Healdsburg Real Estate

Healdsburg Real Estate

Welcome to Healdsburg, California—a charming gem nestled in the heart of Sonoma County. Known for its picturesque landscapes and vibrant community, Healdsburg offers a unique blend of small-town charm and sophistication that captivates both residents and visitors alike.

As you stroll through the tree-lined streets, you’ll discover a delightful mix of boutique shops, art galleries, and gourmet restaurants, all showcasing the region’s rich cultural heritage and culinary prowess. The town’s central plaza is a hub of activity, hosting lively farmers' markets and seasonal festivals that celebrate local artisans and the bountiful harvests of the surrounding vineyards.

Healdsburg is renowned for its world-class wineries, making it a haven for wine enthusiasts. With over 400 wineries in the nearby area, you can indulge in tastings that highlight the region's exceptional varietals, from bold Zinfandels to elegant Chardonnays. The scenic beauty of rolling vineyards and majestic oak trees creates an idyllic backdrop for outdoor activities, including hiking, biking, and kayaking along the Russian River.

Families will appreciate Healdsburg’s excellent schools and welcoming community spirit, while nature lovers can explore nearby parks and trails that showcase the stunning Sonoma County landscape. Whether you’re looking for a weekend getaway or considering a permanent move, Healdsburg’s enchanting atmosphere and rich offerings make it a truly remarkable place to call home. Discover the magic of Healdsburg, where every corner tells a story and every experience is a celebration of life.

Newest Listings in Healdsburg

$1,295,000
3 Beds ⋅ 3 Baths ⋅ 326065513 MLS
Tucked along the banks of a year-round creek, this fully remodeled 2,178 sq ft retreat blends thoughtful design with the kind of privacy that's increasingly rare in wine country. Set on a .55-acre lot, the property has been re-envisioned from the studs up, balancing warm, contemporary finishes with an easy connection to the land around it. The main house offers 2 bedrooms and 2 bathrooms in a serene setting with a usable yard, abundant deck space, and oak trees surrounding the property. Extensively renovated to feel timeless and elegant in wine country. Features include extensive use of fire resistant metal siding on the exterior, newer cabinetry, slab countertops, new appliances, hardwood floors, fully remodeled bathrooms and a fully functional interior elevator. Attached yet fully separate, the guest quarters add a private 1-bedroom, 1-bathroom living space ideal for visiting family, a home office, or rental income potential. Step outside and the creek frontage becomes the true centerpiece of the property, offering a rare sense of seclusion and a direct connection to nature just minutes from town. Whether you're looking for a full-time residence, weekend escape, or multigenerational setup, 14183 Chalk Hill Rd delivers a rare combination of privacy, water frontage, and move-in-ready polish.

14183 Chalk Hill Rd, Healdsburg
$1,495,000
3 Beds ⋅ 2 Baths ⋅ 326064711 MLS
Set along one of Healdsburg's most picturesque streets, this rare find features two separate bungalow-style homes on a spacious 1/4 acre parcel just minutes from Healdsburg Plaza. With turn-of-the-century character and a just-remodeled interior, the primary home (#133) is a perfect blend of historic and new. Classic bungalow-styling features two bedrooms and one bathroom, approximately 750 sq.ft. of living space, all updated to please the modern aesthetic. Tall ceilings and windows, LED lighting, an inviting front porch, new cabinetry and appliances, luxury vinyl plank flooring, and an energy-efficient mini-split system make this home ready for you to move right in and enjoy. The second home is set to the back of the parcel with its own private entrance and separate house address. Built in a cottage style, this sweet unit is one bedroom, one bath with approximately 647 square feet of living space. The interior is freshly painted with new lighting fixtures. Both homes have air-conditioning, laundry, separate detached garages, and fully fenced yards. This property is truly unique. Two homes on a 1/4 acre lot, two separate addresses, two electric meters, and two water meters. Whether you're envisioning a private family compound, a wine country getaway with guest accommodations, multi-generational living, or the flexibility of a primary residence paired with a second home, the possibilities are as timeless as the homes themselves. Just 0.7 mile from celebrated Healdsburg Plaza, enjoy the perfect balance of neighborhood charm and world-class dining, wineries, and boutique shopping.

135 Sherman St, Healdsburg
$2,900,000
3 Beds ⋅ 2 Baths ⋅ 326065911 MLS
Nestled in the heart of Healdsburg's highly sought-after West Dry Creek Valley, this exceptional Wine Country retreat offers the perfect blend of privacy, natural beauty, and relaxed luxury. Set on approximately 3.04 acres and surrounded by renowned vineyards and wineries, the property captures the essence of Wine Country living. The single-level residence features 3 bedrooms and 2 bathrooms with the potential for future expansion, offering the possibility of adding up to two additional bedrooms (buyer to verify). Designed for effortless indoor-outdoor living, the beautifully landscaped grounds provide an idyllic setting for entertaining family and friends. Enjoy warm summer days by the sparkling in-ground pool and spa, host memorable barbecues on the expansive outdoor living areas, or simply relax while taking in the picturesque vineyard views that border two sides of the property. Whether you're seeking a full-time residence, weekend escape, or Wine Country getaway, this rare West Dry Creek offering combines an unbeatable location with exceptional potential in one of Sonoma County's most coveted destinations.

5968 W Dry Creek Rd, Healdsburg
$695,000
3 Beds ⋅ 3 Baths ⋅ 326062554 MLS
3-Bedrooms, 2-1/2 Baths Home close to Healdsburg Golf Course, Russian River, Downtown Healdsburg Plaza. Located near Clubhouse and Pool with Russian River Access, Close to Badger Park which has a Dog Park, Community Gardens.

849 Falcon Way, Healdsburg
$950,000
4 Beds ⋅ 2 Baths ⋅ 326065240 MLS
Wine Country Gem with four APNs, over 1/2 acre of land and river access! This spacious, rustic charmer offers a timeless ambiance with vintage character, modern comfort, and an extraordinary natural setting. The home's two levels each have their own living area and expansive wrap-around decks, showcasing breathtaking panoramic views of the iconic Russian River. Two bedrooms on each level allow for exceptional flexibility for entertaining, working from home, or accommodating guests. Additional highlights include a large, bright kitchen and dining area, abundant windows, and private wine storage. Step outside and enjoy spectacular river vista views and seamless indoor-outdoor living. The generously sized lots provide a peaceful retreat with access to the Russian River beach, perfect for kayaking, swimming, relaxing, or simply enjoying the beauty of Wine Country. Ideally located just minutes from Healdsburg's renowned downtown plaza, world-class wineries, acclaimed restaurants, and boutique shopping. This unique property offers an unparalleled opportunity to own a distinctive riverfront retreat in one of Sonoma County's most sought-after destinations. Don't miss your chance to own this exceptional Vintage Healdsburg home.

2031 Madrone Ave, Healdsburg
$16,000,000
326066203 MLS
Matrix Winery is a landmark 44-acre winery estate situated along Healdsburg's iconic Westside Road corridor in the heart of the Russian River Valley. Anchored by a valuable 50,000-case winery permit, the property features an established tasting room open for tours and tastings with wine warehouse-office and extensive paved parking area. Beautiful landscaped grounds, winery production facility, and approximately 20 acres of premier estate hillside vineyards planted primarily to Pinot Noir, Chardonnay, Zinfandel, and Petite Sirah. The turnkey grounds boast two scenic reservoirs, an extensive paved internal road network, and panoramic valley views. Located just minutes from downtown Healdsburg and the Plaza, the parcel presents rare development upside with potential subdivision into two ~20-acre parcels, each offering multiple prime building sites for a legacy compound or custom estate residence.

3291 Westside Rd, Healdsburg
$2,450,000
3 Beds ⋅ 3 Baths ⋅ 326066250 MLS
Sweeping Dry Creek Valley views, 6.5 acres, and a coveted West Dry Creek Road address set the stage for this special Healdsburg Wine Country property, just minutes from Healdsburg Plaza. Surrounded by vineyards and mature redwoods, the setting offers privacy and a remarkable connection to one of Sonoma County's most celebrated destinations for cycling, wine tasting, dining, and outdoor recreation. The single-level main residence features three bedrooms plus a flex room and three full bathrooms, with an open kitchen, spacious great room, expansive windows that take full advantage of the surrounding views, and an easy connection to the outdoor spaces. Fresh exterior paint, updated interior light fixtures, and refreshed landscaping give the property a renewed feel while leaving it ready for your personal touches and vision. An unfinished two-story ADU offers additional space and future possibilities, while an agricultural barn provides added flexibility for vineyard operations, equipment, storage, a workshop, or other agricultural uses. Two separate access points provide convenient entry to the residential and vineyard areas. Approximately two acres are planted with Zinfandel vines, further connecting the property to the landscape and character of Dry Creek Valley. With world-renowned wineries and scenic cycling routes nearby, along with the restaurants, boutiques, tasting rooms, and energy of Healdsburg Plaza just minutes away, this is a rare opportunity to own a substantial Wine Country property in one of Healdsburg's most sought-after locations.

3025 W Dry Creek Rd, Healdsburg
$875,000
3 Beds ⋅ 2 Baths ⋅ 326066241 MLS
Excellent neighborhood (with no pesky HOA dues to pay or association to have looking over your shoulder:), easy walk to downtown. Access to bicycle trail that routes down Johnson St. to Healdsburg Plaza and businesses in the area. Quiet cul-de-sac location. Has been a rental for decades. Owner is a quality contractor who has built many custom homes in the Healdsburg area. Short walk to the City Pool which adjoins the high school.

243 Theresa Ct, Healdsburg
$1,289,000
3 Beds ⋅ 1 Baths ⋅ 326066461 MLS
Escape to Wine Country with this inviting single-story home set behind a private gate on 2.4 acres in the heart of Alexander Valley. Featuring 3 bedrooms, 1 full bath,Escape to Wine Country with this inviting single-story home, privately set back from the road behind a gated entrance on 2.4 acres in the heart of Alexander Valley. Featuring 3 bedrooms, 1 full bath, and a single-car garage, this well-proportioned home offers comfortable living with the space, privacy, and serenity that only acreage can provide. Lovely outdoor patios, a hobby vineyard, raised garden beds, approximately 28 Italian olive trees, and a variety of fruit trees enhance the outdoor experience, creating a peaceful country setting just minutes from the celebrated restaurants, boutique shopping, and vibrant scene of Healdsburg and Geyserville. What makes this property truly special is its potential: the current home is ideally suited to serve as an additional dwelling unit (ADU) for a future main residence. The elevated hilltop building site offers a beautiful setting with pastoral views for that next chapter. Your dream home is within reach. This gated property offers rare flexibility, opportunity, and the quintessential Wine Country lifestyle in Sonoma County's beautiful Alexander Valley. and a single-car garage, this well-proportioned home offers comfortable living with the space and serenity that only acreage can provide. Lovely outdoor patios, a hobby vineyard, raised garden beds, approximately 28 Italian olive trees, and a variety of fruit trees enhance the outdoor experience, creating a peaceful country setting just minutes from the celebrated restaurants, boutique shopping, and vibrant scene of Healdsburg and Geyserville. What makes this property truly special is its potential: the current home is ideally suited to serve as an additional dwelling unit (ADU) for a future main residence. The elevated hilltop building site offers a beautiful setting with pastoral views for that next chapter. Your dream home is within reach. This gated property offers rare flexibility, opportunity, and the quintessential Wine Country lifestyle in Sonoma County's beautiful Alexander Valley.

1240 Alexander Valley Rd, Healdsburg
$895,000
2 Beds ⋅ 2 Baths ⋅ 326065600 MLS
Beautifully rebuilt and move-in ready, this stunning 2-bedroom, 2-bath cottage home offers the perfect blend of luxury finishes, thoughtful craftsmanship, and an unbeatable Healdsburg location. Situated directly across the street from Russian River access, enjoy the best of outdoor living while being minutes from downtown Healdsburg's world-class restaurants, renowned wineries, and boutique shopping. This fully permitted renovation features elegant marble countertops, designer Ann Sacks tiles, premium Waterworks faucets, and sophisticated Visual Comfort lighting. The cottage is equipped with high-end Fisher & Paykel appliances (refrigerator, microwave, and dishwasher), a Viking gas range and a stacked interior washer and dryer. The yard boasts river views and a newly completed river rock retaining wall, poured driveway and walkways, with an outdoor patio. Additional highlights include engineered hardwood floors, Pella aluminum-clad windows, WUl-compliant exterior Hardie shingles and TruExterior trim, spray foam insulated walls and ceiling throughout the house and garage and off-street parking for up to four cars plus an attached single-car garage. An exceptional opportunity to own a beautifully finished home in one of wine country's most desirable locations.

1914 Redwood Dr, 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
$2,495,000
2 Beds ⋅ 3 Baths ⋅ 326065293 MLS
Just four blocks from the vibrant Healdsburg Plaza, this beautifully reimagined residence blends timeless craftsmanship with exceptional indoor-outdoor living. Thoughtfully renovated over the years, the home offers sophisticated single-level living with a chef's kitchen featuring a Wolf range, soapstone countertops, dual sinks, a generous center island, custom cabinetry, and built-in dining with flexible guest accommodations. The spacious primary suite was redesigned to include a luxurious spa-inspired bath, soaring vaulted ceilings, and an expansive dressing room, creating a tranquil retreat. A comfortable second bedroom and beautiful second full bath provide inviting accommodations for family and guests or an ideal work-from-home space. Throughout the home, custom millwork, art lighting, built-in speakers, radiant fireplace heat, two HVAC systems, and instant hot water provide everyday comfort and convenience. Designed for unforgettable entertaining, the outdoor spaces feature a multi-level cedar deck with a recessed therapeutic spa, expansive stone patios, gas fire feature, water fountain, outdoor kitchen connections, mature landscaping, fruit trees, and multiple seating areas surrounded by exceptional privacy. Adding incredible versatility is an approximately 813-square-foot detached studio and garage with soaring ceilings, loft, full bath, laundry, extensive storage, and separate climate control - ideal for many purposes, including creative pursuits, a home office, or flexible living. With Savant whole-property audio, beautifully curated gardens, and an unbeatable location moments from world-class dining, tasting rooms, shopping, and the Healdsburg Plaza, this is an exceptional opportunity to enjoy the very best of Wine Country living.

328 Piper St, Healdsburg
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