Woodside CA Real Estate & Homes for Sale

One of the BEST gated estates in Woodside's most prestigious area. This majestic one-of-a-kind estate features an enchanting private lake, a long scenic winding driveway, 7+ lush acres, EXTENSIVELY REMODELED 5 bd/5.5 ba primary residence with guest house. Approximately 8238 sq ft of total living space, an energy efficient metal roof, dual pane windows/doors, sub zero refrigerator/ freezer, 3 separate heating systems, a gourmet kitchen, gym, bocce ball court, pool, greenhouse, 3 wells, a sand beach to launch boats onto the private lake, a 6-stall remodeled horse stable with railed riding area, rose garden & areas for a future tennis court/a riding arena. It is quintessential of fine living where numerous weddings & fundraisers exceeding 500+ people have been hosted. Secluded yet conveniently located to Stanford, Sand Hill Rd, tech companies, SF & San Jose International Airports. This property represents a RARE opportunity to own one of the most unique properties in all of Woodside.

Surrounded by natures beauty and western hill views at the end of a long, private lane, this property feels miles away yet is just 4 blocks from the town. Custom built 10 years ago, the craftsmanship showcases extraordinary detail at every turn. The chorus of natural materials, beginning with the all-stone foyer, extends throughout the home giving it a lodge appeal with walnut and mahogany finishes and custom windows and doors throughout. The awe-inspiring setting is highlighted by western hill views with outdoor kitchen, spa, fire pit, plus vast level lawn and terrace. The main residence is positioned on 4 acres with 4 bedrooms, 5 baths, 2 offices, gym, basement, 3 car garage with rooftop veggie garden. Recreational amenities are plentiful with a life-size chessboard, putting green and basketball court, plus a lower level devoted to games, media, wine, & fitness. Access to acclaimed Woodside School makes this the ultimate place to call home. 1 acre adjacent lot could be sold as well.

Come relax and sooth your soul in this 1850+ sq ft, 3 bedroom, 2 full bath, open space sanctuary surrounded by the redwood canopy. Enjoy summertime with your friends and family on the wraparound decks under the whimsical forest. Explore the magic that the mountain has to offer: walk to famous Alice's restaurant, drive a few minutes to awarded Thomas Fogarty winery, hike the nearby state parks, bike the Santa Cruz mountains. Own half an acre of coveted Bay Area land located strategically between two major highways for an easy commute to San Francisco or San Jose. This is true California living in a natural and mystical preserve just minutes away from thriving Silicon Valley.Located on a private hideaway street, Property offers expansion potential.

Don't wait on this exceptional Woodside Glens gem- comprehensively renovated down to the studs in 2021! Immerse yourself in nature in this pristine 4 bedroom, 2 bath home just a short walk to town and the award-winning Woodside Elementary School! Combining top quality with chic contemporary style, enjoy peaceful country living with a carefully conceived design aimed to maximize light, space and privacy. Wonderful open floor plan features a gourmet chef's kitchen fitted with top of the line Thermador appliances, customized cabinetry, and Mirage wide plank white oak flooring. Main floor features two brs, incl. spacious primary suite and walk-in closet. Downstairs are 2 more brs, multi-use bonus/storage rooms and state of the art home theatre. Multiple decks for al fresco enjoyment and fenced flat grassed yard provide space to play outdoors and low-traffic street with easy bike, walkability and xlarge .52 ac lot offers amazing potential for expansion, garage + ADU!

Tucked away yet close-in, this Woodside Glens home is the perfect blend of comfort and country privacy. The home is surrounded with the natural beauty of the area with front and rear decks that take advantage of morning sunrises and evening sunsets. Redwood finishes the exterior, and cathedral ceilings inside showcase clear-heart redwood, also used as an accent wall for the living room fireplace. The kitchen and bathrooms are remodeled with absolute designer style in bright white with perfectly selected finishes in tile, marble, and granite. A potential fourth bedroom/play room with its own exterior access, is positioned between two bedrooms, bookshelves line the hallway, and the primary suite opens to a private front deck. The lower level offers extensive room for storage plus finished bonus office space, ideal for todays needs. Located less than one mile from the Town Center, plus access to acclaimed Woodside Elementary School - a very special place to call home.

Opportunity knocks! 263 Ferndale Way offers an oversized lot of 34,195 square feet with a beautiful cabin-style home. Plumbing, insulation, electrical all updated in 1983. The home offers 3 bedrooms, 1 bathroom, and 775 square feet of living space. Upstairs, you will find an open concept kitchen/living area along with an abundance of natural light and vaulted ceilings. Some potential options with this property includes a potential SB9 lot split (to be verified with San Mateo county) or building your dream home right away! Due to the fact there is a residence, conventional financing should be available! All public utilities. Come and see for yourself all the potential this property has to offer. Rarely available lots in the heart of Emerald Hills!

Competitive price per sqft! 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.

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 other applications. 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.

Complete privacy set way back from the street on 5.6 acres just one mile from famed Alice's Restaurant. Lodge style ambiance throughout with wood paneled wainscot and towering ceilings plus expansive windows and sliding glass doors. Spacious living room, formal dining room, large family room, and open design kitchen with high-end appliances. 2 offices plus 3 bedrooms and 3.5 baths. Private upstairs wing for primary suite with its own view deck plus second upstairs wing with 2 bedrooms. Numerous detached workshops for storage or hobbies. Professional greenhouse, pond, huge deck for outdoor living plus vast stretch of lawn for recreation. Miles of hiking, biking and equestrian trails nearby. Barn & horse corrals. Large attached 3 car garage plus 1 car detached.

This estate (known as "Hilltop House") is a masterful combination of timeless French architecture, by Gardner Dailey circa 1935, and luxurious updates for 21st century living. Spanning ~3.4 acres, the setting is quintessential Woodside, set far back from the street with added layers of privacy from redwood groves and a vast meadow adjoining a conservation easement with unobstructed views. The 3-story residence is classically appointed with hardwood floors, refined millwork, and grand formal rooms complemented by a parlor, entertainment bar, library and chef's kitchen. Personal quarters are many with a total of 8 bedrooms, including the lavish multi-room master suite, plus extended family living quarters with full kitchen, and lower-level staff quarters. The impressive grounds include a pool, tennis court, and sun-swept lawns ready to host family or philanthropic events. Located in the heart of central Woodside just minutes to Stanford, Silicon Valley and 2 airports. Woodside Elementary

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.

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.

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.

Seller says sell-submit offers!

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 faade 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.

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).