Woodside CA Real Estate & Homes for Sale

Nestled on one of the most coveted streets in Atherton, this custom-built estate epitomizes refined living with its impeccable design & superior craftsmanship. Upon entry through the contemporary steel & glass doors, guests are greeted by grand living & dining rooms. The chef's kitchen is a culinary masterpiece, featuring top appliances, center island & walk-in pantry. The kitchen seamlessly flows into the inviting great room, where the soaring ceiling, cozy fireplace & stacking doors lead to the outdoor terrace, blurring the lines between indoor & outdoor living. The backyard oasis, complete with pool, spa, outdoor loggia with fireplace, firepit & outdoor kitchen, is surrounded by mature perimeter privacy hedging. The upper level offers a luxurious primary suite with vaulted ceiling, fireplace, private office & spa-inspired bath. Three additional en suite bedrooms & a kids' lounge complete the upper level. The lower level features a 5th bedroom suite with private entrance, rec room & glass-enclosed wine cellar. Additional highlights include an executive office, 3-car garage & gated entry. Experience unparalleled luxury living in this exceptional Atherton estate, where every detail has been thoughtfully curated for the discerning buyer seeking the epitome of California living.

Stunning Hacienda Compound with Separate Guest House, Pool House, and Greenhouse Amidst Beautifully Landscaped Courtyards. Formal Entry Elegant Living Room. Separate Office with Built-ins. Formal Dining Room. Chef's Kitchen with Center Island, Wolf Appliances, and Breakfast Room Opens to Spacious Family Room with Fireplace and Built-ins. Primary Suite Retreat Features Double Sinks, Stall Shower, Stone Soaking Tub, and Two Walk-in Closets. 4 Spacious Bedrooms. 4.5 Bathrooms. Upper Level Features Spacious Loft and Full Bathroom. Lower Level Features Expansive Wine Cellar. Interior Features Include High Ceilings, Multi-Zone Heating and Airconditioning, Laundry Room, and Vaulted Ceilings. Separate Guest House Includes Kitchen, Fireplace, and Full Bathroom. Separate Pool House Includes Full Bathroom. Lovely Landscaped 2.86 +/- Acre Lot with Sparkling Pool, Enclosed Courtyards, Mature Cactus Gardens and Landscaping, and Hand Laid Stonework. Award Winning Portola Valley Schools.

At the end of a cul-de-sac in the premier Circus Club area, this property was built in 2012 w/inspiration from the villas in Urbino, Italy. The entire property is masterfully finished w/an array of imported materials from the antique French roof tiles to the lavish exterior stone. Inside & out, an endless succession of design embellishments ...hand-scraped ceiling beams & walnut floors, rare stone surfaces, & hand-plastered walls & ceilings. Behind the scenes, distributed audio, programmable lighting,& a home automation system. Luxurious amenities highlighted by an extraordinary wine cellar, a home theater, & recreation lounge w/bar. Spacious terraces provide a seamless connection to the outdoors, some through fully retractable stacking walls of glass doors. This extraordinary property has a 1-bedroom guest house, outdoor dining & entertainment complex, & a saltwater pool & spa. A timeless masterpiece of enduring character & quiet elegance in the heart of the San Francisco Peninsula.

Welcome to this stunning Woodside residence, where modern elegance meets timeless charm. Built in 2010, this home combines stone, wood, and striking red accents to create a captivating exterior. Circular driveway beckons you towards the welcoming entryway. Step inside to discover a light-filled haven boasting 3 bedrooms and 2 baths. The airy sunroom immediately off the entry sets the tone for the bright and inviting atmosphere found throughout. Spacious kitchen, you'll be greeted by high ceilings and a magnificent chef's island complete with a gas cooktop and warming drawer - perfect for culinary enthusiasts. The sunlit eating area features custom built-in buffet cabinets offering ample storage for all your needs. The living room is a sanctuary of comfort, Nestled within is a cozy wood-burning stove. Step outside onto the deck or patio, where you can bask in the serene ambiance of the outdoors amidst mature shade trees. This outdoor space provides endless possibilities for entertaining. Retreat to the master bedroom, complete with its own ensuite bathroom and outdoor access via a light-filled French door. Whether relaxing indoors or enjoying the tranquility of the outdoor spaces, this Woodside gem offers the perfect blend of modern luxury and natural beauty.

Please call listing agent at 650-398-5384 for open house. Your very own nature retreat is here calling your name. Located on 5.45 acres of lush green land, this home is your ticket unlimited bliss. On arrival you are greeted with a handsome wooden gate opening onto an expansive forecourt, welcoming you back home. Surrounded by nature and crisp, fresh air, your mind and soul begin to relax before you step foot into your home. Composed of five bedrooms, four and half bathrooms, spacious living space and office, and a kitchen fitted to the nines, this home has everything you need plus absolute privacy and a stunning view out to the bay. Come and visit this gem for yourself. It will certainly make you think twice about missing out on this opportunity.

One of the most extraordinary properties on the SF Peninsula on almost 18 acres. The property has endless potential (including zoning for commercial use) and has been used to raise horses, to showcase a car aficionados collection, and to host philanthropic and social events easily up to 200 guests, all the while serving as a comfortable venue for everyday living. 5-floor main residence from the 10+ car garage to a viewing room at the top of one of the turrets. Personal quarters include multiple apartments plus tremendous, dedicated office space. The barn is a matching masterpiece with both buildings hand-crafted by local and international artisans with individual details taking up to a year to complete. Magnificent grounds include a 4-tee golf practice area, RC car track, resort-inspired pool and spa, and direct access to miles and miles of hiking and equestrian trails in bordering Wunderlich Park. Woodside or PV schools. 17 minutes to Woodside town center.

Price Improvement! Estate home situated in a quiet & serene park like setting tucked away from the street. This gated property is located in the heart of Portola Valley, a short stroll to Town center, Famers market, Summer concerts, Just a few minutes drive to 280 & Sand Hill Venture Row. 5 bedrooms/3.5 fully remodeled baths with a unique welcoming feeling. Primary suite with a freshly remodeled bathroom & walk-in closet. Located on a wooded yet sunny 1.3 acre's. The 3,600 s.f. Home has a gourmet Chef's kitchen, Calcutta marble, custom cabinets, commercial grade appliances, gas range/oven, Liebherr refrigerator, breakfast bar, and bench seat storage. Large formal living room with high ceilings and slider to outdoor entertaining area. Separate family room/library with high ceilings. hardwood floors throughout. Double pane windows throughout. Inside laundry and abundance of storage cabinets. Two outdoor living rooms for entertaining. Raised planters for a vegetable & herb garden, Space ideal for a chicken coop, Tons of usable lawn space, On cooler nights, there is a spacious theater that insures many hours of entertainment. Wonderfully high ceilings & high end custom finishes throughout. No detail was ignored This home speaks of quality Come home to style and comfortable elegance.

PERMIT READY! EXTREMELY RARE OFFERING! - EXISTING 4-STORY EXQUISITE MASTERPIECE! The BEST forested HOME CAMPUS ideal for Family/Executive, Live/Work/Educate/Entertain! Grand & Awe-Inspiring -blend your own elegant & luxurious dream home w/ your chosen modern corporate component. Own your "Private Getaway" estate set superbly among majestic California Redwoods. Picturesque & Private, this park-like setting sanctuary perched spectacularly atop Woodside, projects dramatically high entryways, soaring ceilings, a multitude of decks, filtered city views & incredible mountain views from nearly every room! "Ahh!" moments abound! REMODEL - APPROVED 2021 PLANS allow for a total of 7 BR, 8 Full BA, 6 Half BA, & boasting 19,000+/-sf of living space w/ attached (interior) ADU on 5+ acres, above-garage addition, full gym w/ sauna, 20-seat home theater, wine cellar, infinity pool, tennis court & jogging path. (SMC Plan. Dept. approval is recommended for stables, putting green or exterior ADU).

This stunning Portola Valley gem is set back from the street on almost one-third acre. Beautifully updated, this move-in ready home boasts one-level living with a level yard in the front and a private terrace in the back. Inside, newly refinished hardwood floors, an updated kitchen, and bathrooms with designer touches throughout provide elegance and style throughout the tastefully appointed country home. Expansive windows provide abundant natural light into the living spaces. The finished garage offers additional play & storage space with potential for a family room. The gated front motor court provides plenty of parking. The level yard, fresh landscaping & new pavers make it perfect for entertaining & outdoor activities. Additionally, the home's sizeable lot provides various expansion options. Conveniently located near Hwy 280 and Sand Hill Rd venture capital centers, this home is perfect for commuters. Walkable to PV schools, Village Square, the library, the Farmer's Market, and trails on the Woodside/Portola Valley loop, it is a true Portola Valley gem!

Step in to your own private wooded wonderland, located in the idyllic Santa Maria/Russell area... Enter the light filled living room with fireplace, high ceilings and built in bookcase; then flow to the open air kitchen, with large island & adjacent dining area. The front yard has an expansive lawn and majestic oak with rope swing, and includes a decked in area for cozy outdoor dining with built in overhead gas heater. The side yard is perfect for BBQ's or sipping sunset wine, with plenty of room for a steaming hot tub. Very nice indoor/outdoor house with French doors or sliders to the exterior on both levels. Open space on two sides, and with front door access to the extensive trail network including a path to the skyline & Alice's Restaurant....113 Tynan Way situated in the heart of Portola Valley but still close-in to freeway access...come live in magical Portola Valley and close to shopping, dining and freeway access.

Incredible Opportunity! Mostly original 3 bedroom/2 bathroom mountain cottage on a large parcel PLUS 3 ADDITIONAL parcels comprising 2 ADDITIONAL home sites (and ADU's) on over 2 beautiful acres. The 4 Assessor Parcel Numbers are: 075-181-100 (24,000 sf), 075-183-010 (18,000 sf), 075-173-110 (30,000 sf) & 075-173-120 (20,000 sf). Senate Bill 9 should assist/improve development options and opportunities. Value is in both the existing home and potential for a total of 3 houses and 3 ADU's. Many options: build out together, live in one as you build others, or keep for future use. Great for extended family or friends. Exclusive Portola Valley and Woodside Schools. The properties have bay views, Cal Water, and a nice mix of trees. Some of the parcels are accessible via Sequoia Way. First time on market in 50 years.

Contemporary with clean lines and total privacy, secluded in the redwoods on 5.6 acres just off Skyline with midway convenience to either Highway 92 or Woodside Road. Absolute privacy and most recently used as a professional recording studio. 3 beds plus an office or reading room with flexible use. Living room open to adjacent step up dining room just off the formal entry. Spacious kitchen with gas cooktop in the island, a large oven with microwave above, side by side refrigerator/freezer and nearby laundry room. The kitchen, informal dining, and family room are open to walls of glass overlooking the forest with access to the patio deck. Large primary suite with custom closet system and modern sleek bathroom. Significant backup generator in the event of power outages. Acclaimed Woodside Elementary School. Miles of hiking trails all around.

This exceptional hilltop residence features dramatic bay views from Mt. Diablo to the coastal mountain range. The Hamptons-inspired shingle home has the ambiance of a resort retreat and the privacy that comes with being adjacent to 5000+ acres of Open Space yet minutes from the heart of Silicon Valley, A giant office suite, complete with lounge, meeting area and private deck is perfect for work from home with high speed internet access supplied by Etheric Networks. A separate library, professional gymnasium, and acres of land to run and play makes this a true sanctuary for all ages.. There are 5 bedrooms and 4.5 bathrooms including a stunning master wing with a private master deck. The outdoor spaces include a pool and patio as well as 4000~ square feet of ipe deck, covered porch with fireplace, outdoor kitchen, and lovely native landscaping. Starwood is a gated private road. The end of road privacy is further enhanced by private trail access from your front door to Open Space.

Tucked away in privacy in sought after Portola Valley with direct views of Windy Hill. The classic traditional home features a colorful palette, fine hardwood floors, and traditional millwork, presenting a blend of timeless appeal and potential to infuse contemporary elegance into its classic structure. Spanning one level, each room flows easily from one to the other with formal living spaces, a tremendous eat-in kitchen, and a step-down family room opening to a spacious deck capturing exquisite Windy Hill views. Separate wing with 3 bedrooms, each with en suite bath, plus there is an additional full bath. The primary suite, kitchen, and dining room open to the level rear grounds with ample room for play and entertaining as well as a possible potential site for a pool. Excellent Portola Valley schools.

Spectacular!...is the best description with its 270-degree unparalleled views of the Western Hills and enhanced by a host of thoughtful upgrades, this stunning contemporary masterpiece by Tobin Dougherty seamlessly blends bold architectural design with the natural landscaping of the knoll top site and is absolutely move-in-ready. Located in sought-after central Portola Valley on a quiet cul-de-sac, this architectural gem is not only perfectly set up for indoor/outdoor private entertaining, but is also surrounded by nature and trails, offering a lifestyle where outdoor activities, excellent schools, and local conveniences are all within easy reach, making it an epitome of sophisticated Silicon Valley living; features floor to ceiling windows, advanced iPad-based home automation, upgraded state-of-the-art digital theater, a gourmet chefs kitchen, outdoor patios off each bedroom, sauna, a recently added private office/4th bedroom. Plans previously drawn for additional 750 sf guest house. Come see this amazing home!

Extensively updated, light and bright, in lovely natural surroundings on a quiet cul de sac. Close to Ladera shopping, restaurants, Stanford, trails, and excellent schools. Indoor/outdoor living with natural views you will enjoy! Wide plank hardwood floors, gourmet kitchen, large center island open floor plan to the family room. New Thermador appliances, new cabinets, white quartz counter tops/backsplash. Kitchen nook surrounded by windows and center island includes seating. Updated bathrooms are white marble or porcelain tile, Restoration Hardware vanities, designer mirrors and light fixtures. Great room aka formal living/formal dining room is drenched in natural light. Doors open to expansive decks the length of the home providing serene views and entertaining venues. Spacious primary bedroom on the main level features 3 closets, a private deck, skylights and a RH style bathroom suite. 3 large bedrooms on the lower level (one shows as a workout room). Custom ViewRail glass stairwell and hardwood stairs. Updated laundry room, wine room and huge storage area. Almost 1/2 acre, some flat and some gently sloping. Portola Valley Ranch offers a social community center, 2 swimming pools, workout facility, dog park, tennis courts, playground, and vineyards. PVR is truly a staycation.

Nestled on 2.5 acres in the coveted Blue Oaks neighborhood, this awe-inspiring 4 bedroom, 4.5 bath residence boasts a timeless interior & sweeping Western Hills views. Step into the sun-drenched foyer, making way for towering ceilings, a stunning living room & custom-colored, white oak hardwood that flows from room to room. Style & functionality combine as a butlers pantry guides you from the formal dining room to a spacious gourmet kitchen. Off the kitchen you will find a large family room, with vaulted ceiling, a stone fireplace & incredible views. In addition this home has 2 dedicated offices, one on each level which provides flexibility for everyday living. Impress guests w/ a 10,000-bottle wine cellar, a media room and gym area. A 3-car garage w/ EV charging adds endless convenience. A sprawling yard provides beauty, multiple entertaining areas & privacy. Fill your weekends by exploring community amenities while being minutes from highly regarded schools, shopping, & dining.

Completed in 2006, this magnificent vineyard estate is the perfect place to escape from the fast daily pace of Silicon Valley. The approximately 41 acres are as peaceful as they are beautiful, with spectacular top-of-the-world San Francisco Bay views. Arriving on the front terrace is as if stepping into the Italian countryside. The scale of the home is destined for grand entertaining spilling out to exceptional front and rear terraces. The kitchen is a culinary retreat with commercial-quality appliances, and the wine cellar awaits a sizable collection. Multiple rooms for everyday living, a theatre, plus a well-being center with spa, steam, and sauna add luxurious touches. Both 5660 Alpine Road and APN 080-040-120 are being offered for sale together.

UP UP AND AWAY to this Skyline Retreat above the Hustle and Flow of the city. Escape the stress and noise making this your own poetic escape! First time on the market. This 163 acres is considered 'THE SWEET SPOT' of the original 3000 acre purchase. The main house overlooks a 3 acre spring fed pond, green pastures and the ocean. Horse barns, guesthouses, workshops and an airstrip are all included in this private secluded oasis right above Stanford and the Silicon Valley. Fresh ocean air, fertile soil and peace and tranquility have contributed to the longevity for many generations. Experience 200 year old redwoods, Sequoia Giants, native oaks, rivers, horse trails, rolling hills and fields of poppies and daffodils. Come take a walk or swim and get a taste of what this unique property has to offer.