1929 and purchased directly from the original homesteaders, this historic legacy property has been a cherished family retreat since 1991. The contractor-owner has meticulously maintained and upgraded the estate as a true labor of love.Offering the pinnacle of luxury glamping, the property features two distinct, privately situated cabins and a custom sauna-bathhouse. The bathhouse sits directly above a bountiful, spring-fed swimming hole perfect for a refreshing cold plunge set against the majestic backdrop of a massive, towering rock wall. Sharing a boundary line with the 6,000-acre Austin Creek Wilderness Area, this expansive acreage offers ultimate privacy with limitless potential, including ample room for additional tent cabins or custom improvements.

8800 Mill Creek Rd, Healdsburg
$1,149,000
5 Beds ⋅ 3 Baths ⋅ 326043689 MLS
Ideally located in Healdsburg's highly desirable Parkland Farms neighborhood, this spacious 5-bedroom, 3-bath home offers approximately 2,500 sq ft just minutes from the Healdsburg Plaza, renowned wineries, restaurants, shopping, parks, and scenic walking trails. Designed with both comfort and functionality in mind, the flexible floor plan features a full bedroom and bathroom on the main level, formal living and dining rooms, fresh interior paint, updated flooring, plantation shutters, and an open-concept kitchen, dining, and family room centered around a cozy gas fireplace. French doors lead to the backyard, creating seamless indoor-outdoor living. Upstairs, the generous primary suite offers a walk-in closet, soaking tub, and dual-sink vanity, while three additional bedrooms and an upstairs laundry room provide plenty of space for family or guests. Outside, enjoy a low-maintenance backyard complete with a built-in BBQ, outdoor kitchen, paver patio, detached two-car garage, and gated driveway, perfect for entertaining and everyday living. With its unbeatable location, versatile layout, and easy access to everything Healdsburg has to offer, this home is the perfect place to enjoy Wine Country living.

367 Arabian Way, Healdsburg
$715,000
2 Beds ⋅ 2 Baths ⋅ 326043516 MLS
Nestled at the end of a quiet cul-de-sac and just a few minutes' walk from the Healdsburg Plaza, this polished 2-bedroom, 1.5-bath condominium punches well above its square footage. Whether you're planting roots in Sonoma County, searching for a seamless second home, or adding a smart asset to your portfolio, 366 Piper delivers on all fronts. Natural light pours through every window, and the interior has been finished with a level of care you don't often see at this price point. The living room centers around a gas fireplace with a custom concrete mantel understated, warm, and genuinely stylish. In-wall TV wiring and a hydraulic wall mount handle the tech side without cluttering the space. The primary suite is calm and well-considered, with a ceiling fan, recessed lighting, and a full bathroom. A full-size vented washer and dryer are tucked neatly within the suite a small detail that makes a big difference day-to-day. Out back, a low-maintenance patio gives you an outdoor perch without the upkeep ideal if you're splitting time between properties and don't want a yard demanding your attention. The big-ticket items have already been handled: new roof, gutters, and hot water heater (all 2020), plus central air conditioning. The HOA replaced roofs and gutters community-wide in 2019 and has exterior improvements on the horizon, fully funded through reserves. Additional storage sits above the parking area. HOA fees cover management, exterior maintenance, and grounds so your weekends stay yours. Healdsburg's best restaurants, tasting rooms, and boutiques are a short walk away. This is the kind of place that just makes life a little easier.

366 Piper St, Healdsburg
$13,500,000
4 Beds ⋅ 5 Baths ⋅ 326040209 MLS
Located just minutes from downtown Healdsburg, this stunning architectural Wine Country estate crowns 20 acres at the gateway to Dry Creek Valley. A scenic drive leads to a dramatic arrival courtyard framed by fountains and gardens designed by Roche + Roche Landscape Architects. Masterfully designed by acclaimed architect Jeffrey Trapold and built in 2008 by award-winning builder JMA Jim Murphy & Associates, the estate artfully blends rural vernacular architecture with contemporary craftsmanship, positioned to capture cinematic views of Dry Creek Valley, Mount Saint Helena, Geyser Peak, and the surrounding vineyards. Soaring cathedral ceilings, expansive walls of glass, and seamless indoor-outdoor living define the residence throughout. Resort-inspired amenities include a swimming pool, spa, bocce court, fountains and beautifully curated gardens. Guests and family are comfortably accommodated in two detached poolside guest suites and a separate two bedroom guest cottage privately set along the drive. An extraordinary architectural estate where privacy, design significance, and breathtaking natural beauty converge in one exceptional Dry Creek Valley setting.

437 W Dry Creek Rd, Healdsburg
$15,500,000
3 Beds ⋅ 5 Baths ⋅ 326041867 MLS
Bell Mountain Ranch - A rare Sonoma wine country compound where luxury, terroir, and stewardship converge. Set at the base of Bell Mountain in the heart of Sonoma County, this extraordinary estate offers a complete wine country lifestyle across approximately 19 acres of Regenerative Organic Certified vineyard at the intersection of the Alexander Valley, Russian River Valley, and Chalk Hill AVAs. A private estate residence is perched on a knoll with expansive vineyard and valley views, complemented by a pool, guest accommodations, and outdoor living spaces designed for both relaxation and entertainment. At the entrance to the property, a separate five-bedroom residence currently serves as an office and meeting space, offering flexibility for extended living, staff housing, or additional guest use. The gated property unfolds through vineyard blocks, meadows, heritage oaks, and scenic natural landscapes, with three ponds, a seasonal creek, established water resources, and solar infrastructure supporting both sustainability and agricultural operations. Anchoring the estate is a purpose-built, +/-18,000 sq ft, three-level winery featuring full production infrastructure, a barrel cellar, and cave, supporting small-lot premium winemaking with approved capacity for up to 30,000 cases annually. Thoughtfully designed hospitality entitlements allow for by-appointment tastings, vineyard tours, and private events centered around a scenic tasting barn beneath mature oaks overlooking a tranquil pond. Bell Mountain Ranch represents a rare opportunity to acquire a fully integrated wine country estate that seamlessly combines luxury living, premium vineyard land, hospitality, and winemaking in one exceptional offering. As you'll see in the digitally altered photos and video-be sure to watch to the very end-Bell Mountain Ranch invites a broader vision. Imagine a private putting green overlooking Mount St. Helena, the tasting barn transformed into a clubhouse, and the winery reimagined as a climate-controlled gallery for a luxury car collection. Picture pickleball, tennis, and bocce courts nestled among the vineyards and heritage oaks. The residences could become a private members' retreat, creating an extraordinary destination in Sonoma Wine Country. Bell Mountain Ranch isn't just what it is today-it's what it's uniquely positioned to become.

13414 Chalk Hill Rd, Healdsburg