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

$1,995,000
2 Beds ⋅ 3 Baths ⋅ 326077999 MLS
Rare downtown retail with parking and two upstairs apartments with current CUP (conditional Use permit) for vacation rental. 3,348 square feet total comprises 1627 square feet of retail or office space below, 914 square feet front apartment and an 807 square feet rear apartment above. Enjoy this ideal location, just a short stroll to Healdsburg Plaza, local markets, and award-winning restaurants. 2 to 4 blocks from more than 10 restaurants. Plus, recently installed fire sprinklers system for added safety. Or live above your shop.

440 Center St, Healdsburg
$2,300,000
4 Beds ⋅ 4 Baths ⋅ 326077589 MLS
Rare opportunity in the heart of Downtown Healdsburg! This unique property offers a flexible layout and an exceptional location just moments from the Healdsburg Plaza, including restaurants, shops, and all that downtown Healdsburg has to offer. The main building, is currently configured as a office (previously a dentist office) including a separate 1 bedroom 1 bath apartment. It was a previously a single family home that was separated into 2 units. Also including an semi attached duplex which provides a one-bedroom, one-bath unit and a two-bedroom, one-bath unit. Ready for its next chapter, this distinctive property offers an exciting opportunity for a buyer with vision. Bring your imagination and explore the potential of this special downtown offering. A tour is truly the best way to appreciate the property, it's layout, and it's location. Property also listed under Multi Unit Income MLS # 326076960

231 Matheson St, Healdsburg
$2,300,000
326076960 MLS
Rare opportunity in the heart of Downtown Healdsburg! This unique property offers a flexible layout and an exceptional location just moments from the Healdsburg Plaza, including restaurants, shops, and all that downtown Healdsburg has to offer. The main building, is currently configured as a office (previously a dentist office) including a separate 1 bedroom 1 bath apartment. It was a previously a single family home that was separated into 2 units. Also including an attached duplex which includes a one-bedroom, one-bath unit and a two-bedroom, one-bath unit. Ready for its next chapter, this distinctive property offers an exciting opportunity for a buyer with vision. Bring your imagination and explore the potential of this special downtown offering. A tour is truly the best way to appreciate the property, it's layout, and it's location. Property also listed under Multi Unit Income MLS #326077589

231 Matheson St, Healdsburg
$1,295,000
2 Beds ⋅ 1 Baths ⋅ 326069450 MLS
Escape to a one-of-a-kind retreat on approximately 11.5 secluded acres in the hills above Healdsburg. With no neighboring homes in sight, this peaceful property offers exceptional privacy and sweeping views across forested hills and distant ridgelines. Designed for indoor-outdoor living, expansive decking, a swimming pool, hot tub and outdoor shower create an inviting setting for entertaining, unwinding and enjoying the surrounding natural beauty. Fruit and citrus trees further enhance the relaxed country atmosphere. The home features two bedrooms and one bathroom with a steam shower, along with a detached office ideal for working from home or pursuing creative projects. A whole-property automatic generator provides additional peace of mind. An architecturally distinctive barn, already plumbed for sewer and water, offers flexible space for storage, equipment, a workshop or recreation, along with intriguing potential for conversion into additional living space, subject to applicable permits and approvals. A rare private sanctuary just outside Healdsburg.

4565 Mill Creek Rd, Healdsburg
$250,000
326076980 MLS
Beautiful sun drenched 1 acre (+) property located south of the town of Healdsburg. This spacious parcel comes with the end of the road privacy, beautiful native oaks, pasture views and room to breathe. Come see what it feels like to be on this special property, near world class wineries and restaurants, and enjoy the space. Explore the possibilities.

659 Red Tail Rd, Healdsburg
$2,295,000
4 Beds ⋅ 3 Baths ⋅ 326060632 MLS
Exceptional 5-acre Wine Country retreat sits on a quiet country lane just five minutes from the Historic Healdsburg Plaza. One of four estate parcels with established CCR's, featuring a private, beautifully updated single-story home surrounded by a 3.5-acre Petite Sirah vineyard, 20+ mature olive trees, and a charming redwood grove. Detailing a 6-bedroom standard septic system, plans for a 2-bedroom ADU, existing Short-Term Rental (STR) permit, 90 GPM shared well, underground utilities including natural gas, and AT&T fiber optic service. Recent improvements include a newer roof, HVAC system, and tankless water heater. An exceptional opportunity to enjoy the best of Wine Country living with outstanding flexibility as a primary residence, weekend retreat, or income-producing investment.

531 Limerick Ln, Healdsburg
$1,850,000
3 Beds ⋅ 2 Baths ⋅ 326076503 MLS
Thoughtfully crafted by JMA Construction and maintained with pride, this graceful 3-bedroom, 2-bathroom Healdsburg residence pairs warmth and convenience with timeless style, within 2,186 square feet indoor space flowing easily to delightful outdoor spaces. An artfully crafted landscape shelters a hidden deck at the front, leading you inside to discover warm and welcoming rooms with lovely red oak hardwood floors throughout the main area. Abundant natural light pours in from a strategically placed skylight over the kitchen making the contemporary counter tops and stainless steel appliances shine. A desk area between the kitchen and dining room meshes good workspace with additional pantry storage. Choose from one of many options for formal or informal meals, from the ample kitchen bar area, to the cozy breakfast nook, formal dining room or outside on one of the decks. The spacious formal dining room and cozy family room both open to the central deck with views of the hills, Fitch Mountain, and the adjacent golf course. The primary suite features a walk-in closet and an updated bathroom with a soaking tub, perfect for unwinding after a long day. The sliding door extends this bedroom to its own outdoor deck, a private space for rest and reflection. When you are ready, pop around for golf at Tayman Park or head downtown for the best of Healdsburg's cafes, restaurants, the Farmer's Market, Tuesday Concerts in the Plaza or the True West Cinema offerings. Become part of an exceptional Healdsburg neighborhood!

412 Fairway Ct, Healdsburg
$1,995,000
4 Beds ⋅ 3 Baths ⋅ 326076165 MLS
A sweet peach in bucolic and relaxing Healdsburg, California. Located just 8 blocks east of downtown and the vibrant Healdsburg Square, this extremely well maintained and loved home is in the heart of the Sonoma County wine country and the coveted Greens neighborhood. Built in 1989, this 2,648sf, two story home sits on a generous 10,000sf lot and features a beautiful, private, landscaped backyard with an amazing pool and spa. There are 4 bedrooms and 3 full baths. The main level front entry opens to a vaulted, light filled living room, formal dining area, beautifully upgraded kitchen with quartz counters and connected TV / sitting area with wood burning fireplace. There is a bedroom and full guest bathroom on the main level as well. The kitchen and sitting area access the a covered back porch / deck which runs the entire westside of the house. The upper level features the primary bedroom with walk-in closet, and upgraded-remodeled bathroom plus two additional bedrooms and second full bathroom. Relax and enjoy the gorgeous in-ground pool and spa, surrounded by mature landscaping with fruit trees and lush foliage. The back yard is fully fenced and creates a sense of peace and privacy. The thoughtfully landscaped front yard with magnificent peach tree enhances and compliments the well tended and pride of ownership which abounds in the Greens neighborhood. There is an oversized two car garage with ample storage. Greens Drive ends in a cul-de-sac with little car traffic and disruption, and a feeling of sanctuary abounds. The Russian River, Memorial Beach, and Fitch Mountain are right out your back door as well as the legendary dining and amazing wineries Healdsburg is known for world wide.

421 Greens Dr, Healdsburg
$3,300,000
3 Beds ⋅ 2 Baths ⋅ 326047788 MLS
Set in the heart of Downtown Healdsburg, this stunning, single-story, turnkey home pairs historic character with modern craftsmanship. Originally built in 1903 and masterfully remodeled in 2007, the home showcases pride of ownership throughout and is just moments from the Plaza, acclaimed dining, the farmers market, and Healdsburg's renowned tasting rooms. The welcoming front porch invites you to slow down and enjoy the rhythm of downtown life, from morning coffee to an evening glass of wine and a friendly hello to neighbors passing by. Inside, 10-foot ceilings, hardwood floors, and abundant natural light create an airy, inviting space. The generously sized bedrooms offer versatile space for family, guests, or a dedicated home office. The kitchen features custom cabinetry, quartz countertops, and a sunny breakfast nook, while the living room centers around a classic fireplace. The home also has dual-zone HVAC. Step onto the spacious back porch, which seamlessly extends the living area into the outside. Situated on a 9,240-square-foot lot, the property offers an exceptional opportunity to enjoy outdoor living in one of Wine Country's most coveted locations. The back patio and porch provide summer shade and an inviting setting for al fresco dining, entertaining, gardening, and enjoying Healdsburg's exceptional Wine Country climate. A detached garage and generous driveway provide ample parking, while the property also offers potential for an ADU. Originally built in 1904 as the John McClish House, a storied wedding gift from the neighbors to a newly married couple, 325 Fitch Street is a rare piece of Healdsburg history, thoughtfully reimagined for modern Wine Country living. With its generous in-town lot, thoughtful updates, and enviable location, 325 Fitch Street offers something highly sought after: a private Wine Country residence paired with the extraordinary convenience of being just steps from the very best of Downtown Healdsburg.

325 Fitch St, Healdsburg
$3,399,000
3 Beds ⋅ 3 Baths ⋅ 326072729 MLS
Establish your own wine country headquarters on approximately 15 acres in one of Sonoma County's most compelling settings. Perfectly positioned in the countryside yet just minutes from downtown Healdsburg and Geyserville, the property offers the rare combination of privacy, tranquility, and effortless access to two of Wine Country's most celebrated destinations. The residence is defined by soaring exposed-beam ceilings, abundant natural light, and a warm, refined aesthetic in touch with its surroundings. An expansive deck extends the living space outdoors, with sweeping views across Dry Creek Valley and the surrounding hillsides. The land invites a life well lived. A vanishing-edge pool enjoys full sun, while a majestic oak creates a natural canopy for outdoor dining and relaxation. Fruit trees, raised garden beds, expansive lawn, pizza oven, and approximately 4.5 acres of Zinfandel, Petite Sirah, and Sauvignon Blanc vines further root the estate in its authentic wine country setting. Inside, natural materials and exposed wood create warmth and permanence, while a central hearth anchors the home and its gathering spaces. The qualities that are nearly impossible to recreate - the setting, privacy, orientation, panoramic views, and connection to the surrounding landscape are already here and exceptional. The substantial barn provides a welcoming entertainment space and remarkable flexibility, with room to gather, spread out, and imagine a variety of uses. Combined with the property's rare 4,000-case winery production permit, it expands the possibilities for enjoying the property and creating a truly personalized Wine Country experience. A vacation rental permit provides further versatility. Private and immersive yet remarkably convenient, 1750 Lytton Springs Road offers something increasingly difficult to find: a property where residence, vineyard, recreation, hospitality, and wine country lifestyle come together in one extraordinary setting.

1750 Lytton Springs Rd, Healdsburg
$2,850,000
4 Beds ⋅ 4 Baths ⋅ 326073904 MLS
Wine Country living at its finest. Experience the best of Wine Country living from this beautifully appointed Eastside Road property, ideally situated at the end of a private lane on 2.11 acres. Surrounded by mature trees and backing to a neighboring vineyard, the setting feels peaceful and tucked away while remaining just minutes from Healdsburg and Windsor. The 3,474 sq. ft. home offers 4 bedrooms and 3.5 baths and lives like a single level, with the primary suite and dedicated office on the main floor. The primary bath adds a touch of luxury with heated floors and a steam shower. At the heart of the home is a spacious open kitchen designed for gathering and entertaining, featuring a marble island with five-burner gas cooktop, farmhouse sink, built-in refrigerator and freezer, double ovens, built-in espresso machine, microwave drawer and 48-bottle wine refrigerator. The open layout offers generous entertaining space, while large windows frame the surrounding greenery and bring the Wine Country setting indoors. A custom four-panel NanaWall accordion door opens the living space to the outdoors, creating a seamless connection for indoor-outdoor entertaining. Outside, enjoy the fully fenced PebbleTec pool and spa, bocce ball court and plenty of room to relax, gather and take in the Wine Country setting. Additional features include temperature-controlled wine storage, solar panels and a Tesla charger. Whether enjoyed as a full-time residence, second home or with an eye toward potential vacation rental use, this Eastside Road property offers exceptional Wine Country versatility. Peaceful and tucked away, yet close to acclaimed wineries, restaurants, shopping and all that Healdsburg and Windsor have to offer, with convenient access to the greater Bay Area.

10934 Eastside Rd, Healdsburg
$3,000,000
4 Beds ⋅ 3 Baths ⋅ 326075117 MLS
Come see what everyone is talking about! Rare Healdsburg Opportunity! Character, Space & Possibility. Opportunities like this rarely come to market in the heart of Healdsburg. Set on nearly one-third of an acre on one of Healdsburg's most desirable streets, this unique property offers an exceptional combination of location, character, privacy, and versatility. Bordering Tucker Street and Alley 2, the quintessential single-level Craftsman features 3 bedrooms, 1.5 bathrooms, laundry room, mudroom, and basement, root cellar.'' Enjoy classic front-porch living and a private backyard with an established orchard. Privately accessed from Alley 2, the detached 840-square-foot, 1-bedroom, 1-bath ADU, built in 2004, offers its own entrance, parking, and full-length deck overlooking the orchard, perfect for guests, family, or a private retreat. And the possibilities continue: the property may have the potential to become two separate lots. The combination of nearly one-third acre, alley access, an existing ADU, and a prime downtown location is exceptionally rare. Whether you envision a family compound, multigenerational living, a guest retreat, or exploring the potential of two properties, this is a truly special opportunity to create your own Healdsburg lifestyle. Rarely does a property with this location, land, and potential become available. Come experience it for yourself.

425 Tucker St, Healdsburg
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