Healdsburg Real Estate

Healdsburg Real Estate

Welcome to Healdsburg, California, a hidden gem nestled in the heart of Sonoma County’s wine country. Known for its idyllic charm and vibrant community, Healdsburg offers a perfect blend of small-town warmth and upscale sophistication. With its tree-lined streets, historic architecture, and picturesque town square, this enchanting city invites you to explore its unique character and rich heritage.

Healdsburg is renowned for its world-class wineries and vineyards, making it a paradise for wine enthusiasts. The surrounding rolling hills and lush landscapes create a stunning backdrop for outdoor adventures, from hiking and biking to kayaking along the Russian River. The city’s commitment to sustainability and local agriculture is evident in its thriving farmers’ market, where residents and visitors alike can savor fresh, seasonal produce.

Culinary delights abound in Healdsburg, with a diverse array of restaurants, cafes, and bistros that showcase the region's farm-to-table philosophy. Whether you're indulging in a gourmet meal or sipping a glass of locally crafted wine, the culinary scene here is sure to impress.

Culturally rich and community-focused, Healdsburg hosts numerous festivals and events throughout the year, celebrating everything from art and music to food and wine. The warm and welcoming atmosphere makes it easy to forge connections and build lasting friendships.

Whether you’re looking to settle down in a charming home or seeking a weekend getaway, Healdsburg’s unique blend of relaxation and excitement makes it an ideal destination. Discover the magic of Healdsburg—where every day feels like a celebration of life!

Newest Listings in Healdsburg

2590 N Fitch Mountain Rd, Healdsburg
$299,000
2 Beds ⋅ 1 Baths ⋅ 326089919 MLS
Opportunity knocks with this diamond in the rough. A unique opportunity with 2-units in the highly desirable Fitch Mountain neighborhood of Healdsburg. Bring your toolbelt to make this property shine as a river retreat, fix and flip, or future rental property. Bring your creativity and unlock the potential in one of Sonoma County's most sought after locations.

2590 N Fitch Mountain Rd, Healdsburg
220 North St, Healdsburg
$1,950,000
3 Beds ⋅ 2 Baths ⋅ 326090239 MLS
Just steps from the Healdsburg plaza, stands a classic Victorian home built in 1900 with 10-foot ceilings and an abundance of historic character. The generously sized bedrooms are filled with natural light, the expansive kitchen and open floor plan make this the perfect wine country residence. The backyard has plenty of room for gardening while enjoying the above ground lap pool. The attached 628 sq ft ADU is ideal for family, friends or guests. Enjoy your morning coffee on the front porch while you watch the world go by on the peaceful section of North Street.

220 North St, Healdsburg
951 Trentadue Way, Healdsburg
$2,500,000
4 Beds ⋅ 4 Baths ⋅ 326088365 MLS
Meticulously designed with attention to every detail in this 4 bedroom, 4 bathroom home, including auxiliary dwelling unit. Finely crafted finishes, and bathed in natural light, showcasing the very best of Healdsburg. A short walk or bike ride to the Healdsburg Square Plaza. As you enter the property, you are greeted by a canopy of Heritage olive trees, and enter through the 10' custom French iron entry door, to 12' ceilings and a sophisticated entry flanked by the bespoke beamed ceiling dining room, featuring built-in cabinetry and a wine refrigerator on your right. To the left is an amply sized office or bedroom. A climate controlled wine storage wall built to store up to 21 cases of your favorite wine provides a sleek transition to the main living areas. The chef style kitchen is perfect for culinary enthusiasts, and connects to the great room, featuring a marble fireplace and a continuation of ceiling beams. Your eyes are drawn to yet another Heritage olive tree, ripe and ready to harvest in the backyard entertaining space, boasting stacking doors for a seamless continuity from indoor to outdoor living. Professionally landscaped, manicured grounds, created for little to no maintenance. Celebrate each entertaining space including outdoor covered dining patio , BBQ kitchen, cozy lounge area with fire pit, and a tranquil fountain rounding out this private retreat. Designed with attention to every detail, this residence embodies contemporary sophistication. Close to world class wineries and dining, Sonoma County Airport and the coast. Less than an hour to San Francisco.

951 Trentadue Way, Healdsburg
560 Matheson St, Healdsburg
$2,395,000
3 Beds ⋅ 3 Baths ⋅ 326084611 MLS
Half a mile from the Healdsburg Plaza, on one of the most attractive stretches of Matheson Street, this three-bedroom home has been extensively reimagined while keeping its original charm. Light fills every room, and a wraparound porch sets the tone for slow mornings and long evenings outside. The remodeled kitchen anchors the main level with custom cabinetry, a pantry, and a large gathering counter, while a 16-foot slider opens straight to the deck and garden. A new gas fireplace and refinished oak floors warm the living room. Upstairs, all three bedrooms have vaulted ceilings giving a real sense of space, and the primary bath's soaking tub overlooks the garden. New Andersen windows and doors, roof, Hardie siding, heat and air conditioning, and a tankless water heater are just some of the many recent improvements. Set on a very private lot, the professionally designed gardens offer bluestone patios, a sunken garden, and a six-person hot tub. Location, light, and an extensive renovation, all in one. Must see to appreciate.

560 Matheson St, Healdsburg
6697 Westside Rd, Healdsburg
$22,000,000
12 Beds ⋅ 14 Baths ⋅ 326086344 MLS
Set within Healdsburg's famed Russian River Valley, the Flax Estate and Vineyard spans 52 acres of privacy, stunning contemporary architecture, and world-class wine country living. Spanning two private parcels, this secluded retreat seamlessly balances contemporary luxury with its historic farmhouse and its direct Russian River access. The property is anchored by a dramatic, contemporary main residencea four-bedroom, four-and-a-half-bath masterpiece thoughtfully designed around majestic heritage oaks. Floor-to-ceiling glass, frames sweeping, uninterrupted views across the valley floor to the region's iconic peaks: Mount St. Helena, Fitch Mountain, and the Geysers. Steeped in history, the estate's historic six-bedroom, six-bath farmhouse once owned by the acclaimed actor Fred MacMurray exudes timeless Wine Country with interiors by celebrated designer, Ken Fulk. Its grounds feature a resort-style wellness complex complete with a 75-foot swimming pool, oversized spa, stand-alone gym, and sauna. Surrounding this pool area is a tennis court, bocce court, outdoor shower, and manicured fruit orchards alongside vibrant flower and vegetable gardens. A more recently built, unique entertainment barn offers a sophisticated setting for hosting memorable parties. Positioned near the private entrance to the property sits a beautifully rebuilt two-bedroom, one-bath cottage providing flexible accommodations for family, guests, or resident staff. At the heart of the estate lies a 26 acre, organically farmed vineyard producing world-class Pinot Noir and Chardonnay. Exclusively managed and crafted by DuMOL Winery, the vineyard's "Flax Estate" designate consistently produces highly sought-after vintages revered by collectors worldwide. Few properties so effortlessly unite architectural distinction, storied history, world-class viticulture, and the natural beauty o f the Russian River making Flax Estate Vineyard a truly singular offering in the heart of Wine Country. The property is offered turn-key and furnished.

6697 Westside Rd, Healdsburg
1840 Redwood Dr, Healdsburg
$1,160,000
2 Beds ⋅ 2 Baths ⋅ 326084605 MLS
Fitch Mountain Beauty with Endless Possibilities! Set on approximately 1.5 acres, this special Fitch Mountain property offers two homes, beautiful natural light, and lovely views of the Russian River. The main residence features soaring vaulted ceilings, warm wood floors, and a spacious kitchen with double ovens and a stunning farmhouse sink. A separate two-bedroom, one-bath guesthouse provides wonderful flexibility for extended family, guests, or additional living space. With a detached garage, ample parking, storage sheds, and plenty of room to make it your own, this property offers a rare combination of charm, versatility, and potential. A wonderful opportunity in a beautiful Fitch Mountain setting!

1840 Redwood Dr, Healdsburg
119 Chiquita Rd, Healdsburg
$1,050,000
4 Beds ⋅ 4 Baths ⋅ 326084628 MLS
Welcome to 119 Chiquita Rd and 1620 Winding Creek Way! Recently built in 2021, this incredible combination of main residence and ADU opens up endless opportunities when it comes to multi-generational living, rental income or whatever living situation would work best for you! The main residence is a two story 3 bedroom & 3 bathroom craftsman with an open layout and large side yard. The ADU has a separate entrance off of Winding Creek Way and is a 1 bedroom & 1 bathroom with stackable washer and dryer, full kitchen and dining area. All of this just minutes from downtown Healdsburg and the amazing wineries the region has to offer.

119 Chiquita Rd, Healdsburg
318 Mason St, Healdsburg
$1,075,000
2 Beds ⋅ 1 Baths ⋅ 326086217 MLS
Looking for a Vintage home with charm and potential in downtown Healdsburg? This 2-bedroom home plus a versatile bonus room sits on a desirable lot just a few blocks to downtown Healdsburg. Featuring high ceilings, updated windows, a convenient detached garage and a side yard with gardening beds and mature fruit and shade trees. Built in or around 1870 this home has had updates over the years yet captures the historic character of early Healdsburg and is positioned in the path of progress. Mason street is considered a highly desirable local favorite due to the low traffic flow and the close proximity to town. Offering so many possibilities with the option to move right in, make it an amazing restoration project or buy for investment. Now is the time to get into the community and enjoy all that Healdsburg has to offer including boutique shopping, fine dining, seasonal farmers markets, free live music events in the Plaza and quaint coffee shops.

318 Mason St, Healdsburg
180 Sawmill Cir Unit #407, Healdsburg
$2,925,000
2 Beds ⋅ 2 Baths ⋅ 326086310 MLS
Experience the pinnacle of Wine Country living in the heart of downtown Healdsburg with this exclusive condo hotel offering at The Residences at Alyvia. This limited collection of 12 luxury residential condominiums is seamlessly integrated within a full-service 53-room hotel within the emerging Mill District community. Each residence is legally mapped as a condominium, governed by a condominium association, and managed by the esteemed Mayacama Hospitality. Owners enjoy a highly personalized lifestyle, including a custom arrival experience in which the team pre-stocks their favorite refreshments, arranges their personal amenities prior to entry, and provides a licensed storage unit for personal belongings. The Alyvia advantage provides a rare connection to the prestigious Mayacama Golf Club. Ownership includes the opportunity to establish a membership with Charter-level access, providing preferred golf privileges for owners, their families, and guests. While in residence, owners enjoy priority spa and restaurant reservations, private cabana opportunities, and full access to the wellness center, including fitness and pool. Designed for both personal enjoyment and effortless ownership, this property under City entitlements utilizes a professional Rental Management Agreement. Revenue is shared through a transparent 50/50 split of net rental income. Monthly HOA dues of $1,386.25 conveniently cover all essential utilities, including water, electricity, gas, and internet. This is a legacy opportunity to own a piece of Healdsburg's finest hospitality. Views are representative of the building's offerings; actual views vary based on unit location.

180 Sawmill Cir Unit #407, Healdsburg
250 Monte Vista Ave, Healdsburg
$929,000
3 Beds ⋅ 2 Baths ⋅ 326084301 MLS
Welcome to 250 Monte Vista Avenue, a beautifully updated 3-bedroom, 2-bath home offering approximately 1,450 square feet of comfortable living space. Ideally located on the south side of March Avenue near Lupine, this inviting home is just a quick stroll to downtown. Great curb appeal welcomes you with a newer garage door and front door, while numerous updates throughout provide added peace of mind for the next owner. Improvements include a newer roof, windows, flooring, and additional updates helping minimize many of the major expenses that can come with homeownership. Step outside to a private backyard designed for relaxing and entertaining, complete with a spacious deck, ambient lighting, and hot tub. With no HOA and a convenient location close to town, this move-in-ready home offers an ideal combination of comfort, privacy, and convenience.

250 Monte Vista Ave, Healdsburg
775 Florence Ln, Healdsburg
$1,599,000
3 Beds ⋅ 3 Baths ⋅ 326082598 MLS
775 Florence Lane offers a welcoming blend of comfort, style, and Wine Country living on a peaceful lane just minutes from downtown Healdsburg. This beautifully updated three-bedroom, two-and-one-half-bath home is filled with natural light and features a spacious, functional floor plan with a dedicated dining room and versatile flex space ideal for a home office, reading room, or lounge. The thoughtfully designed kitchen features a Sub-Zero refrigerator, Viking range, and room for a wine refrigerator tucked behind a sliding barn door. The primary suite provides a private retreat with a stylish ensuite bath and walk-in closet. Designed for effortless indoor-outdoor living, the beautifully landscaped and private backyard features an outdoor arbor kitchen area, expansive deck, fire pit, hot tub, and multiple gathering spaces perfect for relaxing or entertaining under the Wine Country sky. The generous backyard also offers room for a pool, providing an exciting opportunity to further enhance the outdoor living experience. A charming front arbor with views of Fitch Mountain provides another peaceful place to unwind. Ideally located near downtown Healdsburg's renowned dining, shopping, tasting rooms, and vibrant Wine Country lifestyle.

775 Florence Ln, Healdsburg
235 Clear Ridge Dr, Healdsburg
$2,695,000
4 Beds ⋅ 5 Baths ⋅ 326084099 MLS
Healdsburg Living with Views, Character & Room to Gather - This stunning residence offers an expansive, open-concept great room with soaring cathedral ceilings that create a sense of grandeur and openness. The seamless flow between the kitchen, living, and dining areas is perfectly complemented by a large front deck perfect for capturing stunning sunsets. These inviting spaces extend effortlessly to a beautifully landscaped, terraced backyard, where you'll find a luxurious built-in spa, enchanting landscape lighting, expansive green space, and plenty of room to cultivate your own garden. The primary suite, thoughtfully positioned on the main floor, offers both convenience and privacy, while the upper level features two spacious en-suite guest bedrooms and a versatile loft space ideal for a home office or additional living area. For even more flexibility, the remodeled lower level boasts a bedroom, bathroom, den, and its own private entrance, all with great natural light and views. This exceptional property also includes a solar array, a charming hobby vineyard, and a wealth of other amenities, making it a truly unique and remarkable home.

235 Clear Ridge Dr, Healdsburg
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