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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
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
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
360 March Ave, Healdsburg
$1,895,000
326066553 MLS
Excellent investment opportunity in Healdsburg, conveniently located just minutes from the historic Healdsburg Plaza, with easy access to restaurants, shopping, wineries, and everyday amenities. This freshly updated four-plex features four spacious 2-bedroom, 2-bath units, each offering approximately 850 square feet of living space. Every unit includes in-unit laundry, separate utility meters, and a dedicated carport with private storage. The two ground-floor units enjoy private patios, while the upstairs units feature private balconies. With fresh updates, desirable amenities, and a convenient Healdsburg location, this turnkey property is an excellent opportunity for investors or owner-occupants seeking rental income in Sonoma County.

360 March Ave, Healdsburg
2460 W Dry Creek Rd, Healdsburg
$1,295,000
3 Beds ⋅ 2 Baths ⋅ 326080729 MLS
Experience the ultimate Wine Country lifestyle at this chic and stylishly updated 3 bedroom, 2 bathroom ranch-style retreat, ideally situated in the legendary Dry Creek Valley. Tucked peacefully down a private lane along side of a picturesque creek, this property delivers a serene country atmosphere while keeping you just minutes from the vibrant energy of downtown Healdsburg's historic plaza! Set on a sprawling, level 0.65-acre parcel, the property is framed by picturesque rolling hills along one of the region's most iconic stretches for world-class cycling and boutique wine tasting. The interior features a stunning upscale renovation, artistically balancing contemporary style with timeless warmth. The light-filled, single-level layout offers gorgeous flooring, an inviting living area, and a beautifully updated kitchen complete with modern cabinetry, countertops and newer appliances. Out back, you'll find a spacious detached office equipped with a mini-split for year-round heating and cooling. Whether you need a dedicated work-from-home space, a private gym, or a creative studio, this versatile outbuilding adapts effortlessly to your vision. Step outside to discover endless possibilities on the expansive, usable lot, perfect for outdoor entertaining, weekend gatherings, or sprawling gardens. Complete with an attached garage and plenty of extra parking, this turnkey gem offers the rare combination of privacy, acreage, and prime Healdsburg proximity. Your wine country sanctuary awaits!

2460 W Dry Creek Rd, Healdsburg
1421 Spruce Way, Healdsburg
$1,174,000
4 Beds ⋅ 3 Baths ⋅ 326081675 MLS
Completely remodeled and thoughtfully designed, this Healdsburg property offers two separate residences with inviting indoor-outdoor living. The single-level, open-concept main home features 3 bedrooms, 2 beautifully updated bathrooms, new appliances, striking high-beamed ceilings, energy-efficient mini-split systems and indoor laundry. Both residences benefit from newer roofs and windows, new fencing and fresh landscaping. The fully permitted ADU includes 1 bedroom, 1 bathroom and indoor laundry. Expansive folding doors open to its private outdoor living area, creating a welcoming space for relaxing or entertaining. Separate rear access through an automatic gate adds privacy and convenience. With distinct living spaces and outdoor areas, the property offers flexibility for extended family, guests or potential rental use. A distinctive staircase leads to additional flexible space suited to a home office, workout room, yoga studio or creative retreat. Conveniently located within a 5 minute drive to Downtown Healdsburg, wineries, restaurants and near Charles M. Schulz-Sonoma County Airport, this property presents a rare opportunity to enjoy two residences in the heart of Wine Country.

1421 Spruce Way, Healdsburg
620 Coghlan Rd, Healdsburg
$7,745,000
326080900 MLS
A rare opportunity to acquire six legal parcels totaling 10.48 acres in an elevated setting above Healdsburg, offering exceptional scale, privacy, panoramic views, and long-term flexibility. With multiple parcels already in place, the property presents a compelling opportunity for future resubdivision, investment, or a multi-generational vision, subject to applicable approvals. At the heart of the offering is an approximately 4,000 sq ft, 4-bedroom, 3 full/2 half bath residence positioned at the top of the property and surrounded by sweeping valley and mountain views. Thoughtfully designed, the home features a main entry floor with the primary suite, great room, chef's kitchen, dining area, and spacious laundry room, all oriented toward the extraordinary vistas. Walls of glass fill the interiors with natural light, while French doors open to a wraparound covered porch for seamless indoor-outdoor living. The chef's kitchen features premium appliances and a built-in espresso station, flowing into a dining area with dramatic glass-front wine display. The primary suite offers a gas fireplace, generous walk-in closet, hidden storage, and direct access to the laundry room, while the lower level features a spacious family room with fireplace and wet bar, three bedrooms, two full baths, and covered patio. Gated and private, this six-parcel offering combines an exceptional existing residence with significant land and future potential, all just minutes from downtown Healdsburg. Whether envisioned as a private estate, long-term investment, or future development opportunity, the property offers a rare chance to shape an expansive piece of Sonoma County real estate while enjoying a remarkable home and setting today. Also includes APNs 002-610-018, 002-610-020, 002-610-023, 002-610-024, & 002-392-026. Just the house and its parcel are listed separately in Residential as 775 Benjamin Way, listing #326080943.

620 Coghlan Rd, Healdsburg
775 Benjamin Way, Healdsburg
$3,995,000
4 Beds ⋅ 5 Baths ⋅ 326080943 MLS
Perched above Healdsburg, this exceptional private estate property captures sweeping valley and mountain views that stretch for miles. Set on its own approximately 1.2-acre parcel, the 4-bedroom, 3 full bath/2 half bath residence is thoughtfully designed for the owners to live primarily on a single level, with expansive windows and walls of glass framing the extraordinary scenery and filling the interiors with natural light. The main entry floor includes the primary suite, great room, chef's kitchen, dining area, half bath, and spacious laundry room, all positioned to take full advantage of the panoramic vistas. The chef's kitchen features premium appliances and a built-in espresso station, flowing seamlessly into the dining area with its dramatic glass-front wine display. French doors open to a wraparound covered porch, creating effortless indoor-outdoor living against a backdrop of mountains and valley. The primary suite is a private sanctuary with its own gas fireplace, generous walk-in closet, hidden storage, and direct access to the laundry room. Downstairs, a spacious family room with gas fireplace and wet bar opens to a covered patio overlooking the surrounding landscape. A flexible space near the attached two-car garage offers versatility for a gym, office, or walk-in pantry. Gated and private, the property offers a rare combination of elevated views, privacy, and proximity to downtown Healdsburg. A distinctive Sonoma County setting for enjoying the landscape, entertaining, and embracing the best of wine country living. Property also listed in combination with 5 vacant land parcels in Land, 620 Coghlan Road, listing #326080900.

775 Benjamin Way, Healdsburg
33 S University St S, Healdsburg
$2,550,000
326080246 MLS
Single Tenant Leased Investment or Owner-User Opportunity. Well suited for a Tax Deferred 1031 Exchange, Investor, or Owner-User. Very clean, well located, and secure light industrial property currently occupied by a long term credit Tenant. The Subject Property is leased to Santa Rosa Lead Products, a division of Mayco Industries, the largest manufacturer of fabricated lead-based products in the United States, who has occupied this light industrial Property since 2003, executed their fifth lease extension on a 5 year extension which now runs through March 31, 2028. The current Tenant has expressed a desire to occupy the Subject Property on a longer term basis depending on the desires and plans of a New Owner.

33 S University St S, Healdsburg
3323 Mill Creek Rd, Healdsburg
$799,900
2 Beds ⋅ 1 Baths ⋅ 326078865 MLS
A rare opportunity to own a vintage creekside cabin in one of Healdsburg's most captivating natural settings. Set on approximately .88 acre along Mill Creek, this 1920 log-style retreat has been held by the same family for generations and offers the kind of character and sense of place that simply can't be recreated. The 2-bedroom, 1-bath cabin is oriented toward the surrounding woods and creek, with mature trees framing the property and creating a peaceful backdrop for weekends away or a more permanent escape. Spend afternoons by the water, evenings in the hot tub beneath the trees, and mornings taking in the quiet of this special setting. A brand-new roof is an important recent improvement, while a detached shed and under-house laundry and storage add practical utility. Served by well and septic. For those who value authenticity, nature and the opportunity to bring their own vision to a property with genuine history, 3323 Mill Creek Road is a sweet piece of old Healdsburg. Probate sale, limited photos have been virtually staged.

3323 Mill Creek Rd, Healdsburg
17698 Healdsburg Ave, Healdsburg
$1,700,000
5 Beds ⋅ 4 Baths ⋅ 326079671 MLS
North side of Healdsburg this 6+ acre property down a country lane sitting on a slight knoll with spectacular views. This is Healdsburg as it was meant to be. Priced to sell

17698 Healdsburg Ave, Healdsburg
447 Monte Vista Ave, Healdsburg
$1,345,000
4 Beds ⋅ 4 Baths ⋅ 326074275 MLS
NEW PRICE: $1,345,000 Plus a seller credit toward the buyer's rate buy-down An Incredible Opportunity in Healdsburg Built in 2018, this thoughtfully designed property offers two separate residences on one lot. It's ideal for multigenerational living, private space for an adult child, caregiver or nanny, or additional rental income. The Main Residence A bright, single-level 1,708-square-foot home with three bedrooms and two-and-a-half baths. High ceilings, custom cabinetry and hardwood floors flow into a welcoming great room anchored by a fireplace. The chef's kitchen, with quartz countertops and stainless steel appliances, is made for gathering, and a separate formal dining room adds space for entertaining. Two bedrooms share a Jack-and-Jill bath, and the private primary suite sits at the back of the home with a walk-in closet and a well-designed bath. The ADU A fully permitted 538-square-foot, one-bedroom residence with quartz countertops, its own laundry, air conditioning, a new refrigerator and a new water heater. It's move-in ready. Two Homes, Fully Independent Each residence has its own address, separate utilities, and its own washer and dryer (included). That level of flexibility is increasingly hard to find. The Setting A generous lot with room for a pool and outdoor retreat, about one mile from the Healdsburg Plaza and its acclaimed restaurants, tasting rooms, boutiques and community events. Beautifully maintained and essentially turnkey, 445-447 Monte Vista Avenue combines newer construction, single-level living and the rare advantage of two homes in one Wine Country property. Seller credit subject to an accepted purchase contract and lender approval. ADU rent and financing terms not guaranteed.

447 Monte Vista Ave, Healdsburg
1593 Cali Ln, Healdsburg
$556,370
2 Beds ⋅ 3 Baths ⋅ 326078995 MLS
Beautiful contemporary townhome with laminate flooring, open spacious kitchen with stone counter tops, gas stove, washer/dryer, refrigerator and a 2 car garage. This home is a Below Market property available to First time home buyers.

1593 Cali Ln, Healdsburg
778 S Fitch Mountain Rd, Healdsburg
$2,695,000
3 Beds ⋅ 3 Baths ⋅ 326078118 MLS
Under a mile from the Healdsburg Plaza, South Fitch Mountain Road bends into oak shade, and this home sits behind that screen of trees, opposite the golf course and private enough that the town feels farther than it is. Set on 0.3368 acres, rare this close to downtown, the 1939 single-level home was extensively remodeled in 2020: three bedrooms, three full baths, and approximately 2,265 square feet, all on one floor. The remodeled kitchen anchors the main level with concrete counters and a restraint that lets the architecture speak. The great room opens beneath a vaulted ceiling, oversized windows framing the yard, the majestic oaks, and the golf course beyond, and a wood-burning fireplace holds the living room through winter. The primary suite sits at one end with generous closets, a marble and tile bath, and an indoor/outdoor shower; a quiet office sits at the other, a split plan that keeps work and rest separate. Single-level flow dissolves the boundary between living space and garden. Outside, a custom in-ground pool anchors the grounds, gas-heated for swimming well into fall, with a gazebo for shade and dinners that run late. The third-acre lot is level, mature, and screened by trees, garden and greenbelt in every direction. Next door, 11-acre Badger Park offers direct Russian River access, one of only two public river-access points in Healdsburg, plus athletic fields, community gardens, a riparian trail, and off-leash dog areas. Must see to appreciate the rare combination of single-level design, a large private lot, and a setting this close to the Plaza and the river.

778 S Fitch Mountain Rd, Healdsburg
983 Grove St, Healdsburg
$5,750,000
5 Beds ⋅ 8 Baths ⋅ 326077869 MLS
The modern aesthetic of this Healdsburg residence is purposeful, emphasizing craftsmanship, proportion and premium finishes. Thoughtfully conceived and expertly executed, this 4BR home with 1BR/1.5BA ADU is built with metal roof and 2x6 construction. Inside, 10 ' ceilings, wide-plank white oak floors, and a custom metal staircase set a sophisticated tone. The living space is anchored by a striking linear fireplace, 10' x 10'-dimensional tile clad wall and limestone bench hearth. The chef's kitchen is appointed with Miele appliances, touch-to-open refrigeration, quartzite counters, an integrated induction cooktop, full bar area, wine and beverage refrigeration, plus prep area and butler pantry. Upstairs, vaulted ceilings and natural light define a secondary lounge and guest bedrooms. The primary suite opens to a private garden and features a spa bath with freestanding tub, walk-through rain shower, Kohler smart toilet, and a bespoke dressing room with LED-lit makeup station. Bathrooms throughout showcase custom vanities, marble tile, and wall-hung fixtures. Seamless indoor-outdoor living, curated landscaping and gated rear access. Some images have been digitally enhanced. Those and all unaltered images are available in the photo gallery.

983 Grove St, Healdsburg
440 Center St, Healdsburg
$1,895,000
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
224 Matheson 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

224 Matheson St, Healdsburg
224 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

224 Matheson St, Healdsburg
4565 Mill Creek Rd, 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
531 Limerick Ln, 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
421 Greens Dr, Healdsburg
$1,795,000
4 Beds ⋅ 3 Baths ⋅ 326076165 MLS
A mere 8 blocks east of the vibrant Healdsburg Plaza, 421 Greens Drive offers you a tranquil respite, complete with resort style pool and spa in an oversized, sun-splashed back yard. Here you can recharge and restore to face the world again, fortified by world class, farm to table dining and wine, sophisticated shopping and convivial surroundings. 421 Greens has been meticulously maintained, smartly upgraded and is peacefully located on a tranquil street with minimal through traffic--one of the characteristics that have made the coveted Greens neighborhood so special over the years. Built in 1989, this 2,648sf, two story home sits on a generous 10,000 sf lot, featuring fresh drought resistant landscaping, raised garden beds and thriving fruit trees. The main level front entry opens to a vaulted, light filled living room, formal dining area, beautifully upgraded kitchen with quartz counters and newer stainless appliances. The kitchen opens to a comfortable sitting area with a wood burning fireplace, all overlooking the lush backyard and pool. A covered back porch extends the living area to the entire west side of the house. The kitchen and sitting area offer access to the porch and backyard. The upper level features a gracious primary bedroom suite with walk-in closet and upgraded bathroom. Two additional bedrooms and second full bathroom complete this level. The main level contains a fourth bedroom and full bath. Relax and enjoy the gorgeous in-ground pool and spa, surrounded by mature landscaping with fruit trees, raised garden beds and lush foliage. The back yard was recently fully re-fenced and creates a sense of peace and privacy. The thoughtfully landscaped drought resistant front yard complements the well tended pride of ownership which abounds in the Greens neighborhood. An oversized two car garage with ample storage plus driveway provide pleanty of parking for you and your visitors. Greens Drive ends in a cul-de-sac with little car traffic and disruption, completing the feeling of sanctuary. In addition to the Healdsburg Plaza, 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
1750 Lytton Springs Rd, 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
114 Lavender Cir, Healdsburg
$860,000
3 Beds ⋅ 3 Baths ⋅ 326074223 MLS
Light-filled and impeccably finished, this three-bedroom, two-and-a-half-bath residence offers refined living just minutes from the Healdsburg Plaza. The main level opens as a single, gracious expanse, where kitchen, living, and dining spaces flow together beneath rich hardwood floors. A full suite of upgraded appliances, custom cabinetry, and quartz countertops anchor the kitchen, with designer fixtures throughout the bathrooms and a pedestal sink lends the powder room a note of understated elegance. A coveted main-level primary suite offers everyday ease with its en suite bath and walk-in closet. Beyond the interior space, a private patio has been transformed by extensive landscape enhancements into a true outdoor sanctuary with a gas grill, dining table for evenings that unfold without hurry. It is the rare space that makes an ordinary Tuesday feel like an occasion. Two additional bedrooms and a full bath await upstairs. An attached one-car garage and a designated parking space just steps from the front door complete the picture. Residents of Sorrento Square enjoy a bocce court, barbecue area, and a tranquil fountain with bench seating. Beyond the gates, Healdsburg's celebrated wineries, restaurants, and shops are all within easy reach, with public transportation close at hand.

114 Lavender Cir, Healdsburg

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