Healdsburg Real Estate

Healdsburg Real Estate

Welcome to Healdsburg, California, a charming gem nestled in the heart of Sonoma County. Known for its picturesque landscapes, world-class wineries, and vibrant downtown, Healdsburg offers a unique blend of small-town charm and sophisticated living. With the Russian River meandering through its lush surroundings, this idyllic city invites residents and visitors alike to bask in its natural beauty and enjoy a laid-back lifestyle.

Healdsburg is renowned for its thriving wine culture, boasting over 400 wineries in the surrounding area. Whether you're a connoisseur or simply enjoy the occasional glass, you'll find an abundance of tasting rooms and vineyards that showcase some of the finest wines in California. The annual Healdsburg Wine & Food Experience highlights the region's culinary talents, featuring local chefs and their exquisite pairings.

Beyond its wine, Healdsburg is home to a vibrant arts scene, with galleries, theaters, and live music venues that celebrate the creative spirit of the community. The historic Plaza, lined with charming boutiques and farm-to-table restaurants, is the perfect place to unwind, shop, and savor the flavors of the region.

Outdoor enthusiasts will love the nearby hiking and biking trails, as well as the opportunities for kayaking and fishing along the Russian River. The city's mild Mediterranean climate allows for year-round enjoyment of its natural surroundings.

In Healdsburg, you'll find a welcoming community that values connection, creativity, and sustainability. Whether you're looking to settle down or simply explore, this enchanting city offers a lifestyle that is as rich and diverse as the wines it produces. Come experience the magic of Healdsburg—where every day feels like a getaway!

Newest Listings in Healdsburg

$2,150,000
326061006 MLS
Discover an extraordinary opportunity to create a custom luxury residence within the prestigious Montage Healdsburg Estate Collection. Estate Homesite 16 offers approximately 13,030 square feet in a peaceful setting surrounded by native oak woodlands, providing the perfect canvas for an architecturally significant Wine Country estate. Ideally positioned within the sought-after north-side Estate neighborhood, the homesite blends exceptional privacy with immediate access to the celebrated amenities of Montage Healdsburg. This lot is contiguous to Estate Homesite 15 (MLS #326060965), and when acquired together, the combined area presents a singular opportunity to build an unparalleled legacy residence. Originally designated for the striking Estate Home F architectural concept, this homesite was designed to accommodate an approximately 4,206 square foot contemporary residence featuring four bedrooms plus a den, five-and-one-half baths, dual primary suites, dramatic floor-to-ceiling glass, expansive covered terraces, an extended lap pool, spa, and exceptional indoor-outdoor living spaces that seamlessly connect with the surrounding natural landscape. Ownership includes access to the exceptional Montage lifestyle, featuring Spa Montage, Hazel Hill restaurant, resort pools, fitness center, concierge services, miles of private walking trails, and the unmatched service and hospitality that define one of the world's premier luxury resort brands. Located only minutes from downtown Healdsburg and surrounded by Sonoma County's most celebrated wineries and culinary experiences, Estate Homesite 16 represents a rare opportunity to create a custom residence within one of California's most exclusive resort communities.

125 Woodlands Drive, Healdsburg
$2,150,000
326060965 MLS
Introducing one of the final opportunities to create a legacy estate within the exclusive Montage Healdsburg residential collection. Arguably the best homesite within the enclave, Estate Homesite 15 encompasses approximately 16,743 square feet, making it one of the largest homesites within the coveted Estate Collection. Nestled among mature oak woodlands and thoughtfully positioned to maximize privacy, this exceptional property offers an extraordinary setting for a custom Wine Country retreat. This lot is contiguous to Estate Homesite 16 (MLS #326061006), and when acquired together, the combined area presents a singular opportunity to build an unparalleled legacy residence. Originally designated for the stunning Estate Home E architectural concept, the homesite was envisioned to accommodate an approximately 4,362 square foot contemporary residence featuring four bedrooms plus a den, four-and-one-half baths, a dramatic detached primary suite, expansive great room, private pool and spa, generous outdoor entertaining spaces, and seamless indoor-outdoor living designed specifically to embrace the Sonoma lifestyle. Ownership includes privileged access to the world-renowned amenities of Montage Healdsburg, including Spa Montage, Hazel Hill restaurant, resort pools, fitness center, concierge services, miles of scenic walking trails, and the legendary hospitality synonymous with the Montage brand. Just minutes from the historic Healdsburg Plaza and surrounded by award-winning wineries, Michelin-starred dining, and endless outdoor recreation, Estate Homesite 15 represents one of the last opportunities to create a custom legacy residence within one of Northern California's most prestigious luxury resort communities.

115 Woodlands Drive, Healdsburg
$2,195,000
5 Beds ⋅ 5 Baths ⋅ 326052623 MLS
A newly built wine country retreat at 1071 Trentadue Way pairs a main residence with a fully independent, detached ADU: ~2,540 square feet, five bedrooms, and four and a half baths in all, with room for multigenerational living, a home office, a studio, or long-term guests. The main home offers ~1,740 square feet across three bedrooms and two and a half baths; the detached ADU adds ~800 more, with two bedrooms, two baths, a full kitchen, and its own private entrance. A deck and private yard make indoor-outdoor living and gathering easy. Inside the main home, an open layout sits beneath nine-foot ceilings and oversized windows. The finishes are clean and considered: waterproof stone composite floors, Caesarstone quartz countertops, Bosch appliances, and matte black hardware. Built-in storage runs throughout, from bedroom wardrobes to hallway closets. The primary suite occupies its own private hall, with cathedral ceilings, a walk-in closet, and a bath with radiant heated floors, Kohler fixtures, and a glass-enclosed rain shower. Built with California in mind: a steel frame and Hardie fiber cement siding for wildfire resistance, all-electric systems with built-in solar to keep energy costs low, and a high-efficiency heat pump. Whole-home MERV-13 air filtration and filtered water at every tap. 1071 Trentadue Way is a rare new-construction offering: polished design, lasting durability, and the flexibility of a detached second home in the heart of Healdsburg wine country, where the historic plaza, Michelin-starred dining, tasting rooms, and the wineries of the Dry Creek, Alexander, and Russian River valleys all converge.

1071 Trentadue Way, Healdsburg
$1,200,000
2 Beds ⋅ 2 Baths ⋅ ML82051891 MLS
Some land doesn't ask you to compromise. This one just hands you a blank canvas and gets out of the way. 7.6 private acres of oak-studded hillside along Mill Creek, on one of Healdsburg's most private residential lanes, minutes from the Plaza's restaurants, tasting rooms, and downtown energy; close enough to bike in when you feel like it. The existing 1962 structure conveys as-is and offers the possibility of a full renovation or a clean start, opening the door to a custom-designed home built exactly to your vision. Zoned RRD B6 40 within unincorporated Sonoma County, with OAK and RC50/50 combining zones reflecting its oak habitat and riparian corridor. Offered as-is. Buyer to independently verify water source, septic, well, zoning, and all development potential. This is land that rewards a builder's eye and a clear sense of what could be.

2346 Mill Creek Lane, Healdsburg
$3,895,000
4 Beds ⋅ 2 Baths ⋅ 326044664 MLS
Built in 1868, this striking Greek Revival residence was built by pioneering settler John D. Hassett and quickly became known to locals as Hassett's Ranch, one of the most prestigious homes of its era. 94 W Grant offers the rare combination of historic lineage, modern livability, and an exceptional location in the heart of Sonoma County wine country. Rich in character and architectural significance, the home offers four spacious bedrooms and two baths across gracious living spaces. Period details along with ceiling heights nearing 11-foot tall blend seamlessly with modern features, including air conditioning, hardwood floors, a welcoming living room with a brick fireplace, a formal dining room with built-in cabinetry, and a thoughtfully designed chef's kitchen suited for contemporary living. Situated on nearly half an acre, lush with mature trees, citrus, and flowering gardens, the grounds are as thoughtfully composed as the home itself. Amenities include a heated pool and spa, a putting green, multiple outdoor spaces for entertaining, and a nearly 1000 sqft carriage house, already served by water and electricity, with soaring 15-foot ceilings. Healdsburg's celebrated downtown plaza only moments away, places Michelin-starred dining, world-class wine tasting, art studios, and boutique shopping at your doorstep. A home that has stood for close to 160 years is not simply real estate, it is a piece of California history. Its next chapter awaits. Call for private appointments.

94 W Grant Street, Healdsburg
$2,750,000
3 Beds ⋅ 2 Baths ⋅ 326039501 MLS
An extraordinary opportunity in the heart of Healdsburg's Wine Country, 5091 Dry Creek Road is the kind of property that rarely comes to market, and almost never with this level of potential. Set on approximately 8 acres of beautiful, flat land with 5.5 acres of established vines, this is a compelling blend of lifestyle, vision, and long-term upside in one of Sonoma County's most picturesque settings. At the center of the land sits a beautifully preserved 1,300 sq ft original coach house, currently classified as an ADU, offering immediate charm and flexibility. The possibilities are exceptional: enhance and enjoy the existing structure as a guest house, creative retreat, or income-producing residence, while building a spectacular new main home on the property. With permits already in place for a second well, the groundwork has been laid for something truly special. This is more than just a land offering, it is a canvas for creating a remarkable Wine Country estate. The setting is private, picturesque, and quintessentially beautiful. Surrounded by vines, open skies, and the effortless beauty that defines this stretch of Healdsburg. To help bring that vision to life, the marketing materials also include imagery of the newly built home located at the lower end of the property. While that residence is not included in the sale, it offers a powerful sense of what can be achieved here and the caliber of home this land can support. Rare, flexible, and rich with possibility 5091 Dry Creek Road is a legacy opportunity in one of California's most desirable wine country locations.

5091 Dry Creek Road, Healdsburg
$8,400,000
4 Beds ⋅ 6 Baths ⋅ 326029056 MLS
Rarely does a home of such architectural intention arrive on the market. Conceived by BAR Architects & Interiors a celebrated San Francisco firm whose work runs through the fabric of California's finest resort communities this 5,642 square foot site-responsive residence is expressed with an unmistakable fluency in luxury living. The design is organized under a signature butterfly roof, a floating canopy that intentionally hides the home from the street, revealing the structure only as you descend into a sequence of glass-walled volumes. The Genova Builders 4BR/5.5BA floor plan is anchored by a dramatic central fireplace and a professional kitchen featuring integrated appliances and honed natural stone surfaces. The living spaces flow effortlessly to 1,511 SF of wraparound decking, dissolving the boundary between the natural wood flooring and the rolling hills. Elevated details include premium designer fixtures, a temperature-controlled wine room, soaking tubs, outdoor showers, a media room, and a private pool. THE MONTAGE ADVANTAGE - Offered fully furnished and uniquely set up for the Montage Rental Program, this property is a turn-key hospitality asset from day one. Ownership provides seamless access to the resort spa, zero-edge pools, and a 24-hour concierge, which serve as a literal extension of the home. Located on one of the community's most private homesites, 175 Sycamore Court offers the rare duality of a secluded retreat with world-class resort amenities just steps away.

175 Sycamore Court, Healdsburg
$1,495,000
326023313 MLS
Located within the luxurious, esteemed and branded Montage Healdsburg community is one of the best view Homesite's remaining at 105 Juniper Court. This corner homesite boasts of privacy and quintessential Sonoma County rolling hill and distant vineyard views. Tucked away in Heritage Oaks while also allowing inspiring views and ample sunlight. This build-ready corner homesite also allows easy access and is very walkable to the communities exclusive Owner's only Clubhouse as well. Once your home is built, enjoy glimpses of Geyser Peak, sunsets and the beautiful rolling hills of Alexander and Dry Creek Valley.

105 NW Juniper Court, Healdsburg
$475,000
41127274 MLS
HEALDSBURG, CA A sprawling 72-acre parcel of land at 11311 Pine Flat Road has been listed for sale, offering a rare opportunity to create a private sanctuary amidst the rolling hills of Sonoma County. With a diverse landscape of open meadows and mature timber, this property presents a blank canvas for a variety of ventures, from a grand estate home with breathtaking views to a tranquil recreational retreat. The property is situated in a region known for its stunning natural beauty, with the potential for panoramic vistas of the Alexander Valley, the Mayacamas Mountains, and the iconic Mt. St. Helena. The land is zoned for timberland, forest, and agricultural uses, opening the door to possibilities such as a private vineyard, an olive grove, or a sustainable forest habitat. Its generous size and secluded location ensure unparalleled privacy and a deep connection with nature. Located on the scenic Pine Flat Road, a paved, dead-end route that winds through the Audubon Canyon Ranch, the property is a haven for outdoor enthusiasts. The area is renowned for its challenging and picturesque cycling routes and is in close proximity to the recreational opportunities of The Geysers and the Russian River.

11311 Pine Flat, Healdsburg
$1,750,000
326020221 MLS
Estate Homesite North 19, located at 135 Hawthorn Court in Healdsburg, California, within the esteemed and luxurious Montage Residences Healdsburg community presents a rare opportunity to build a custom home in one of Sonoma County's premier luxury resort-style communities. Positioned on a high point in the community and amidst it's rolling hills, this 11,006 sq. ft. luxury homesite sits on an elevated setting with southeast exposure, offering morning and afternoon light and views across vineyards and surrounding hillsides. Located just steps from The Residential Club and Montage Healdsburg amenities, the site features a generous building envelope and flexibility for a custom-designed residence. A home study sketch is included to provide additional architectural inspiration if needed. Owners enjoy access to The Residential Club, featuring a private pool, fitness center, gathering spaces, and a dedicated residential concierge team, along with the services and resort amenities of Montage Healdsburg. Just minutes from downtown Healdsburg's wineries, restaurants, and boutiques, the community offers a distinctive blend of privacy, natural beauty, and resort-style living in Northern Sonoma County.

135 Hawthorn Court, Healdsburg
$995,000
326020061 MLS
Located within the esteemed, Forbes Five Star Montage Healdsburg Resort and Community is Estate Homesite North 18, 100 Valley Oak Circle which offers a private, build-ready luxury homesite in the heart of Sonoma's wine country region. Set among rolling hills and oak groves, estate lot enjoys a northeast-facing exposure with treetop views, a tranquil creek gently behind its lot and soft morning light. Conveniently located within walking distance of The Residential Club and just moments from Montage Healdsburg resort amenities, including Spa Montage and on-site dining, the homesite offers both privacy and proximity. The site allows for a thoughtful custom residence with a generous building envelope and includes a home study sketch to provide design inspiration as you envision your wine country retreat. Owners enjoy access to The Residential Club, featuring a private pool, fitness center, gathering spaces, and a dedicated residential concierge team, along with the services and resort amenities of Montage Healdsburg. Just minutes from downtown Healdsburg's wineries, restaurants, and boutiques, the community offers a distinctive blend of privacy, natural beauty, and resort-style living in Northern Sonoma County.

100 Valley Oak Circle, Healdsburg
$2,150,000
41116765 MLS
Welcome to 838 Dry Creek Rd. Imagine owning your own 9.63+/- acre piece of paradise among the vines in the Dry Creek Vally. You will be surrounded by bucolic wine country beauty but just (7) minutes to town and all that Healdsburg has to offer. Think farmers market, boutique shopping and fine dining not to mention out door sports like golf or river rafting. You will be the envy of your friends. This property is a blank canvase just waiting for your imagination. Buy and hold or build right away. You cannot go wrong. Get away from it all in the middle of it all. Creekside front access with Riparian rights make this property special. Don't wait.

838 Dry Creek, Healdsburg
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