Healdsburg Homes for Sale

Healdsburg Homes for Sale

Welcome to Healdsburg, California – a picturesque gem nestled in the heart of Sonoma County. Known for its stunning vineyards, charming downtown, and vibrant arts scene, Healdsburg offers a perfect blend of small-town charm and sophisticated living. With its rolling hills and breathtaking landscapes, this city is a haven for outdoor enthusiasts and wine lovers alike.

Healdsburg is renowned for its world-class wineries and tasting rooms, making it a top destination for those who appreciate the finer things in life. Stroll through the historic plaza, where you'll find an array of boutique shops, gourmet restaurants, and local art galleries. The community hosts numerous events throughout the year, including the popular Healdsburg Wine & Food Experience, which showcases the region's culinary talents and exceptional wines.

When it comes to homes for sale in Healdsburg, you’ll discover a diverse selection that caters to various lifestyles. From charming Victorian-style houses to modern luxury estates, the real estate market here offers something for everyone. Many properties boast stunning views of the vineyards and mountains, providing a serene backdrop for your daily life. Whether you’re looking for a cozy cottage or a sprawling ranch, Healdsburg’s real estate options are sure to impress.

Living in Healdsburg means embracing a lifestyle filled with adventure, culture, and community. With its friendly residents and welcoming atmosphere, it’s no wonder why so many people are eager to call this beautiful city home. Explore the homes for sale in Healdsburg today and discover the perfect place to create lasting memories in this enchanting corner of California.

Newest Healdsburg Homes for Sale

951 Trentadue Way, Healdsburg
$2,500,000
4 Beds ⋅ 4 Baths ⋅ 326088365 MLS

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
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
434 Alexander Valley Rd, Healdsburg
$2,350,000
4 Beds ⋅ 4 Baths ⋅ 326082146 MLS
A rare opportunity in the heart of Alexander Valley, this beautifully updated 3,113 sq. ft. home offers exceptional versatility, two primary suites, owned solar with battery backup, and an impressive four-car garage setup in a sought-after wine country setting. Featuring 4 bedrooms plus an office and 3.5 baths, the thoughtfully designed floor plan includes a primary suite on each level, ideal for multigenerational living, guests, or added privacy. Every bedroom features a spacious walk-in closet, while the upgraded kitchen with pantry opens seamlessly to the dining area, creating an inviting space for everyday living and entertaining. Owned solar with backup battery adds efficiency and convenience. A newly installed reverse osmosis system provides filtered drinking water to the kitchen sink and refrigerator, complemented by an additional water treatment system located behind the original garage. Two separate two-car garages, including a recently built garage with workshop bay, offer outstanding space for vehicles, storage, hobbies, and projects. Set on approximately 5 acres, the property features a gravel access road leading to a flat, elevated area at the top, showcasing beautiful bird's-eye views of the surrounding wine country and offering exciting potential to explore a future ADU, guest house, studio, or other use, subject to approvals. Enjoy the space, flexibility, and beauty of Alexander Valley, all within easy reach of Healdsburg, renowned wineries, exceptional dining, and the best of Sonoma County wine country.

434 Alexander Valley Rd, Healdsburg
231 Zinfandel Rd, Healdsburg
$2,650,000
4 Beds ⋅ 5 Baths ⋅ 326082790 MLS
An extraordinary opportunity to own this spacious custom-built home in Healdsburg's sought-after Vintage Hills, thoughtfully designed for comfortable living, entertaining, and indoor-outdoor enjoyment. Set on a private 1-acre, fully useable parcel at the end of a cul-de-sac, this 4-bedroom, 3.5 bath home offers approximately 3,400 sq. ft. of living space, abundant natural light, beautiful views overlooking the westerly hills and a wonderful blend of comfort and privacy. The main level lives like a single-story home, featuring a formal living and dining area with fireplace, chef's kitchen with breakfast area, adjoining family room, separate laundry room with sink and half bath, and a gracious oversized primary en-suite with walk-in closet. Two additional bedrooms and a full bathroom complete the main level. Also included is a spacious lower level with a private entrance that offers incredible flexibility with a large game room, kitchenette and an additional bedroom and full bath. Perfect for overnight guests and entertaining. Step outside to a full-length ground-level deck with multiple entertaining areas overlooking the built-in pool and spa with cascading waterfall. The expansive grounds with a firepit, mature landscaping, raised garden beds and fruit trees offer plenty of room to entertain, relax and enjoy the peaceful country setting. An oversized detached shop/barn with its own half bath provides excellent space for hobbies, storage, projects, or additional workspace. This property offers the convenience of city services while maintaining a private, country-like setting, all just minutes from the Healdsburg Plaza.

231 Zinfandel Rd, Healdsburg
234 Lincoln St, Healdsburg
$2,095,000
3 Beds ⋅ 3 Baths ⋅ 326083089 MLS
Charming, sweet, surprising, with understated warmth and a designer touch throughout. Rest easy with a brand new roof as of October 16th. Strollable to the Plaza in one direction, or to Summer's Market in the other. Old-Healdsburg combines with 'new' Healdsburg here to create a blend that just may capture your heart. Experience natural light, elegance, a private, heated lap pool, room to play, garden, add-on/re-create, or simply be -- in the company of some of Healdsburg's finest assets...her beloved trees. Verify with the City, but have been told the grand front yard tree may be removed if the eventual new owner elects to. This reenvisioned home is a host's delight with the kitchen as the centerpiece. Come together with ease inside or outside. Or, retreat to a unique sanctuary separateness, as desired. 2 of the 3 bedrooms are en-suites, promising comfort and practical living. A portion of the attic space is sheet rocked, and offers 2 skylights, a window, lights/outlets, and approximately 8 feet of head space at its peak. This area totals approximately 120 sqft (not reflected in the tax roll square footage noted - buyer to verify). A detached 1-car garage near the pool invites imagination. Beloved by the current owners for more than 30 years, the baton awaits. Come home to Healdsburg.

234 Lincoln St, Healdsburg
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