Woodside CA Real Estate & Homes for Sale

One of the BEST gated estates with PANORAMIC views of the Western Hills. This beautiful single story home is on approximately 1.29 acres in Woodside Hills and has the following features: 4 spacious bedrooms, 3 bathrooms, a detached cottage with bathroom, remodeled gourmet kitchen, large 3-car detached garage, a huge private driveway with space for over 10+ cars, an outdoor bar, putting green and a bocce ball play area. Additional features include large wood burning fireplace, airy and open floor plan with a fantastic layout conducive to privacy with amazing views from almost all the rooms. Excellent private location close to highway 280, downtown Woodside, downtown Redwood City, Stanford University, Sand Hill Road, tech companies, SFO International airport, & shopping! This one-of-a kind property is absolutely unique. Must see!

An Expansive Bay View Retreat! Surrounded by nature & abundant in privacy, this exceptional Woodside residence offers premier living on over 7 acres. Stunning panoramic views envelope the property highlighted by sunrise views each day and city lights by night. The floor plan is open & flowing with approximately 3,095 square feet over three levels taking complete advantage of the breathtaking view. There are 4 bedrooms & 3 baths in total, the expansive primary suite retreat offers an oversized bath & walk in closet. The rest of the spacious bedrooms are equally ideal, one w/ loft, one w/ oversized walk-in closet and one with its own access to the outdoors - a perfect bedroom or office. Fine California indoor & outdoor living is highlighted with vast decking around, sprawling level lawn, mature trees & gorgeous views. Rounding out the property is the 2-car garage, huge laundry room, ample storage & abundant light. A perfect scenic escape yet close to everything.

Sophisticated move-in-ready home on the hill. Designer finishes and professional design used to re-imagine a timeless classic: a Contemporary cabin in the redwoods! This gorgeous home was recently gutted, renovated and transformed into a one-of-a-kind modern retreat. Located in Kings Mountain area, home to some of the best hiking and biking trails around, you'll find this fully fenced, nearly flat property. A huge, detached 2+ car garage has room for a workshop or hobby area. You'll also find two quaint/rustic structures here, awaiting your improvements. Highly acclaimed Kings Mountain Elementary School and Mountain House are just down the street. Take Hwy 92 for a 30 minute trip to San Francisco, San Mateo, Stanford... maybe even the East Bay!

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.

Cozy Studio cabin nestled in the Redwoods. This adorable home boasts an updated kitchen and bathroom with all new electrical and plumbing. Brand new water resistant LVT flooring throughout. New propane wall heater keeps this home nice and warm during the winter. Summers can be spent enjoying the views from the back deck or the front porch looking out to the redwood trees. This home is located in the Kings Mountain area of San Mateo County. Kings Mountain is a wonderful community that offers small town charm while still being close enough to 92 and Woodside Rd. to commute to work. This home is centrally located, just a short walk to the Mountain House for a delicious dinner, the firehouse which is known for the annual Kings Mountain Art Fair and countless other community events. There is also an abundance of nearby hiking trails. Potential to expand the home. Easy 15 minute drive to Downtown Woodside, San Mateo and Half Moon Bay.

Extraordinary, contemporary home privately tucked away on a magnificent compound of almost 12 acres with unbelievable Bay views. The home's design boasts soaring ceilings, walls of glass and myriad decks which create an indoor-outdoor living environment. The floorplan supports casual everyday living and recreation, but with multiple office spaces, it allows for a perfect life-work balance. Large, primary bedroom with sitting area and attached office/nursery. Gourmet chef and caterer's kitchen. The home is rich in detail, but its natural environment is the soul of the property. Resort like landscaping and outdoor entertainment spots. There are an abundance of amenities: guest house, gym, infinity pool, fire pit, retractable awning, spa, vineyard spot, orchard, two level lawns, 6 car garage with workshop, generator, two wells for irrigation, access to Wunderlich Park. After a long day out, you'll breathe a sigh of relief when you return home to your private retreat. 16379skylineblvd.com

Beautiful 5 bedroom, roughly 3,574sf, Spanish Revival home with sweeping bay views on approximately 1 acre. A formal sitting room offers vaulted ceilings, fireplace, and sliding glass doors to an expansive outdoor veranda great for entertaining. Kitchen into great room works beautifully and offers eat-in area, wet bar and sliding door onto balcony perfect for al fresco dining. Large grass field for recreation and sports. Four car finished garage with storage. Sought-after Roy Cloud school. Private location, yet minutes to Canada Road, downtown Woodsides Roberts Market, Bucks, the Village Bakery.

Completely remodeled country luxury home with a Craftsman flair, this home has it all. Outstanding views in a park-like private setting, sun-swept grounds of 2.7 acres, plus a pool, spa, sauna, and steam shower for health and well-being. Remodeled interiors are absolutely beautiful lofty ceilings, fine hardwood floors, and views that reach out to the East Bay hills, the South Bay, & the Western hills. Formal venues are complemented by a tremendous chefs kitchen & family room combination plus there is a lower-level recreation room opening to the pool. The 4 spacious bedrooms arranged over 3 open levels with a luxe primary suite on the main level. Rounding out the property is a large, well-appointed barn that provides for equestrian use or added bonus spaces - with an existing upstairs room, ideal for todays home office needs. This home is an excellent option to escape the fast pace of the SF Peninsula. A close-in location, Portola Valley School and the SF Peninsula, Freeways, Airports.

More photos+ coming soon! AMAZING RARE OPPORTUNITY in perfect location in the Woodside Glens- first time on MLS, this gracious Spanish colonial single story 3 br, 2 ba home is located on EXTRA LARGE .66 acre sun-drenched, fully fenced and gated lot. Elevated yet mostly flat, while away peaceful afternoons by the completely private fenced pool or lounging in the enclosed patio overlooking the massive grassed yard, gardens and fruit trees, all facing a dramatic 180-degree backdrop of Western Hills views! Completing this extraordinary compound are two separate driveways, a two-car attached garage AND a detached 1236 sq ft 5-car garage with studio guest apartment. And yet there's more: an exterior ~100 sq ft office/work space/shed, room for 6+ more cars off street parking on site and a covered carport big enough for an Airstream! Not to be missed, your Woodside dream home awaits!

Situated on 3.0 private acres, this move-in-ready approx. 4,865 sq ft elegant Contemporary Villa is a designers dream! Impress your guests with an experience they will remember as they enter the home to a large, high-ceilinged living room overlooking a long rear infinity pool showcasing jaw-dropping views of Western Hills. The home features a host of desired amenities, such as high ceilings, an efficient one-level layout and multiple sets of indoor/outdoor French Doors and the current owners added in a variety of further improvements which range from high end designer touches in virtually every room, a reconfigured and improved gourmet chefs kitchen, a new travertine entry and courtyard, an expanded and gated travertine stone driveway framed by splashes of new colorful landscaping. The property should also have further development potential (main home expansion or new guesthouses, check with Town Planning). In convenient Woodside location with easy access to Sand Hill Road and I-280

Fantastic Woodside retreat in a beautiful setting amongst the redwoods. This 4-bedroom 2 bathroom home has vaulted ceiling with tons of natural light, a large open living area off of the spacious kitchen make the home perfect for entertaining. The house also features a detached garage with studio, sunny deck and spacious backyard. An idyllic peaceful setting, close to town with easy access to the coast.

Welcome to this peaceful redwood retreat! Located at the end of a private road, this 3 bedroom and 3 bath home with family room offers unrivaled privacy and tranquility. Extensive hiking trails right outside your front door. Existing barn with room for a corral. The kitchen flows into the dining area nook then opens to the spacious living room with full views of the redwoods. From here, one can continue on to the expansive deck, off of the living room which allows for full enjoyment of this magical setting. The cozy, en suite primary bedroom features a skylight and fireplace. Two bedrooms and second full bath, complete the main level. Downstairs is a large family/office/au-pair suite with full bath and laundry. Beautiful hardwood floors throughout. Propane fueled, automated generator. Two car garage with an extra third garage bay - currently set up as an extensive workshop. Portola Valley schools. 10 minutes to 280.

This amazing 30 acre ranch in beautiful rural Woodside with breathtaking views of the coastal hills can be your own personal getaway. There are so many options for this rare piece of property: Horse Ranch with riding arena, cattle, vineyard, family retreat or personal residence, the possibilities are endless. Sitting at the end of a small country road behind a private gate is this 3 bedroom, 2 bath 2200 sq ft ranch style home. Fix up or build your dream home!!! The property has 2 ponds, creek, natural spring, pasture land and partial ocean views from the property!!!! A beautiful 30 min. drive through towering redwoods and rolling hills takes you from the congestion on Silicon Valley/280 to your own private retreat.

Understated Elegance in beautiful Woodside! Tranquility greets you as you step into the private Zen Garden entrance of this Mid-Century Masterpiece. Inside you will find a grand living room with a wall of windows showcasing beautiful views across the canyon to the Bay. The large deck off the living room is perfect for entertaining. The kitchen, tastefully updated, has custom cabinets, granite countertops, plenty of storage and a wonderful skylight bringing in an abundance of natural light. The casual dining area has 2 sets of doors leading back out to the zen garden or the pergola near the running waterfall where you can enjoy privacy, peace and quiet. This single level custom home was built with precision and care and the original family has kept this home impeccably maintained. The Primary bedroom has sliding glass doors showcasing stunning views and a private sitting area.The addl oversized bedrooms are great for growing families. Detached shed great for home office!

Presiding on approx 3 acres on one of Woodside's most premier streets, this is an outstanding opportunity with a wealth of possibilities. The vast level land borders a seasonal creek and is dotted with redwood groves, heritage oaks, and stretches of sun-swept open land. The classic main home exudes mid-century style, and spanned by a covered porch, plus a, newer guest house. Either home could be enjoyed as is today or while awaiting plans for remodeling or potentially building new in this fabulous setting. The treasured location offers all the privacy and rural feel for which Woodside is known, yet is just minutes to Sand Hill Road venture capital centers and Stanford University. Woodside town center is less than 2 miles away and miles of hiking, biking, and riding trails are all around, including The Horse Park at Woodside. Whether an equestrian estate, executive retreat, or family compound, this property stands ready enjoy the quintessential Woodside lifestyle.

See ML81860545 in MLS Lots & Land priced at $1,999,000. Build your dream home on 2.3 acre private retreat lot with your own preferred contractor. Price is for the land, plus significant site improvements, the approved construction drawings and building permits. Property includes in place site utilities (600 amp electrical service, 2 20,000 gal water storage tanks, on site water well approx 12 gallons per minute production, septic tank and leach field, storm drainage and retention pond, propane gas tank, site grading and retaining wall for the new house foundation, site grading and retaining wall for the new driveway and turnaround, rough framed 2 story garage and in-law unit with roof trusses, $200,000 Fleetwood Custom Windows. County records lot size varies from the Contraction drawings. Buyer to verify. Construction Drawings are for a 7354 sq ft house (living space) consisting of a 6485 sq ft main house, 869 sq ft rough framed in-law unit above garage. The 3 car garage is 869 sq ft.

This magical and historic home is a tranquil retreat situated on over one acre of useable land with plenty of sun. One of only a few original redwood log cabins remaining in the area, this home has been creatively expanded and beautifully remodeled. The home has high ceilings, and an expansive kitchen with stone countertops, stainless steel appliances and a stone deck perfect for indoor/outdoor entertaining. The over sized room above the garage can be a recreation room, family room, guest room or office and has a separate entry. Side yard has a terraced stone wall fruit orchard and fenced area for animals with a chicken coop. The half acre adjacent parcel features a large flat area, its own driveway, its own water meter, and building potential. With desirable Portola Valley schools (plus bus service) and nearby hiking, biking and horse trails, this home offers incredible Santa Cruz mountain immersion while being only 15 minutes from Hwy 280 for commuting to all Silicon Valley!

This Contemporary & Captivating home on 2.4 acres with 180 degree western views, is a masterful expression of contemporary style and artistry. Extending over 3850 sq ft comprising entry, living room, dining room, family kitchen, 4 bedrooms, 3.5 baths, 1 half bath, 3 office spaces, breakfast sunroom, wine storage and 3 car garage.Relax on the private patio space, arbor and backyard with hot tub, garden area and grass yard with lovely views of the western hills. Property has an area on lower portion ideal for an ADU or guest unit. This incredible location is ideal for hiking, biking and Award-winning Woodside Elementary school.

Enjoy the timeless appeal of this spacious mid-century modern home on approx. 1.84 acres. Breathtaking and magical setting... walking paths meander through imposing redwoods, spring-fed pond with waterfall, pool & inviting outdoor living spaces. 4620 sq. ft. 5 bed 3 bath home with open-concept floor plan flowing seamlessly...living room to sun room, to great room and kitchen. Walls of glass bring in the striking surroundings and open to multi-level Ipe & Redwood decks. Featured design elements showcase upstairs cat-walk looking down upon great room and functioning to join the spacious master suite and private master living area The master floor is enhanced by imposing stone fireplace, dramatic beamed ceilings and private decks, while suns fills the space through a large array of windows and doors. This one-of-a-kind property is served by the Portola Valley and Woodside Schools. Easy access to the heart of the Peninsula and Silicon Valley. Private road. Please no drive-bys.

Don't miss this opportunity in beautiful and neighborly Woodside Glens! This home needs work, so bring your imagination and make it yours. The kitchen, dining area, and living room are combined in an open floor plan with high ceilings and large windows overlooking a lovely seasonal creek. Two bedrooms one full bath upstairs and one bedroom and a full bath downstairs, plus a family room with outside entrance. Decks on both levels, and your own parking pad with four spaces. All this on a quiet cul de sac close to downtown Woodside's shops and restaurants, Library and Woodside Elementary School (k-8). Quick access to Highway 280 at Woodside Road.

Two Exceptional Homes on 1.45 Acres Minutes to Town Center! Welcome to your own peaceful valley in central Woodside. Less than one mile from the town center, this 1.45-acre lot offers two exceptional homes a newly renovated 5-bedroom main residence plus a fabulous 1,535-square-foot 3-bedroom second home all tied together with sun-swept level grounds dotted with mature oaks plus a farmers market-worthy vegetable garden with full enclosure. Each home has its own driveway and private entrance as well as individual outdoor living spaces. The finishes in each are superb with cottage-chic sophistication, gourmet kitchens, and abundant natural light. Adding the finishing touch to this rare property is its walk or bike access to award-winning Woodside Elementary School. Welcome home!

Peaceful country cottage, framed by its white picket fence w/wisteria draping home & garage is situated in a SUNNY grove w/ stately redwoods on 2+ acres. Cozy LR features a fireplace & tucked away day bed, great reading area or a place to unwind. Expansive paneled windows outline the side yard w/ brick patio & views overlooking the peninsula. Kitchen/Dining room w/cabinets galore are freshly painted w/new SS refrigerator & dishwasher. Master has w/b fireplace, hand painted tiles & closet stretching the entire wall. Home is light filled & brings in the beautiful outdoor scenery throughout. Appeal never ending w/Dutch door, interior cottage doors finished off w/patina handles, original recessed hardwood floors & newly painted exterior & interior. Hot tub, separate work shed attached to garage & a chicken coop. Open level yard features adjacent area that could be used for a cutting garden or small vineyard. PV schools, hiking, Alice's & nearness to the Village of Woodside.

EXTREMELY RARE OFFERING - EXQUISITE MASTERPIECE! The BEST forested 4-story HOME CAMPUS ideal for Corporate Live/Work/Educate/Entertain! 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! Grand & Awe-Inspiring, blend your own contemporary, elegant & luxurious dream home w/ your chosen modern corporate component. "Ahh!" moments abound! Approved Plans for 7 BR, 8 Full BA, 6 Half BA, boasting over 19,000sf of living space w/ attached ADU on 5+ acres, call for a generous remodel of the existing residence, an above-garage addition, full gym with sauna, 20-seat home theater, wine cellar, infinity pool, tennis court & outdoor jogging path. Stables or putting green are optional. (SMC Plan. Dept. approval recommended).

This estate (known as "Hilltop House") is a masterful combination of timeless French architecture and luxurious updates for 21st century living. Spanning ~3.31 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 lower and upper level have been freshly painted. This classically appointed home has hardwood floors, refined millwork, grand formal rooms complimented by a parlor, entertainment bar, library and chef's kitchen. Personal quarters are many with 8 bedrooms, including a multi-room master suite, plus extended family 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 international airports. Woodside Elementary

Amazing opportunity to own in highly desirable prestigious Woodside. PRICED TO SELL! Welcome to this peaceful redwood retreat with stunning views and serene natural forest- fully remodeled This charming home has 3bd and 2 1/2 bath, high-end appliances kitchen, home gym, 2 fireplaces, wine cellar, balconies, extensive wrap around deck, huge 4 car garage and backup generator. The large guest unit has a separate and private entrance (1bd, 1 bath, full kitchen, living /dining area, office and backyard). Walking distance to local restaurants. Easy access to hiking trails, Woodside village, 280, Stanford Shopping Center and downtown Palo Alto.