luxury real estate for sale St. Helena, United States

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.

A Rare Convergence of Location, Zoning, and Opportunity Properties combining premier location, proven surrounding values, development flexibility, and true scarcity rarely reach the market - this is one of those moments. Set within established, highly sought-after residential neighborhoods, this offering carries intrinsic value that extends well beyond its current improvements. Recent comparable sales in the immediate area reflect strong, sustained demand - underscoring a valuation opportunity rooted in location alone. What sets this property apart is its rarity: a parcel of this size, in this setting, carrying Medium Density zoning, is a genuinely uncommon find. That scarcity - paired with the exclusivity of the surrounding market - is not easily replicated. Whether the goal is long-term hold, ground-up development, or income generation, this property delivers the flexibility and fundamentals to support it. In a market defined by limited inventory and rising demand, opportunities of this caliber don't wait.

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.

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.

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.

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!

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.

Tucked away in a serene west-side enclave just moments from St. Helena's vibrant Main Street, this thoughtfully refreshed single-level residence offers everyday ease and plenty of charm. The 3-bedroom, 2-bathroom home spans 1,663 square feet of light-filled interiors, anchored by a spacious open-concept kitchen that flows effortlessly into the living and dining spaces, designed with both connection and comfort in mind. Outdoors, mature landscaping frames inviting spaces to gather, dine, and unwind offering a seamless extension of Napa Valley living in one of St. Helena's most sought-after neighborhoods.

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**

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

Located on the valley floor and set among vineyards just north of St. Helena, 1181 York Lane offers a private, four-structure compound (main house, studio, cottage, and office/gym) with a flexible layout in a relaxed setting. The two-story main residence is thoughtfully arranged with two bedrooms on the lower level, while the upper floor is dedicated to daily living, an open kitchen, dining, and living room, along with the primary suite plus powder room. The kitchen features marble countertops, Sub-Zero refrigerator, and Viking gas range with hood. Interiors are oriented toward the property's landscaped grounds, creating a calm, private atmosphere. Detached guest and studio spaces capture vineyard and hillside views, providing separation for visitors, extended living, or creative use. A converted garage, currently used as an office, offers additional flexibility as a workspace, studio, or gym. Outdoor areas include deck spaces, mature landscaping, and a pool set naturally within the grounds. The property offers convenient access to St. Helena while maintaining a more private, country setting.

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.

Scenic Lot in Deer Park - Minutes from Downtown St. Helena Take in stunning views from this prime lot in Deer Park, ideally located just minutes from downtown St. Helena and approximately one mile from St. Helena Hospital. Canon Park Drive is conveniently accessible via both Sanitarium Road and Deer Park Road. The previous home on the property was a beautifully remodeled 4-bedroom, 3-bath residence (renovated in 2019). Disclosures include building plans, water and easement agreements, and tree care documentationall available upon request. The building site has been cleared, including removal of some dead trees, and the lot was last professionally surveyed in 2016. https://509canonparkdr.com/

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.

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.