Completely reimagined by designer Josh Chandler and JAC Designs, this residence transcends its historic roots with an architectural vision that is at once bold, inventive, and deeply livable. Expanded in 2005 and thoughtfully updated in 2010, the home embodies a contemporary/industrial farmhouse aesthetic while introducing sculptural forms, striking materials, and a curated sense of artistry. Set behind a gated entry and tucked off the street, the 3,600 sq. ft. layout flows with remarkable openness. Light moves through vast windows, skylights, and French doors, connecting nearly every room to outdoor courtyards, patios, and gardens. The facade and interiors reveal Chandler's signature balance of innovation and warmth: reclaimed wood, polished and glazed concrete, limestone, and custom metalwork are paired with refined cabinetry, integrated lighting, and expressive architectural lines. The main living area with tall ceilings, anchored by a monumental European-style fireplace framed in limestone and reclaimed wood. Bespoke details custom wire chandeliers, built-in shelving, and corrugated metal accents to further enrich the interiors with personality and texture.
Set within a private country setting, this exceptional orchard ranch features over 200 mature olive trees spread across 2.57 acres of serene landscape. Offering a perfect balance of rural charm and modern comfort, the property includes an updated single-level main residence, a separate single-level second dwelling, and additional structures, together creating a peaceful, self-contained compound. Located less than 10 minutes from downtown St. Helena and only 2.5 miles from Lake Hennessey, the setting feels worlds away while remaining conveniently close to town. The main residence includes approximately 2,110 square feet and offers 2 bedrooms and 2.5 bathrooms with a spacious, inviting layout. Rustic hardwood and large-format stone floors, paired with a wood-burning fireplace, add warmth and character, while expansive sliding glass doors create an easy connection between indoor and outdoor living. The kitchen is both charming and functional, featuring a breakfast nook, granite countertops, high-end appliances, bar-top seating, and a generous walk-in pantry. A private flex room with a separate entrance provides versatility for a home office, gym, or creative space. Outdoors, the property truly shines. A covered back patio offers the perfect setting for entertaining or quiet relaxation, taking in sweeping views of the manicured olive orchard, neighboring vineyards, and surrounding mountains. A charming, updated 910 square-foot guest house and an 805 square-foot storage building are accessed via a gravel pathway or a separate entrance off Rossi Road, enhancing both privacy and usability. This olive orchard ranch offers a rare blend of peaceful country living just minutes from town. Whether you choose to cultivate and harvest your own olive oil or simply slow down and enjoy the privacy and bucolic surroundings, the setting invites a more intentional way of life.
Nestled just a block from downtown St. Helena's Main Street, the charming yellow two-story farmhouse, built in 2002, sits on a serene 0.35-acre lot with beautiful landscaping and lots of privacy. The property has a well drilled in 2002 perfect for maintaining the lush surroundings - and City water for domestic use. Inside, the 3316 sq ft home offers a spacious layout with 4 bedrooms, 3.5 baths, living room, family room and formal dining room with an attached 2-car garage. With its warm ambiance and sprawling communal areas, it's ideal for a few people or a larger family. The high ceilings, crown molding, abundant natural light, and custom built-ins throughout are nice features and a nod to more traditional architecture. The backyard is designed for entertaining or just relaxing, featuring a large pergola-covered deck (seasonally laden with wisteria), long-bench seating and a built-in BBQ grill. The grounds are beautiful with decades of love that went into the gardens and a must see of the property. A greenhouse and a lovely water feature adorn the backyard that accentuates the quiet serenity found here at 1330 Pine. The home has Tesla solar and three back up batteries.
Tucked away in a quiet, private setting beside scenic vineyards and towering trees, this charming older stucco home offers a wonderful opportunity to create something truly special. A large deck wraps along two sides of the home, perfect for relaxing, entertaining, or enjoying peaceful vineyard views. Inside, you'll find a spacious kitchen, a sunny dining room, indoor laundry hook-ups, and central heat. The home features a second bedroom and bath with a separate exterior entrance and its own private patioideal as a guest suite, extended living space, or potential rental room. Additional highlights include a basement garage with storage room, plus ample space to park an RV or add a storage unit. Set on a large 1 acre lot with room to garden. This property is full of charm and potential, making it a great place to remodel and truly make your own while enjoying country living surrounded by Napa Valley charm. This is the first time this well loved property has been on the market in decades. Don't sit on this one! Come see this lovely setting and cute cottage while it is still available.
Charming Napa Valley retreat with flexibility, potential, and location. Situated on a corner lot with abundant privacy provided by mature trees and lush bushes, this home is just minutes from the heart of downtown St. Helena. Featuring hardwood floors and an inviting interior that exudes warmth and character, the home is well-maintained while offering opportunities to personalize and enhance according to your vision. The bright, sun-filled kitchen offers a functional layout currently equipped with all essential appliances, including a wine refrigerator. A cozy corner by the window provides the perfect spot for morning coffee or a quick breakfast, while the space as a whole presents an excellent opportunity to bring your personal vision to life through updates and finishes. The side door in the kitchen opens to a covered patio, extending the entertaining space outdoors, perfect for alfresco dining or relaxed Napa Valley evenings. The expansive backyard provides a transformable canvas for a garden, reimagined landscaping, or creating an enhanced outdoor living area. The detached garage includes over 400 square feet of additional space, providing flexibility for a private office, studio, fitness room, or refined storage solution. Whether you're seeking a primary residence, weekend wine country getaway, or investment opportunity, this property delivers endless possibilities. Enjoy easy access to wineries, boutiques, galleries, and restaurants that define the Napa Valley lifestyle.
This stunning St. Helena country estate spans 1.27 acres, featuring impressive architectural details & high-pitched ceilings that evoke a sense of grandeur & openness. Artfully shaped windows & various ceiling angles add visual interest & architectural character. The main house, featuring a dramatic high-ceiling entry, bamboo floors throughout, two fireplaces, a library/office, a wine cellar, a chef's kitchen with a butler's pantry, & a grand entertaining bar adjacent to the family room, opens to the backyard patio. The primary suite is truly an oasis; a pitched ridge skylight immerses the interior, the primary bedroom with a sitting area opens to a balcony, & a spacious primary bathroom with beautiful marble finishes & spa-like amenities. The guest house features a living room, 2 fireplaces, a kitchen, a large bedroom suite, & an oversized 4-car garage with a workshop. Gorgeous natural stone walls beautifully embrace the exquisite garden entry, and the backyard is a serene bucolic garden setting, featuring a large pool & spa, water fountain, & a spacious patio for outdoor dining/entertaining. The grounds are truly a vision - matured trees, beautiful floral & succulent gardens, fig trees, & vegetable beds that add to the allure of the Napa Valley lifestyle.
Welcome to Daisy Hill, a stunning retreat nestled in the serene beauty of St. Helena 2 miles from downtown and one mile from Meadowood Resort that sleeps up to 16 people. The main house with space for 12 and the two casitas for another 4! With its exquisite craftsmanship, breathtaking landscapes designed by Johnathan Plant, and luxurious amenities, it offers an unparalleled experience for those seeking a tranquil and private haven just minutes from shopping and dining. Sited on a bucolic country lane and originally custom-built in 2001, the two-story Craftsman-style home of stucco and wood siding showcases its timeless elegance. Designed for an elevated style of family living and entertaining, Daisy Hill includes the primary residence with 4 bedrooms, 4.5 baths, an outdoor dining pavilion and kitchen, a parlor/gym with a full bath, two guest casitas ensuite with private entrances, a pool with waterfall edge, bocce ball court, lighting and sound throughout, walking trails and seemingly endless, mature, lush gardens and tranquil nooks. Heavenly retreat.
Located in the heart of St. Helena, this newly built gem blends luxury and functionality across a 3,800 SF main residence + ADU on a beautifully landscaped in-town lot. The 5BD, 5BA property showcases white oak cabinetry and floors, 11-foot ceilings, and custom finishes throughout. A sliding glass wall seamlessly connects the great room to a private outdoor retreat featuring a 38x20 pool with spa and Baja shelf, outdoor kitchen with Sedona grill, and a built-in fire pit. The primary suite enjoys a private terrace with views of the Mayacama mountains, a spa inspired bath, and a generous walk-in closet. Additional amenities include a flexible office/gym space and a fully appointed ADU. A rare in-town St. Helena offering for those seeking modern design with effortless indoor-outdoor living in one of Napa Valley's most desirable locations.
Experience the quintessential Napa Valley lifestyle from this beautiful single-level residence in St. Helena's desirable and peaceful Signorelli neighborhood. Only a few level blocks from world-class dining, boutique shops, and tempting tasting rooms, this well-appointed 3 bedroom (option for a fourth bedroom), 2.5-bath home is ready for you to enjoy. Inside, soaring ceilings and warm hardwood floors create an inviting open-concept layout. The gourmet kitchen is a true centerpiece, featuring an oversized island, high-end appliances, and built-in bench seating with inspiring views of the backyard sanctuary. The private primary suite is a true retreat, offering a luxurious bathroom and direct exterior access to the spa. The family and living rooms each have a cozy fireplace, making them ideal for intimate gatherings or a relaxing night with a good book. A dramatic tasting room is located under a second level space that could be an office, fourth bedroom, or private retreat. Outside, the meticulously landscaped grounds beckon, featuring multiple seating areas beneath structured trellises, an English garden, and manicured roses all connected by charming gravel pathways. This is 806 Chiles Avenue, where luxury meets tranquility.
This prime property, located at the end of a quiet lane, just south of downtown St. Helena, enjoys vast vineyard and mountain views, along with a wealth of development and improvement opportunities. The 2BR/1.5BA classic mid-century ranch style home features a spacious living room with fireplace, remodeled kitchen and a versatile dining/office space, all of which overlook the property's expansive 0.8 acres. The residential compound includes a 2-car garage with laundry facility and a 2-story barn, perfect for parties, exercise, yoga, wood working or overflow parking. Water is plentiful here, sourced from both an on-site well and city water. The property's sizable spread provides space to add all kinds of outdoor amenities that one might imagine: vineyard, vegetable gardens, fruit trees, a chicken coop, pool, pickle ball court. The possibilities are many. An approved wet weather septic perc affords multiple options for expanding the existing residence or building from scratch. Whether you love it as is, or as a place to manifest your Napa Valley vision, this offering, unique for its location, size and views, is a rare Wine Country gem.
Set just north of town along a classic stretch of Highway 29, this 26 acre St. Helena residence and vineyard offering presents a rare opportunity to steward a special piece of Napa Valley. At the center of the property sits an original 1966 residence encompassing 2,668 square feet. The home reflects its era and is ready for thoughtful restoration or re-imagining, providing a strong foundation for a future vision that honors the land. A pool, vineyard roads, and a classic cypress-lined approach reinforce the estate's character. Approximately 7.44 acres of vineyard are planted to Cabernet Sauvignon, Cabernet Franc, and Sauvignon Blanc, framed by rolling hills, mature trees, and long vineyard views in every direction. Surrounded by neighboring vineyards and estate holdings, this property offers a sense of continuity with Napa Valley's agricultural heritage, while remaining moments from downtown St. Helena. A rare offering where patience and vision meetan authentic Napa Valley opportunity defined by land, scale, and setting.
An incredible opportunity to acquire this shockingly beautiful Napa Valley estate. Exquisitely updated modern contemporary residence, unquestionably one of the most striking and elegant estates in St. Helena. It is truly the ultimate retreat for individuals who value privacy. This entertainer's dream will exceed any expectations for Napa Valley luxury living. Experience unsurpassed & breathtaking views from its magnificent mountain perch on nearly 14 acres of solitude and grandeur. A spectacular great room accented with soaring ceilings & massive fireplace, compelling interior spaces for museum-quality art, stunning light fixtures, fabulous primary suite adjacent to office/library, gym/recreation/media room, & luxurious private guest suites. Grand and modern epicurean-style kitchen with commercial-grade appliances to curate exquisite Napa Valley fine dining at home. Banks of French doors allow direct access to a striking pool veranda, expansive lawns, sports court, gorgeous lavender gardens, & a spacious courtyard for outdoor dining & entertaining.
Situated in one of St. Helena's most desirable in-town neighborhoods, this beautifully maintained single-level residence offers +/- 2,020 square feet of thoughtfully designed living space with two bedrooms and two baths. The light-filled interior features an inviting fireplace and a comfortable flow among the living room, dining area, and kitchen, creating an ideal setting for both everyday living and entertaining. The kitchen is well appointed with a large center island, abundant cabinetry, and generous counter space. The primary suite includes direct access to the garden, a spacious ensuite bath with dual sinks and granite counters, and a walk-in closet. An additional bedroom, a full bath, and a versatile office or flex spaceideal for guests, remote work, or creative pursuits and currently outfitted with a discreet Murphy bedcomplete the efficient single-level floor plan. The private, fenced backyard offers pergola-covered patios, raised garden beds, a potting shed, and space for outdoor enjoyment. A detached two-car garage and ample storage add convenience. Ideally located close to downtown St. Helena's renowned restaurants, tasting rooms, boutique shops and community amenities, this home offers an exceptional blend of in-town living, functional design, and turnkey condition a rare opportunity in today's market. Don't miss your chance to experience the quintessential Napa Valley lifestyle just moments from the heart of town.
Located just three blocks from the heart of downtown St. Helena, 921 Chiles Avenue offers an exceptional opportunity to enjoy wine country living with close-to-town convenience. Built in 1998, this well-maintained residence features +/-1,351 sq ft with three bedrooms and two and a half baths in a thoughtfully designed layout. The main level includes light-filled living spaces with a welcoming fireplace, an open flow ideal for everyday living, and a functional kitchen with ample cabinetry and workspace. All bedrooms are situated upstairs, including a comfortable primary suite with en-suite bath and generous closet space. The private side yard provides an outdoor setting for entertaining, gardening, or quiet relaxation, while the two-car garage offers convenient parking and storage. Situated in one of St. Helena's most desirable in-town neighborhoods, this home is moments from renowned restaurants, tasting rooms, shops, and the weekly farmers market. Well suited as a primary residence, weekend retreat, or investment property, 921 Chiles Avenue combines location, livability, and classic Napa Valley appeal in a rarely available downtown setting.
Your own pied-a'-terre in the wine country is ready for your personal touches, on a quarter acre lot, large enough to consider a second unit. This 3 bedroom, 2 bathroom home is full of opportunity. Ample bedroom sizes, open concept, plenty of parking, and a bounty of fruit trees, make this the not-to-be-missed St. Helena single family home. Located just 7 minutes to a local gourmet grocer, 14 minutes to The French Laundry, and surrounded by vineyards and famed world class Napa Valley wineries.
Renovated 1880 home. Door and door knocker are original. Architecture of time period remains the same. This home has been carefully renovated, preserving entry parlor. Fantastic wine celler or small basement. Modern addition of central heat/air, and tankless water heater. One could add thier own touches, possible ADU addition, check with the City of St. Helena. Back yard is ample, and includes original artist studio, or storage area. Beautiful large backyard deck. Easy walk to many ameneties; The olive oil factory, Gotts, Charter oak restaurant. Quiet and loved neighborhood.
Set on 40 private acres above the renowned Meadowood Resort, this exceptional estate captures the essence of Wine Country luxury. A gated entrance leads up a secluded driveway to a stunning modern-industrial residence, where exposed steel elements, soaring 25-foot ceilings, and walls of glass create a striking yet inviting atmosphere. Built in 2006, the home is designed for both grand entertaining and everyday comfort. The spacious great room flows seamlessly into a lofted living area, while all en-suite bedrooms provide privacy and tranquility. An elevator connects each level, and the gourmet kitchen complete with an expansive butler's pantry caters to culinary excellence. Outdoors, the redesigned grounds offer a resort-like experience with a terraced landscaping, an in-ground pool, a poolside cabana with bath, and built-in outdoor kitchen complemented by a stunning wood burning fireplace. Expansive lawns are complemented by grand staircases, olive orchards set among gravel pathways and seating areas, bocce ball court and lush landscaping enhance the serene setting. Located just minutes from world-class wineries, fine dining, and the best of St. Helena, this estate is a rare opportunity to own a true Napa Valley retreat.
Welcome to a private Valley-floor retreat in the heart of St. Helena, where timeless elegance meets effortless indoor-outdoor living. This exceptional 4-bedroom, 4.5-bath residence spans approximately 4,789 square feet and is thoughtfully designed for both refined entertaining and everyday comfort. A dramatic great room with soaring ceilings anchors the home, flowing seamlessly into the gourmet kitchen featuring a generous center island, premium appliances, and an adjacent dining area ideal for hosting gatherings large or small. Natural light fills the interior, creating a warm and inviting atmosphere throughout. The primary suite is a true sanctuary, offering a private balcony, expansive walk-in closet, and a spa-inspired bathroom complete with steam shower and Jacuzzi tub. Two additional bedrooms feature en-suite baths, while a fourth bedroom is conveniently located near a full bathideal for guests, an office, or flexible living arrangements. Outdoors, enjoy a below-ground pool, multiple patio spaces, and the tranquil setting that defines Valley-floor livingperfect for relaxed afternoons and memorable evenings. Additional features include central heating and air conditioning, a whole-home sound system, and a fireplace for cozy nights. Approved ADU plans provide future flexibility and added value. Located just moments from downtown St. Helena's renowned dining, shopping, and wineries, this home offers an exceptional Wine Country lifestyle.
Located at the end of a private country lane just moments from downtown St. Helena, this refined single-level estate offers understated elegance, quiet privacy, and a rare sense of calm. The main residence is designed for seamless indoor-outdoor living, featuring natural light, serene garden outlooks, and partial vineyard views from the family room and the spacious primary suite. The grounds are a standout feature, characterized by layered, intentional landscaping with large stepping-stone pathways, mature plantings, and multiple outdoor areas designed for relaxation. An authentic Japanese-inspired tea house with traditional Shoji doors creates a peaceful setting for guests or relaxation. A detached studio provides flexible space for creative work, fitness, or a private office. The attached ADU, with its own entrance, full kitchen and bath, offers excellent versatility for hosting or extended stays. Throughout the property, storage is abundant, and every space has been planned with comfort and ease in mind. This is rare St. Helena offering that blends tranquility, thoughtful design, and proximity to town an exceptional retreat in the heart of Napa Valley.
Build Napa Valley's next legendary winery! Located on the corner of Zinfandel Lane and Silverado Trail and situated on 19-plus acres lies Napa Valley's next great winery estate. This rare offering includes winery permit approvals for 30,000 gallons of production, excellent visitations, events and more. Also included, approved plans for a 12,500-plus square foot winery designed by storied architect Howard Backen. This beautiful property features a sprawling 13-acre vineyard with breathtaking views of the surrounding mountains and valley; as well as an estate residence, 2 bedroom cottage and classic wood barn. Additional plantable acreage and potential for a wine cave. The main residence is 2,643 square-feet with detached 3 car garage, 3 baths, a pool, and offers spectacular views of the vineyard and beyond. Come claim a piece of Napa Valley's legacy!
Beautifully reimagined by Seller, and well maintained, this rare 3 bedroom, 2 bath home manufactured in 2015 is a standout! The owner has thoughtfully invested approximately $120,000 in quality upgrades, including a whole-house air and water filtration system, new hot water heater, and smart thermostat. The primary bathroom features new plumbing, while Interior updates feature new countertops throughout, tasteful hardware, new flooring in two bedrooms, and a new washer and dryer. Every detail reflects the owner's commitment to quality and meticulous care. It's a happy home awaiting its next steward.
Charming 1940s in-town bungalow on a spacious double lot! This delightful home showcases all the classic features of the era coved ceilings, original light fixtures, rich hardwood floors, and abundant built-ins along with a full basement offering ample storage. The home includes two bedrooms, one bath, and a versatile breakfast room or office that enhances its livability and charm. Outside, a detached two-car-plus garage anchors the rear of the property, while an abundance of mature fruit trees dot the oversized city lot, creating a private and inviting outdoor retreat.
Experience Napa Valley living in this single-level home in an ideal location on St. Helena's west side. Set on a desirable large corner lot, this 2,374 sq ft residence blends modern sophistication with effortless comfort. Expansive windows bathe the interiors in natural light, while a wood-burning fireplace provides the living room warmth and charm. The inviting chef's kitchen showcases a generous island, premium appliances, sleek countertops, and custom cabinetry enhanced by the rare luxury of its own fireplace, perfect for cozy mornings. Three spacious bedrooms and two-and-a-half baths include a serene primary suite with dual sinks, a separate tub and large shower. Two additional bedrooms with a shared bath offer versatility for family, guests, or a home office. Mature trees and lush landscaping create a tranquil backdrop for alfresco dining, gardening, or relaxation. Room for a pool and/or hot tub. A large two-car garage with automatic door, plus a garden shed, provide ample storage. Just moments from world-class wineries, acclaimed restaurants, and boutique shopping. This home is ready for your personal touches and provides the perfect opportunity to embrace the best of St. Helena living.
A magnificent 3662 sq ft, 4 beds, 3.5 baths, three-level custom home in a quiet west-side St. Helena neighborhood just blocks from downtown. Divided between three levels, each floor encompasses a refined balance of contemporary living and familial comforts. The main floor features a large great room, dining area, modern kitchen with quartzite countertops, contemporary cabinets, sub-zero refrigerator, wolf range, and modern finishes. Warming both atmosphere and ambiance, the great room features an oversized wood-burning fireplace and floor to ceiling windows. Optimizing privacy, the master bedroom is located on the main floor with its own private patio access separated from the 2nd-floor guest bedrooms. The media room, fully redone large garage, and ample storage complete the bottom floor. The home's beautiful decks have been refinished. Upgrades include Tesla solar for efficiency.
Perched above the valley floor with sweeping vistas stretching from St. Helena toward Calistoga, this exquisitely renovated hillside sanctuary offers the perfect blend of luxury, comfort, and conveniencejust moments from the charm of Main Street, St. Helena. Designed for both full-time living and weekend escapes, this home features two elegant en suite bedrooms, and an additional bedroom with a private bath, plus a stylish office space. Wide-plank French oak floors and soaring vaulted ceilings create an open, airy ambiance, while a cozy fireplace in the living room invites you to unwind in style. Throughout the home, custom-curated Designers Guild window treatments and wallpaper infuse a sophisticated, modern flair. Step outside to the expansive west-facing decks, which provide the perfect setting for sunset gatherings, al fresco dining, or simply soaking in the stunning scenery. A detached yoga studio/office offers a tranquil escape for work, creativity, or mindful relaxation. A spacious storage building and a two-car carport at street level complete the home.
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Saint Helena is located in California. Saint Helena 94574 is less family-centric than the surrounding county with 28.53% of the households containing married families with children. The county average for households married with children is 32.08%.
