luxury houses for sale St. Helena, United States

Nine Rare Acres, Sweeping Down-Valley Views, and Room to Grow in St. Helena. Nine private acres above St. Helena, with sweeping views down Napa Valley and the rare opportunity to create a family compound or a generational retreat. The view changes with the seasons: new green in spring, full canopies in summer, harvest gold in fall, and morning fog and yellow mustard in winter. The four-bedroom main residence, guest house, and swimming pool are suited as much to a quiet weekend as to a summer of visiting family. The house frames the valley rather than competing with it. What makes this property particularly unusual is the land itself. Spanning three legal parcels, it offers the potential, subject to county approval, for a lot line adjustment that could create one or two additional building sites. In St. Helena, where acreage of this scale rarely comes on the market, it's an opportunity to create something that can be enjoyed for generations. Listing includes AI-generated images illustrating the property's potential.

Nestled on 10.3± acres in a private gated oasis at the base of Glass Mountain, this modern Mediterranean villa embodies the quintessential Napa Valley lifestyle. Surrounded by sweeping vineyards and renowned for the region's rich volcanic soil and obsidian rock with neighbors such as Hundred Acre, the property is located just minutes from downtown St. Helena. Designed for seamless indoor-outdoor living and a true farm-to-table experience, the property features a total of 4,660± square feet with four bedrooms, a loft, and three bathrooms across the main residence and guest house. A series of French doors open to intimate courtyards and expansive outdoor entertaining areas, including an 80-foot solar-heated pool with pergola, outdoor fireplace lounge, al fresco dining courtyard with built-in barbecue and tranquil water feature, and majestically landscaped olive and fruit tree orchards including white and mission fig, peach, pear, apple, nectarine, lemon and lime. The main residence spans 3,552± square feet and offers two bedrooms plus a loft and two bathrooms. Expansive great room style living areas, including family room with fireplace and gourmet kitchen, open to a wraparound veranda with views of the stunning grounds. Spacious and luxurious main ensuite with fireplace and seating area open to private courtyard with outdoor fireplace. The detached guest house provides 1,108± square feet two bedrooms, one bathroom and full kitchen ideal for guests, extended family, or a private retreat. At the heart of the property is a 4±-acre Cabernet Sauvignon vineyard, with additional plantable acreage available. Additional amenities include a high-producing 98± GPM well, temperature-controlled wine cellar with capacity for approximately 3,000 bottles, and a five-car garage with workshop. Detached exercise/art studio and equestrian facilities complete the estate with a four-stall barn, tack room, riding arena, paddocks, stable, and chicken coop offering the perfect balance of luxury living, winemaking potential, and country lifestyle in the heart of Napa Valley.

Experience relaxed Wine Country living in this beautifully updated single-level residence, ideally situated beside the vineyards in desirable St. Helena. Offering three bedrooms and approximately 2,088 square feet, the thoughtfully designed interior features hardwood flooring, sophisticated Neolith countertops throughout, an inviting living room with fireplace, and a well-appointed kitchen with stainless steel appliances, double ovens, and a built-in refrigerator. Generous windows and doors create a seamless connection to the professionally designed grounds, where expansive decks, a spacious patio, outdoor dining areas, and a firepit provide an exceptional setting for entertaining or quiet relaxation. Vineyard and mountain views enhance the sense of place, while temperature-controlled wine storage, an interior laundry room, central heating and air conditioning, and an attached two-car garage add everyday convenience. Set on approximately one-quarter acre with mature landscaping and no HOA, this charming property captures the effortless indoor-outdoor lifestyle for which Napa Valley is celebrated.

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.

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.

Morning swims, afternoons exploring wine country, and evenings gathered around the fire1547 Allyn brings the pleasures of Napa Valley home. Set on beautifully landscaped grounds in the heart of St. Helena, this newly constructed residence pairs refined contemporary design with the ease of in-town living, creating a private retreat moments from the town's celebrated restaurants, boutiques, and tasting rooms. Encompassing approximately 3,800 square feet across the main residence and a fully appointed ADU, the five-bedroom, five-bath property balances generous gathering spaces with intimate places to unwind. Eleven-foot ceilings lend an airy elegance, while white oak floors, custom cabinetry, and thoughtfully selected finishes bring warmth and continuity throughout. At the heart of the home, a sliding glass wall opens the great room to an outdoor setting designed for long, leisurely days and memorable evenings. A 38-by-20-foot pool with an integrated spa and Baja shelf anchors the private grounds. An outdoor kitchen with a Sedona grill invites alfresco dining, while a built-in fire pit offers a welcoming place to linger over a glass of wine as the evening cools. The primary suite provides a serene escape, with a private terrace framing views of the Mayacamas Mountains, a spa-inspired bath, and a generous walk-in closet. A flexible office or gym accommodates the rhythms of daily life, while the ADU offers a beautifully appointed setting for guests. A distinctive new-construction offering in one of Napa Valley's most desirable towns, 1547 Allyn captures a coveted balance: the privacy of a wine country retreat and the pleasure of having St. Helena close at hand.

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.

Behind the gates of Meadowood Resort, one of Napa Valley's most storied settings, lies a private world unto itself. Set on 40 hilltop acres above the resort grounds, 860 Meadowood Lane is a singular architectural estate defined by scale, privacy and sweeping views across the Napa Valley. Designed in the modern-industrial tradition and built in 2006, the 4,723-square-foot residence makes a statement from the moment you enter. Soaring 25-foot ceilings, exposed structural steel, an elevator and expansive views from nearly every room define the interior, while the setting unfolds across olive orchards, mature landscaping and exceptional outdoor living spaces. The home is designed for living at full scale, with three bedrooms, three full and two half baths, a butler's pantry and dramatic interior volumes that feel both sophisticated and comfortable. The architecture is distinctive, the materials substantial and the natural light exceptional. Outside, a resort-caliber pool and cabana, outdoor kitchen with fireplace and bocce court create a setting made for entertaining and enjoying Napa Valley's indoor-outdoor lifestyle. A remarkable great lawn provides an additional sense of openness and scale, while other areas of level land offer flexibility for future detached structures such as a guest house, barn or garage, subject to applicable approvals. Above all, this is a land and privacy story. Forty acres, more than ten times the size of many properties along Meadowood Lane, with commanding views, usable land and a setting just minutes from downtown St. Helena and The Napa Valley Reserve. A rare combination of acreage, privacy, infrastructure and architectural distinction in one of St. Helena's most coveted locations.

Offered for the first time since its completion in 2010, Failla Winery Estate presents a rare opportunity to acquire a fully operational, fully entitled winery and hospitality destination in the St. Helena AVA, one of Napa Valley's most desirable locations. The offering includes the real estate only; the Failla winery brand and business are not included. Situated on nearly 17 acres along Silverado Trail, the estate offers exceptional visibility, accessibility, and branding potential. A vineyard-lined drive leads to a historic farmhouse tasting room and an extraordinary underground cave winery and tasting room, creating an unforgettable visitor experience near two luxury resorts. Permitted for 10,500 cases annually under its 25,000-gallon permit, the property includes approximately 20,641 square feet across six structures. The centerpiece is a 13,276-square-foot underground cave featuring production facilities, barrel and library storage, private tasting rooms, and hospitality spaces. Additional improvements include a 4,020-square-foot crush pad, barrel storage barn, pump house, and a residence currently serving as a second tasting venue. Expansion plans could allow the cave to grow to approximately 27,225 square feet while increasing permitted production capacity to 33,000 cases annually. Located in the prestigious St. Helena AVA, the estate features a prolific well producing approximately 200 gallons per minute, 3.5 acres of head-trained, dry-farmed Zinfandel, and the potential for approximately three additional vineyard acres, subject to approvals. The underground cave is one of the property's greatest assets. Replicating a fully entitled cave winery and tasting room of this scale today would require years of permitting, complex engineering, and substantial capital investment. A buyer acquires a turnkey production and hospitality facility while avoiding the time, cost, and entitlement risks of new construction. Beyond its replacement-cost advantage, the cave provides naturally stable temperatures ideal for barrel aging, wine storage and production, and reducing energy and climate-control costs while helping protect valuable inventory. The unique cave wine tasting setting enhances premium hospitality and creates a distinctive destination that is increasingly difficult to replicate in Napa Valley. Purpose-built winery estates of this caliber rarely become available, offering an exceptional combination of location, infrastructure, operational efficiency, and value.

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.

Tucked away in a serene St. Helena setting, this inviting residence blends timeless charm with comfortable elegance. A welcoming wraparound porch sets the tone for relaxed wine country living, while soaring ceilings create a dramatic sense of space upon entering the great room. Anchored by a striking fireplace, the expansive living area serves as the heart of the home, ideal for both everyday living and entertaining. The thoughtfully designed kitchen features a generous center island, granite countertops, and updated cabinetry, offering both style and functionality for the culinary enthusiast. A short hallway leads to two well-appointed bedrooms, including an impressive primary suite with a spacious sitting area, walk-in closet, and a tranquil retreat-like atmosphere. Just off the dining area, a versatile room provides the perfect space for a home office, library, or creative studio. Completing the property is an attached two-car garage and additional driveway parking for guests. Conveniently located just minutes from downtown St. Helena, enjoy easy access to renowned restaurants, boutique shopping, wineries, and the exceptional lifestyle that defines Napa Valley living.

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.

Durham Ranch is Ken Fulk's treasured Napa Valley retreat, shared with family and close friends for decades. Set on 76 private acres in the renowned town of St. Helena, the property offers a rare balance of seclusion and access, where open land, ancient oaks, and seasonal streams create a profound sense of escape, yet proximate to restaurants, wineries, and cultural life of Napa Valley. Originally a modest cattle ranch dating to the 1940's, the property was thoughtfully restored and reimagined by celebrated designer Ken Fulk as a place to gather, celebrate, and disconnect. The vision honors the spirit of the classic California ranch while introducing a modern design sensibility. Durham Ranch embodies effortless living, inspired design, and strong provenance in a bucolic setting with the potential to add more dwellings subject to Napa County approval. At the heart of the compound is the restored ranch cottage, 1,200 Sq Ft, with two bedrooms and one-and-a-half baths. Bluestone floors, board-and-batten walls, and open-rafter ceilings create a timeless ranch aesthetic, while reclaimed materials, including historic fence boards used for cabinetry, salvaged tractor springs converted to barstools, and 1920s Parisian lighting, connect the interiors to a deeply rooted history. A screened porch overlooks the pool and surrounding landscape. Nearby, the 3,200 Sq Ft steel barn serves as the ranch's social centerpiece. With soaring 33-foot ceilings, the space was designed for private gatherings and large-scale entertaining, accommodating up to 200 personal guests comfortably. Plans by George Bevan inspire future conversion to living space, offering flexibility for the next steward of the property. Guest experiences extend across the ranch. Two safari-style tent cabins are perched on a wooded hilltop overlooking the valley, while the Cowboy Shack, originally conceived as a traveling art installation, serves as a playful hideaway or entertainment bar. Outdoor living unfolds across thoughtfully designed spaces connected by Ipe boardwalks. A 45x16 ft heated pool with full-length baja shelves anchors the entertaining area, complemented by bocce, terraces, and lawns shaded by magnificent oaks. The landscape includes seasonal streams, a natural spring, and miles of scenic terrain. Offering privacy while remaining within minutes of downtown St. Helena, Durham Ranch represents a rare opportunity to steward a deeply personal and authentic Napa Valley retreat.

Napa Valley Water Views. Unparalleled Privacy. An Extraordinary Estate. Perched above the shimmering waters of Lake Hennessey, this extraordinary 100 acre estate offers a rare combination of breathtaking natural beauty, exceptional privacy, and refined Napa Valley living. Just minutes from the Silverado Trail in St. Helena, the property occupies a spectacular setting where panoramic lake views, rolling vineyards, and expansive open landscapes create an unparalleled sense of tranquility and seclusion. At the heart of the estate, an exquisitely remodeled 8,500 sq. ft. main residence embodies understated luxury and timeless sophistication. Thoughtfully designed for both intimate living and grand entertaining, the home features four bedrooms, four full and two half baths, two private offices, a light-filled solarium dining room, a chef's kitchen with an expansive pantry, and a wine cellar. Rich architectural details, including Venetian plaster walls, floor-to-ceiling Chinkapin oak pocket doors, custom ironwork, walnut hardwood, and French limestone flooring, reflect an exceptional level of craftsmanship throughout. Designed to embrace its remarkable surroundings, the estate offers a seamless connection between indoor and outdoor living. An infinity-edge pool appears to merge with the waters of Lake Hennessey, creating a breathtaking backdrop for relaxation and entertaining. Two beautifully appointed detached guest residences, approximately 1,000 and 1,200 sq. ft., provide luxurious accommodations for family and guests, complemented by a separate 60-foot lap pool. Beyond the residences, manicured gardens, elegant fountains, and thoughtfully designed outdoor gathering spaces create a private sanctuary. A full-size tennis court, bocce court, and approximately one acre of prized Pritchard Hill Cabernet Sauvignon vines further enrich the quintessential Napa Valley lifestyle. A world apart, yet moments from the heart of Napa Valley, this exceptional estate offers a level of privacy, scale, and natural beauty that is increasingly difficult to find. A rare opportunity to experience Wine Country living at its most extraordinary.

A modern Wine Country retreat, offering refined architecture, curated outdoor living, and western vineyard views that define the St. Helena lifestyle. Set on a quiet lane above the valley floor, this newly rebuilt residence blends clean lines, exquisite finishes and copious amounts of glass to frame the landscape at every turn. The home's 2,100sq. ft. layout is anchored by a vaulted great room with exposed beams, designer lighting, a sculptural kitchen and charming butler's pantry. Custom cabinetry, gorgeous quartzite slab counters and premium appliances complement the space. Three ensuite bedrooms provide comfort and privacy, while a separate powder room serves guests. The outdoor environment is resort‑caliber: a newly constructed pool and spa, expansive decks, patios, and tiered landscaping that steps gracefully toward the view. Morning light washes across the valley; evenings settle into a soft western glow over vineyards and wooded hillsides. Complementing the main residence is a new 500 sq. ft. pool/guest house a flexible space for visitors, office, or studio use it expands livability and enhances the property's versatility. 104 Camino Vista offers the rare opportunity to step directly into a modern, turnkey St. Helena home. Thoughtfully designed with clarity, simplicity, and style.

Set against the spectacular backdrop of Napa Valley's western hills, this 15.44 +/- acre vineyard estate offers something increasingly rare: extraordinary views, abundant space, two legal parcels and the freedom to imagine an even more expansive wine country compound. The setting is breathtaking. A 6.44 +/- acre terraced Cabernet Sauvignon and Sauvignon Blanc vineyard sweeps away from the residence, opening to panoramic views across the valley and to the Vaca Mountains beyond. Located on the cooler western slope, the property feels wonderfully removed from the world, yet downtown St. Helena is just eight minutes away. Two legal parcels create exceptional possibilities for the future. With the ability to adjust the lot line, the second parcel offers the potential for another main residence, guest house and ADU, subject to applicable approvals - an extraordinary opportunity to create a multi-generational estate with separate residences for family and friends. Already, the property lives as a relaxed and welcoming compound. The 3,856 +/- sq ft main residence includes four bedroom suites and opens extensively to the landscape through tall French doors. A soaring great room with cathedral ceiling and wood-burning fireplace provides a natural gathering place, while the remarkably spacious kitchen was designed for many hands to cook, visit and linger together. Nearby, the original stone cottage has evolved into a charming guest house with an en-suite bedroom, game room and additional flexible spaces. Beyond the residences, the estate becomes a private playground. Hike the acreage, wander through the vineyard and beneath magnificent oaks, keep horses, play tennis, swim in the 45-foot pool, explore the seasonal creek or head up the gentle hillside to the stream-fed pond. An expansive wraparound deck and broad lawn overlook the vineyard, creating an extraordinary setting for outdoor dining, celebrations and long afternoons with family and friends. A spa, tennis court with viewing patio and approximately 1,000 sq ft barn add to the possibilities. Old stone walls, towering cypress, fruit trees and mature landscaping give the property a sense of permanence and character that cannot be newly created. The Cabernet Sauvignon vineyard has contributed to wine awarded 97 points by Robert Parker. Part vineyard estate, part family compound and part private playground, this is a place to gather, explore and create an entirely personal Napa Valley legacy.

Ultimate St. Helena jewel estate majestically set high on a hilltop, near the Meadowood resort; this French Provencal-style estate on 13+ acres offers panoramic views of St. Helena and is beautifully executed with sweeping slate roofs, curved stone walls, and bow windows throughout. Enter through a leaded-glass double door into a grand foyer that opens to formal living spaces defined by intricate bow windows and Rumford fireplaces. Adjacent to it, the expansive family room is bathed in natural light, with a circle of windows and a fireplace, and overlooks serene estate grounds. The grand formal dining room flows effortlessly into a spacious chef's kitchen featuring a built-in indoor grill, custom cabinets, marble countertops, Wolf appliances, a walk-in pantry, and a large eat-in area for casual family dining. The private primary suite is a sanctuary of luxury, featuring high ceilings, a fireplace, two elegant walk-in closets, and a spa-inspired bath with radiant-heated floors, a tumbled-marble shower, a soaking tub, and a dual vanity. The library, recreation room, and additional bedrooms are generously sized and complemented by beautifully appointed baths, a separate guest house, and an outdoor kitchen. The basement is the ultimate underground man-cave, a modern subterranean luxury space, a cave-like wine cellar, and an art/treasure/collector's sanctuary with a heavy vaulted safe, plus an extensive English-style pub or high-end lounge, finished with rustic copper and tin-stamped ceilings, dark wood floors, and moody ambient lighting. Outdoor living is equally spectacular, featuring expansive patios, beautiful waterfalls cascading to the pool and spa, meticulously maintained grounds framed by the estate's timeless slate roof and copper gutters, a variety of fruit and olive trees, and extensive walking trails, all of which complete this extraordinary property.

Architect-designed Spring Mountain estate set down a private lane adjacent to Keenan Vineyard, with panoramic valley and vineyard views from nearly every principal room. Fully renovated from 2003 to 2005, the home combines timeless architecture with exceptional craftsmanship, including custom walnut paneling and hand-finished woodwork throughout. The chef's kitchen features Wolf, Sub-Zero, and Thermador appliances, two dishwashers, generous workspace, a casual dining area, and an adjoining family/TV room for everyday living. The expansive primary suite takes full advantage of the setting with sweeping views, outdoor access, a fireplace, office area, and secret passage to the richly paneled library. A new in-ground pool with hot tub and fire pit creates a private outdoor retreat surrounded by the natural beauty of Spring Mountain. Elsewhere on the property are a paved, full-size tennis court and approximately 1 acre of planted vineyard with room to expand. Additional features include a wine cellar, Savant smart home system, multiple wells, and Culligan water treatment. A rare combination of privacy, architecture, vineyard surroundings, and expansive Napa Valley views, all roughly 10 minutes from downtown St. Helena.

The York-Alexander house, built in 1877 by Silas York of the early pioneer York family, offers a glimpse into Napa Valley's glorious past. Sited on almost 11 acres amidst impressive stands of grand oaks, expansive lawns, and exquisite gardens, this magnificent historic residence is a unique example of the Italianate architecture of the time. The 5BR/3.5BA home features a double parlor with wood burning fireplace, a romantic formal dining room, an airy primary suite with balcony, and an inviting sunroom with walls of windows providing soft morning light and views of the property's verdant grounds. The property enjoys a wealth of venues for large scale entertaining and quiet relaxation: a spacious dining terrace, a heated salt water pool and spa, tennis court, an immense vegetable garden, and a pleasant tree-covered allee with views of the property's 5.2 +/- acre Sauvignon Blanc vineyard. The offering includes two legal parcels and deeded access both from Lodi Lane and Hwy 29.

On coveted Fir Hill Drive - a quiet west-side country lane with rare ownership turnover - this thoughtfully reimagined home offers a combination of privacy, scale, and valley floor setting seldom found so close to town. Surrounded by vineyards, neighboring estates, and mature trees across nearly two landscaped acres, the property captures the serenity of country living while remaining moments from the dining, wine, and culture that define Napa Valley. The interiors are precise and considered, featuring herringbone and wide plank oak floors, custom millwork and steel detailing, Fleetwood doors, designer lighting, and curated finishes throughout. The chef's kitchen opens naturally into formal and informal living spaces designed to move effortlessly between intimate daily living and large-scale entertaining. Outside, a 25-yard lap pool anchors professionally designed grounds that include expansive lawns, multiple terraces, and layered indoor-outdoor living spaces intentionally created for gathering, retreat, and year-round enjoyment. This is a rare opportunity to own a true St. Helena estate in one of the town'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.

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.

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.

Introducing a St. Helena custom-built estate, the extraordinary expression of refined Wine Country living. Set on approximately 3.2 acres with sweeping views of acclaimed Newton Vineyard, this newly constructed residence blends contemporary sophistication with natural beauty, showcasing exceptional architectural details and curated finishes throughout. A private drive winds through the scenic western hills, where handcrafted rock walls frame the property's own hobby cabernet vineyard and olive grove, creating a tranquil and timeless sense of arrival. Inside, light-filled living spaces feature soaring ceilings, warm natural textures, and surround sound throughout, while the grand great room, with its cathedral wood coffered ceiling, opens to stunning vineyard vistas, creating an inviting setting for both intimate gatherings and large-scale entertaining. The home offers four en-suite bedrooms, a dedicated office, and a versatile media or auxiliary living space. One can't go far without wandering into the luxurious primary suite with 10-foot glass doors, layered vineyard views, and a spa-inspired bath with elevated designer finishes. At the center of the home, the gourmet kitchen is both functional and striking, featuring LG Signature appliances, an 800-bottle wine room, a range with a built-in air sous vide, custom cabinetry, an oversized island, and a statement copper-painted hood. Additional highlights include custom built-ins throughout, a metal roof, solar with backup battery, and huge flex space above the spacious four-car garage. Outdoors, the lifestyle continues with a pool, limestone pool deck, custom pizza oven, and BBQ, perfect for entertaining against a stunning vineyard backdrop. Completing the experience, Newton Vineyards extends a rare privilege for those who desire it, offering the owner the ability to roam and enjoy nearly 500 acres of its surrounding estate land, enhancing the sense of privacy and connection to the landscape. Located within the gated enclave of Madrona Ranch and just minutes from renown downtown St. Helena, this is a rare opportunity to be the first to call 2509 home.