Woodside CA Real Estate & Homes for Sale

This incomparable property is a tour de force of contemporary styling w/many rooms enjoying signature solarium glass walls & glorious views. A recent & extensive renovation inside & out transformed the home into a remarkably chic & sophisticated estate of more than 8,500 SF total on just over 3 acres. There is a tremendous sense of volume throughout created by towering ceilings, entire walls of glass,& subtle level variations between rooms. Every inch has been beautifully rendered w/the highest quality & craftsmanship plus behind-the-scenes amenities have been added or upgraded for security, automation, solar power, backup generator, and fire suppression. The grounds are equally transformed into stunning venues for outdoor living w/pool, spa, bocce court, and barbecue kitchen. Located on Woodsides premier corridor, this extraordinary property is just two miles to the center of town, close to Sand Hill Road venture capital centers and Stanford University, and two international airports.

Situated on one of Woodside's premiere streets this beautiful 3 acre view property is ready to build new or remodel. Plans by renowned architect, Tim Chapelle of Arcanum Architecture. Reports have been completed to build your dream home or renovate existing charming 5800 square foot home. This property includes 2 guest houses a 2-car garage, pool, 4-stall barn with paddock. This property features expansive lawn area and meandering pathways throughout. Just minutes from the Town of Woodside and highly acclaimed Woodside School, Highway 280, Stanford University, Sand Hill Road venture capital centers and midway between two international airports.

First time on the market in over 4 decades, this gated treasure is situated on a private street on just over 2 acres. Surrounded by nature, this home is a one-of-a-kind retreat. The fountains and koi pond set a stage upon entry that is both calm and comforting. Dramatic large wood beams and a high ceiling welcome you into the main great room. Windows highlight the natural surroundings from almost all of the rooms. The main residence contains 4 bedrooms and 2.5 bathrooms. Adjacent to the garage is a 2-bedroom guest house with a living room and kitchen. There is an additional Studio under the Primary bedroom with a separate entrance. There are multiple structures that all contain living areas. If tranquility and nature are important, this healing retreat is something you must come and experience.

Extensively Remodeled Home Energy efficient Metal roof, double pane windows and doors, 3 separate heating systems and levels Gourmet Kitchen with two La Cornue ovens, sub zero refrigerator and freezer Fully equipped gym, Bocce Ball Court, Pool and Pool/guest house with kitchen and two bathrooms, Green House, fenced planting beds, Private lake, Sand beach which to launch boats from, 6 stall remodeled Stable with railed riding area,Rose Garden, Private Gate Entrance, High Ceilings, areas for tennis court , riding arena, 1.5 minutes to 280 freeway, 25 minutes to San Francisco and San Jose airport, Close to downtown Woodside's restaurants and shopping 5 minutes ,Heart of Silicon Valley Hosted weddings and fundraisers exceeding 500 people

Country Home & Barn on One Level Acre with Western Hill Views. Set almost at the end of a long, private lane for complete privacy from the street, this home feels miles away from everything, yet is just 4 blocks from town. An enchanting 2-bedroom, 2-bath country home & equestrian facilities span the 1-acre lot, level land and amazing views, offering all kinds of possibilities. Each bedroom is en suite; one with large office and sliding glass doors. Large rear deck, with fire pit and barbecue, steps down to the vast lawn. An attached 2-car carport with large storage room and wiring for Tesla charger. Rounding out the property, the two-stall barn with tack room and fenced corral and easy trail access. Enjoy the property today or while planning for building an entirely new home for the future. The adjoining 1.1-acre lot, at the end of the lane, is also available for sale providing even more options at this exceptional location. Access to acclaimed Woodside Elementary School (K-8).

Located at the very end of a long lane, this 1.1 Acre property has complete privacy from the main st, is just 4 blocks from Woodside town center, and has access to acclaimed Woodside Elementary. The setting is quintessential country, the long driveway leads past an open sun-swept meadow & oak trees arriving at the home. The covered front door opens to a traditional foyer; beautiful wide-plank wood floors throughout. Open design for living, dining, & kitchen; a fireplace in ledgestone; windows wrap around two walls. The remodeled kitchen is topped in granite, including breakfast seating at the peninsula; stainless steel appliances and track lighting. 2 bedrooms, each with lighted ceiling fan & glass doors to a spacious rear deck. Attached 2-car garage w/ custom built-ins & laundry area. Quality updates throughout, a lovely spot to move in & enjoy today. Opportunity to expand / build new; adjoining 1-acre parcel, also for sale, increases options for estate living in a superb location.

Located in historic Sky Londa, this home is surrounded by lush landscaping, stunning redwood trees and the natural beauty of the area. The home sits on a .86 acre lot (per county) and provides a tranquil setting for entertaining and everyday living. A generous use of windows and skylights fills the home with natural light and views of the surroundings at every turn. The focal point of the sizable first floor is the expansive, airy, eat-in kitchen with deck access, that connects seamlessly to the living room and dining room areas. A large office with a private entry, built-in wall unit and stone, wood burning fireplace is located off the front porch. A large bonus room, also with private entry, is on a lower level and accessed from the lower yard. Enjoy the beauty of the Skyline community and nearby hiking trails from this serene property while being conveniently located to Highway 84 and popular Alices Restaurant.

Dazzling whole-home renovation, resort-like amenities on 3 acres, and access to acclaimed Woodside Elementary School, it's all here. This stunning home combines glamorous high style with country seclusion on the prestigious west-side just two miles from the town center. 3 levels with breathtaking interiors that include stunning expanses of natural stone slabs that double as works of art. 2 dedicated offices, fitness center, theatre, refrigerated wine storage, and grand rooms for entertaining. 4 spacious bedrooms, each with en suite bath, include one on main level and upstairs primary suite plus there is a large detached guest house with 2 bedroom suites. The grounds are designed for health and wellness with pool, spa, tennis court, and walking/jogging path around the entire property and there is a small vineyard. Truly a home to be savored.

Featuring amazing Western Hill views in the highly sought after Mountain Home corridor in Central Woodside, this 3.5 acre gated estate is being offered for the first time in nearly 60 years. Situated at the end of a quiet cul-de-sac, come see this timeless treasure, comprised of a classic two story California Craftsman main home, an adjacent carriage house set up for entertaining, a pool and peaceful pathways through the mostly flat grounds. Ideal for indoor/outdoor entertaining, the main home has large living and dining rooms with French doors opening out to a spacious brick entertaining patio framed by mature heritage oaks and world class English Gardens showcasing the spectacular western sunsets. Upstairs, relax in a spacious primary suite and light-filled home office, near the additional four bedrooms. Enjoy the privacy and tranquility of this fully-fenced property within close proximity to Town Center shops, restaurants within close driving distance to Silicon Valley & airports

10+ location in Woodside School District. Walk to town shops and school. Quiet country lane off, just off historic Mountain Home Road, this property awaits your estate home. The lot of approximately 3.84 acres offers the utmost in privacy. The land is level with sun-swept open expanses of lawn and meadows with mature trees and perimeter foliage that enhances the privacy. Owned by the same family for more than 65 years, the property comprises a vintage ranch home and caretaker cottage, pool, tennis court, and sport court. This premier central Woodside location is bordered by legacy properties, benefits from access to acclaimed Woodside Elementary School (K-8), and is less than one mile from the town center.

Lovely home on a quiet street in Woodside! Vaulted ceilings, decks galore and canyon/redwood views make this home a functional mountain retreat. The living room is adjacent to the kitchen and includes a cozy fireplace. A sunroom overlooks the redwood forest, and opens onto a spacious back deck. The 3 bedrooms feature large closets, one with an attached balcony. The in-law unit has a separate entrance, bathroom, bedroom and kitchenette. The unit has plenty of room for a vacation rental or long term rental to supplement your mortgage payment. The 4/10ths of an acre are flat and include a side yard for a dog or kids to enjoy. Abundant parking includes a parking area for 10+ vehicles alongside paved parking in front. High speed internet and excellent cell service make this a practical oasis. Only 15 minutes to 280, 20 mins to Stanford, and 15 mins to the beach. Come home to your mountain retreat in Woodside!

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On the hunt for the ultimate Woodside getaway where you can leave behind the hustle and bustle of everyday life? Set on a majestic 2 acres, this spectacular residence provides an ideal blend of luxury and tranquility, all just moments from everything San Francisco has to offer. A long driveway, lush redwoods, and a contemporary fa?ade greet you. Inside, discover a bright, welcoming layout with crisp white tones, soaring ceilings, and fine finishes throughout. Warm up in front of the stately fireplace in your well-sized living room or take advantage of one of the extensive decks framing verdant vistas. Your gourmet kitchen comes fitted with modern appliances, ample cabinetry, and an eat-in bar. Dine in your adjacent dining room where tray ceilings add to the captivating ambiance. At the end of a tiring day, rejuvenate in your secluded retreats, or savor a nightcap outdoors with 360 degrees of pure nature. As a bonus, you'll have a private library and an attached 7 garage.

Serene, very private and very quiet 3+/- acre property, only 5 minutes to Woodside town center surrounded by oaks, redwood and manzanita trees. Set on a knoll the property borders Huddart Park and watershed property and features the highly desirable beautiful western hill views. The 3-bedroom, 2-bath (current 3rd bedroom used as office), inviting home has rustic tones with an abundance of natural light. Large primary bedroom with walk in closet and recently updated en-suite bathroom. Light and bright, well laid out kitchen and updated second bathroom. Multiple outdoor dining and seating areas to enjoy this peaceful natural setting and views, fruit trees and several flat areas for potential ADU or pool sites. 2 covered horse stalls with runouts, tack room, sand arena/turnout area, larger main barn/workshop, outdoor shower. Barn is aprox. 20'x34' Easy trail access into Huddart Park, Woodside Elementary School, close access to 280 and Sand Hill. Truly must be seen to appreciate.

This expansive, custom built home has so much to offer and such tremendous future potential! The generous floor plan offers approx. 9,800 square feet of living space w/ soaring ceilings in the formal entryway, a gourmet kitchen, 6 en-suite bedrooms, home office, & a fully equipped guest/caretaker's apartment above the 6 car garage. Breathtaking views from almost every room w/ expansive decks on every level to take in the surrounding beauty of this mountain retreat. The current landscaping is a relative blank slate and the potential to create a custom outdoor oasis is unlimited! There is plenty of room to add a swimming pool, pickle ball court, hardscaping, or whatever fantastic outdoor living area you would like to create! This gated home was incredibly well engineered and offers exceptional privacy & yet is still an easy commute to San Francisco, Palo Alto, or San Jose.

A great home on 5.5+ acres with so much potential! Enjoy the stunning views from the living room, dining room, kitchen, primary bedroom, and outdoor patios! Move in, transform or potentially build new in this private setting. The two-story house has 5 spacious bedrooms, and 4.5 bathrooms. Upon entering, you are greeted by soaring ceilings and expansive windows and skylights that offer ample natural light and a view into the private backyard. The eat-in kitchen is highlighted by a huge center island, peninsula with extra seating, and large glass doors leading to the outdoor patio. The large patio is perfect for BBQs, alfresco dining or star gazing in the summer time. The main level has the master suite with dual vanities, shower ,spa stub and private balcony. The lower level has a total of 2 bedrooms and 2 full bathrooms, including an in-law unit with kitchen ,bathroom, and a separate entry. Excellent Portola Valley schools. Perfect for vacation rental. Rental income ~$18K-$20K/month

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 make 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.

One of Americas grandest estates, the Green Gables Estate is a fabulous combination of mans and natures best, including its exquisitely scaled main residence, world class gardens, six additional homes, a stunning 100+ yard Roman Pool, three swimming pools, a beautiful stone tea house, a large spring-fed reservoir (sustaining much of the estates irrigation needs) and bountiful vegetable and flower gardens. The estate also offers opportunities to create new residential structures, develop vineyards, add an equestrian center or expansive orchards. With its two private roads, wooded trails, and endless tranquility, this incredible estate is the ultimate family compound or inspiring corporate retreat. With its seven homes situated on 74 private acres, featuring breathtaking panoramic views of the Western Hills, it is remarkably situated in the heart of Silicon Valley and is blessed with an idyllic climate as well as location; San Francisco international airport is just 20 minutes away.

Long time owner is ready to sell. Best deal in Prime Central Woodside, 3 level acres with Pinot & Merlot wine vineyards & Sweet Concord & Table Grape vineyards, Numerous Fruit Trees all maintained organically without use of pesticides. Main Ranch home with 4 bedrooms 3,535 sf, Guest house #1-1,915sf, Guest house #2-640 sf, Guest house #3-730sf and an ADU/ Pool bathroom 300sf Totaling 7,120 sf per attached Floor Plan Visuals Drawing. Additionally a horse corral, Property is zoned for 6 horses. Excellent Schools and easy commute access bordering Sand Hill Road & Whiskey Hill Roads.

PERMIT READY! EXTREMELY RARE OFFERING! - EXISTING 4-STORY EXQUISITE MASTERPIECE! The BEST forested HOME CAMPUS ideal for Corporate 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 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).