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Meticulously designed with attention to every detail in this 4 bedroom, 4 bathroom home, including auxiliary dwelling unit. Finely crafted finishes, and bathed in natural light, showcasing the very best of Healdsburg. A short walk or bike ride to the Healdsburg Square Plaza. As you enter the property, you are greeted by a canopy of Heritage olive trees, and enter through the 10' custom French iron entry door, to 12' ceilings and a sophisticated entry flanked by the bespoke beamed ceiling dining room, featuring built-in cabinetry and a wine refrigerator on your right. To the left is an amply sized office or bedroom. A climate controlled wine storage wall built to store up to 21 cases of your favorite wine provides a sleek transition to the main living areas. The chef style kitchen is perfect for culinary enthusiasts, and connects to the great room, featuring a marble fireplace and a continuation of ceiling beams. Your eyes are drawn to yet another Heritage olive tree, ripe and ready to harvest in the backyard entertaining space, boasting stacking doors for a seamless continuity from indoor to outdoor living. Professionally landscaped, manicured grounds, created for little to no maintenance. Celebrate each entertaining space including outdoor covered dining patio , BBQ kitchen, cozy lounge area with fire pit, and a tranquil fountain rounding out this private retreat. Designed with attention to every detail, this residence embodies contemporary sophistication. Close to world class wineries and dining, Sonoma County Airport and the coast. Less than an hour to San Francisco.
…By Healdsburg Sotheby's International Realty
Set on approximately 1.32 acres along one of Sonoma Valley's most coveted Eastside streets, 1265 Castle Road brings together a 3,818-square-foot contemporary main residence, detached one-bedroom guest house, resort-inspired pool and spa, and beautifully landscaped grounds overlooking neighboring vineyards. Built in 2019 and located just moments from Bartholomew Park and the historic Sonoma Plaza, the private, gated estate offers three bedrooms, three bathrooms, and a dedicated office that can function as a fourth bedroom within the main residence. Expansive Marvin windows and doors fill the interiors with natural light and create a seamless connection to the surrounding landscape. Italian porcelain flooring, mahogany ceilings, radiant heat, and thoughtfully selected finishes lend warmth and refinement to the home's clean architectural lines. Designed for both everyday living and effortless entertaining, the residence features generous gathering spaces and a chef's kitchen with premium Miele appliances and a walk-in scullery, all flowing naturally to the outdoors. Meandering garden paths connect mature landscaping, raised garden beds, fruit trees, berry plantings, and wide-open spaces that embrace the property's vineyard-view setting. An outdoor kitchen, fire pit, multiple areas for dining and relaxation, gated entry, and dog run further enhance the grounds. Solar power, battery storage, extensive irrigation, and a living roof complement the estate's thoughtful design and environmentally conscious systems. Pairing contemporary architecture with the relaxed indoor-outdoor lifestyle for which Sonoma is known, 1265 Castle Road is a private and beautifully realized retreat in one of the valley's most sought-after locations.
…By Sotheby's International Realty - Wine Country – Sonoma Brokerage
Welcome to 2158 Mount Olive Drive, lovingly maintained and situated in Santa Rosa's highly desirable Montgomery Village neighborhood. Located only a half mile from the updated Montgomery Village Shopping Center with Mendocino Farms, Anthropologie, Free People, Apple Store, Monti's & more! With a spacious backyard, multiple indoor living areas, and seamless indoor-oudoor flow from both the open-concept kitchen/family room and primary suite, this home is perfectly suited for both entertaining and everyday living.This single-level home was thoughtfully designed with 1,936± sq ft of living space, a welcoming formal entryway, formal dining room, a primary suite, 2 guest bedrooms, living room, family room, indoor laundry, and exceptional storage space in hallway cabinets. Enjoy your beautifully landscaped yard complete with a large deck, sports court, raised garden bed, 2 sheds, automatic sprinklers, charming arbor, and meandering paths. Mature plantings, including a Japanese maple, ivy, Silver maple, Redwoods, liquid amber, agapanthas, rosemary, meyer lemon tree, camellias, roses, succulents, azalea, and trumpet vine create a lush and private environment. Truly an exceptional setting to host dinner parties or unwind with your favorite book in the evenings. The generous primary bedroom features an updated ensuite bathroom with an additional closet and sleek dual sink vanity. Staying organized is a breeze with your 2-car garage which includes multiple storage cabinets, a built-in work bench and durable epoxy floors. This home is ideally located within minutes of Whole Foods, Oliver's Market, Hwy 12, Hwy 101 access, Howarth Park, Annadel, Starbucks & more.
…By Artisan Sotheby's International Realty
Prestige meets park-like setting on this 5.95± acre parcel adjacent to Skyfarm and Fountaingrove, in the historic Riebli Valley. At 1055 Sundown Trail you will find country living adjacent to the city, near shopping, world class wineries and golf, as well as the Sonoma County Airport. Dwelling built in 2021, featuring 3 bedrooms, 2 bathrooms, with all the comforts of wine country living. Includes a covered porch, large carport, citrus and olive trees, garden beds, places to dine, lounge, play, Plenty of room to raise livestock, or start your hobby vineyard. Property includes several seasonal creeks, with waterfalls, multiple building sites for possible additional structures. Storage shed and tractor also included.
…By Healdsburg Sotheby's International Realty
Discover the opportunity to build your custom dream home on this exceptional 1.63± acre homesite in prestigious Skyfarm. Enjoy panoramic valley and mountain views, a premier location surrounded by luxury residences, and easy access to Healdsburg, Sonoma County Airport, world-class wineries, and the Fountaingrove Golf Club.
…By Healdsburg Sotheby's International Realty
The Vineyard Estates is a private collection of four ultra luxury homes behind a single gate in the heart of wine country, each situated on expansive acreage with exceptional architecture and an uncompromising standard of finish. Every home is fully integrated with Domovita.AI, the first residential AI concierge platform ever built into a home at the time of construction, and each is equipped with a state of the art wildfire defense system. Residents enjoy access to Drakes Ranch, a fully managed pastoral estate where vineyards are being planted, animals roam the land, and a fishing pond is underway. Ownership also comes with a curated portfolio of lifestyle partnerships spanning private wine allocations and cellar access at some of the region's most celebrated producers, exotic car membership, trackside hospitality, world class sporting and social experiences, and wellness memberships. Opportunities of this nature are rare, and this one is without precedent. Chardonnay, Lot 13, is a single story residence offering 4,930 square feet of living space on 4.0 acres, designed by Sean Bailey Design and built by Dotto Construction. The home features four bedrooms plus a dedicated office, four and a half bathrooms, and a thoughtfully composed floor plan that includes a wine room, rec room, family room, prep kitchen, mud room, and courtyard, all flowing seamlessly to the outdoors. Dual two car garages totaling 1,305 square feet, a pool and spa, an outdoor kitchen and cabana, covered porches, a fire pit, a sauna, and an outdoor shower complete a compound that is as well considered outside as it is within. Every surface has been specified with intention, from the hand applied limewash plaster walls and natural stone throughout to the full professional appliance suite and designer plumbing fixtures in every bath. Situated on a private road within The Vineyard Estates, Chardonnay delivers single story living at its finest, with the space, privacy, and lifestyle infrastructure that defines this one of a kind community.
…By Sotheby's International Realty - Wine Country – Sonoma Brokerage
This striking contemporary residence perfectly articulates the art of arrival, by intentionally merging the best of bold design, warm modern materials, and refined indoor-outdoor living. A tiered approach to the main residence creates a dramatic sense of reveal to this exquisite estate framed by curated landscaping and soft, integrated lighting. The smooth earthen-hued stucco façade blends with natural wood cladding, expansive windows, and glass walls; creating an interplay of geometry, scale and luminosity that is inviting and timeless. A dramatic great room anchors the open-concept layout that flows effortlessly between the living and dining space, where designer lighting and minimalist detailing reinforce the sophisticated, uncluttered feel that is deeply connected to its natural surroundings. A wall of glass opens to a heated screened porch; a dramatic see-through linear fireplace connects the great room to the exterior dining pavilion, dissolving the boundaries between inside and out. A floating staircase blends engineering precision with artful expression, and the minimalist, yet highly functional, kitchen enhances livability and effortless entertaining. A companion structure was completed in 2023 and finished to the same exacting standard as the main residence, completing this cohesive and functional estate compound. The upper level features a beautifully appointed 2-bedroom, 2-bath guest residence, with private deck and views. The lower level is equally well-conceived, offering abundant storage in a spacious 3-car garage, a gym with adjacent full bath, and a sophisticated executive office with the quiet and separation that serious work demands. An architecturally integrated estate barn with dedicated storage and workshop, blends utilitarian purpose with a refined private office. Thoughtfully sited among olive orchards, curated fruit and citrus groves, and raised-bed gardens, it supports an agrarian lifestyle that includes the production of estate olive oil. Life in the wine country happens outside. A resort-style lap pool and spa, pizza oven, built-in grill, fire pit, and multiple entertaining areas are defined by intentional landscaping, creating spaces for gathering and retreat. With solar power, battery storage, a backup generator, and smart-home automation serving the entire property; the property offers a rare blend of modern luxury with self-reliance. A phenomenal wine country showcase, where curated minimalism and quiet luxury converge harmoniously with the land. This is wine country living without compromise, located approximately 70 miles from San Francisco and set in Dry Creek Valley and nearby Healdsburg. Popular wine industry events, a central plaza dotted with an abundance of award-winning restaurants featuring the best in “farm-to-table” cuisine, art galleries and chic boutiques makes Healdsburg the “small town with big class”.
…By Sotheby's International Realty - San Francisco Brokerage
Designed by award-winning architect George Miers of Swatt Miers, 429 Chestnut Avenue is a newly completed contemporary residence positioned above Sonoma Valley with sweeping 270-degree views. Completed in 2025, the approximately 3,766-square-foot home offers three bedrooms, three full bathrooms, two half bathrooms, an office, and an oversized two-car garage. Walls of glass frame spectacular valley views and dramatic sunsets, while custom finishes throughout include poured-in-place terrazzo features, wide-plank quarter-sawn white oak floors, custom cabinetry, slab marble bathrooms, and premium Sub-Zero and Wolf appliances. The upper level is dedicated to the primary suite with private balcony, fire pit terrace, and panoramic views. Outdoor spaces include a swimming pool, reflecting pool, entertaining terraces, and gathering areas designed to maximize the property's extraordinary setting. Solar power, battery backup systems, Lutron HomeWorks, Sonos audio, EV charging, and fire suppression complete this exceptional architectural offering.
…By Annonceur International
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.
…By Annonceur International
Situated on rolling bench land high above the southern Alexander Valley within the exclusive Hall Ranch community, this extraordinary ∼40.11-acre estate property offers an unparalleled canvas for a world-class wine country lifestyle, notably benefiting from no Hall HOA Architecture Review process. The site comes fully prepared with architecture plans for a contemporary luxury compound featuring a 7,838 +/- sq ft estate residence, a 990 +/- sq ft pool house, 4,765 +/- sq ft of patios, and a professional swimming pool. Encircled by rolling vineyards, ancient oak woodlands, and sweeping meadows, the parcel commands spectacular, panoramic views over a private lake, the iconic Alexander Valley wine country, and the charming towns of Healdsburg, Geyserville, and the Jimtown store. Anchored by 8 +/- acres of premium hillside Cabernet Sauvignon vineyards, the property features a ready-to-build foundation complete with paved roads, a water well, underground power, and completed percolation testing. Enjoy absolute country privacy and serenity just minutes from world-class wineries, Healdsburg's vibrant downtown shopping, restaurants, the airport, and beautiful Lake Sonoma. Website: 746artisancircle.jmbland.com
…By Annonceur International
Located on a quiet street in Kenwood, this updated 3-bedroom, 3.5-bath home sits on approximately 0.5 acres surrounded by 23 mature redwood trees with views of Sugarloaf Ridge and nearby vineyards. Remodeled by Synergy Architects and Designers, the approximately 2,200 sq ft residence features classic contemporary styling and an open living, dining, and kitchen area designed for entertaining. Quartz countertops, textured walls and ceilings, a marble and tile fireplace surround, and a suspended kitchen vent hood create distinctive design elements. Large sliding glass doors provide broad access to the spacious backyard dotted with redwoods and peach trees. The front yard features mound gardens and a long paved driveway with embedded lighting. Additional highlights include an attached 3-car garage with epoxy flooring and built-in storage, Bosch refrigerator (2026), new carpeting (2026), Generic generator (2020), water heater replacement (2019), and Nest smart home features.
…By Annonceur International
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