luxury real estate for sale Rutherford Road, United States

Moments from downtown St. Helena, along a quiet country lane, this private property is defined by a single-level main residence, detached guest house, and a landscape designed for gathering and connection. The main home is designed for everyday living, with light-filled interiors that connect naturally to the outdoors. A living room anchored by a gas fireplace and expansive windows flows into a thoughtfully equipped kitchen with Viking range, wine storage, dual dishwashers, and an island with prep sink and seating. The dining room, complete with a built-in bar, offers direct access to the outdoors, reinforcing the home's indoor-outdoor rhythm. Additional spaces include a media room, private office, and flexible-use areas. The primary suite opens to the rear patio and pool, with an adjoining space suited for an office, or gym. A second bedroom and multiple baths complete the main residence, while the detached guest house offers additional living spaces. Outdoors, mature redwoods and cedar frame the setting, with a broad lawn, bocce court, pool and spa, and multiple gathering areas. A well-equipped outdoor kitchen with fire feature and covered seating extends the living experience. This is a property designed for gathering, defined by privacy, and quietly positioned where Napa Valley begins to slow.

Located on the cooler western slope of Napa Valley, this stunning vineyard retreat offers the perfect blend of tranquility and luxury. A beloved venue for family weddings and exclusive events, it has attracted notable guests, including famous golfers Arnold Palmer and Billy Casper who were entertained there during Transamerica Golf Tournaments at Silverado in the 1980s and 1990s. Spanning 15.44 +/- acres across two legal parcels, the contemporary country compound is framed by breathtaking views of its 6.44 +/- acre terraced Cabernet Sauvignon and Sauvignon Blanc vineyard and to the Vaca Mountains beyond. The main residence features four bedroom suites, a spacious kitchen with sitting and casual dining areas, and a great room with cathedral ceiling and wood-burning fireplace. French doors throughout offer strong indoor-outdoor flow. The charming guest house, created from the property's original stone cottage, features an en-suite bedroom with a separate entrance, a game room with a striking stone wall interior, an attached bath, plus additional spaces providing options for versatile living. Other features include a 45-foot-long pool, spa, 5000 +/- sq ft deck, an expansive lawn, pond, tennis court, barn, mature landscaping, and a seasonal creek.

This is such a spectacular property in so many ways. Location extraordinaire, sitting in the heart of Oakville with expansive views of the neighboring vineyards and picturesque Far Niente and Harlan wineries beyond. The seasonal To Kalon stream boarders the western side of the property. There are actually 3 homes that make up this rare offering. The main structure, which is the original Oakville Schoolhouse built back in the late 1800's, consists of two homes with a common wall. There is a 2bed/2ba single story home on one side and a 2bed/2ba two story on the other side, where the second story loft could also be used as a third bedroom. In addition to the main structure there is a detached 1bed/1ba cottage. Each of the living spaces has an outdoor space to take advantage of views and wine country lifestyle. Also included is a detached 3 car garage/storage space. If you are looking for a special property unlike anything on the market, you need check this out.

Set at the end of a quiet cul-de-sac along Napa Valley's iconic Silverado Trail, this gated 4.25 acre estate offers a rare combination of privacy, natural beauty, and future potential. Nestled among mature oak trees and dramatic rock outcroppings, the property unfolds as a secluded private oasis, where winding pathways connect a collection of outdoor living spaces thoughtfully integrated into the landscape. The three-bedroom, two-and-a-half-bath residence reflects the craftsmanship and design sensibilities of its era, presenting as exceptionally well cared for while offering a compelling opportunity for modernization and personalization. A short walk from the main residence leads to a private pool, spa, and sun terrace tucked into the lower portion of the property. Above, an expansive lawn overlooks the pool and serves as the centerpiece for outdoor entertaining, connecting seamlessly to a built-in outdoor kitchen, pizza oven, and lounge area with sweeping views across the estate. On the opposite side of the property, a private tennis court provides an amenity rarely found within such a tranquil setting and newly installed well in 2025. Whether enjoyed in its current form or reimagined for the future, the property's true value lies in its remarkable setting with an extraordinary blend of mature trees, usable acreage, recreational amenities, and privacy just minutes from Napa Valley's renowned wineries, restaurants, and downtown conveniences. A rare opportunity to create a legacy Wine Country retreat in one of Napa Valley's most desirable locations.

Set on approximately 14 acres near Joseph Phelps Winery, 480 Taplin Road is a Cape Cod-inspired estate designed for entertaining and multi-generational living. The main residence, detached carriage and pool houses provide 7,900 sq ft of conditioned space surrounding a heritage black oak. Interiors showcase wide-plank floors, a sunken living room with fireplace, formal dining room, a chef's kitchen with marble counters, Thermador range and Sub-Zero appliances, and a primary suite with dual closets and spa bath. A residential elevator serves all levels, including a 4,700-bottle wine cellar, and an upstairs bonus room with an en suite guest room and two offices (one currently staged as a bedroom). The carriage house offers two en-suite bedrooms and a kitchenette; the pool pavilion features a full kitchen, changing room, outdoor shower, and half bath beside a heated infinity-edge pool and spa. Fruit trees, gardens, multiple terraces, bocce court, solar, two wells and extensive infrastructure complete the offering. This is a Napa Valley retreat that gracefully balances comfort, elegance and resort-style amenities, just eight minutes from downtown St. Helena.

A Napa Valley estate of extraordinary scale and beauty. Set across 100± acres just minutes from the Silverado Trail in St. Helena, this remarkable private compound unfolds above Lake Hennessey with sweeping water and vineyard views, exceptional privacy, and an extraordinary collection of residences and amenities. At the heart of the estate is a newly remodeled 8,500± sq. ft. residence, where refined architecture meets relaxed Wine Country living. Four bedrooms, four full and two half baths are complemented by two private offices, a sun-filled solarium dining room, wine cellar, chef’s kitchen, and expansive pantry. Venetian plaster walls, floor-to-ceiling Chinkapin oak pocket doors, custom ironwork, walnut hardwood and French limestone floors bring warmth and sophistication throughout. An infinity-edge pool seemingly disappears into the lake beyond, while two detached guest houses—approximately 1,000± and 1,200± sq. ft. — enjoy their own 60-foot lap pool. Beyond the residences, mature gardens and fountains frame a series of intimate and grand entertaining spaces. A full-size tennis court, bocce court, approximately one acre of coveted Pritchard Hill Cabernet vines, and spectacular Lake Hennessey views complete this one-of-a-kind Napa Valley retreat. Private, timeless and virtually impossible to replicate.

Welcome to Napa Valley's most serene and prestigious winery estate, where heritage, luxury, and unparalleled winemaking potential converge in the heart of St. Helena. This historic, fully operational winery spans 5.67 +/- acres along Silverado Trail, between Meadowood Resort and Auberge du Soleil, offering immediate revenue potential with extraordinary expansion opportunities, ideal for winemakers, entrepreneurs, or hospitality visionaries. The 5,500 +/- sq. ft. production facility features 6,200 +/- sq. ft. of crush pad space, 82,000 gallons of tank storage, and a 6,000 +/- sq. ft. warehouse with a permit to double in size. Permitted for 40,000 gallons annually, with a waste-water upgrade to reach 100,000 gallons, this turnkey, high-capacity facility is perfect for estate winemaking and custom crush clientele. Solar electric power ensures sustainability. The newly remodeled tasting room, within a charming guesthouse, is ideal for private tastings, luxury lodging, or events. A bocce court and expansive deck showcase panoramic views of vineyards, rolling canyons, and the tranquil Napa River, creating an unmatched, peaceful retreat. Highly coveted hospitality entitlements allow daily tastings for up to 48 guests, plus 69 exclusive marketing events per year, maximizing brand visibility and revenue streams. The 3,518 +/- sq. ft. Craftsman-style home with an additional studio is perfect for guest accommodations, short-term rentals, or VIP stays. A lawn and olive grove along with numerous gardens and fruit trees, enhance the estate's beauty and provide an idyllic setting for exclusive wine releases, private gatherings, and weddings. The estate includes ample parking for 35+ vehicles. With immediate income streams, high-production potential, and premier hospitality offerings, this custom crush facility and full-production winery is a rare Napa Valley residential and commercial opportunity.

14+/- acres in one of Yountville's most desirable locations, this offering presents a rare opportunity to create a legacy estate. With a proposed 7,500+/- sq ft main residence, an 800+/- sq ft guest house, and a conceptual 8,000+/- sq ft barn or winery site illustrating future possibilities, the property blends luxury living with long term value while offering an estimated $700,000 in savings as plans were submitted and are now in final review prior to Napa County's implementation of a new construction tax impacting larger residences. A future buyer could also change the plans, allowing them to tailor the home to their preferences while still capturing the associated cost savings. The planned residence features 5 bedrooms, 5 bathrooms +2 half bathrooms, an infinity edge pool, elevator, and sweeping valley vistas framed by neighboring Del Dotto vines, along with approximately one acre on the property suitable for a potential hobby vineyard. Accessed by a quiet country road and a private vineyard lane, the estate promises ultimate seclusion while remaining moments from downtown Yountville and the famed Del Dotto wine caves. Offered at $14,500,000 for the land + projected building costs, this is a chance to own a completed estate with potential for value far exceeding the cost to build, representing an exceptional investment in Napa Valley's most sought after area. Land is available for purchase on its own for $3,995,000. Also listed in MLS as #326004100.

14+/- acres in one of Yountville's most desirable locations, this offering presents a rare opportunity to create a legacy estate. With a proposed 7,500+/- sq ft main residence, an 800+/- sq ft guest house, and a conceptual 8,000+/- sq ft barn, illustrating future possibilities, the property blends luxury living with long term value while offering an estimated $700,000 in savings as plans were submitted and are now in final review prior to Napa County's implementation of a new construction tax impacting larger residences. A future buyer could also change the plans, allowing them to tailor the home to their preferences while still capturing the associated cost savings. The planned residence features 5 bedrooms, 5 bathrooms +2 half bathrooms, an infinity edge pool, elevator, and sweeping valley vistas framed by neighboring Del Dotto vines, along with approximately one acre on the property suitable for a potential hobby vineyard. Accessed by a quiet country road and a private vineyard lane, the estate promises ultimate seclusion while remaining moments from downtown Yountville and the famed Del Dotto wine caves. Offered at $14,500,000 for the land + projected building costs, this is a chance to own a completed estate with potential for value far exceeding the cost to build, representing an exceptional investment in Napa Valley's most sought after area. Land is available for purchase on its own for $3,790,000.

Welcome to 1357 Magnolia Avenue, a stunning 2015-built residence nestled among mature oaks on one of St. Helena's most desirable tree-lined streets. Quiet and peaceful, this property offers 3 bedrooms, 2.5 bathrooms, and 2,108 square feet of refined living space, delivering the ultimate Napa Valley lifestyle with unparalleled peace of mind. Step inside to soaring ceilings, abundant natural light, plantation shutters, and gleaming hardwood floors. The chef's kitchen features premium stainless steel appliances and granite countertops, seamlessly flowing into a spacious living area anchored by a cozy gas fireplace. Wine enthusiasts will appreciate the dedicated, temperature-controlled wine storage space. The generous primary suite serves as a private retreat, complete with custom closet organizers and a spa-like en-suite bath featuring double vanities and an elegant dual-head tile shower. Furthermore, the attached two-car garage is fully optimized with extensive extra overhead storage, ensuring ample space for vehicles and belongings. Priced at $1,495,000, 1357 Magnolia Avenue isn't just a home, it is a secure, high-reward gateway to the very best of wine country living.

Perched at the top of Whitehall Lane, this beautiful single-story Napa Valley residence captures the very best of wine country living. Set against a backdrop of sweeping vineyard and valley views, the five-bedroom home offers a rare combination of privacy, charm, and effortless indoor-outdoor living. Designed for comfort and ease, the single-level floor plan is ideal for both full-time living and relaxed weekend escapes. Generous living spaces are filled with natural light, while large windows frame the surrounding landscape and bring the beauty of Napa Valley indoors. The home's inviting character, thoughtful layout, and warm wine country atmosphere create a setting that feels both elegant and approachable. Outside, a hobby vineyard enhances the property's sense of place and offers the romance of owning a piece of Napa Valley's agricultural heritage. Whether enjoyed as a personal passion project, a scenic backdrop, or a defining feature of the estate, the vineyard adds authenticity and charm to the property. From sunrise over the valley to golden evenings overlooking the vines, every part of this home is designed to celebrate its remarkable setting. Located moments from St. Helena's renowned restaurants, wineries, and boutiques, the property offers a peaceful retreat with convenient access to the heart of wine country. Additionally, the barn has been converted into a two bedroom guest house

Once in a lifetime, an opportunity emerges that transcends the ordinary definition of real estate. Glendale Ranch, a property spanning over 2,000 acres just 3 miles from Main Street, St. Helena, is one of Napa Valley's last great private estates, a self-contained world of rolling oak woodlands, ancient Douglas fir forests, cascading waterways, and heritage vineyards that have produced legendary Napa wine for over a century. Glendale offers absolute seclusion and world-class accessibility. A sanctuary that has sheltered visionary stewards from the Younts to the Rutherfords. Astounding ecological diversity rivals any protected parkland in the region, making Glendale one of the most biodiverse private landholdings remaining in the Napa Valley. At the center of it all is the historic White House, built in the 1880s, perched atop a grassy knoll with soaring ceilings, wrap-around porches, and timeless grandeur. Three additional homes across 17 parcels make this an extraordinary opportunity for a private family compound. Water is among Glendale's most extraordinary assets. A 7-acre private lake, ponds, wells, and the year-round Conn Creek with secured water rights collectively form one of the most robust water systems in Napa. Infrastructure, from 1.5 miles of paved roads to 5.5 miles of improved dirt roads and an extensive network of utilities and water, offers countless possibilities bound only by imagination. You are invited to become the next steward of Napa Valley's largest and most irreplaceable estate.

Charming St. Helena Retreat with Timeless Woodwork & Dual Living Spaces. Nestled in the heart of St. Helena, this inviting Napa Valley home blends classic craftsmanship with comfortable living. Rich woodwork throughout creates a warm, sophisticated atmosphere that embodies wine country charm. The thoughtfully designed layout features two spacious living roomsideal for both relaxed everyday living and effortless entertaining. Natural light fills the home, highlighting the detailed finishes and enhancing its welcoming feel. Located just minutes from downtown St. Helena's renowned restaurants, boutiques, and wineries, the property offers the perfect balance of tranquility and convenience. Ideal as a full-time residence, weekend retreat, or Napa Valley getaway.**New roof in 2025 and home is completely earthquake retrofitted**

Perfectly situated just one block from downtown St. Helena, this immaculate 3-bedroom, 2-bathroom home is move-in ready and waiting for you to create your Napa Valley dream yard. Set on an expansive lot, the property offers ample space for a pool, ADU, bocce court, lush gardens, or all of the above. Inside, the home has been beautifully remodeled with a bright, open floor plan, a stylish kitchen, and seamless indoor-outdoor flow. The primary suite boasts a spacious walk-in closet with laundry, while the flexible office/third bedroom adapts to your needs. With unbeatable walkability to world-class dining, boutique shops, and top-rated schools, this rare offering combines turnkey comfort with limitless outdoor potential in the heart of Wine Country.

Sophisticated Fully Furnished Modern Farm Estate in the Heart of St. Helena Nestled in the world-renowned Napa Valley, this exceptional St. Helena estate reimagines wine country living. A masterclass in modern farmhouse design, the property seamlessly blends clean architectural lines and contemporary luxury with the warm charm of its agricultural heritage. Listing Description Every detail of this bespoke estate is crafted to elevate the everyday experience. The main residence features soaring vaulted ceilings. At the heart of the interior is an open-concept great room and a chef's kitchen, equipped with premium integrated appliances, custom cabinetry and an oversized waterfall quartz island. The spaces flow effortlessly to the exterior, where the expansive covered loggia, between the main home and guest retreat, blurs the lines between indoor sophistication and outdoor relaxation. The primary suite serves as a private oasis and features access to the exterior spa. Outside, the manicured grounds transform into a private resort. Features include an outdoor kitchen, a firepit lounge and relaxing water feature. Located just minutes from the historic boutiques, Michelin-starred dining, and premier wineries of downtown St. Helena, this legacy estate offers the rare combination of privacy and urban convenience.

Welcome to 900 Chiles Avenue, a beautifully refreshed home offering exceptional value in the heart of St. Helena. Move-in ready, it features new carpeting, fresh interior paint, new linoleum flooring, and a new dishwasher. Raised garden beds provide the perfect space to cultivate flowers, herbs, or vegetables, while the low-maintenance yard allows more time to enjoy Wine Country living. Ideally located near shopping, dining, parks, and local amenities, this property is an outstanding opportunity for a primary residence, weekend retreat, or investment. Possibly the best value in St. Helena. Seller Financing Available to qualified Buyer.

Discover this iconic Napa Valley compound blending historic architecture with sophisticated modern design. Set on a private 3.11 +/- acre parcel near the world famous Meadowood Resort and The Napa Valley Reserve, this Estate is surrounded by idyllic vistas offering an incomparable lifestyle just minutes from downtown St. Helena. The Estate encompasses 5,775 +/- sq ft of living space across 4 structures. The Queen Anne-style main residence (c. 1895) features luminous living spaces with handsome wood-paneled detail and a penthouse primary suite with sitting room, spa bath and terrace, while 2 farmhouse style guest cottages provide luxurious accommodations. Renowned interior designer Jay Jeffers reimagined every detail with timeless sophistication and modern flair, creating interiors that flow seamlessly to outdoor living. The historic red barn offers a lounge, recreation loft, and more parking. A 5-car stone-clad garage with environmental control was designed for discerning car collectors. Expansive flagstone terraces, heated pool/spa, bocce court, fruit orchard, and curated gardens complete this idyllic setting. With dual gated entries, a spacious motor court, and advanced security, Meadowood Estate is a rare opportunity to own one of Napa Valley's most exceptional properties.

Welcome to 2501 Pinot Way in the heart of St. Helena, CA. This extensively renovated single-story contemporary home offers the ultimate in modern design and luxurious amenities, making it the epitome of Wine Country living. With 5 bedrooms and 3.5 baths, this 3,541 sq ft estate sits on a generous 24,293 sq ft lot offering the ultimate in privacy and tranquility. The brand new kitchen boasts upgraded appliances, perfect for the culinary enthusiast. Enjoy the expansive landscaped backyard on more than half an acre, complete with an oversized pool, spa, and a Tahitian style 3-roof cabana featuring a shaded seating area and fire pit. The primary bedroom suite offers a ensuite bathroom with a jetted tub and walk-in closet, while the formal entry leads to light-filled living spaces throughout. The U-shaped floor plan layout allows for direct access to the outdoor garden courtyard, creating a seamless indoor-outdoor flow providing ample room for entertainment and relaxation. The two gas fireplaces add warmth and ambiance to the modern interior. Experience the best of St. Helena living in this meticulously remodeled home. Conveniently located on a quiet cul-de-sac, this serene retreat is just a short walk to downtown St. Helena's charming shops and upscale restaurants and wine bars.

Rare opportunity to live among the vines in the heart of St. Helena. Nestled at the end of a quiet cul-de-sac, this single-level, three-bedroom, two-bath home offers privacy and sweeping views of the Spottswoode Vineyard and a tranquil creek. Expansive windows fill bright, open living spaces designed for relaxation and easy entertaining. The spacious backyard is perfect for gatherings, overlooking the vineyard and creek beyond. Just a short walk or bike ride to Main Street shops and restaurants, this special property blends serenity and convenience. New roof installed in 2024.

A 1910 Edwardian on the west side of St. Helena, two blocks from Main Street, remodeled with period appropriate restraint. Four bedrooms, a wrap-around porch, private pool and spa area and a separate guest apartment with private entrance. The income entitlement is what makes it singular. A buyer acquires a residence and a working hospitality asset on the same deed. Few in-town properties offer the option to live, host, or earn, and fewer still let an owner choose between them year to year. The property introduces itself with a meticulously landscaped front yard, greeting the guest with the vibrancy and color of roses, the structure of manicured hedges and the aromas of several fruit trees. A formal staircase leads to the wraparound porch landing, into the main level, which has been thoughtfully renovated to integrate 1910 sophistication with contemporary comforts. Two ensuite bedrooms, an additional powder room, a chef kitchen and living room/dining room combo sit on this level. Through an internal staircase, the descent to the floor level brings access to the bottom bedroom suites, a large sliding door leading to the private pool area and a second kitchen. It is uncommon for a single address to accommodate so many ways of living. A family home or a quiet investment held for the season, all within two blocks of Main Street, and all at the owner's discretion.

Summer splash pad! Let's party! In the heart of St. Helena, Newly built modern retreat pairs fine design with effortless living. 3,800 SF main residence and ADU! Beautifully landscaped in-town lot. With 5 bedrooms and 5 baths, the home showcases white oak cabinetry and floors, 11-foot ceilings, and bespoke finishes throughout.Sweeping sliding glass wall opens the great room to a beautiful outdoor setting with a 38' x 20' pool and spa an outdoor kitchen and fire pit. The primary suite offers a private terrace with Mayacama Mountain views, a spa-inspired bath, and huge walk-in closet. Complete with a flexible office or gym and a fully appointed ADU, this is a rare St. Helena offering for those who want modern style, indoor-outdoor ease, and only blocks from fine dining and fab shopping!

Set amidst the rolling vineyards just outside the charming town of Yountville, this exceptional Mediterranean-inspired estate blends timeless architectural design with refined modern luxury. Built in 2018, the two-story residence offers 4 bedrooms and 4.5 bathrooms, thoughtfully appointed with high-end finishes and artisan details throughout. Rich wood floors, soaring ceilings, and expansive windows frame panoramic vineyard views, while multiple balconies invite seamless indoor-outdoor living. The main level features a luxurious primary suite with spa-like bath and private terrace, offering the ease of single-level living within a grander floorplan. At the heart of the home, a gourmet kitchen is outfitted with professional-grade appliances, custom cabinetry, and an oversized island ideal for both entertaining and everyday living. A dedicated wine cellar and intimate tasting area provide an enviable setting for collectors and oenophiles alike. Beyond the main residence, a beautifully finished 1-bedroom, 1-bath guest cottage with a full kitchen offers elegant accommodations for visitors. The property also boasts a resort-style pool, landscaped grounds, and a small block of Cabernet vines capturing the essence of Napa Valley living at its most luxurious. Just minutes from world-renowned dining and wineries, this extraordinary estate is a rare opportunity to own a private retreat in one of wine countrys most coveted locations.

Inspired by the architecture of the Edwardian era, this historic beauty was built in 1905 by the MacKinder family and later became the home of Starr Baldwin, past publisher of the St. Helena Star. It holds a prominent place among the grand residences on the notable first block of Spring Mountain Road, just moments from downtown on St. Helena's coveted west side. The classic white shiplap exterior and generous wrap-around front porch sit gracefully beyond an expansive front yard and welcoming landscape. From the street, the home conveys the quiet presence and proportion characteristic of its era. Inside, the 3,506 sq. ft. residence offers the spacious public rooms, refined architectural detail, and tall, well-placed windows one expects of a distinguished early 20th-century home. High ceilings, original millwork, and oak and fir floors reflect the craftsmanship of the period. The four-bedroom layout includes a formal entry, an elegant double parlor with wood-burning fireplace, and a formal dining room with original built-in buffet. A light-filled breakfast room/den and a bright kitchen with white cabinetry overlook the gardens and pool. The four upstairs bedrooms retain their historic detailing and generous proportions Below, an old-fashioned basement includes a temperature-controlled wine cellar, adding both character and function. A detached 685 sq. ft. ADU, converted from a former barn, provides two additional bedrooms, a full bath, and flexible lounge spacewell suited for guests, extended family, or a private office. Outdoors, a broad and sunny back porch opens to a heated pool with integral spa and safety cover, surrounded by established landscaping. Boxwood hedges, crepe myrtle trees, and mature plantings frame the property, creating privacy and a garden setting that complements the home's historic architecture. Substantial in scale yet comfortable in feel, this offering is a rare opportunity to own a significant piece of St. Helena's architectural heritage in one of Napa Valley's most desirable residential neighborhoods.

Incredibly rare residential building/development opportunity awaits with this large lot located on famed Silverado Trail at Yountville Crossroad. This 4.93+/- acre parcel invites your creative ideas to turn it into your dream property. Panoramic vineyard views of the Yountville AVA provide an epic setting for endless possibilities and golden sunsets. A visit to this property is a must to get the full scope of the options available and to fuel your creativity. Plans/renderings/elevations are also included to help you realize the potential. A short jaunt down Yountville Crossroad puts you right in the middle of world famous downtown Yountville and all of the dining, wine tasting and shopping it is known for.