Refine Search
Sort by
13000 Los Amigos Rd, Healdsburg
$9,400,000
325100234 MLS
This is truly a one-of-a-kind Healdsburg Legacy Ranch, first time on the market in many decades. 'Highland Acres Ranch' has an expansive 1,160 acres. The lands of this ranch extend from near 101 & Healdsburg Ave to Alexander Valley with Fitch Mountain & the Russian River near its Northern border & Chalk Hill near its Southern border. It includes very private Russian River frontage below Alexander Valley. There are 2 parcels: 2303 Bailhache Ave with 520 acres & 13000 Los Amigos Rd with 640 acres. You enter this ranch through the beautiful St. Francis vineyards off Los Amigos Rd just South of downtown Healdsburg. There is an existing access road through the vineyards going to its 26-acre building envelope that features panoramic city light views extending to the hills along the Sonoma coast. Before the Kincade fire in 2019, this ranch had a family compound built within the 26- acre building envelope. There are 2 certified septic systems & 2 domestic wells with fully restored PG&E electricity service ready to build with. There were 2 homes, as well as barns & outbuildings, that existed before, which the county's Resiliency Program Guidelines should qualify to replace, saving a substantial amount of $ in permit fees & also shorten the building permit approval time substantially.

13000 Los Amigos Rd, Healdsburg

2843 Wright Ranch Ln, Healdsburg
$7,900,000
4 Beds ⋅ 4 Baths ⋅ 326017235 MLS
Sited upon a naturally protected contour on 113 acres in one of Northern California's most desirable wine country settings, The Clearview Estate is a luxury vineyard estate near Healdsburg in Sonoma County, offering remarkable privacy, unobstructed sweeping views, and refined living in the heart of wine country. Just minutes from the Michelin-starred dining of Healdsburg, renowned wineries, and Sonoma County Airport, and approximately 1 hour from San Francisco, the property offers a rare balance of privacy and accessibility. The gently rolling landscape includes 7.5 acres of premium Cabernet Sauvignon vineyard under lease, offering the perks of vineyard ownership without the responsibilities of management. A five-mile trail network winds through open meadows, seasonal creeks, and around a tranquil reservoir below the residence, creating an exceptional setting for hiking, mountain biking, horseback riding, and exploring the natural beauty of the land. The 4,288 sq. ft. custom residence, built by respected wine country builder Total Concepts, reflects authentic farmhouse architecture with vaulted ceilings, expansive windows, and seamless indoor-outdoor living. The formal living room flows into the dining room with exposed beams and folding glass doors opening to outdoor spaces and a screened porch with fireplace. The kitchen features a generous butcher-block island, elevated appliance selection, walk-in pantry, and abundant windows framing the surrounding landscape. The entire second level is dedicated to the primary suite, offering vaulted ceilings, fireplace, multiple view balconies, spa-inspired bath with soaking tub, and dual walk-in closets. A private guest wing with its own living area, bedroom, sleeping loft, and covered porch provides comfortable accommodations for visitors. A temperature controlled wine cellar offers ample storage for collectors. Outdoor amenities include an infinity-edge pool and spa, bocce court, fire pit, and multiple gathering areas overlooking the property's inspiring landscape. Resting near converging creeks and heritage oaks, a distinctive party barn offers flexible space for a car collection, studio, workshop, or memorable gatherings. Grid-tied solar, multiple wells, water storage, and fenced pastureland complete this exceptional Healdsburg wine country estate. Experience a lifestyle defined by the land itself.

2843 Wright Ranch Ln, Healdsburg

131 Sawmill Cir Unit #401, Healdsburg
$7,800,000
3 Beds ⋅ 4 Baths ⋅ 326040350 MLS
Experience the pinnacle of Healdsburg living in this newly constructed, full-floor penthouse where world-class architecture meets the serene beauty of the preserve. Accessible via a private elevator entrance, this residence was designed by the visionary firm Olson Kundig, recently honored in the 2025 AD100, defining modern sophistication within the exclusive Mill District enclave. The expansive single-floor layout is anchored by a true chef's kitchen featuring premium Miele appliances, a high-performance gas range, and a dedicated wine room. For effortless hosting, a discreet butler's pantry provides an additional sink and secondary dishwasher. The heart of the home flows seamlessly from the kitchen through the open-concept dining and living areas, where oversized sliding doors retract to create a breathtaking open wall experience. This merges the interior with a massive private deck spanning over 2,000 square feet. This outdoor sanctuary, complete with a full kitchen, sink, and BBQ, offers the perfect vantage point for golden hour sunsets over the preserve. The primary suite serves as a true retreat with direct terrace access, an oversized walk-in closet, and a spa-like soaking tub. Two additional bedrooms feature private en suite bathrooms, complemented by a dedicated home office and a powder room. Coming in Summer 2026, the Mill District's world-class amenity suite will feature a private lap pool, a designer pool deck, and a sophisticated Residents' Lounge tailored for entertaining. Wellness enthusiasts will appreciate the state-of-the-art Fitness Center and Movement Studio, offering a balanced environment for high-performance training and yoga. Experience this unrivaled sanctuary perfectly positioned just a short stroll from Healdsburg's iconic dining and tasting rooms.

131 Sawmill Cir Unit #401, Healdsburg

no property photo
$6,700,000
4 Beds ⋅ 6 Baths ⋅ 326018994 MLS
Perched atop a sun-kissed knoll in the rolling hills of Healdsburg just minutes from the famed Plaza, this breathtaking gated estate radiates the timeless romance of the Italian countryside. Sweeping 360 views of vine-draped valleys and golden hills create a setting straight from a Tuscan dream. The main residence is a harmonious blend of rustic charm and modern luxury, with warm stucco walls, clay tile roof, and stone paths winding through fragrant gardens and olive trees. Inside, soaring ceilings, a private elevator, butler's kitchen, and wine cellar evoke refined living. French doors open to patios perfect for dining under the stars, while the sparkling pool, spa, and full bath changing room invite leisurely afternoons. A 1-bedroom guest cottage offers serene vineyard views and private repose. Across 23.5 acres, life flourishes with vegetable and flower gardens, fruit trees, and two chicken coops. This is a place to gather, savor, and dream where every detail whispers romance, rooted in the heart of wine country.

Healdsburg

9110 Chalk Hill Rd, Healdsburg
$6,500,000
6 Beds ⋅ 6 Baths ⋅ 326000256 MLS
Don't miss this truly exceptional Healdsburg estate, offering gated, private living on one of the most coveted roads in the area. A private bridge crosses a seasonal rocky creek, leading you into a serene, park-like setting where an enchanted pond with swimming and boat docks is framed by mature trees and a fenced orchard garden. Nearby, a newer RV creates the perfect hub for weekend campouts, swimming, barbecues, volleyball, and lakeside relaxation. Continue up the drive to the recently built modern farmhouse, completed by local builders in 2023. Inside, soaring ceilings and expansive walls of glass capture breathtaking, uninterrupted panoramic views from every room stretching across the Mayacamas, Mt. St. Helena, and rolling vineyard-lined valleys. The main residence features four bedrooms and three-and-a-half baths, a stunning great room, expansive outdoor decks, and deep garages with a large motor court ideal for car enthusiasts and entertainers alike. An adjacent ADU offers two bedrooms and two baths, its own fireplace, and equally impressive views, positioned above an expansive six-car garage and workshop. Set on approximately 100 acres with thoughtful improvements throughout, this rare wine country offering combines privacy, recreation, and refined living. A truly special property awaiting its next discerning buyer!

9110 Chalk Hill Rd, Healdsburg

6323 W Dry Creek Rd, Healdsburg
$4,450,000
4 Beds ⋅ 4 Baths ⋅ 326041213 MLS
Set in coveted Dry Creek Valley, just outside Healdsburg, this idyllic country property rests on an elevated 3.9 acres overlooking iconic vineyards and pastoral landscapes. A winding country lane leads to the gated entry, where sweeping views of the valley and surrounding mountains unfold, setting the scene for a lifestyle defined by quiet luxury, natural beauty, and a sense of ease that reveals itself over time. Thoughtfully transformed and expanded in 2014, the three-bedroom residence draws on a classic farmhouse aesthetic, reinterpreted through a clean, modern lens. The dramatic Great Room, anchored by soaring 15ft. ceilings, a Lennox gas fireplace, walls of windows and French doors, flows seamlessly onto an expansive entertaining deck overlooking the valley and pool below. The chef's kitchen features Thermador appliances, Pietra Grigio natural stone countertops, a striking end-grain black walnut island, and a charming window seat nook. The main-level primary suite offers vineyard views, deck access, a spacious walk-in closet with laundry, and a spa-inspired bath with dual custom vanities, a freestanding soaking tub, radiant floor heating, and a Toto Japanese toilet. Two additional spacious guest bedrooms, one with private patio, and a dedicated office with built-in cabinetry, and additional laundry, complete the lower level. A thoughtfully designed flex space, currently a workout room, is adaptable for media room, work or creative pursuits. A charming 390 sf guest house offers ideal accommodations for guests, complete with a sleeping loft, Murphy bed, full kitchen with island, living area, and full bath. The 3-car garage and adjacent shed provide plenty of storage and space for hobbies. Outdoors, resort-style amenities abound: a solar-heated lap pool with integrated cover, a wood arbor with retractable shade for lounging and outdoor dining, a fenced vegetable garden with raised beds, extensive landscaping, and a pickleball court. Practical highlights include a metal roof, cement board siding, private well with UV filtration/water softener, whole-home backup generator, solar power with battery backup, and an EV charger outlet. A rare offering in Sonoma Wine Country, located only 15 minutes to the charming town of Healdsburg.

6323 W Dry Creek Rd, Healdsburg

10533 Westside Rd, Healdsburg
$3,958,090
5 Beds ⋅ 6 Baths ⋅ 326056737 MLS
Imagine leaving the pace of everyday life behind. As you wind along the iconic Westside Road beneath towering redwoods, you arrive at your private gate and immediately feel the world slow down. The birds are singing, a gentle breeze dances through the vineyard leaves, and your pool sparkles in the afternoon sun, a quiet invitation to settle into the rhythm of Wine Country. From the moment you arrive, you know you've found a place that feels exactly as it should. 10533 Westside Road is more than a home, it's a sanctuary where architecture and nature exist in perfect harmony. Thoughtfully designed for this extraordinary setting, every space embraces the surrounding landscape. Warm wood tones, expansive walls of glass, and a timeless palette of slate, granite, and metal blur the line between indoors and out. While the home's clean architectural lines create a striking presence, subtle curves soften the design, lending an organic elegance that feels both sophisticated and welcoming. Built in 1990, the residence offers three spacious bedrooms and three-and-a-half bathrooms, each thoughtfully positioned to provide both privacy and comfort. Every room captures a unique view, allowing the natural beauty outside to become part of everyday living. Just beyond the main home, the beloved pool house, affectionately known as The Hut, offers a magical retreat of its own. Complete with a kitchenette, full bath, and cozy loft, its industrial-style windows frame a picturesque lily pad-filled pond where the gentle chorus of frogs provides nature's evening soundtrack. The estate continues to unfold with a versatile barn featuring an upper-level one-bedroom, one-bath space with a kitchenette and flex room. With the recent expansion of the septic system from two to five bedrooms, the opportunity now exists to transform this into a remarkable guest residence for extended family, visitors, or additional living space. Below, the barn offers ample room for a workshop, storage, or creative pursuits. As guests arrive, they're welcomed by the lower barn at the entrance, where twinkling market lights create an unforgettable first impression. Whether hosting intimate weekends, milestone celebrations, or peaceful evenings under Sonoma's star-filled skies, every corner of this property was designed to bring people together while offering room to breathe. And you're only minutes away from downtown Healdsburg as well as West County activities.

10533 Westside Rd, Healdsburg

320 Center St, Healdsburg
$3,750,000
326001179 MLS
Rare opportunity to own one of the most iconic retail buildings in the heart of downtown Healdsburg, prominently located on the premier corner of Healdsburg Plaza. 320 Center Street is a beautifully preserved mixed-use property featuring a high-visibility ground-floor retail space and two residential apartments above. Built in 1857, the building offers a compelling blend of historic charm and modern functionality. The ground-floor retail space is currently available and suitable for owner-occupancy and providing flexibility for a variety of uses. The upstairs residential units remain occupied, offering additional income potential. This property is well-suited for investors, 1031 exchange buyers, or end-users seeking a flagship presence in Wine Country.

320 Center St, Healdsburg

1315 W Dry Creek Rd, Healdsburg
$3,400,000
3 Beds ⋅ 5 Baths ⋅ 325055488 MLS
Experience the pinnacle of wine country living at this exceptional Dry Creek Valley estate, set on 25.9 private acres surrounded by world-class vineyards. This stunning home offers 4 bedrooms, one a newly added in-law unit, 4 full baths, and 2 powder rooms, masterfully blending modern sophistication with natural beauty. Expansive terraces, manicured grounds, and panoramic vineyard views create a breathtaking backdrop for entertaining, from al fresco dinners under the stars to poolside lounging and golden hour wine tastings. Every space is designed for both celebration and serenity. Inside, the open-concept Great Room flows seamlessly to the outdoors, ideal for gatherings large or small. A chef's kitchen, soaring ceilings, and a serene primary suite offer elegant comfort. Walls of glass and clean architectural lines bathe the home in light and warmth. Whether hosting a sunset soiree or savoring a quiet glass of wine, this estate embodies the best of the Healdsburg lifestyle--refined, relaxed, and undeniably luxurious.

1315 W Dry Creek Rd, Healdsburg

699 Grove St, Healdsburg
$3,351,700
4 Beds ⋅ 3 Baths ⋅ 326015708 MLS
Timeless elegance meets modern Wine Country living in this beautifully reimagined 1937 residence, just moments from downtown Healdsburg and set on an expansive +/-.33-acre lot. The home offers four bedrooms and three full baths, including a spacious main-level primary suite with a fireplace, two walk-in closets, and a spa-like bathroom. The living room is perfectly sized and would transform to any aesthetic - it's that good. The kitchen is timeless, with a gas range, island, marble counters, pantry, and breakfast area. The feel is gracious and updated, with a nostalgic appeal, featuring a wonderful basement, sprawling bedrooms on the upper level, and a covered porch. It's the modern appeal that sets it apart, though, with thoughtful updating and everyday needs met. The backyard is a private retreat. A sparkling in-ground pool is framed by lush landscaping and raised garden beds, a trellised dining area, and a built-in barbecue. The large detached office provides flexibility and could be a recreational room, art studio, or potential ADU. Just blocks from the Healdsburg Plaza, you'll enjoy the beloved restaurant scene, fun wine tasting, summer concerts on the square, and our weekly farmers' market. A true Healdsburg gem.

699 Grove St, Healdsburg

1541 Chablis Rd, Healdsburg
$3,325,000
5 Beds ⋅ 4 Baths ⋅ 326033487 MLS
Welcome to Healdsburg! A sprawling single-level home set on 1.4 acres in Healdsburg's coveted Vintage Hills neighborhood. Perfectly marrying the charm of country living with the convenience of city services, all tucked away on a peaceful lane that embodies the best of Wine Country living. This property is as practical as it is beautiful, offering exceptional energy efficiency with an owned solar system and a brand-new 40-gallon-per-minute well, keeping utility costs impressively low. Step inside and discover warm hardwood floors that lead you through the home's thoughtful layout. At its heart, you'll find the formal living room with a cozy gas fireplace and chef's kitchen ideal for entertaining. All 5 bedrooms are privately situated on the east side of the home, with the primary bedroom in the rear and opening to the backyard. The family room, rec room, office, and laundry are on the west wing of the home, also opening to the backyard, creating a harmonious indoor-outdoor flow. Step outside to your resort-like grounds. Gather with family and friends on your covered patio with cooling misters for hot days and ceiling heaters for chilly evenings. Spend your days lounging by the pool, and nights stargazing in the hot tub or circling around the fire pit. A ton of room for recreation with a huge lawn & a driveway spacious enough to set up a pickleball court. The east side of the property borders a seasonal creek and offers the beginning of an abundant homestead, with a chicken coop and an orchard of over 50 fruit trees. Additionally, there is a detached 4-car garage with an overhead door leading to the backyard. All of this and just a short 7-minute drive to the Healdsburg Plaza and 1 hour to the Golden Gate. This is an ideal property for full-time residences or a Wine Country retreat.

1541 Chablis Rd, Healdsburg

425 Tucker St, Healdsburg
$3,300,000
4 Beds ⋅ 3 Baths ⋅ 326075117 MLS
Come see what everyone is talking about! Rare Healdsburg Opportunity! Character, Space & Possibility. Opportunities like this rarely come to market in the heart of Healdsburg. Set on nearly one-third of an acre on one of Healdsburg's most desirable streets, this unique property offers an exceptional combination of location, character, privacy, and versatility. Bordering Tucker Street and Alley 2, the quintessential single-level Craftsman features 3 bedrooms, 1.5 bathrooms, laundry room, mudroom, and basement, root cellar.'' Enjoy classic front-porch living and a private backyard with an established orchard. Privately accessed from Alley 2, the detached 840-square-foot, 1-bedroom, 1-bath ADU, built in 2004, offers its own entrance, parking, and full-length deck overlooking the orchard, perfect for guests, family, or a private retreat. And the possibilities continue: the property may have the potential to become two separate lots. The combination of nearly one-third acre, alley access, an existing ADU, and a prime downtown location is exceptionally rare. Whether you envision a family compound, multigenerational living, a guest retreat, or exploring the potential of two properties, this is a truly special opportunity to create your own Healdsburg lifestyle. Rarely does a property with this location, land, and potential become available. Come experience it for yourself.

425 Tucker St, Healdsburg

2998 W Dry Creek Rd, Healdsburg
$3,107,500
3 Beds ⋅ 3 Baths ⋅ 326020277 MLS
Just four miles from downtown Healdsburg along picturesque West Dry Creek Road, this newly built modern farmhouse offers a refined take on Wine Country living in one of Dry Creek Valley's most sought-after locations. Set on an a low-maintenance 1/3 acre parcel, this three-bedroom, three-bath residence seamlessly blends contemporary design with relaxed country elegance. At the heart of the home, a dramatic, living room with vaulted 20 foot ceilings creates an inviting light-filled gathering space. The adjoining gourmet kitchen is thoughtfully appointed for both entertaining and everyday living, featuring a Lacanche gas range, Wolf ventilation hood, Sub-Zero refrigerator, and temperature controlled wine cooler, Miele dishwasher, stone countertops and custom cabinetry throughout. Designed for effortless indoor-outdoor flow, the main living room doors slide open to a patio overlooking neighboring vineyards. This is an ideal setting for dining, entertaining, or simply enjoying the tranquil rhythm of Dry Creek Valley. This exceptionally low maintenance parcel offers a built in bocce court, sufficient space for raised bed gardening or a future swimming pool. Additional highlights include a standing seam metal roof, a 27 kilowatt Tesla Powerwall energy system, laundry room, a one car garage with EV charger, a high-producing well and state-of-the-art filtration system, providing a reliable water source. This is truly a rare and exceptional opportunity to own a thoughtfully designed brand new, luxury retreat in Healdsburg's renowned Dry Creek Valley.

2998 W Dry Creek Rd, Healdsburg

519 Horse Barn Rd, Healdsburg
$3,100,000
4 Beds ⋅ 4 Baths ⋅ 326014284 MLS
Tucked just minutes from the heart of downtown Healdsburg, this striking newer home offers a rare blend of modern design & privacy with a wine country lifestyle ease. Set amid meadow views, gardens, and forested hills, the property delivers true single-level living with seamless indoor-outdoor flow-perfect for everyday comfort and effortless entertaining. Glass-walled Nano doors open the expansive great room to the outdoors, creating a natural extension of the living space and framing serene natural surroundings. The chef's kitchen anchors the home with an oversized eat-in island along with a Wolf gas cooktop & vented hood in relationship with Sub-Zero refrigerator and separate wine refrigerator. The thoughtfully designed floor plan boasts high-end finishes with hardwood floors throughout inclusive of two private primary en-suite bedrooms plus two additional guest bedrooms that share a full bath, all on one level. A dedicated office and flexible additional room offers space for work, media, or recreation, complemented by high-speed Starlink internet. Outside, professionally landscaped grounds create a resort-like setting featuring a heated infinity-edge pool, separate spa and expansive deck with accent lighting along with both dining and lounging areas sprinkled amongst recreational amenities inclusive of bocce court, sand volleyball court and horseshoe pits. There is a private well with a complete Reverse Osmosis system installed for properly treated water to use everywhere around the home. The setting feels secluded yet is incredibly convenient - just five minutes to Healdsburg Plaza and moments from renowned wineries in Dry Creek, Alexander Valley, and the Russian River. Sustainably built with an owned 9.36kWh solar power system and eco-conscious design, this home balances luxury with efficiency and comfort. Whether used as a full-time residence or a refined Wine Country retreat, 519 Horse Barn Road offers an exceptional lifestyle in one of Sonoma County's most desirable locations.

519 Horse Barn Rd, Healdsburg

9981 W Dry Creek Rd, Healdsburg
$3,045,000
3 Beds ⋅ 3 Baths ⋅ 325043445 MLS
Welcome to 9981 West Dry Creek, an exquisite estate and the final residence on this notable road. On the market for the first time in 26 years, this custom-built Santa Barbara-style home offers a unique mix of seclusion and stunning natural surroundings, with rose gardens, olive trees, and more encircling the property. Spanning over approximately 3,300 square feet on 49+/- acres, the residence includes three generously sized bedrooms and 2.5 baths, all thoughtfully designed for modern living. The home's interior is an ode to smart, elegant design, boasting an open-concept kitchen, a cozy breakfast nook, a sophisticated living room, and a formal dining roomideal for both intimate gatherings and grand entertaining. A serene hallway, mirroring a cloister-style covered porch, leads to a convenient half bath, a laundry room, and independent bedroom ensuites, ensuring both comfort and privacy. At the end of the exterior-covered walkway, you'll find a spacious two-car garage, approximately 428 square feet, with an unfinished second floor offering limitless possibilities for a gym, office, media room, or an ADU. With access to seasonal creeks, trails ideal for hiking and ATV rides, this property is ideal for those who value a connection with nature.

9981 W Dry Creek Rd, Healdsburg

206 Old Rossi Pl, Healdsburg
$2,998,000
4 Beds ⋅ 4 Baths ⋅ 326065364 MLS
Welcome to Old Rossi Place! Tucked along a peaceful cul-de-sac in the heart of Healdsburg, stands a true single-level, modern farmhouse, featuring stunning vaulted, wood beamed ceilings and French Oak flooring throughout, with four spacious bedrooms and four full bathrooms. Three of the four bedrooms include private en suite baths, providing comfort and privacy for both family and guests. The chef's kitchen serves as the home's centerpiece, outfitted with a Wolf range and steam oven, built-in Sub-Zero refrigerator with dedicated wine column, dual dish washers, and beverage coolerperfect for hosting gatherings of any size. Outdoors, a sparkling pool invites relaxed afternoons under the Sonoma County sun, surrounded by mature landscaping that gives the property an established, welcoming character seldom seen in new construction. Whether entertaining poolside or simply unwinding, these spaces feel polished yet relaxed. Just a short stroll to the Healdsburg Plaza, where renowned wineries, exquisite shopping and Michelin-star restaurants await perfectly placing you at the center of wine country's best dining and tasting. Thoughtfully designed, beautifully finished, and ready for its first owners, this home blends contemporary style with timeless charm. Truly a rare pairing of quality construction and an unbeatable location.

206 Old Rossi Pl, Healdsburg

423 Matheson St, Healdsburg
$2,900,000
3 Beds ⋅ 4 Baths ⋅ 326014169 MLS
This landmark Healdsburg residence, set along a storybook stretch of downtown Healdsburg, strikes the perfect balance of distinctive architectural style with modern sensibility. Historic Matheson Street is a highly coveted address consistently celebrating the city's most valuable and sought-after real estate. Stately 3BR Queen Anne home embodies its classic character with design-forward interiors, single-level living and an adaptable floor plan. Elegant living room and formal dining room grace the entry with distinctive moldings, soaring coved ceilings, and generous windows that frame sun filled interiors, while an adjacent lounge or den provides an intimate space for TV, games, or pre-dinner gatherings. At the heart of the home, a beautifully renovated kitchen features a large central island with prep sink, abundant custom cabinetry, pantry storage, and premium Viking appliances. The serene primary suite overlooks the rear garden and sauna and features a fireplace, sitting area, and direct access to the deck. Two additional bedrooms with ensuite bath in one and the other has a convenient half-bath. Generous laundry room with kitchen office adds everyday convenience, while a basement provides generous storage space and fully racked wine cellar. Set on nearly one-third of an acre, the grounds offer space for gardens and ample parking, an amenity rare for in-town properties. A driveway along the side of the main home leads to an open auto court at the rear of the property, and an additional two-level residence expands the livability of this property. Interior stairs connect a beautifully appointed ADU, with full bath, modern kitchen, and garden access to a spacious room with full bath downstairs, providing generous guest accommodation, income opportunity, or dynamic live-work compound in the heart of town. Located just two blocks from boutiques, galleries and celebrated dining surrounding Healdsburg Plaza, immersed in the best of Healdsburg living. A rare in-town opportunity, just steps to the Plaza, where enduring architecture and gracious design elevate modern living.

423 Matheson St, Healdsburg

716 University St, Healdsburg
$2,870,000
4 Beds ⋅ 3 Baths ⋅ 326042447 MLS
In town Healdsburg home. This Stunning single-story 4-bedroom home is on a spectacular .45 acre lot and has privacy and views. Renovated in 2025, this high-end Mid-Century style home has designer touches, plenty of space for gathering and entertaining and a sparkling pool that was recently resurfaced. Tucked back off University, this sun filled property has mature landscaping and views to Fitch Mountain and beyond. Inside you will be delighted by the chefs kitchen with stainless steel appliances, wine fridge, wide plank French Oak floors, gorgeous Taj Mahal quartzite countertops and an oversized peninsula with bar seating and storage. The kitchen space is expansive with great workspace and includes a breakfast area. Off the kitchen there is an additional room, filled with windows that would make a great light filled reading nook or sunroom and has a sliding door that provides access to the outdoor patio. The great room consists of the living room with a wood burning fireplace connecting with a dining area that offers views to the pool. Enter the primary suite with a sliding door that opens to a patio with views and a luxurious bathroom with soaking tub and walk in shower. In addition, there are 3 spacious guest bedrooms, one with a built-in desk and another full bath with double sinks and a powder room off the laundry room. The laundry room, with new washer and dryer also has a work sink and additional storage and a walk-in pantry. Step outside into the park like backyard and relax, swim, work on a garden or enjoy your detached flex space that is currently staged as a private gym/studio. This rare parcel is set amongst other estate homes and just a few blocks from downtown Healdsburg. For efficiency it has two heat pumps and owned solar. More room to grow so talk to the city about adding a pool house or ADU. An amazing place to call home!

716 University St, Healdsburg

10934 Eastside Rd, Healdsburg
$2,850,000
4 Beds ⋅ 4 Baths ⋅ 326073904 MLS
Wine Country living at its finest. Experience the best of Wine Country living from this beautifully appointed Eastside Road property, ideally situated at the end of a private lane on 2.11 acres. Surrounded by mature trees and backing to a neighboring vineyard, the setting feels peaceful and tucked away while remaining just minutes from Healdsburg and Windsor. The 3,474 sq. ft. home offers 4 bedrooms and 3.5 baths and lives like a single level, with the primary suite and dedicated office on the main floor. The primary bath adds a touch of luxury with heated floors and a steam shower. At the heart of the home is a spacious open kitchen designed for gathering and entertaining, featuring a marble island with five-burner gas cooktop, farmhouse sink, built-in refrigerator and freezer, double ovens, built-in espresso machine, microwave drawer and 48-bottle wine refrigerator. The open layout offers generous entertaining space, while large windows frame the surrounding greenery and bring the Wine Country setting indoors. A custom four-panel NanaWall accordion door opens the living space to the outdoors, creating a seamless connection for indoor-outdoor entertaining. Outside, enjoy the fully fenced PebbleTec pool and spa, bocce ball court and plenty of room to relax, gather and take in the Wine Country setting. Additional features include temperature-controlled wine storage, solar panels and a Tesla charger. Whether enjoyed as a full-time residence, second home or with an eye toward potential vacation rental use, this Eastside Road property offers exceptional Wine Country versatility. Peaceful and tucked away, yet close to acclaimed wineries, restaurants, shopping and all that Healdsburg and Windsor have to offer, with convenient access to the greater Bay Area.

10934 Eastside Rd, Healdsburg

433 Tee Ct, Healdsburg
$2,850,000
4 Beds ⋅ 4 Baths ⋅ 326016348 MLS
This beautifully designed custom 4,000 s.f. home is situated on a spacious, fully landscaped, and private .39 acre parcel. An amazing location, just a short distance to downtown Healdsburg and the Plaza. Dozens of upgrades include: Pool, spa, remodeled kitchen and baths, walk in wine cellar, playroom, 3 car garage and multiple designer touches throughout. Additonally, located on the ground level there is bedroom and full bathroom with direct access to the exterior. The floor plan opens to the huge shaded deck, patio and BBQ area. The mature landscaping and trees offer privacy and a perfect backdrop for entertaining and relaxation. The koi pond and pergola also provide additional enhancement to the outdoor experience. This is truly a wonderful opportunity to enjoy all of what the wine country has to offer!

433 Tee Ct, Healdsburg

12076 Cloud Ridge Rd, Healdsburg
$2,750,000
6 Beds ⋅ 4 Baths ⋅ 326026338 MLS
Situated amidst the redwoods in Healdsburg's scenic Mill Creek, this nearly 43-acre property blends peace, privacy, and timeless design. Accessed by a private road, the main home is a 4BD/3BA Craftsman built from first-growth redwood from the property, with one bed and bath conveniently located on the main level. A spacious paver patio wraps the home, offering the perfect spot to soak in the views. Inside, the great room features a wood-burning stove, hardwood floors, and expansive picture windows that invite the outside in. The remodeled kitchen boasts a Wedgewood range, built-in Viking fridge, custom cabinetry, and a walk-in pantry. A large mudroom/laundry area sits just off the kitchen for added functionality. All 3 baths remodeled as well. Brand new heating sytem! Down the road, a separate guest cabin offers a full kitchen, wood floors, indoor laundry, wood stove, two bedrooms & full bath, and a wraparound deck that basks in sunlight. An additional secluded redwood deck creates a peaceful escape ideal for art, yoga, or summer fun. Both homes and the well system are powered by owned solar and a Generac generator. Just 15 minutes to downtown Healdsburg's restaurants, tasting rooms, and Hwy 101 this retreat offers complete privacy without sacrificing convenience. **Seller fianancing possible**.

12076 Cloud Ridge Rd, Healdsburg

171 Sawmilll Cir Unit #203, Healdsburg
$2,550,000
2 Beds ⋅ 3 Baths ⋅ 326029300 MLS
Canopy at Mill District offers a serene sanctuary designed by world-renowned AD100 architect Olson Kundig. Residence A203 is a brand-new home featuring two bedrooms, two-and-a-half bathrooms, and a versatile den, all perfectly perched on the second floor. The heart of the home is an open floor plan, with a gourmet kitchen flowing seamlessly into the living and dining areas. Large floor-to-ceiling sliding doors lead to the private balcony equipped with a built-in BBQ, making it the perfect place for morning sunrises and effortless indoor-outdoor living. The interior is defined by rustic sophistication and luxurious finishes, including Italian-made cabinetry, Miele appliances, stone countertops, and temperature-controlled wine storage. The primary suite serves as a true retreat, featuring a large walk-in closet, a spa-like bathroom with a soaking tub, and a dedicated desk area. The second bedroom also offers a walk-in closet and an ensuite bathroom with a walk-in shower. For added flexibility, the den is perfect for a home office, a fitness space, or a cozy second seating area, while a pantry and laundry room off the kitchen provide additional functionality. Canopy represents a rare opportunity to enjoy a meticulously designed home in the most desirable location in wine country. The 10- acre Mill District community will also include a boutique hotel, a swimming pool, and a fitness center. Located in the heart of Healdsburg, this home blends urban vibrancy with resort-like amenities. You are just a short walk from the charming plaza, Michelin-starred restaurants, and world-class tasting rooms.

171 Sawmilll Cir Unit #203, Healdsburg

829 Healdsburg Ave, Healdsburg
$2,500,000
326021852 MLS
Development opportunity in Downtown Healdsburg. This approximately one-acre property currently includes five, detached residential rental units, and three outbuildings with ample parking. Zoned ORM, this property could be re-developed into multi-family units (possibly up to 15 units) and/or offices and is located not in the path of progress but in the heart of progress. It is situated near one of Healdsburg's busier intersections (Powell Avenue and Healdsburg Avenue so promises excellent visibility and exposure. This property represents a unique opportunity for investors and developers to capitalize on Healdsburg's growth and prime downtown location. Whether pursuing residential, office, or mixed-use projects, the potential for a high return on investment is significant.

829 Healdsburg Ave, Healdsburg

15119 Grove St, Healdsburg
$2,450,000
3 Beds ⋅ 4 Baths ⋅ 326021490 MLS
In-Town Healdsburg Farmhouse Estate on 2.16 Acres: Set on a rare 2.16-acre parcel in downtown Healdsburg, this exceptional property offers remarkable flexibility - whether envisioned as a private family compound, future development opportunity, or a turnkey wine country retreat. The thoughtfully designed single-level farmhouse spans approximately 3,326 square feet and features three generously sized bedroom suites, each with its own en suite bath, for a total of 3.5 bathrooms. Vaulted ceilings, warm hardwood floors, and a beautifully appointed chef's kitchen create a refined yet relaxed living environment. A welcoming wraparound porch overlooks the meticulously landscaped grounds, where outdoor living takes center stage. Enjoy a resort-style setting with a large pool and spa, outdoor kitchen, and an expansive entertaining deck designed for gatherings beneath the wine country sky. Above the detached three-car garage you will enjoy a private flex space with full bathroom and laundry. With its rare acreage, prime in-town location, and endless possibilities, this is a truly unique opportunity to own a remarkable piece of Healdsburg wine country.

15119 Grove St, Healdsburg

10936 Eastside Rd, Healdsburg
$2,300,000
3 Beds ⋅ 3 Baths ⋅ 326034866 MLS
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

801 Dry Creek Rd, Healdsburg
$2,100,000
4 Beds ⋅ 3 Baths ⋅ 326030457 MLS
Set on approximately 1.5 private acres in the heart of Dry Creek Valley, this historic wine country estate captures the essence of Sonoma living. Timeless, relaxed, and quietly spectacular. Originally designed in a classic Victorian style and thoughtfully renovated, the main residence offers four bedrooms and two and a half baths, filled with natural light, warmth, and character at every turn. Beyond the main home, the property unfolds into a true lifestyle compound. A charming detached ADU, finished entirely in rich knotty pine and complete with its own kitchen and bath, offers an inviting retreat for guests, extended family, or creative pursuits. Entertaining here is effortless and unforgettable. The expansive barn both functional and atmospheric sets the stage for gatherings large or small, from intimate dinners to celebratory events. Outdoors, a 20-person jacuzzi invites evenings under the stars, surrounded by mature trees and sweeping valley views that stretch across the prestigious Dry Creek landscape. Every corner of the property has been curated to embrace the beauty of its surroundings from enchanting gardens and open spaces to peaceful vantage points that take in vineyard and ridge views. Just minutes from the Healdsburg Plaza, yet feeling a world away, this is a rare offering where history, versatility, and wine country lifestyle come together in one extraordinary setting.

801 Dry Creek Rd, Healdsburg

519 Johnson St, Healdsburg
$1,995,000
4 Beds ⋅ 3 Baths ⋅ 326035415 MLS
Exceptional opportunity in the heart of Healdsburg's historic district - just three blocks from the Plaza. This rare property features two separate homes plus two detached accessory spaces on an ~8,060 SF lot, offering incredible flexibility for multi-generational living, rental income, or a primary residence with guest accommodations. The front home (circa 1939) has been thoughtfully restored, blending timeless character with modern updates. Period details such as coved ceilings, archways, and hardwood floors are complemented by a renovated kitchen, updated windows, and a beautifully preserved vintage bath. A detached studio with full bath and an attached garage add versatility. The newer rear bungalow (built 2010) offers a bright, open-concept layout with 9-foot ceilings, abundant natural light, and seamless indoor-outdoor flow. Features include a well-appointed kitchen, gas fireplace, heated bathroom floors, and its own detached accessory room - ideal for a home office, studio, or guest overflow. Both residences enjoy private outdoor spaces with mature landscaping, patios, grape arbors, and fruit trees, creating a peaceful compound setting just moments from world-class dining, tasting rooms, and the vibrant Healdsburg Plaza. A unique blend of historic charm and modern convenience in an unbeatable in-town location.

519 Johnson St, Healdsburg

655 W Grant St, Healdsburg
$1,990,000
3 Beds ⋅ 3 Baths ⋅ 326028576 MLS
Set on nearly half an acre in the heart of Healdsburg's coveted Dry Creek valley floor, this warm and inviting 3-bedroom, 3-bathroom retreat offers a lifestyle rooted in beauty, comfort, and connection to the land. Surrounded by neighboring vineyards, framed by majestic mountain views, and kissed by mature redwoods, the property feels like a private sanctuary while remaining just minutes from the charm of downtown. Life here unfolds outdoors as much as it does inside. Multiple patios create distinct spaces for gathering, dining, and unwinding, while a wood-fired oven and artful bocce court invite long, laughter-filled evenings. Garden beds and abundant fruit trees offer a farm-to-table experience right at home, and the peaceful setting is accompanied by birdsong, rustling leaves, and breathtaking sunrises and sunsets that paint the sky daily. Inside, the fully remodeled residence blends thoughtful design with effortless indoor-outdoor flow. The main living space is both striking and welcoming, featuring vaulted ceilings, a stunning rock fireplace, and seamless connection to the kitchen, perfect for entertaining or enjoying quiet nights in. Natural materials and textures ground the home in its surroundings, creating a sense of authenticity and calm. A detached workshop and garden shed provide exciting potential for a guest space, studio, or creative retreat, adding flexibility to this already special property. Whether hosting lively gatherings, tending the garden, or simply soaking in the serenity, this is a place to slow down, savor, and truly feel at home. Warm, unique, and beautifully built, this is Healdsburg living at its finest.

655 W Grant St, Healdsburg