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151 Sawmill Cir Unit #204, Healdsburg
$1,995,000
1 Beds ⋅ 2 Baths ⋅ 326040316 MLS
Representing the last remaining one-bedroom plus den residence at Canopy at Mill District, Residence B204 is a masterfully designed sanctuary envisioned by world-renowned AD100 architect Olson Kundig to blend modern architectural pedigree with serene natural beauty. This brand-new home offers a treehouse-like atmosphere, featuring large floor-to-ceiling windows that frame majestic redwoods and overlook the tranquil preserve. The expansive open layout seamlessly connects the living and dining areas to a gourmet kitchen appointed with Italian-made MandiCasa cabinetry, premium Miele appliances, wine storage, and elegant stone countertops. The light-filled living space extends onto a private balcony with a built-in BBQ, ideal for indoor-outdoor entertaining against a backdrop of lush greenery. The primary suite features a generous walk-in closet and a spa-inspired bath with a deep soaking tub, while the versatile den is supported by a separate full second bathroom. Residents enjoy exclusive access to The Poolhouse, a private health and social retreat steps away, featuring a lap pool, expansive sun deck, a sophisticated Residents' Lounge with a demonstration kitchen and fireplace, and a state-of-the-art Fitness Center. Situated in the heart of Healdsburg, this enclave offers a sophisticated, walkable lifestyle moments from the historic plaza, Michelin-starred dining, and world-class tasting rooms. Photos shown may be of the actual unit, a model home, or a similar residence within the building.

151 Sawmill Cir Unit #204, Healdsburg

2167 Redwood Dr, Healdsburg
$475,000
1 Beds ⋅ 1 Baths ⋅ 326040326 MLS
Cute as a button! A perfect vacation house or starter home tucked away by the Russian River on Fitch Mountain, this 1946 cottage has been restored and updated for easy living. Walking distance to the river and hiking trails, close to everything Healdsburg has to offer. One bedroom, one bath, 650 square feet on the main level, plus a loft that adds real living space beyond the listed square footage. With a new roof, recent paint, new carpet, and tile bathroom with a claw-foot tub, the work's already done. Enjoy the covered porch wrapped in fragrant star jasmine. The back doors open to a private, fenced yard with decks, a picnic spot, and an outdoor shower for rinsing off after a day at the river. Forced-air heat and an on-demand water heater cover the essentials. No HOA and no shared walls - just easy living in an eclectic river community. A place to steal away for vacation or to enjoy every day.

2167 Redwood Dr, Healdsburg

216 Foss Creek Cir Unit #B, Healdsburg
$675,000
2 Beds ⋅ 2 Baths ⋅ 326038269 MLS
Located just a short stroll from the world-renowned Healdsburg Plaza, this beautifully upgraded upper-level condominium offers the perfect blend of Wine Country charm and modern comfort. Thoughtfully updated throughout, the unit features an open-concept kitchen and dining area with a breakfast bar, stainless steel appliances, a built-in wine refrigerator, and custom cabinetry ideal for entertaining or everyday living. Rich cherry wood flooring greets you at the entry, while recent upgrades include a new heating and air conditioning system for year-round comfort. Built-in features and quality finishes elevate the space, offering a turnkey opportunity for those seeking a sophisticated yet low-maintenance lifestyle. Whether you're searching for a full-time residence or the ultimate weekend escape, Foss Creek Villas delivers with its serene setting, community pool, and unbeatable location near acclaimed restaurants, tasting rooms, and boutiques.

216 Foss Creek Cir Unit #B, Healdsburg

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

401 Matheson St, Healdsburg

620 Dry Creek Rd, Healdsburg
$1,745,000
4 Beds ⋅ 4 Baths ⋅ 326037487 MLS
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

4951 W Soda Rock Ln, Healdsburg
$3,950,000
4 Beds ⋅ 4 Baths ⋅ 326034879 MLS
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

5520 W Soda Rock Ln, Healdsburg
$14,500,000
4 Beds ⋅ 3 Baths ⋅ 326036977 MLS
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

2 W Soda Rock Ln, Healdsburg
$5,850,000
3 Beds ⋅ 2 Baths ⋅ 326034895 MLS
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

1084 Red Tail Rd, Healdsburg
$1,675,000
3 Beds ⋅ 2 Baths ⋅ 326036719 MLS
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

1099 Dry Creek Rd, Healdsburg
$4,495,000
4 Beds ⋅ 7 Baths ⋅ 326035090 MLS
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

6355 Mountain View Ranch Rd, Healdsburg
$4,875,000
3 Beds ⋅ 4 Baths ⋅ 326035397 MLS
Discover an extraordinary Wine Country retreat where peaceful seclusion, natural beauty, and understated luxury come together in Healdsburg's coveted Dry Creek Valley. The 3,678 square-foot main residence and charming 650 square-foot guest cottage provide an ideal setting for weekend retreats, remote work, and entertaining. Spanning approximately 40 acres of rolling vineyards and scenic hills, this private sanctuary offers breathtaking views of Geyser Peak, Mount St. Helena, and the valley below. A place to escape the demands of urban living, reconnect with nature, and embrace tranquility. Two gated entrances ensure privacy and serenity. Inside, vaulted ceilings, exposed beams, a floor-to-ceiling stone fireplace, and expansive windows create an inviting atmosphere. A well appointed kitchen with professional-grade appliances complements the home's effortless elegance. The main-level primary suite offers a wellness hub with a private view deck and spa-inspired bathroom. Additional bedrooms, a spacious family room, wet bar, utility room, and dedicated wine storage provide comfort and flexibility. Outdoors, a spectacular 50-foot saltwater pool and spa invite relaxation. Imagine mornings spent meditating overlooking the vineyards, meandering among olive and fruit trees, and quiet evenings beneath the Wine Country sky. Approximately 13.16 acres of farmed vineyards feature European varietals, with an established winery relationship offering continuity and ease of management. Whether seeking a luxurious second home, an ideal remote-work setting, or a beautiful primary residence, this exceptional estate offers space to recharge, reflect, and reconnect. A rare opportunity to experience intentional living in the Sonoma County wine country.

6355 Mountain View Ranch Rd, Healdsburg

97 Kennedy Ln Unit #36, Healdsburg
$455,000
2 Beds ⋅ 2 Baths ⋅ 326035850 MLS
Welcome to easy Healdsburg living, just minutes from the historic downtown plaza, wineries, restaurants, boutique shopping, and the Russian River. Built in 2015 and updated throughout, the home features a bright open-concept layout, natural light, and modern finishes. Improvements include updated lighting and fixtures, dimmable living and dining room lighting, newer appliances, and cooling units in each room. It includes a flex room ideal for guests, a home office, hobby space, or additional sleeping area. Outside, enjoy low-maintenance landscaping and peaceful outdoor spaces. Unlike many manufactured home communities, there is no separate land lease or monthly space rent. The property may also be rented to tenants, providing flexibility for investors, second-home buyers, or rental income. This property offers comfort, convenience, and flexibility in the heart of Wine Country.

97 Kennedy Ln Unit #36, Healdsburg

695 Chiquita Rd, Healdsburg
$2,199,000
3 Beds ⋅ 3 Baths ⋅ 326033684 MLS
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

1633 Dry Creek Rd, Healdsburg
$2,995,000
2 Beds ⋅ 3 Baths ⋅ 326033984 MLS
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

5143 Dry Creek Rd, Healdsburg
$4,495,000
4 Beds ⋅ 4 Baths ⋅ 326034406 MLS
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

317 Alexander Valley Rd, Healdsburg
$1,995,000
2 Beds ⋅ 2 Baths ⋅ 326033954 MLS
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

438 Matheson St, Healdsburg
$4,195,000
4 Beds ⋅ 4 Baths ⋅ 326029964 MLS
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

2563 Mill Creek Rd, Healdsburg
$1,400,000
2 Beds ⋅ 3 Baths ⋅ 326032489 MLS
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

1017 Westside Rd, Healdsburg
$2,350,000
4 Beds ⋅ 4 Baths ⋅ 326031365 MLS
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

280 Long Acres Pl, Healdsburg
$2,795,000
4 Beds ⋅ 5 Baths ⋅ 326031086 MLS
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

25 W Grant St, Healdsburg
$6,500,000
10 Beds ⋅ 11 Baths ⋅ 326030556 MLS
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

10957 Westside Rd, Healdsburg
$1,795,000
2 Beds ⋅ 1 Baths ⋅ 326028639 MLS
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

1212 N Fitch Mountain Rd, Healdsburg
$3,195,000
5 Beds ⋅ 3 Baths ⋅ 326025290 MLS
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 814 sf 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 opens to stunning views, lush garden back patio. Spacious primary bathroom with tub, walk-in shower and double sinks. There is an ensuite guest bedroom downstairs. Upstairs are three enchanting bedrooms featuring built-in bookshelves and cabinets plus a full bathroom. 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 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 home. SEE VIDEO at end of FACTS and FEATURES

1212 N Fitch Mountain Rd, Healdsburg

6165 W Dry Creek Rd, Healdsburg
$740,000
4 Beds ⋅ 4 Baths ⋅ 326024033 MLS
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

735 Johnson St, Healdsburg
$2,450,000
3 Beds ⋅ 2 Baths ⋅ 326006835 MLS
Location, location, location! Located just half a mile from the Healdsburg Plaza, 735 Johnson Street sits on 1/4 acre lot within the coveted Johnson Street Historic District; a neighborhood known for its architectural character, walkability, and enduring charm. Originally built in 1995, the home offers about 2,000+ SqFt of thoughtfully arranged living space with 3 bedrooms and 2 bathrooms. A formal living room with a fireplace and wet bar create a welcoming space to gather, while the dedicated dining room and breakfast nook provide multiple options for daily meals or special occasions. The gourmet kitchen features granite countertops and connects easily to both indoor and outdoor dining areas. A separate den/home office offers privacy for focused work, creative pursuits or separate family room. A large backyard deck extends the living space and invites quiet moments in the fresh air. Below, a partial basement includes a workshop space, large wine cellar and additional storage. At the rear of the property, a large detached two-car garage provides ample room for parking, gear, or future guest house or ADU location. This large lot could fit a pool, a large garden or bocce court. The home is well-maintained with a layout that encourages personalization over time. Other features include an electronic gate with private driveway, rainwater collection system, solar array, front and back porches and clean basement storage. Don't miss this opportunity to live on Johnson Street! (Property is now income producing with monthly rent to owners.)

735 Johnson St, Healdsburg

4395 Pine Flat Rd, Healdsburg
$7,950,000
5 Beds ⋅ 6 Baths ⋅ 326017030 MLS
Welcome to 4395 Pine Flat Rd, an elegant Healdsburg estate offering some of the most breathtaking views in Sonoma County. Just minutes from downtown yet worlds away, this extraordinary property blends luxury, comfort, and resort-style amenities on 10+ mostly usable acres. The Main Residence consists of a four-bedroom, five-bathroom home is designed for both entertaining and everyday living. High ceilings, rich wood floors, and expansive windows frame vineyard and mountain vistas at every turn. Highlights include: Chef's kitchen with bar seating and seamless flow to the outdoor dining pavilion, formal dining room and multiple living spaces including a family room, library/office, gym, and wine cellar, main-level suite perfect for guests or multi-generational living, upstairs primary suite with private balcony, sitting area, and generous storage. A spacious detached studio offers flexible use for guests or extended family. Its outdoor entertainment area, complete with fireplace, is ideal for gatherings under the stars. This estate was made for relaxation and play, featuring a sparkling pool & hot tub, tennis court & bocce court, outdoor kitchen & vineyard-view dining, orchard, rose gardens, and raised garden beds, serene spots for birdwatching or simply doing nothing at all.

4395 Pine Flat Rd, Healdsburg

801 Samantha Ct, Healdsburg
$2,295,000
5 Beds ⋅ 4 Baths ⋅ 326016409 MLS
Nestled at the end of a quiet cul-de-sac in one of Healdsburg's desirable residential settings, 801 Samantha Court presents a rare opportunity to reimagine an exceptional property into something truly extraordinary. Set on a private, park-like parcel shaded by majestic oaks, the property enjoys sweeping views, remarkable tranquility, and a seamless connection to nature. Free from HOA restrictions yet bordering two neighboring HOA open spaces, the setting offers a wonderful sense of privacy and serenity. The home offers an expansive chef's kitchen that opens to generous outdoor decks, creating an effortless flow between indoor and outdoor spaces. Whether hosting elegant dinner parties, holiday celebrations, or leisurely weekend gatherings, the home provides an inviting backdrop for every occasion. An additional approximately 1,600 square feet of versatile space offers exceptional flexibility for a variety of lifestyle needs. Two spacious recreation rooms, a dedicated gym/wine cellar, and abundant storage further enhance the property's versatility. For the automotive enthusiast or serious collector, the impressive eight-car garage is a particularly rare and compelling feature, offering extraordinary space to house a prized collection, pursue automotive projects, or accommodate recreational vehicles and hobbies. Outdoors, the beautifully terraced grounds offer endless possibilities for relaxation and entertaining. Natural stone retaining walls define inviting outdoor spaces, while expansive decks provide idyllic settings for dining, lounging, and enjoying the surrounding landscape. An oversized treehouse adds a sense of whimsy and adventure, while a thoughtfully positioned firepit captures picturesque Healdsburg views and provides a front-row seat to Fourth of July fireworks. With its substantial footprint, distinctive architectural elements, exceptional garage capacity, and peaceful natural setting, 801 Samantha Court offers a remarkable canvas for a thoughtful transformation. An opportunity to create a truly special Healdsburg retreat, where privacy, possibility, and an expansive lifestyle come together.

801 Samantha Ct, Healdsburg

936 Valley View Dr, Healdsburg
$1,175,000
3 Beds ⋅ 2 Baths ⋅ 326003322 MLS
Own the Altitude. Positioned along Valley View on the preferred side of Fitch Mountain, this approximately 2,200 square foot residence delivers what cannot be recreated: elevation and horizon. The main living level sits upstairs exactly where it belongs so daily life meets open sky. Living room, kitchen, and primary suite are oriented toward expansive views and natural light. Downstairs, a generous family room and two additional bedrooms provide separation and flexibility. Built in the 1980s and offered in original condition, this is not about finishes. It's about fundamentals. In a neighborhood where homes range from approximately $1.2 million to over $3.5 million, this offering represents entry into one of Healdsburg's most compelling ridgeline settings. Front and rear decks extend the footprint outward and invite reinvention. Tucked at the end of an easement, the property offers privacy without isolation within the City of Healdsburg and minutes to downtown. Elevation is permanent. The rest is up to you.

936 Valley View Dr, Healdsburg

920 Lytton Springs Rd, Healdsburg
$2,995,000
3 Beds ⋅ 3 Baths ⋅ 326012134 MLS
Exceptional Healdsburg! Two 10 acre parcels being sold together are set among utterly noble surrounds and gorgeous panorama of rolling terrain, meticulous vineyard rows, oak woodlands, pastoral and distant mountain views anchored by our silent guardian, Mt St. Helena. This setting remains one of the prettiest you'll see, one of the most serene you'll experience. And yet just 10 minutes away is historic and dynamic downtown Healdsburg , Geyserville's rustic charm, the Dry Creek General Store & Tavern. Lake Sonoma's Recreation is a quick 15 minute drive. This quiet countryside, expressive with an active pollinator garden, fruit orchard - citrus, plum, apples, figs, asian pears and young 2019 cabernet vines planted and nourished in rich Dry Creek benchland soil notable for producing ultra premium wines. The single story home built on a gentle rise commands a 360 vantage point. Vibrant views & seasonal light illuminate every room, this 2600 sq.ft. of comfort can be expanded upon & updated to suit your own stylistic preferences resulting in a countryside haven you won't want to leave! The home's 1988 vintage offers superb building integrity, a separate office, open dining into living with warm wood finished ceilings, 3 bedrooms, 2.5 baths, finished basement for wine and cold storage. The entire property is served by solar. Separately, there's a 850 sq.ft. shop and the original cabin remains with some utilities. Its condition reflective of its age, but it brings great value for potential guest house, ADU or farm stay use. The adjacent 2nd parcel, 1730 Chiquita is separately accessed and improved with a high producing well. Perced (2006) for a 3 bedroom system, possibly 4, it too is planted in premium cabernet for a total of 12.2 acres of vines. A thriving ecosystem of herons and ducks, dragonflies and others find rest on the adjacent one acre foot aerated pond; they're a joy to watch while in flight below the reflecting water. DA zoning and two separate parcels allow for further development potential and other agricultural/equestrian options. The Sonoma County Airport is within a 15 minute proximity. This exquisite 20 acres summons a lifestyle abundant with natural soundscapes, tranquility, starry skies, sunrise's golden light & sunset's liquid fire that also cultivates reciprocity in wine country enterprise. Not to be missed! Property Website: https://910lyttonspringsrd.com/

920 Lytton Springs Rd, Healdsburg

397 Parkview Dr, Healdsburg
$1,148,275
3 Beds ⋅ 3 Baths ⋅ 326010888 MLS
Discover the perfect blend of natural beauty and downtown convenience in this spacious 3-bedroom, 2.5-bathroom Healdsburg retreat. Ideally located just steps from Byron Gibbs Park and a scenic 1.5 mile stroll to the iconic Healdsburg Plaza, this home offers immediate access to world-class dining, shopping, and tasting rooms. The light-filled, open layout is designed for seamless entertaining, flowing directly onto an expansive back deck that overlooks a peaceful stream. Wander across the bridge to discover a rustic chicken coop area, a charming canvas for your "farm-to-table" dreams or a creative garden project. For those needing extra space, the property features two separate garages, providing ample room for vehicles, a home gym, or a dedicated workshop. Ready for its next chapter, this home comes thoughtfully refreshed with brand-new interior and exterior paint, as well as plush new carpeting upstairs. This turn-key sanctuary allows you to move right in and start enjoying the quintessential Wine Country lifestyle from day one.

397 Parkview Dr, Healdsburg

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