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366 Piper St, Healdsburg
$715,000
2 Beds ⋅ 2 Baths ⋅ 326043516 MLS
Nestled at the end of a quiet cul-de-sac and just a few minutes' walk from the Healdsburg Plaza, this polished 2-bedroom, 1.5-bath condominium punches well above its square footage. Whether you're planting roots in Sonoma County, searching for a seamless second home, or adding a smart asset to your portfolio, 366 Piper delivers on all fronts. Natural light pours through every window, and the interior has been finished with a level of care you don't often see at this price point. The living room centers around a gas fireplace with a custom concrete mantel understated, warm, and genuinely stylish. In-wall TV wiring and a hydraulic wall mount handle the tech side without cluttering the space. The primary suite is calm and well-considered, with a ceiling fan, recessed lighting, and a full bathroom. A full-size vented washer and dryer are tucked neatly within the suite a small detail that makes a big difference day-to-day. Out back, a low-maintenance patio gives you an outdoor perch without the upkeep ideal if you're splitting time between properties and don't want a yard demanding your attention. The big-ticket items have already been handled: new roof, gutters, and hot water heater (all 2020), plus central air conditioning. The HOA replaced roofs and gutters community-wide in 2019 and has exterior improvements on the horizon, fully funded through reserves. Additional storage sits above the parking area. HOA fees cover management, exterior maintenance, and grounds so your weekends stay yours. Healdsburg's best restaurants, tasting rooms, and boutiques are a short walk away. This is the kind of place that just makes life a little easier.

366 Piper St, Healdsburg

22549 River Rd, Geyserville
$1,370,000
3 Beds ⋅ 2 Baths ⋅ 326043225 MLS
Character, Charm and Value!! This is a perfect second home or county comforts of full-time living with small acreage and easy maintenance. Welcome to the charming town of Geyserville. Just minutes from potential opportunity to membership of a private lake among other recreational possibilities in Geyserville. Pass through the gate into a sun-drenched private courtyard, perfectly suited for morning coffee or evening entertaining, before stepping through a beautiful arched front door into this hidden oasis among the trees. Tucked on a lush .62 acre lot. This Alexander Valley gem draws you in with warm materials and an effortless indoor-outdoor flow. Inside, white oak hardwood floors run throughout beneath vaulted ceilings. The combination living and dining room is anchored by a fireplace and framed by expansive windows with Alexander Valley views expands onto private deck. The kitchen features updated cabinetry, an island and peninsula, ample storage, and a built-in wine cooler, with thoughtful built-in cabinetry woven throughout the home adding both character and practicality. Each bedroom has its own personality. The first opens via French doors directly to the garden, while the second features custom built-in storage and a reading nook framed by windows looking out. A dedicated office leads into the primary suite, where vaulted ceilings with gorgeous, exposed beams and breathtaking views set a serene tone. The primary bathroom is finished entirely in marble, with a generous tiled shower, freestanding soaking tub, and double vanity with a custom marble countertop. Outside, a wraparound porch extends your living space into the landscape, while a hot tub shaded by a sprawling fig tree and a picturesque neighboring barn evoke the very best of rural Sonoma living. A detached studio with a half bathroom and pellet stove offers exceptional flexibility as a guest suite, gym, or private office, outdoor shower and a separate storage shed adds further versatility to this truly special property.

22549 River Rd, Geyserville

200 Foss Creek Cir Unit #A, Healdsburg
$649,000
2 Beds ⋅ 2 Baths ⋅ 326033818 MLS
Experience the charm, convenience, and lifestyle of Healdsburg from Foss Creek Villas, a sought-after community just minutes from the downtown Plaza, renowned restaurants, tasting rooms, boutique shopping, parks, and the Foss Creek Pathway. This 2-bedroom, 2-bath condo offers a smart and inviting single-level layout designed for comfort, privacy, and everyday function. The heart of the home features a welcoming living area with fireplace, dedicated dining space, and access to a private outdoor patio area, creating an easy flow for relaxing, entertaining, or enjoying a quiet morning coffee. The bedroom layout is especially appealing, with each bedroom and full bath positioned on opposite sides of the home. This thoughtful separation gives the condo a spacious feel and offers flexibility for guests, a home office, or shared living. The kitchen offers a comfortable space for everyday cooking and entertaining, with a brand-new refrigerator and stove, valued at approximately $3,000. Condo was just painted and a new water heater installed. Additional features include central heating and air conditioning, designated exterior parking, and access to community amenities including a pool, patio area, clubhouse/community room, and workout room. Set in one of Healdsburg's most convenient locations, this Foss Creek Villas condo offers comfort, convenience, and the best of Wine Country living.

200 Foss Creek Cir Unit #A, Healdsburg

824 Prince Ave, Healdsburg
$1,095,000
3 Beds ⋅ 2 Baths ⋅ 326041198 MLS
Downtown Healdsburg Gem | Blocks to Healdsburg Plaza Location is everything, but privacy is the ultimate luxury. Tucked back from the street, this 3-bedroom, 2-bathroom residence offers an unexpected level of seclusion and quiet just blocks from the Healdsburg Plaza and everything it has to offer. The interior is defined by an effortless, open-concept flow. The kitchen offers a versatile layout with the perfect footprint to add a custom center island, and transitions seamlessly into a generous common room. This flexible space easily accommodates a large dining table or additional lounge seating, while dual doors lead to the exteriorallowing the home to live much larger than its footprint and pulling natural light into every corner. Both guest bedrooms are situated off the front living area, while the primary suite is thoughtfully tucked away at the rear of the home to ensure maximum privacy. Twin patios lead directly off the kitchen, creating a seamless transition for indoor-outdoor living. An additional slightly elevated concrete patio near the garden beds, providing many spaces for lounging and outdoor dining. A spacious driveway ensures effortless arrivals and complements the oversized two-car garage.

824 Prince Ave, Healdsburg

2167 Redwood Dr, Healdsburg
$475,000
1 Beds ⋅ 1 Baths ⋅ 326040326 MLS
Cute as a button! A perfect vacation house or starter home tucked away by the Russian River on Fitch Mountain, this 1946 cottage has been restored and updated for easy living. Walking distance to the river and hiking trails, close to everything Healdsburg has to offer. One bedroom, one bath, 650 square feet on the main level, plus a loft that adds real living space beyond the listed square footage. With a new roof, recent paint, new carpet, and tile bathroom with a claw-foot tub, the work's already done. Enjoy the covered porch wrapped in fragrant star jasmine. The back doors open to a private, fenced yard with decks, a picnic spot, and an outdoor shower for rinsing off after a day at the river. Forced-air heat and an on-demand water heater cover the essentials. No HOA and no shared walls - just easy living in an eclectic river community. A place to steal away for vacation or to enjoy every day.

2167 Redwood Dr, Healdsburg

216 Foss Creek Cir Unit #B, Healdsburg
$675,000
2 Beds ⋅ 2 Baths ⋅ 326038269 MLS
Located just a short stroll from the world-renowned Healdsburg Plaza, this beautifully upgraded upper-level condominium offers the perfect blend of Wine Country charm and modern comfort. Thoughtfully updated throughout, the unit features an open-concept kitchen and dining area with a breakfast bar, stainless steel appliances, a built-in wine refrigerator, and custom cabinetry ideal for entertaining or everyday living. Rich cherry wood flooring greets you at the entry, while recent upgrades include a new heating and air conditioning system for year-round comfort. Built-in features and quality finishes elevate the space, offering a turnkey opportunity for those seeking a sophisticated yet low-maintenance lifestyle. Whether you're searching for a full-time residence or the ultimate weekend escape, Foss Creek Villas delivers with its serene setting, community pool, and unbeatable location near acclaimed restaurants, tasting rooms, and boutiques.

216 Foss Creek Cir Unit #B, Healdsburg

97 Kennedy Ln Unit #36, Healdsburg
$474,000
2 Beds ⋅ 2 Baths ⋅ 326035850 MLS
Welcome to easy Healdsburg living, just minutes from the historic downtown plaza, wineries, restaurants, boutique shopping, and the Russian River. Built in 2015 and updated throughout, the home features a bright open-concept layout, natural light, and modern finishes. Improvements include updated lighting and fixtures, dimmable living and dining room lighting, newer appliances, and cooling units in each room. It includes a flex room ideal for guests, a home office, hobby space, or additional sleeping area. Outside, enjoy low-maintenance landscaping and peaceful outdoor spaces. Unlike many manufactured home communities, there is no separate land lease or monthly space rent. The property may also be rented to tenants, providing flexibility for investors, second-home buyers, or rental income. This property offers comfort, convenience, and flexibility in the heart of Wine Country.

97 Kennedy Ln Unit #36, Healdsburg

2563 Mill Creek Rd, Healdsburg
$1,400,000
2 Beds ⋅ 3 Baths ⋅ 326032489 MLS
Eight minutes from the Healdsburg plaza, Mill Creek Road gives way to a forest canopy and the kind of quiet that makes you exhale. That's the setting for 2563 & 2560 Mill Creek Rd combined to offer an almost 1 acre property, modern designed 2 bedroom, 2.5 bathroom 1,409 sqft home, genuine nature immersion, and one of the most compelling income opportunities in Healdsburg today. A striking modern home with floor-to-ceiling windows, warm oak plank floors, and an open-concept layout built for living well. The kitchen anchors the main level with a large island, wine fridge, stainless appliances, and floating shelves. Multiple glass sliders dissolve the boundary between inside and out, opening to an expansive deck for dining and entertaining, gravel path, dedicated patio, hot tub, cold plunge, and sauna the kind of amenity stack that earns five-star reviews or creates quality memories. Both ensuite bedrooms sit upstairs, framed by forest views on every side. Cross Mill Creek Road to the south parcel: a fully fenced half-acre with Mill Creek frontage, mature trees, flat open terrain, and a large storage shed ideal for recreation or leisure. Must see to appreciate this unique offering.

2563 Mill Creek Rd, Healdsburg

6165 W Dry Creek Rd, Healdsburg
$740,000
4 Beds ⋅ 4 Baths ⋅ 326024033 MLS
New co-ownership opportunity by Pacaso: Own one-eighth this professionally managed, turnkey home. Olive Grove is set along a private driveway on West Dry Creek Road in Healdsburg, where ancient olive and fruit trees frame the approach to a renovated hillside compound. The board and batten exterior with a metal roof reads as modern and grounded against the surrounding hillside, with a main residence, a detached bedroom suite and a detached office and gym arranged across more than three private acres. The great room is Olive Grove's centerpiece, with a dramatic wood-plank vaulted ceiling, an oversized gas fireplace and walls of glass that frame the private orchard and West Dry Creek Valley beyond. Sliding doors open the full width of the living space to the outdoors. The kitchen has white cabinetry, stainless appliances and an 11-foot island lit by weathered zinc pendant lights. The primary suite has a walk-in closet and an en suite bath with a soaking tub, dual vanity and marble shower. Two additional bedrooms and baths complete the main residence. The pool and hot tub sit among the ancient trees with hillside views behind, and the outdoor kitchen and fire pit extend the entertaining spaces across the broad decks. Downtown Healdsburg is a short drive away, with the town's celebrated restaurant row on the plaza, the Saturday Healdsburg Farmers Market and the tasting rooms of Dry Creek Valley all within easy reach. Olive Grove is fully designed, furnished and managed by Pacaso. Owners arrive to find the home exactly as it should be, every time.

6165 W Dry Creek Rd, Healdsburg

936 Valley View Dr, Healdsburg
$1,175,000
3 Beds ⋅ 2 Baths ⋅ 326003322 MLS
Own the Altitude. Positioned along Valley View on the preferred side of Fitch Mountain, this approximately 2,200 square foot residence delivers what cannot be recreated: elevation and horizon. The main living level sits upstairs exactly where it belongs so daily life meets open sky. Living room, kitchen, and primary suite are oriented toward expansive views and natural light. Downstairs, a generous family room and two additional bedrooms provide separation and flexibility. Built in the 1980s and offered in original condition, this is not about finishes. It's about fundamentals. In a neighborhood where homes range from approximately $1.2 million to over $3.5 million, this offering represents entry into one of Healdsburg's most compelling ridgeline settings. Front and rear decks extend the footprint outward and invite reinvention. Tucked at the end of an easement, the property offers privacy without isolation within the City of Healdsburg and minutes to downtown. Elevation is permanent. The rest is up to you.

936 Valley View Dr, Healdsburg

397 Parkview Dr, Healdsburg
$1,148,275
3 Beds ⋅ 3 Baths ⋅ 326010888 MLS
Discover the perfect blend of natural beauty and downtown convenience in this spacious 3-bedroom, 2.5-bathroom Healdsburg retreat. Ideally located just steps from Byron Gibbs Park and a scenic 1.5 mile stroll to the iconic Healdsburg Plaza, this home offers immediate access to world-class dining, shopping, and tasting rooms. The light-filled, open layout is designed for seamless entertaining, flowing directly onto an expansive back deck that overlooks a peaceful stream. Wander across the bridge to discover a rustic chicken coop area, a charming canvas for your "farm-to-table" dreams or a creative garden project. For those needing extra space, the property features two separate garages, providing ample room for vehicles, a home gym, or a dedicated workshop. Ready for its next chapter, this home comes thoughtfully refreshed with brand-new interior and exterior paint, as well as plush new carpeting upstairs. This turn-key sanctuary allows you to move right in and start enjoying the quintessential Wine Country lifestyle from day one.

397 Parkview Dr, Healdsburg

1625 Madrone Ave, Healdsburg
$1,295,000
3 Beds ⋅ 2 Baths ⋅ 326008753 MLS
Charming 3-bedroom, 2-bath home in a prime Healdsburg location, offering the perfect blend of comfort, scenery, and Wine Country lifestyle. Just minutes from downtown Healdsburg and the Healdsburg Tayman Park Golf Course, this property provides both everyday convenience and easy access to world-class dining, tasting rooms, and outdoor recreation.The true highlight of this home is its sweeping panoramic views. From sunrise to sunset, the property captures wide-open vistas of rolling hills, vineyards, kayaks on the Russian River and hot air balloons in the summer months. Large windows and outdoor living spaces are thoughtfully oriented to take full advantage of the scenery, creating a constant connection to the natural beauty that defines Wine Country. The setting feels private and serene, offering a sense of retreat while still being just minutes from the energy and charm of downtown Healdsburg. This rare balance of proximity and perspective is what makes the property so special. Whether you're seeking a full-time residence, weekend getaway, or investment opportunity, this home presents an exceptional chance to enjoy one of Sonoma County's most desirable areas. Plans available for ADU in backyard. A separate 0.27-acre view lot located directly across the street is also available for purchase. This parcel includes a 4-bedroom perc and a circular driveway already in place, presenting a rare opportunity to build a second home, guest house, or future investment property in a highly sought-after neighborhood.

1625 Madrone Ave, Healdsburg

523 Center St, Healdsburg
$899,000
3 Beds ⋅ 2 Baths ⋅ 326001334 MLS
Major Price Improvement NOW $899,000! Exceptional opportunity for an investor, builder, or buyer looking to create value in the heart of Healdsburg. This charming 1922 cottage is currently configured as a 3-bedroom, 2-bath home with approximately 1,250 sq ft and is being offered with fully approved City of Healdsburg plans for a beautifully redesigned 1,403 sq ft modern residence with an open-concept floor plan. Much of the time and uncertainty of the planning and approval process has already been completedbring your contractor and move forward with the project. At this newly reduced price, the combination of an attractive entry point, approved plans, and an exceptional in-town location creates a compelling value-add opportunity. Set on a quiet street just blocks from the renowned Healdsburg Plaza, world-class dining, tasting rooms, and boutique shopping. Review the plans, run the numbers, and bring the visionthe groundwork has already been done.

523 Center St, Healdsburg

131 Sawmill Cir Unit #203, Healdsburg
$999,000
1 Baths ⋅ 325040432 MLS
Located in Healdsburg's premier Mill District neighborhood, this impeccably designed studio in the Canopy collection offers an exceptional blend of style, function, and convenience just steps from the historic town plaza. Nestled among a preserved grove of redwoods and adjacent to a community park, this luxury residence is part of a one-of-a-kind development by world-renowned architects Olson Kundig. Inside, the space has been thoughtfully upgraded with a custom Murphy bed and built-in cabinetry that seamlessly integrates into the modern design, a mounted flat-screen TV with soundbar and subwoofer for a premium home entertainment experience, and electric car charging in the secure underground parking garage. Soaring ceilings and floor-to-ceiling windows bathe the home in natural light and offer tranquil views of the redwoods and park. Everything here is brand new, with high-speed internet, Wi-Fi, and refined finishes that elevate everyday living. Outside your door, enjoy immediate access to Healdsburg's celebrated food, wine, and outdoor lifestyle. Whether you're seeking a stylish wine country getaway or a turnkey pied-a-terre in one of Sonoma County's most desirable communities, Unit 203 at 131 Sawmill Circle offers an unmatched opportunity to live in the heart of it. Also included is the Poolhouse. The Poolhouse is a private social, health and wellness facility, located just steps from Canopy. Centered around a private lap pool and expansive pool deck, The Poolhouse is for the exclusive use of Mill District residents a place where they can refresh, relax, socialize, and entertain.

131 Sawmill Cir Unit #203, Healdsburg