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$2,350,000
3 Beds ⋅ 3 Baths ⋅ 326034866 MLS ⋅ ACTIVE UNDER CONTRACT Status
Ten minutes from the Healdsburg plaza, at the quiet end of Eastside Road, fruit trees scent the air and the energy shifts the moment you turn onto the property. 10936 Eastside Road sits on 3.25 private acres at the end of a dead-end lane a single-level, approximately 1,840-square-foot home with 3 bedrooms plus a bonus room, 3 bathrooms, and a rare blend of privacy, wine-country setting, and resort-style outdoor living. The kitchen anchors the main living space with a generous island at its center, opening into a great room framed by vaulted ceilings and an open-concept layout built for gathering. The primary suite sits apart from the social core of the home quiet and peaceful, the kind of room that delivers a restorative night's sleep. Glass doors dissolve the boundary between the interior and the backyard, drawing the eye through the great room and out to the deck, pool, and grounds beyond. A new pool and spa anchor a backyard built for wine country living, complemented by a covered deck with a hanging swing overlooking the water and a dedicated bocce court set among mature fruit trees and open fields. A second permitted septic system is already in place for a future pool house, offering a clear path to expand the property's usable living space. The 3.25-acre lot delivers the kind of private, wine-country tranquility that feels worlds away while staying minutes from town. Ten minutes to Healdsburg's acclaimed dining and tasting rooms, a short ride to downtown Windsor and the SMART train, and two miles from a neighboring state park with an eligible short-term rental permit in place for buyers interested in occasional rental use. Perfect as a second home, primary residence or as an income property. A true must see to appreciate.

10936 Eastside Rd, Healdsburg
$1,745,000
4 Beds ⋅ 4 Baths ⋅ 326037487 MLS ⋅ ACTIVE Status
Just over a mile from the historic Healdsburg Plaza, 620 Dry Creek Road is a rare compound at the entrance to one of Sonoma County's most celebrated wine valleys. Set on 1.27 level, peaceful acres bordered by redwood trees and open pasture, the property brings together four distinct structures: a 3-bedroom, 2-bath main house with a loft, skylights, fireplaces, and southern views of vineyards and rolling hills; a charming 1-bedroom, 1-bath ADU with its own full kitchen and private yard; a pool house; and a game barn with electricity and soaring ceilings that genuinely surprises. An in-ground pool, hot tub, covered patio, solar panels, Tesla Powerwall battery backup, and a new 200-amp electrical panel round out a property built for living well and entertaining generously. The fully fenced open-sky pasture and ample open parking make this as practical as it is beautiful.

620 Dry Creek Rd, Healdsburg
$3,950,000
4 Beds ⋅ 4 Baths ⋅ 326034879 MLS ⋅ ACTIVE Status
Located in the heart of Sonoma County's renowned southern Alexander Valley AVA, this turn-key 25,000-case winery on 36 acres +/- offers a rare opportunity to own a fully operational, charming wine estate with significant upside potential. The property features a quaint tasting room with inviting outdoor seating, perfect for hosting public tastings, private events, and memorable winery gatherings. A premier elevated estate building site overlooks sweeping panoramic views of Mt. St. Helena and the Mayacamas Mountains, creating an idyllic setting for future expansion or a signature estate home. The winery includes an existing 2,861 sq ft () building, a 4,600 sq ft () crush pad and tank area, and a 12,000 sq ft Sonoma County-approved expansion permit complete with architectural plans. The estate encompasses 23.79 acres +/- of premium vineyards planted to Cabernet Sauvignon, Cabernet Franc, and Chardonnay, with 13.24 acres of new plantings and 10.55 acres of mature vines. Additional improvements include a 1,250 sq ft +/- manager's residence, a 2,500 sq ft +/- farm worker bunkhouse, and fully landscaped grounds. Situated on a peaceful, paved country lane, the property enjoys convenient proximity to Downtown Healdsburg with its world-class shopping, dining, and amenities. It is also close to Lake Sonoma, the Russian River, Sonoma County Airport, and just 20 minutes from Napa County. This is a rare chance to acquire a productive, event-ready winery in one of California's most prestigious wine growing regions ideal for a passionate winemaker, investor, or family seeking a lifestyle property in the heart of wine country.

4951 W Soda Rock Ln, Healdsburg
$14,500,000
4 Beds ⋅ 3 Baths ⋅ 326036977 MLS ⋅ ACTIVE Status
Premier southern Alexander Valley estate, winery, vineyards, cattle ranch along the Russian River in Sonoma County's renowned southern Alexander Valley AVA comprises approximately 320 acres across three parcels, offering an exceptional turn-key wine country property that combines a fully operational 25,000-case winery, productive vineyards, and expansive ranch potential with stunning panoramic views of Mt. St. Helena, the Mayacamas Mountains, Russian River Valley, and Chalk Hill. The holdings include a spacious 3,006 sq. ft. multi-level ranch residence with pool, tennis court, and wine cellar; a charming wine tasting room with outdoor seating; a 2,861 sq. ft. winery building, crush pad, and approved 12,000 sq. ft. expansion; plus manager's residence, large bunkhouse, shop, and livestock facilities. Approximately 120 +/- acres are planted to premium vineyards featuring Cabernet Sauvignon, Chardonnay, Zinfandel, Malbec, Petite Verdot, Cabernet Franc and Sauvignon Blanc, with additional prime acreage ideally suited for further vineyard development. Significant water resources include a large reservoir, irrigation wells, and nearly half a mile of Russian River frontage with beach access. A dramatic ridge-top building site commands sweeping views, while mature forests, oak woodlands, and lush landscaping provide privacy and natural beauty. Zoning supports potential subdivision, and the generous acreage accommodates grazing or other agricultural uses. Conveniently located on a peaceful paved lane just minutes from downtown Healdsburg's acclaimed restaurants and shops, the property offers easy access to Lake Sonoma, the Russian River, Sonoma County Airport, and is only 20 minutes from Napa Valley representing a rare legacy opportunity for a family estate, wine production expansion, or investment in one of Northern California's most prestigious wine growing region.

5520 W Soda Rock Ln, Healdsburg
$5,850,000
3 Beds ⋅ 2 Baths ⋅ 326034895 MLS ⋅ ACTIVE Status
Premier Alexander Valley estate with Stunning Views nestled along a peaceful, paved country lane, this exceptional ranch estate offers breathtaking panoramic views of Mt. St. Helena, the Russian River Valley, the Mayacamas Mountains, vineyards and iconic Chalk Hill valley. The property features a spacious 3,006 sq. ft. (+/-) multi-level ranch residence, complemented by a sparkling inground swimming pool, lush lawns, tennis court, professional landscaping, wine cellar and majestic clusters of redwood trees. Additional improvements include a manager's residence/office, a large shop, livestock shelter, and corrals.The estate is enhanced by approximately 10 +/- acres of premium vineyards planted to Cabernet Sauvignon, Zinfandel, Chardonnay, Petite Verdot, and Sauvignon Blanc. An additional 25 acres (+/-) of prime land are ideally suited for future estate vineyard development. A dramatic ridge-top estate building site offers sweeping, unobstructed views of Mt. St. Helena and the surrounding grassland/oak tree countryside. Zoning allows potential subdivision of the property, while generous acreage supports grazing for cattle or other farm animals. Mature fir, oak, and madrone forests and redwood tree lined meadow provide natural beauty and privacy throughout the property. Conveniently located, the estate is just minutes from the vibrant shops, acclaimed restaurants, and world-class amenities of downtown Healdsburg. It also enjoys easy access to Lake Sonoma, Russian River, Sonoma County Airport, and is only 20 minutes from Napa County.This rare offering combines productive vineyards, expansive ranch potential, and spectacular natural beauty in one of Northern California's most sought-after wine country locations. Website: https://5520wsodarocklane.jmbland.com

2 W Soda Rock Ln, Healdsburg
$1,675,000
3 Beds ⋅ 2 Baths ⋅ 326036719 MLS ⋅ ACTIVE Status
Welcome to your private Sonoma County retreat, set on approximately 1.4 acres of flat, usable land in the heart of California Wine Country. This 3 bedroom, 2 bath home, offers 1,890 square feet of warm, inviting living space with timeless chalet-inspired design and exceptional versatility. Upon entry, your gaze is immediately drawn to soaring cathedral ceilings and striking exposed wood beams that create a dramatic yet welcoming great room. Anchored by a centrally located wood-burning stove, this open-concept living space is ideal for both relaxing and entertaining. A designated dining area flows seamlessly into the kitchen, offering comfort and connection for everyday living. The primary suite is a true retreat, featuring vaulted ceilings, an en-suite bathroom, and a walk-in closet. Two additional bedrooms are thoughtfully positioned on the opposite side of the home with a shared full bath, providing privacy and flexibility for guests or family. The property continues to impress outdoors with expansive, level acreage offering endless possibilitiesfrom gardening and recreation to simply enjoying the peaceful surroundings. An attached two-car garage is complemented by a substantial detached Barn/Shop with over 2,500 square feet of space, ideal for car enthusiasts, hobbyists, or creative pursuits. Additional finished flex space and game room areas provide even more room to work, play, or entertain. Ideally located just up from Merriam Vineyards and minutes from both downtown Healdsburg and Windsor, this property offers the perfect balance of privacy and convenience. Healdsburg is widely recognized as a premier wine and culinary destination, centered around a charming plaza filled with tasting rooms, restaurants, and boutique shops. Surrounded by world-class wineries and celebrated dining, the area delivers the very best of Sonoma County living. A rare opportunity to enjoy space, character, and lifestyle in one of Northern California's most sought-after locations.

1084 Red Tail Rd, Healdsburg
$4,875,000
4 Beds ⋅ 7 Baths ⋅ 326035090 MLS ⋅ ACTIVE Status
Set in the heart of prestigious Dry Creek Valley, just minutes from downtown Healdsburg, 1099 Dry Creek Road is a newly built modern estate that redefines wine country luxury. Designed for seamless indoor-outdoor living, this private 1.6 acre retreat is surrounded by vineyard and mountain views, offering both tranquility and convenience. The main residence spans approximately 3,753 sq ft with 3 bedrooms and 4.5 baths, complemented by a beautifully appointed 1,200 sq ft ADU with 1 bedroom and 1.5 baths, ideal for guests, extended stays, or flexible living. Thoughtfully curated with elevated materials and craftsmanship throughout, the home features French oak flooring, bespoke white oak cabinetry, and marble surfaces including Arabescato Corchia countertops and Bianco Carrara baths. A chef's kitchen with premium appliances anchors the open-concept great room, where walls of glass frame the surrounding landscape and create a seamless connection to the outdoors. Designed for both everyday living and elevated entertaining, the property offers a glass-enclosed wine display, butler's pantry, game room, and library/office. Smart home integration includes Lutron lighting, automated shades, Sonos audio, and whole-home connectivity. Resort-style outdoor living is highlighted by a heated pool and spa, expansive patio areas, curated landscaping, and a turf lawn, perfect for entertaining or relaxing in a serene wine country setting. A rare offering combining modern design, luxury finishes, and an exceptional location just one mile from Healdsburg Plaza, this is turnkey wine country living at its finest.

1099 Dry Creek Rd, Healdsburg
$4,875,000
3 Beds ⋅ 4 Baths ⋅ 326035397 MLS ⋅ ACTIVE Status
Set in the heart of Healdsburg's coveted Dry Creek Valley, this 40+/- acre vineyard estate offers a rare blend of natural beauty and understated elegance. The 3,678+/- square-foot main residence is perfectly positioned to capture sweeping, unobstructed views of Geyser Peak and Mount St. Helena, with vineyards, rolling hills, and the valley floor nestled in between. A charming approximately 650 square foot guest cottage provides a welcoming space for family and friends. The setting is tranquil and secluded with two gated entries and surrounded by gently rolling terrain that evokes a sense of timeless ownership. A dramatic great room anchors the upper level with vaulted ceilings, exposed beams, a floor-to-ceiling stone gas fireplace, and built-in cabinetry. The kitchen is both functional and inviting, designed to connect naturally with guests or offer a quiet place to begin the day. High-end appliances, generous counter space, ample storage, and natural light define the space. The main level also includes the primary suite, guest bedroom, and full bathroom. The primary suite is positioned to take advantage of the views, with access to a private deck. The primary bathroom is spa-inspired with a soaking tub, glass-enclosed shower, and dual sink vanity. The lower level offers a relaxed and flexible living environment, including a spacious family or media room with wet bar and direct access to a deck. A private guest suite with en suite bath, separate entrance, and its own driveway provides ideal accommodations. A wine storage room, laundry, and additional full bath complete this level. Outdoors, a 50-foot saltwater pool and spa are complemented by mature olive trees, fruit trees, raised garden beds, and open grounds. The 13+/- acre vineyard features a curated selection of European varietals. The fruit is currently spoken for by a known brand, and this arrangement can continue. Infrastructure includes an owned solar system, domestic and agricultural wells, generator backup, and a water filtration system. This is a property for those seeking quiet sophistication and an unpretentious yet extraordinary retreat in one of Sonoma County's most desirable vineyard regions.

6355 Mountain View Ranch Rd, Healdsburg
$2,495,000
2 Beds ⋅ 2 Baths ⋅ 326036206 MLS ⋅ ACTIVE Status
Ride your bikes to town from your front door! Welcome to your private Sonoma Wine Country retreat, just five minutes from Healdsburg Plaza. Set on a gated 2.68-acre parcel, this single-level residence offers exceptional privacy and sweeping vineyard views across the Russian River Valley. Designed for effortless indoor-outdoor living, the home is encircled by a newly constructed 2,000-square-foot wraparound deck that seamlessly connects to an in-ground pool and hot tub, both finished in elegant Italian porcelain tile. A three-zone outdoor audio system enhances the experience, creating the perfect setting for entertaining or quiet relaxation. Originally built as an 1880s farmhouse, the home has been thoughtfully renovated to blend historic character with modern comfort. Recent upgrades include a new roof, updated windows, and a state-of-the-art five-zone heating and cooling system. The well-designed floor plan offers privacy and functionality, with two ensuite bedrooms positioned at opposite ends of the home. A detached room with panoramic views provides flexible space ideal for guests, a home office, or a creative studio. At the center of the home, the great room features a striking mid-century modern beam and shiplap ceiling, framed by windows that invite in serene woodland vistas. Modern infrastructure ensures convenience and peace of mind, including high-speed Starlink internet with underground fiber optic distribution and full property Wifi coverage, as well as upgraded 400-amp electrical service. Water systems are equally robust, featuring a rehabilitated well, an advanced treatment system, 25,000-gallon storage capacity, and a new three-bedroom septic system. The grounds are as captivating, with two seasonal creeks bordering the property, mature heritage oaks and redwoods, and over 30 fruit trees. With ample space for gardens, animals, or recreation, this property offers a rare combination of natural beauty, privacy, and refined living, an exceptional opportunity in the heart of Wine Country.

2291 Westside Rd, Healdsburg
$2,199,000
3 Beds ⋅ 3 Baths ⋅ 326033684 MLS ⋅ ACTIVE Status
Set on a generous 1.27 acre lot in a peaceful, private setting, 695 Chiquita Road offers an exceptional opportunity to enjoy the best of Healdsburg living just minutes from Healdsburg Plaza. The 2,767 square foot residence has been completely remodeled, blending modern design and finishes with a warm, inviting Wine Country aesthetic. The home is thoughtfully updated to provide comfortable everyday living as well as effortless entertaining, with light-filled interiors and a seamless connection to the surrounding landscape. Positioned to capture scenic views, the property feels like a true retreat, offering privacy, quiet, and a strong sense of place. The expansive 1.27 acre parcel provides a rare amount of usable land this close to town. There is ample space for outdoor living areas, gardens, a pool, or future expansion. The property also offers excellent potential for an ADU, creating flexibility for guest accommodations, extended family, or supplemental income. Located near the Healdsburg Bike Path, the property provides easy access to biking and walking routes that connect you to the charm and energy of Healdsburg. Just minutes away, the Plaza offers world-class restaurants, tasting rooms, boutique shopping, and a vibrant community atmosphere. With its rare combination of privacy, views, acreage, and a fully remodeled home in a highly desirable location, 695 Chiquita Road presents a compelling opportunity as a full-time residence, weekend retreat, or investment property in the heart of Sonoma County Wine Country.

695 Chiquita Rd, Healdsburg
$2,995,000
2 Beds ⋅ 3 Baths ⋅ 326033984 MLS ⋅ ACTIVE Status
Stunning Dry Creek Valley estate set on 11.91 acres with sweeping views of Mount St. Helena and the Dry Creek ridgeline. This 1,920 SF Mediterranean-style residence is thoughtfully designed for relaxed Wine Country living and effortless entertaining, featuring an open floor plan, vaulted ceilings, and expansive windows that frame the surrounding landscape. Spanish tile floors run throughout the single-story 2BD/2BA home, with the second bedroom opening to a serene courtyard perfect for morning coffee or quiet evenings. At the heart of the home, a well-appointed chef's kitchen with a generous island and abundant storage invites gathering and connection. Outdoors, the property unfolds into a private oasis with multiple entertaining areas, manicured gardens, a tranquil pond, fruit trees, raised garden beds, and meandering pathways leading to a lower patio and pool. While currently surrounded by Zinfandel & Petite Sirah vine, this sustainably farmed property offers exceptional versatility for those who may not wish to maintain vines. With its rich soil and established infrastructure, it presents an ideal opportunity to create your own agricultural vision whether planting olive trees, cultivating fruits and vegetables, or bringing in animals for a small hobby farm or sustainable homestead. The estate is supported by impressive infrastructure, including a high-producing 125+ GPM well, a 4-bedroom installed septic system, owned solar panels, a roof sprinkler system, underground utilities, and four 5,000-gallon water storage tanks. Located just minutes from downtown Healdsburg, 1633 Dry Creek Road offers privacy, flexibility, and the quintessential Wine Country lifestyle. Only 15 minutes from Sonoma County Airport and approximately one hour north of San Francisco, this is a rare opportunity to enjoy both tranquility and convenience in one exceptional property.

1633 Dry Creek Rd, Healdsburg
$4,975,000
4 Beds ⋅ 4 Baths ⋅ 326034406 MLS ⋅ ACTIVE Status
Nestled in the heart of Sonoma County's renowned Dry Creek Valley, this exceptional 67-acre ranch offers a rare combination of premier vineyards, a boutique winery open for public tastings and limited events, and complete privacy on sought-after benchland with premium southwestern exposure. Perched atop a scenic knoll, the estate residence 3200 Sq ft +/- commands sweeping panoramic views over the valley, lush vineyards, and on-site 3K case winery. The property features a dedicated wine tasting building/conversion to 2nd residence, a comfortable apartment, a fully equipped wine-making facility, and ample storage everything needed for a turnkey wine country operation with valuable Dry Creek Road frontage, the estate enjoys direct paved access while maintaining seclusion. Of the 67 total acres +/- approximately precisely 33.02 acres per current vineyard map are planted to premium vineyards, including historic old-vine Zinfandel blocks dating to the 1910s, along with Cabernet Sauvignon, Petite Verdot, Cabernet Franc, and Malbec. These vines thrive on the ideal bench land terroir. Paved roads wind throughout the property, providing effortless internal access while preserving the natural beauty.Tranquil creeks meander through the remaining mature oak and madrone woodlands, complemented by a picturesque small pond that enhances the serene setting. The property strikes a perfect balance between productive agriculture and a peaceful, private retreat. Possible 20 +/- acre subdivision potential for three parcels (See zoning). Conveniently located just minutes from the historic Dry Creek General Store, Lake Sonoma, and the vibrant restaurants, wineries, and boutique shopping of Healdsburg. Sonoma County Airport is only a 15-minute drive away, making this an effortlessly accessible yet wonderfully secluded wine country gem.This is a truly rare opportunity to own a private, productive, and breathtaking 67-acre estate with Dry Creek Road frontage in one of California's most prestigious wine growing regions.

5143 Dry Creek Rd, Healdsburg
$1,995,000
2 Beds ⋅ 2 Baths ⋅ 326033954 MLS ⋅ ACTIVE Status
Set on approximately 4.62 acres along desirable Alexander Valley Road, this versatile wine country property offers a rare combination of usable land, multiple living spaces, and functional improvements. The mostly level parcel features a small old vine Zinfandel vineyard with room for potential expansion, along with ample space for gardens, animals, or additional agricultural use. The main residence includes 2 bedrooms and 2 baths, complemented by an attached 2-bedroom, 1-bath ADU with a separate entrance, ideal for extended living, guests, or rental income. A newly built rectangular pool creates a striking outdoor focal point, perfect for entertaining and enjoying the surrounding valley setting. Additional improvements include an approximately 1,500 sq ft shop, well-suited for storage, hobbies, or workspace needs. Located in the heart of Alexander Valley, just minutes from Healdsburg and near the emerging North Village, this property offers a blend of rural charm, functionality, and convenient access to wine country amenities.

317 Alexander Valley Rd, Healdsburg
$4,695,000
4 Beds ⋅ 4 Baths ⋅ 326029964 MLS ⋅ ACTIVE Status
Nestled on one of Healdsburg's most coveted streets, just a short stroll from the vibrant Plaza, 438 Matheson St. is a stunning example of early 20th-century charm paired with modern-day versatility. Set on a generous corner lot spanning approximately a quarter acre, this property boasts a serene oasis with formal gardens, a sparkling pool, and room to expand with additional flower or vegetable beds. Steeped in character, the over 3,000 sq. ft. home (+/-) spans three thoughtfully designed levels. The main floor has a formal parlor and dining room, a beautifully remodeled gourmet kitchen, and a cozy media room, all anchored by timeless details and abundant natural light. Upstairs, two spacious bedrooms plus an office and two bathrooms share the spotlight with a delightful covered porch, perfect for enjoying quiet moments overlooking the picturesque street below. The versatile lower level opens up endless possibilities, offering space for one to two additional bedrooms, a home office, or even a private theater. Complete with a full bath and laundry room, it's a flexible haven for evolving needs. Outside, a detached garage sparks inspiration with its potentialimagine transforming it into a summer kitchen, guest quarters, or an ADU. Recent upgrades, including fresh interior and exterior paint, a brand-new roof, and a solar system, make this home as efficient as it is enchanting. 438 Matheson seamlessly blends timeless elegance with modern functionality, offering an unparalleled opportunity to live in one of Healdsburg's most desirable locations.

438 Matheson St, Healdsburg
$4,500,000
6 Beds ⋅ 6 Baths ⋅ 326024435 MLS ⋅ ACTIVE Status
Set on approximately 15 acres in Sonoma County, this newly constructed property offers a rare combination of modern design, usable land, and a versatile multi-residence layout. Thoughtfully planned and designed for both everyday living and entertaining, the property provides a seamless blend of indoor comfort and outdoor lifestyle. The main residence features clean architectural lines, an open-concept floor plan, and abundant natural light throughout. Expansive nano-style doors create a strong indoor-outdoor connection, opening to generous decking and surrounding views. The interior offers a functional layout with well-proportioned living spaces, quality finishes, and a natural flow suited to both quiet living and gatherings. In addition to the main home, a fully detached two-bedroom, two-bath residence provides flexibility for guests, extended living, or potential income opportunities (buyer to verify). Positioned separately from the main home, it offers privacy along with its own outdoor areas. The grounds are designed to take full advantage of the acreage, with a balance of open space and curated landscaping. A newly constructed approximately 1,500 square foot barn adds utility for a variety of uses. The property also includes a small hobby vineyard and established gardens with pathways, mature plantings, and seasonal color. Outdoor amenities are a central feature of the property, including a pool, sauna, and multiple areas for seating and entertaining. A well-equipped outdoor kitchen and dining area provide an ideal setting for year-round use, whether hosting or enjoying the surrounding environment. With its combination of new construction, multiple living spaces, and usable acreage, this property presents a unique opportunity to enjoy Sonoma County living with flexibility and privacy, all within a thoughtfully designed setting.

8349 W Dry Creek Rd, Healdsburg
$1,400,000
2 Beds ⋅ 3 Baths ⋅ 326032489 MLS ⋅ ACTIVE Status
Eight minutes from the Healdsburg plaza, Mill Creek Road gives way to a forest canopy and the kind of quiet that makes you exhale. That's the setting for 2563 & 2560 Mill Creek Rd combined to offer an almost 1 acre property, modern designed 2 bedroom, 2.5 bathroom 1,409 sqft home, genuine nature immersion, and one of the most compelling income opportunities in Healdsburg today. A striking modern home with floor-to-ceiling windows, warm oak plank floors, and an open-concept layout built for living well. The kitchen anchors the main level with a large island, wine fridge, stainless appliances, and floating shelves. Multiple glass sliders dissolve the boundary between inside and out, opening to an expansive deck for dining and entertaining, gravel path, dedicated patio, hot tub, cold plunge, and sauna the kind of amenity stack that earns five-star reviews or creates quality memories. Both ensuite bedrooms sit upstairs, framed by forest views on every side. Cross Mill Creek Road to the south parcel: a fully fenced half-acre with Mill Creek frontage, mature trees, flat open terrain, and a large storage shed ideal for recreation or leisure. Must see to appreciate this unique offering.

2563 Mill Creek Rd, Healdsburg
$1,695,000
3 Beds ⋅ 3 Baths ⋅ 326030944 MLS ⋅ ACTIVE Status
Perfectly positioned in the heart of Wine Country, this beautifully updated single-level retreat offers an exceptional blend of privacy, comfort, and natural beauty. Ideally located less than 15 minutes from Healdsburg, 20 minutes from Calistoga, 22 minutes from Sonoma County Airport, and under 30 minutes from downtown Santa Rosa, the property provides convenient access to some of Northern California's most sought-after destinations. Set on approximately 1.15 acres, the property enjoys vineyard views and scenic frontage along Maacama Creek, creating a tranquil setting rich with wildlife and the peaceful ambiance of Wine Country living. Thoughtfully designed for both relaxation and entertaining, the turnkey residence features 3 bedrooms, 3 bathrooms, and approximately 2,225 square feet of light-filled living space. The open-concept floor plan showcases a spacious living room with fireplace, a beautifully updated chef's kitchen with premium appliances, and inviting guest accommodations. High-end finishes and seamless indoor-outdoor flow enhance the home's warm and welcoming atmosphere. Outdoor living is equally impressive, featuring an expansive entertaining deck, stone patio, outdoor kitchen, and beautifully landscaped grounds that capture the essence of Sonoma County's indoor-outdoor lifestyle. A wrap-around driveway offers ample parking in addition to the de-attached two-car garage. Located near Chalk Hill Road and just moments from renowned wineries, vineyards, and fine dining, this private Wine Country retreat presents a rare opportunity to enjoy the best of Sonoma County living in a picturesque creek side setting.

14734 Youngs Rd, Healdsburg
$4,250,000
4 Beds ⋅ 5 Baths ⋅ 326030880 MLS ⋅ ACTIVE Status
Flora Ranch Estate sits on 40+ acres atop a gentle vineyard knoll with a beautiful custom-built Mediterranean inspired home overlooking Alexander Valley, Mt Saint Helena and Chalk Hill with breathtaking panoramic views. Inside the home, warm, inviting spaces feature soaring beam-wrapped cathedral ceilings, an open-concept layout, and serene seating areas throughout to relax amongst the views. Step onto the wrap-around back deck and enjoy the infinity-edge pool and spa, seamlessly blending indoor-outdoor living. The home's lower level reveals a winemaking lounge, small production studio and wine cellar built into the hillside for aging your own estate grown Cabernet Sauvignon. The vineyard is currently sustainably farmed on 15 acres of hillside in ancient volcanic soils. The gentle rolling topography enhances both vineyard character and breathtaking views. Flora Ranch Estate offers a rare opportunity to join, expand or reimagine within Alexander Valley's esteemed wine growing and agricultural community. The rich land is not only planted to award winning grapes but you'll also find flowers, raised garden beds, an irrigated fruit orchard and a picturesque pond draped with large willow trees. Enjoy the peacefulness of gorgeous country living yet just 15 minutes to Healdsburg Plaza, 15 min to Santa Rosa Airport, 20 min to Napa Valley's Calistoga and within district to the highly sought after Alexander Valley School with bus route at the bottom of Flora Ranch Rd. Generational legacy estates like these don't become available very often and your time has come to make this stunning slice of wine country yours at Flora Ranch Estate.

13404 Flora Ranch Rd, Healdsburg
$2,350,000
4 Beds ⋅ 4 Baths ⋅ 326031365 MLS ⋅ ACTIVE Status
Set behind gates on Westside Road and tucked along a private lane in the sought-after Madrona Knolls neighborhood, this Healdsburg residence offers a rare combination of privacy, natural beauty, and close-to-town convenience. Surrounded by mature landscaping with dogwoods, citrus and plum trees, azaleas, rhododendrons, roses, and seasonal color, the setting feels peaceful and established while remaining just minutes from Healdsburg Plaza, acclaimed dining, tasting rooms, and boutique shopping. Inside, soaring approximately 25-foot windows in the great room frame sweeping southern valley views, distant mountains, memorable sunrises, and the changing light across the landscape. Abundant natural light, rich hardwood flooring, and generous living spaces create an atmosphere that is both comfortable and refined. Designed for everyday living as well as entertaining, the home offers four bedrooms and three baths, including two spacious primary suites positioned on opposite ends for privacy and flexibility. At the center of the home, the kitchen, dining, and great room connect naturally and flow to expansive view decks and outdoor gathering spaces. A private wine cellar with tasting area adds to the wine country setting, while the gated grounds provide a sense of retreat. A distinctive offering in one of Healdsburg's most desirable hillside neighborhoods.

1017 Westside Rd, Healdsburg
$2,795,000
4 Beds ⋅ 5 Baths ⋅ 326031086 MLS ⋅ ACTIVE Status
Imagine waking up at 280 Long Acres Place, where the morning sun clears the peak of the Mayacamas Mountains and pours through the home's soaring ceilings. The sheer volume of the great room reflects the vastness of the rolling eastern ridges just outside your window, creating an atmosphere of effortless, airy luxury. This isn't just a house; it's a lifestyle curated for the connoisseur. After a day exploring local vineyards, you return to the Sunset Breeze estate to select a vintage from one of your two professional wine cellars. With a 1,000+ bottle capacity, your collection finally has a gallery of its own. The main residence is both grand and functional, featuring 3 spacious bedrooms and 4 bathrooms, plus a private office designed for quiet focus. When the weekend arrives, the party naturally flows from the high-volume interiors onto the expansive entertaining deck, where the mountain views provide a dramatic backdrop for starlit dinners. For your guests, the 480 sq. ft. detached casita offers total autonomy with its own kitchenette and full baththough it's equally suited as a high-end home gym or creative studio. Moments from the world-class dining of Healdsburg Plaza, this estate offers the rare balance of away from it all and in the heart of it.

280 Long Acres Pl, Healdsburg
$6,900,000
10 Beds ⋅ 11 Baths ⋅ 326030556 MLS ⋅ ACTIVE Status
Price improvement! Exceptional opportunity to own an established 10-room inn in the heart of internationally acclaimed Healdsburg, Sonoma County. Set on over an acre, this inviting property blends timeless charm with modern comfort. Guests enjoy serene garden settings, welcoming common areas and a short walk to the vibrant town plaza offering boutique shops, art galleries, acclaimed restaurants and wine tasting. As well as a vibrant mix of year-round special events, live music and community gatherings. Ideally situated near the airport, Lake Sonoma, and the Russian river, providing both convenience and access to outdoor recreation. Rarely found in this prime location, the expansive grounds offer significant potential for future expansion or enhancement, appealing to investors, developers, or owner-operators seeking a lifestyle hospitality. A turnkey operation with strong appeal as a boutique lodging destination, private retreat or corporate getaway.

25 W Grant St, Healdsburg
$1,795,000
2 Beds ⋅ 1 Baths ⋅ 326028639 MLS ⋅ ACTIVE Status
Off-Grid Oasis | 75+/- Acres of Serenity & Self-Sufficiency. Escape to this rare 75-acre off-grid sanctuary with sweeping views of Black Mountain and beyond. Designed for sustainable, multi-family living, the property features a spacious main home with an open floor plan, large view deck, and BBQ area ideal for outdoor entertaining. A separate guest house offers privacy for visitors or extended family, while a well-equipped workshop and barn provide space for projects, storage, or homesteading. Enjoy established hiking trails, forested paths, open meadows and fruit bearing trees though out property. Solar-powered, this retreat blends comfort with eco-conscious living. A separate 4-acre parcel is included, enhancing both privacy and potential, totaling 80+/- acres. Whether you seek a family compound, creative escape, an independent lifestyle in nature, or a prepared site for future estate, this secluded mountain haven invites you to unplug, unwind, and thrive.

10957 Westside Rd, Healdsburg
$2,095,000
2 Beds ⋅ 2 Baths ⋅ 326026592 MLS ⋅ ACTIVE Status
Tucked behind a private gate at the end of a quiet lane, 1311 West Dry Creek Road unfolds across 66.73 acres of pure Sonoma beauty a secluded haven where nature, possibility, and privacy converge. Just minutes from downtown Healdsburg yet worlds away in peace, this rare dual-parcel sanctuary invites you to create your own legacy estate in one of wine country's most sought-after valleys. The landscape comes alive in springtime, with crystal-clear creeks, heritage oaks, and madrone trees glowing beneath sunlit canopies. Meandering trails lead through forest and meadow, revealing both majestic views and tranquil pockets of serenity along the way. A well-crafted road network connects each space from the welcoming cottage and studio to two premier building sites poised for a future estate of distinction. The existing 2-bedroom, 1-bath cottage with loft sits nestled beside a seasonal creek, surrounded by fruit trees and flowering gardens. Steps away, a spacious detached studio with half bath offers flexibility for guests, art, or wellness pursuits. A connected storage wing adds practicality without sacrificing charm, making these spaces ready for immediate enjoyment while envisioning the property's greater potential. Two remarkable building sites await: a breathtaking hilltop with sweeping vistas across Dry Creek and Alexander Valleys, and a secluded sunlit meadow bordered by trees perfect for an intimate retreat. Thoughtfully installed infrastructure includes a five-bedroom septic system, mountain spring-fed water, ample storage, and advanced filtration. Every element aligns for an effortless start to an extraordinary estate project. Surrounded by vineyard landscapes and just minutes from tasting rooms, world-class restaurants, and downtown Healdsburg, this private wine country acreage offers rarity and readiness in equal measure. As the valley bursts into new life this spring, 1311 West Dry Creek Road stands ready for its next chapter a vision of Wine Country living that is timeless, private, and unforgettable.

1311 W Dry Creek Rd, Healdsburg
$3,450,000
5 Beds ⋅ 3 Baths ⋅ 326025290 MLS ⋅ ACTIVE Status
A Rare Canvas with Expansive Views and Ultimate Privacy on Fitch Mountain. This is a one of a kind opportunity within the town of Healdsburg. Situated on almost an acre lot, 1212 N Fitch Mountain Road is the ultimate foundation for a legacy estate. Drawing directly from the understated elegance of renowned British architect C.F.A. Voysey, this 3,298 sq. ft. main residence and 810 sq.ft. one bedroom ADU have been meticulously restored and expanded over three decades by the founding principal of AXIA Architects. With exacting sympathy for Voysey's signature aesthetic. Divided lite steel windows are strategically placed on at least two sides of every living space, saturating the interiors with natural light and framing picturesque views from every vantage point. The interior details serve as a gallery of artisan craftsmanship, from the living room beams featuring a hand-painted poppy motif to a curated collection of lighting including Italian pendants and handmade sconces. The kitchen has hand-painted Italian wildflower tiles, while both bathrooms feature premium McIntyre tiles with traditional trim. The primary bedroom features stunning views and French doors that open to the back patios The primary bathroom is exceptionally spacious with a 6-foot tub, walk-in shower, and double sinks. There is an ensuite guest bedroom downstairs. Upstairs are three bedrooms featuring built-in bookshelves and cabinets plus a full bathroom and an additional storage room. In 2012, the estate was expanded with a massive garage with room for a shop, exercise room, or studio topped by a private 860 sq. ft. ADU. This one-bedroom unit is suitable for a remote workspace/office, an exclusive guest house for visitors, a private space for a live-in nanny or caretaker or a rental. The residence is bookended by stunning vistas: a southern terrace overlooks Healdsburg and the Russian River Valley, while the north patio, complete with fireplace and fishpond, looks over a spacious lawn to Alexander Valley and the Mayacama Mountains. Surrounded by a curated garden paradise with fruit trees, a vegetable garden, and rose gardens along with a petanque court and multiple outdoor dining spaces, the property is a private sanctuary just 5 minutes to The Plaza and easy access to the Fitch Mountain park and trails and the dog park . The zoning accommodates a pool and pool house and several expansion options. This is the foundation for your wine country family home.

1212 N Fitch Mountain Rd, Healdsburg
$1,395,000
5 Beds ⋅ 4 Baths ⋅ 326022605 MLS ⋅ ACTIVE Status
New construction rarely feels this complete. Designed for effortless living and modern sensibility, this light-filled residence offers a seamless blend of style, function, and flexibility, anchored by wide-plank oak floors, clean architectural lines, and a thoughtful layout that lives beautifully day to day. The heart of the home is a striking open kitchen designed to perform as well as it presents, featuring quartz countertops, an oversized island, and the unexpected luxury of dual dishwashers, a detail that speaks to both entertaining and ease. The adjacent dining area and expansive living space flow naturally to the outdoors, creating a quiet rhythm between indoor comfort and private backyard living. A dedicated entry study provides a refined work-from-home space, while modern lighting and curated fixtures elevate every room. Upstairs, the primary suite is a true retreat, offering a spacious walk-in closet and a beautifully appointed bath with dual sinks and a clean, contemporary finish. What sets this property apart is its versatility. In addition to the 4-bedroom, 2.5-bath main residence, a fully independent studio ADU with its own kitchen and full bath creates opportunity, whether for guests, extended living, or income potential. Framed by low-maintenance landscaping and a welcoming front porch, the property is designed to be both polished and practical. A two-car garage and private outdoor spaces complete the offering. This is not just new construction, it's a home that understands how people want to live today.

109 Paul Wittke Dr, Healdsburg
$2,095,000
4 Beds ⋅ 4 Baths ⋅ 326024573 MLS ⋅ ACTIVE Status
Come and enjoy the elegant architecture of this beautiful custom home, set on over 1/2 acre in the heart of Healdsburg's wine country. Upscale amenities include a chef's kitchen with Viking appliances, Brazilian wood floors and solar with 2 battery backups. The open floor plan offers abundant natural light, walk in pantry, spacious laundry and 2 central air and heating systems. The serene grounds offer a natural habitat, built-in barbecue and fire pit, and an amazing heated in-ground pool.

134 Moonlight Dr, Healdsburg
$1,195,000
4 Beds ⋅ 4 Baths ⋅ 326023920 MLS ⋅ ACTIVE Status
Welcome to 1311 Prentice Drive in the heart of Healdsburg, a rare duplex opportunity offering versatility, comfort, and prime location all in one. This townhome-style property features two well-designed units, each with its own private entrance, one-car garage, in-unit laundry, and separate backyard; perfect for investors, multi-generational living, or owner-occupants seeking rental income. The front unit is a beautifully remodeled 2-bedroom, 2-bath home showcasing modern finishes, updated fixtures, and a fresh, contemporary feel throughout. Move-in ready and thoughtfully upgraded, it offers stylish living with comfort and functionality. The back unit features 2 bedrooms and 1.5 baths and has been well maintained in its original condition. Clean, comfortable, and full of potential, it provides steady rental appeal or an excellent canvas for future updates. Both units enjoy private backyard spaces ideal for relaxing, entertaining, or gardening, creating a sense of separation and individuality rarely found in duplex properties. Located in a central neighborhood close to shopping, dining, parks, and everything Healdsburg has to offer, this property delivers flexibility, income potential, and long-term value in one of Sonoma County's most desirable communities. A smart investment and a lifestyle opportunity, all under one roof.

1311 Prentice Dr, Healdsburg
$740,000
4 Beds ⋅ 4 Baths ⋅ 326024033 MLS ⋅ ACTIVE Status
New co-ownership opportunity by Pacaso: Own one-eighth this professionally managed, turnkey home. Olive Grove is set along a private driveway on West Dry Creek Road in Healdsburg, where ancient olive and fruit trees frame the approach to a renovated hillside compound. The board and batten exterior with a metal roof reads as modern and grounded against the surrounding hillside, with a main residence, a detached bedroom suite and a detached office and gym arranged across more than three private acres. The great room is Olive Grove's centerpiece, with a dramatic wood-plank vaulted ceiling, an oversized gas fireplace and walls of glass that frame the private orchard and West Dry Creek Valley beyond. Sliding doors open the full width of the living space to the outdoors. The kitchen has white cabinetry, stainless appliances and an 11-foot island lit by weathered zinc pendant lights. The primary suite has a walk-in closet and an en suite bath with a soaking tub, dual vanity and marble shower. Two additional bedrooms and baths complete the main residence. The pool and hot tub sit among the ancient trees with hillside views behind, and the outdoor kitchen and fire pit extend the entertaining spaces across the broad decks. Downtown Healdsburg is a short drive away, with the town's celebrated restaurant row on the plaza, the Saturday Healdsburg Farmers Market and the tasting rooms of Dry Creek Valley all within easy reach. Olive Grove is fully designed, furnished and managed by Pacaso. Owners arrive to find the home exactly as it should be, every time.

6165 W Dry Creek Rd, Healdsburg
$9,300,000
4 Beds ⋅ 5 Baths ⋅ 326016481 MLS ⋅ ACTIVE Status
Perched above Healdsburg on six legal parcels totaling 10.48 acres, this exceptional property offers a rare combination of privacy, scale, and long-term flexibility. The residence crowns the top of the property, capturing sweeping valley and mountain views that stretch for miles and create a true sense of arrival. With multiple parcels already in place, the offering presents a compelling opportunity for future resubdivision, investment, or multi-generational vision, if desired. The approximately 4,000 sq ft, 4-bedroom, 3.5+ bath home is thoughtfully designed to live primarily as a single level. The main entry floor includes the primary suite, great room, chef's kitchen, dining area, and spacious laundry room - all positioned to maximize the extraordinary vistas. Walls of glass frame breathtaking scenery and bathe the interiors in natural light. The chef's kitchen features premium appliances and a built-in espresso station, flowing seamlessly into the dining area highlighted by a dramatic glass-front wine display. French doors open to a wraparound covered porch, creating effortless indoor-outdoor living against a backdrop of panoramic views. The primary suite is a private retreat with its own gas fireplace, generous walk-in closet, hidden storage, and direct access to the laundry room. Downstairs, a spacious family room with gas fireplace and wet bar opens to a covered patio overlooking the surrounding valleys and mountains. A flexible space near the attached two-car garage is ideal for a gym, office, or walk-in pantry. Gated and private, with access from Benjamin Way or Coghlan Drive, this 10.48-acre, six-parcel offering is a rare opportunity just minutes from downtown Healdsburg - combining elevated views, usable land, and future potential in one extraordinary estate setting. Also includes APNs 002-610-018, 002-610-020, 002-610-021, 002-610-023, and 002-610-024.

775 Benjamin Way, Healdsburg
$1,295,000
3 Beds ⋅ 3 Baths ⋅ 326006403 MLS ⋅ ACTIVE Status
Tucked away on a private lane in Healdsburg's desirable Clear Ridge neighborhood This custom built, two-story single-family home offers privacy, space, and scenic surroundings. The 2,444 sq. ft. residence features 3 spacious bedrooms and 2.5 bathrooms and a flex room, ideal for full-time living or a weekend retreat. This location is ideal for the bicycling, walking and jogging enthusiasts. It is less than a mile to the entrance of Alexander Valley to the north and also Dry Creek Valley to the west. These two valleys are known the world over NOT just for the beautiful vineyards but also for the wonderful bike riding. There is excellent hiking in the surrounding hills and a walking path close by which leads to downtown Healdsburg. The home includes a 2-car garage plus an attached workshop, offering flexible space for hobbies, storage, or a home gym. The backyard could easily accommodate an outdoor kitchen and furniture in the patio area (please look at Digitally Altered photo). Only 2 minutes to shopping, 3 minutes to catch the freeway and only 4 minutes to downtown. Very centrally located. A rare opportunity to own a country home within city limits with room to breathe in one of Healdsburg's most sought-after areas.

230 Clear Ridge Dr, Healdsburg

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