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$829,000
5 Beds ⋅ 5 Baths ⋅ 326064237 MLS ⋅ ACTIVE Status
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 ⋅ ACTIVE Status
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 ⋅ ACTIVE Status
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
$795,000
3 Beds ⋅ 1 Baths ⋅ 326062859 MLS ⋅ ACTIVE Status
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 ⋅ ACTIVE Status
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
$1,875,500
3 Beds ⋅ 2 Baths ⋅ 326060892 MLS ⋅ ACTIVE Status
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 ⋅ ACTIVE Status
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
$995,000
4 Beds ⋅ 3 Baths ⋅ 326056672 MLS ⋅ ACTIVE Status
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 ⋅ ACTIVE Status
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 ⋅ ACTIVE Status
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
$925,000
4 Beds ⋅ 3 Baths ⋅ 326055787 MLS ⋅ ACTIVE Status
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 ⋅ ACTIVE Status
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 ⋅ ACTIVE Status
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 ⋅ ACTIVE Status
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
$1,100,000
2 Beds ⋅ 2 Baths ⋅ ML82051891 MLS ⋅ Active Status
HEADLINE: THE BLANK CANVAS | 7.6 Acres | Mill Creek | Healdsburg | Just Reduced $100K PROPERTY SUMMARY: Sometimes the best properties aren't the ones with all the answers. They're the ones that ask the right questions. This is 7.6 acres of oak-studded hillside along Mill Creek in one of Healdsburg's most exclusive residential enclaves. Surrounded by estates valued $3M+, this property offers raw potential at an honest price: just reduced to $1,100,000. Eight minutes from downtown Healdsburg. A world away from everything else. You get a clean slate: 1962 structure to reimagine or demolish, development-ready zoning, and no inherited infrastructure complications. What you do with it? That's yours to decide. Septic tested and approved. Water sourcing requires independent verification with Sonoma County and licensed professionals. For the builder who understands land.

2346 Mill Creek Lane, Healdsburg
$769,000
2 Beds ⋅ 2 Baths ⋅ 326019417 MLS ⋅ ACTIVE UNDER CONTRACT Status
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 ⋅ ACTIVE Status
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 ⋅ ACTIVE UNDER CONTRACT Status
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 ⋅ ACTIVE Status
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 ⋅ ACTIVE Status
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 ⋅ ACTIVE Status
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 ⋅ ACTIVE UNDER CONTRACT Status
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
$13,500,000
4 Beds ⋅ 5 Baths ⋅ 326040209 MLS ⋅ ACTIVE Status
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 ⋅ ACTIVE Status
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
$1,095,000
3 Beds ⋅ 2 Baths ⋅ 326041198 MLS ⋅ ACTIVE Status
Downtown Healdsburg Gem | Blocks to Healdsburg Plaza Location is everything, but privacy is the ultimate luxury. Tucked back from the street, this 3-bedroom, 2-bathroom residence offers an unexpected level of seclusion and quiet just blocks from the Healdsburg Plaza and everything it has to offer. The interior is defined by an effortless, open-concept flow. The kitchen offers a versatile layout with the perfect footprint to add a custom center island, and transitions seamlessly into a generous common room. This flexible space easily accommodates a large dining table or additional lounge seating, while dual doors lead to the exteriorallowing the home to live much larger than its footprint and pulling natural light into every corner. Both guest bedrooms are situated off the front living area, while the primary suite is thoughtfully tucked away at the rear of the home to ensure maximum privacy. Twin patios lead directly off the kitchen, creating a seamless transition for indoor-outdoor living. An additional slightly elevated concrete patio near the garden beds, providing many spaces for lounging and outdoor dining. A spacious driveway ensures effortless arrivals and complements the oversized two-car garage.

824 Prince Ave, Healdsburg
$7,495,000
3 Beds ⋅ 4 Baths ⋅ 326039588 MLS ⋅ ACTIVE Status
Exceptional 23 acre Healdsburg estate showcasing approximately 1,500 feet of private Russian River frontage with direct river beach access in the heart of Sonoma County. Rarely does a property offer such an extraordinary combination of extensive private waterfront, complete privacy, breathtaking natural beauty, and enduring legacy value just minutes from downtown. A long private drive meanders through a spectacular landscape of heritage oaks, towering redwoods, native flora, and dramatic rock outcroppings before arriving at a refined riverfront residence gracefully positioned on a peaceful knoll above the river. Designed for understated luxury and seamless indoor-outdoor living, this turnkey residence offers three bedrooms, three-and-one-half baths, curated interiors, bespoke finishes, and timeless board-and-batten architecture that blends harmoniously with its surroundings. The estate's defining feature is its unparalleled connection to the Russian River. Private frontage and direct beach access create an exceptional waterfront retreat for swimming, kayaking, paddleboarding, fishing, and beachfront entertaining. The tranquil riparian setting lives like a private nature preserve, where songbirds, hawks, seasonal waterfowl, and the gentle rhythm of the river create an atmosphere of complete serenity. Designed for recreation and relaxation, the grounds feature curated gardens, a productive fruit orchard, greenhouse, classic redwood barn, private golf practice hole, expansive meadows, and one of California's most remarkable landmark trees a magnificent State Champion Pecan Tree. Enhancing the estate's remarkable privacy, more than 750 acres of permanently protected open space stewarded by the Sonoma Land Trust adjoin the property, preserving the surrounding landscape and providing an extraordinary natural buffer that is increasingly rare in Wine Country. A separate elevated 1 acre parcel with views toward Mount St. Helena offers the potential to create a family compound with a second residence and guest house, further enhancing the estate's flexibility and long-term value. A truly rare offering, this premier riverfront estate combines exceptional privacy and timeless natural beauty for a true legacy property in Healdsburg.

6225 W Soda Rock Ln, Healdsburg
$475,000
1 Beds ⋅ 1 Baths ⋅ 326040326 MLS ⋅ ACTIVE Status
Cute as a button! A perfect vacation house or starter home tucked away by the Russian River on Fitch Mountain, this 1946 cottage has been restored and updated for easy living. Walking distance to the river and hiking trails, close to everything Healdsburg has to offer. One bedroom, one bath, 650 square feet on the main level, plus a loft that adds real living space beyond the listed square footage. With a new roof, recent paint, new carpet, and tile bathroom with a claw-foot tub, the work's already done. Enjoy the covered porch wrapped in fragrant star jasmine. The back doors open to a private, fenced yard with decks, a picnic spot, and an outdoor shower for rinsing off after a day at the river. Forced-air heat and an on-demand water heater cover the essentials. No HOA and no shared walls - just easy living in an eclectic river community. A place to steal away for vacation or to enjoy every day.

2167 Redwood Dr, Healdsburg
$997,000
2 Beds ⋅ 2 Baths ⋅ 326039529 MLS ⋅ ACTIVE Status
Welcome to the desirable Riverside 55+ community! This beautifully renovated 2 bedroom, 2 full bath home is completely move-in ready with stylish updates throughout. Enjoy fabulous tiled bathrooms, a beautifully updated kitchen, spacious living areas, and a large yard perfect for relaxing or gardening. Located in a peaceful neighborhood, 309 Mountain View Drive offers comfort, charm, and easy living all in one perfect package.

309 Mountain View Dr, Healdsburg
$1,650,000
3 Beds ⋅ 3 Baths ⋅ 326036825 MLS ⋅ ACTIVE UNDER CONTRACT Status
Prime Healdsburg Living Meets Incredible Potential. Nestled in the coveted Greens neighborhood, 410 Tee Drive presents a rare opportunity to secure a substantial 2,686 square foot residence in one of Healdsburg's most established enclaves. Featuring a classic wrap around porch and a floor plan designed for effortless flow, this home serves as the perfect canvas for your modern vision. The main level offers multiple living spaces designed for flexibility, anchored by a fireplace that adds warmth to the home's original character. The kitchen flows seamlessly to the backyard, making it an ideal setup for indoor-outdoor entertaining. Upstairs you will find the primary suite with a spacious bathroom featuring a shower and soaking tub, plus a walk-in closet. Two additional bedrooms and a second full bathroom also live upstairs. The oversized two-car garage includes a built-in workshop, while a separate mudroom and utility room complete with a full bathroom is conveniently located between the garage and the main house. The expansive backyard is a gardener's dream, featuring established citrus and fruit trees, a large deck, and dedicated space for a farm-to-table kitchen garden. Whether you are enjoying everything the Healdsburg Plaza has to offer, teeing off at Tayman Park, or exploring the Russian River or trails of Fitch Mountain, the location is truly second to none. Live comfortable in this home or bring your vision to transform this spacious property into your dream home.

410 Tee Dr, Healdsburg
$2,399,000
3 Beds ⋅ 2 Baths ⋅ 326037963 MLS ⋅ ACTIVE Status
Just 2.5 blocks from the heart of the Healdsburg Plaza, the iconic A.W. Garrett House is a rare offering an exquisitely restored 1895 Queen Anne Victorian that blends timeless architectural beauty with modern luxury. Recognized as one of the most ornate and notable examples of Queen Anne cottage architecture in the area, this single-story residence showcases extraordinary period craftsmanship, including a signature turret, gabled rooflines, decorative bargeboard and gable bracing, stained glass windows, intricate sawn detailing, turned columns, and an expansive wraparound verandah that defines its striking curb appeal. Inside, soaring ceilings, rich oak hardwood floors, and beautifully preserved historic character are complemented by thoughtful updates throughout. The chef's kitchen features quartz perimeter countertops, black granite on the island, a 36'' Viking gas range, KitchenAid Professional built-in refrigerator and dishwasher, and elegant finishes designed for both everyday living and entertaining. Updated bathrooms offer quartz countertops and Hansgrohe fixtures, while additional highlights include a full basement, laundry room, beautifully landscaped grounds, a detached two-car garage, and a versatile flex space above the garage ideal for a studio, office, or guest overflow. Lovingly restored with today's conveniences while honoring its architectural legacy, this exceptional downtown Healdsburg property offers a truly rare opportunity to own a landmark home in one of wine country's most sought-after locations.

401 Matheson St, Healdsburg

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