Woodside CA Real Estate & Homes for Sale

Welcome to your dream retreat in the prestigious Skywood area of Woodside. This sunlit, charming home offers a tranquil escape with breathtaking views of Hoover Tower and the Bay from its expansive back deck. The residence features 3 bedrooms and 2 baths. The open floor plan seamlessly connects the dining area to the living room, where a cozy fireplace awaits. Step into the flex space; envision it as a large family room or your private sanctuary with a vaulted ceiling, providing a versatile layout. Enjoy the serenity of your surroundings. The back deck becomes your personal oasis, offering an ideal spot to unwind and take in the panoramic views. This space is designed for the ultimate in indoor-outdoor living. This home boasts modern amenities, including solar panels, a generator for added security, a solar water heating system, and a whole house water filtration system. Embrace sustainability and efficiency. Conveniently located approximately 15 minutes from Highway 280, Roberts Market, and top-rated schools. Commuting is a breeze, allowing you to connect with Silicon Valley and beyond. Experience the best of both worlds - the tranquility of Skywood and the accessibility to urban conveniences. This residence is more than a home; it's a lifestyle. Make it yours!

Welcome to the Redwood Chalet! This stunning 3330 sq ft country home has 5 bedrooms and 3.5 bathrooms - nestled in a redwood forest on 6+ acres - is completely private and still only 5 miles from 280. The spacious living room with its cathedral ceilings and a wall of windows invites an abundance of natural light, creating a warm and peaceful atmosphere. Open the sliding doors and step out onto the deck, where you can enjoy alfresco dining or simply relax, taking in the tranquil surroundings. On the other side of the deck is the remodeled kitchen - granite countertops and stainless appliances - a true chefs delight. The primary en-suite bedroom, is located on the lower level along with 3 more bedrooms with sliding glass doors to the outdoor patios, and 1 full bath. Laundry and a wine cellar. The en-suite guest quarters are located on the top floor. EV charger and fiber optic internet. Detached 2+ bay garage features a huge extra multi purpose room on the second story room. PV Schools.

Privately situated, this serene country home blends comfort with sunshine and seclusion., yet minutes to town. Spanning approximately 1.70 acres of sunlit grounds the home harmonizes perfectly with nature. Whether a primary residence, or a weekend escape from urban living, this home offers utmost tranquility with close-in convenience. A spacious spa set within a wood-paneled building encircled by shoji screen windows. Inside, discover the charm of this 3-BD plus office, 3-BA home, and hardwood floors in most rooms. The welcoming great room with natural light from windows & a glass-lined front alcove, seamlessly combines living, dining, and kitchen. The main level has 3 bedrooms, including a primary suite with sweeping views & deck access. The 4th bedroom, with its own entrance, and bath are on the lower level, along with a spacious project/laundry room. Plus a detached 2-car garage and access to acclaimed Woodside Elementary (K-8) School just down the road.

Rare building opportunity in the heart of the Woodside Glens neighborhood! The property comes with an entitlement to build a 2,375 sf SFR, 440 sq.ft. garage, and attached 800 sq.ft. ADU. Primary Bedroom and 1.5 BA are located on the main level, the lower level has 2 Bdrms and 1 Full BA. The attached 1 Bdrm and 1 BA ADU, also located on the lower level, has a separate entry, a living room, kitchen, and outdoor space. The design has a 2 Car Garage & 2 Car Parking Deck at street level- refer to entitlement plans for details. The lot allows for the development of a new home in this prime location that is quaint and has beautiful views of the oak trees and a seasonal swale. Woodside being one of the valleys most desirable areas, has maintained its rural character while being set directly between Silicon Valley and San Francisco. This wonderful location is just a short distance to downtown Woodside and is minutes away from Downtown Redwood City with a bustling restaurant and cultural scene.

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.

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.

Exceptional half acre+ with bay views, Emerald Hills home built with meticulous attention to detail by its current owner, a renowned artisan in stone and ironwork. Designed with a focus on indoor-outdoor living the home seamlessly extends from the family room to a mostly covered, tiled deck with a fireplace lounge, dining area and well-equipped outdoor kitchen offering a serene and inviting space for everyday living. Vaulted ceilings including living room with fireplace, formal dining room with fireplace, sun room and main floor bedroom. Granite chefs kitchen with views, breakfast room with outdoor patio, plus adjacent family room with fireplace. Upstairs luxurious primary suite with fireplace and sitting room, plus two additional bedrooms and adjoining lounge or office.Lower-level flexible-use room for office, 2-car garage PLUS 735 square feet studio including half bath-possible ADU conversion.Excellent Roy Cloud School, views and vast lawn.One-of-a-kind enchanting home-a must see.

It would be difficult to imagine a more perfect setting. Completely hidden from the road, this 1.06-acre property delivers rare seclusion and breathtaking views - yet its only a half mile from Portola Rd. The 3 bed, 3 bath home offers 2090 sq ft of rustic charm with a design sensibility lifted from the pages of a Ralph Lauren catalog. Rich hand-crafted wood paneling, an authentic detail, wraps the living room. Patio doors lead to a large deck with expansive vistas. The kitchen is inviting and equipped with all the tools to create culinary delights. Expansive windows in the dining room offer views of the surrounding hills. The home also offers a community-owned gigabit-speed fiber network. A lower level has a private entrance and functions as a separate apartment with bedroom, bath, kitchen, and sitting room. The front of the home offers a large patio complete with fountain surrounded by mature trees and fenced for privacy.

Location, location, location! 156 Bardet is just a short stroll to Roberts Market, local restaurants and highly acclaimed Woodside School, plus it offers immediate access to hiking trails and popular biking routes. The mostly original 1949 constructed home provides a wonderful canvas as a charming single level home. Walls of windows fill the living room with sunlight and create a cozy atmosphere within the white washed paneling and hardwood floors. Or capitalize on the almost half acre lot to create your dream home. The property is currently served by septic but connection to City sewer has been paid and is ready for approval. There is much to love about the potential in this centrally located Woodside home.

Picture yourself, immersed in nature, living amongst the redwoods and fruit trees in your own fully fenced, secluded compound. Hidden from the road allowing you the ultimate in privacy. Enjoy the fragrance of fresh air and the Coastal breeze. Sink into soulful bliss and surround yourself in the beauty of nature while enjoying your morning beverage or your telecommute on the sun filled deck. The large great room with stone fireplace is the perfect space to entertain, an additional fireplace in the primary bedroom. Bonus room downstairs. No freeways here, far enough away from the hustle and bustle of the Silicon Valley, yet a short drive to Highways 92 and 280. With a little TLC, this lovely, private and secluded, quiet home would transform into a true gem. Sitting on over a half an acre, this is a real opportunity for the buyer who wants to keep the history and nostalgia of the area while creating a beautiful sanctuary to call their own. Live here or create your own retreat center.

First time on the market! This home is at the highest point on Olive Hill Lane offering views of the bay and western hills. On Woodside's most prestigious street, a stone's throw to town and school. This perfectly situated 3.4+/- acre lot is firmly rooted in natural California aesthetics in complete privacy. It is truly an extraordinary property and not to be missed.

This ground up full renovation of a single story Mid-Century Modern home boasts 3,000 sq ft of living space - including 5 bedrooms and 3 bathrooms. Situated on an approximately 1 acre lot in the highly sought after enclave of Woodside Hills, this spacious residence offers expansive views of the Bay and surrounding hillsides. The open floor plan offers the best in seamless indoor/outdoor living. The completely reconfigured Master Bedroom Suite includes a newly added en-suite bathroom with double sinks, marble tiled shower, and walk-in closet. In the center of the home you will find a chef's kitchen accented with granite and quartz countertops and top-of-the-line Thermador appliances - which opens up to an oversized family room with fireplace and a formal dining room. Yards on all sides of the home have been newly landscaped, with a natural flat green lawn which connects to a magnificent swimming pool. A separate free standing 3 car garage is located adjacent to the home, with a half-moon driveway with 2 entrances that accommodate multiple vehicles. Seller is offering a 2/1 rate buy down starting at 4.25 percent interest rate!

Home for the Holidays! Beautifully staged with new upgrades! You won't want to miss this Woodside paradise! Escape to 2.41 acres offering sweeping views of the surrounding natural beauty with manicured gardens. The main home boasts newly painted interiors, new carpet and an updated kitchen with skylights that enhance the appeal. A large deck off the kitchen offers a perfect place for entertaining with views of the gardens. There are 4 bedrooms and 3.5 baths, a large lower level family room and entertainment area, plus a 2 bedroom 1 bath guest cottage. Classic white fences border the stalls and what could be an arena for horses if desired, and there is a tennis court on the lower level of the property. There is a pool and cabana ready for additional recreation and additional outdoor activities. Whether enjoying today or renovating for the future, this location is superb just steps from Huddart Park, 2 miles from Town Center with access to Woodside Elementary School. Welcome Home! For more photos and video go to www.265greer.com.

Great opportunity for a new home on a level lot with views of Kite Hill in Woodside. Over one-third acre (16,269sf) of level land looking out to Kite Hill Wildflower Preserve. Full architectural plans approved by Town of Woodside are ready for issue of permit saving nearly a year of design time and 9 to 12 months of permitting time. Plans are for a modern farmhouse home with 3 beds, 2.5 baths and attached ADU with 1 full bathroom and large room which also could be a 4th bedroom or home office. Main home: 2,882sf, ADU 499sf, attached 2-car garage 539sf. Total footage: 3,920. Close-in location walk to the town center and acclaimed Woodside Elementary (K-8) School.

A wonderful "Woodside Knolls" home with an ADU/guest house! This property was redone in 2001-2004 as the main house was taken down to the studs and expanded and the ADU/guest house was added then as well. Primary suite is upstairs with views and an additional 3-bd are downstairs with 2-full offices that could be bedrooms as well. Gorgeous backyard with large lawn, expansive patios & verdant vegetable and flowering gardens. The ADU is behind the garage with 2-large front rooms, an eat in kitchen and a full bathroom. Sparkling pool and inground Spa are behind the ADU. 1-acre parcel has both room & privacy!

481 West Maple Way, Woodside is a contemporary gem with awe-inspiring views of the western hills and Crystal Springs reservoir. This home showcases clean lines, soaring ceilings, and an abundance of glass creating a seamless integration with the outdoors. The open-concept layout is ideal for entertaining. A gourmet chef's kitchen with top-of-the-line appliances and a large center island is a focal point. The living and dining areas provide a comfortable and stylish setting from which to admire the view. The master suite is a private sanctuary with a spa-like en-suite bathroom and spacious walk-in closet. The separate studio cottage with full kitchen provides flexibility. Expansive outdoor living spaces include beautiful native plants, a large terrace for al fresco dining, an outdoor living room, soothing hot tub, and putting green. This property combines the best of both worlds serene seclusion and proximity to the vibrant amenities of Silicon Valley and top-rated schools.

Custom rebuilt Hidden Valley / Farm Rd estate will not disappoint! On just over 3.25-acres, this 5,253 sq ft estate home was taken down to the studs, remodeled, expanded and structurally retrofitted over the years. The main residence has a spacious office loft and 4 bedrooms, including a main-level primary suite with 2 couture closet rooms and sumptuous marble bath. The large, detached building with executive office and overhead studio guest house, each with bath and kitchenette. Spacious terrace, pool, and vast stretches of lawn intertwined with walking paths encircling the entire property. Also suitable for up to 6 horses. This magical Woodside area is just minutes to 280, Sand Hill Road, Stanford University, and excellent Portola Valley schools. Luxurious livability, acreage, privacy, and every amenity needed for today.

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.

Fantastic price reduction by $455,000! A Game Changer! This home has always been connected to PUBLIC SEWER SYSTEM-not on septic system), Endless Potential for updating or perfect the way it is! 2,820 sq. ft. MOL, building plans show a rec room downstairs. Home w/high ceilings, big rooms, 3 massive fireplaces, downslope lot w/view of hills, peaceful/secluded. Big 3 car garage + workshop, downstairs, rec room staged as 2nd family room, possible 4th BR, or office, big laundry room + bathroom, could be in-law suite for guests or home schooling, what's your pleasure? Entry level boasts big living room, dining room, kitchen/family kitchen, w/grand fire place, 2 baths & Powder Rm & 3 Bedrooms, Original Owner. Roof is 12 years old MOL, Decks provide views of the hills, front wrap around patio could be changed to lawn, pavers, garden or play area. This property has been lovingly maintained and now ready for your TLC. Surrounded by more expensive Pride of Ownership Homes. A must see!

Interesting opportunity to build on this peaceful, sun-drenched parcel. This land could be a great location for your estate home or quiet get-away. Plenty of room for horses, animals and/or hobby farm, you'll find that you are perfectly situated to access the hiking and riding trails that abound in the open space adjacent to this property. Seller has 2 lots for sale (0-220 and 0-250 Heacox) and the actual address is not yet determined. Land has been surveyed and septic perc tested. Electric pole on site and an old well.

Interesting opportunity to build on this peaceful oak-studded parcel. Sun and shade, flat and grade, seasonal creek, this land could be the location for your estate home or quiet get-away. Room for horses, animals and/or hobby farm, you'll find that you are perfectly situated to access the hiking and riding trails that abound in the open space adjacent to this property. Seller has 2 lots for sale (0-220 and 0-250) and the actual address is not yet determined. Land has been surveyed and septic perc tested. Electric pole on site and area should have plentiful water for a well.

Fabulous new price for this absolutely gorgeous, completely remodeled and upgraded mid-century modern house plus detached guest house set on a mostly level 1.72 acre lot in Woodside that offers much privacy and a large backyard. The main house has five/six bedrooms plus 2.5 baths, plus there is a completely remodeled detached guest house with kitchen, bath, and laundry- total square footage is 4,222 sf. The list of upgrades and amenities is extensive and includes new hardwood flooring throughout, beautiful kitchen, gorgeous landscaping, radiant and conventional heating sytems, a/c, three fireplaces, two 240-volt Tesla chargers, outdoor barbecue area with heaters for comfortable dining, and more. Ample lawn area with room for a pool and sport court. Award-winning Las Lomitas School District. Located on the edge of Atherton, convenient to shopping, Stanford University, 280 and transit.

New Price! Country living at its finest! Welcome to The Lake House. This beautiful, 6 bedroom, 8 bathroom house sits on 4.2 acres with valley views, a private lake along with a private redwood grove. Step into this amazing contemporary country home featuring abundant light, energy efficient metal roof with solar panels supporting tesla power walls, outside gym, dog run, and custom-built tree house. On the main level, there are 3 en suite bedrooms and a separate office, along with living/dining room, eat in kitchen and family room. The lower level offers 3 more bedrooms with a large family/playroom supported by a secondary kitchen area. There are over 4000 sq ft of terraces, with fire pit, for outdoor enjoyment as well as an attached 2 car garage and detached 2 car garage. The private lake is an ideal spot for swimming or fishing. Enjoy the privacy and tranquility of country living, with access to an extensive trail system. Only 3.9 miles from 280. PV schools.

Straight out of a fairy tale, this Woodside estate sits atop over 5 acres of grounds embraced by mature oaks, buckeyes & redwoods. Offering over 3,835 SF of living area & a bonus 1,000 SF of unfinished basement. Huge living room w/ two-story window wall, with views of western hills. The chef's kitchen features professional grade appliances & a central island. A truly great room is graced w/ built-in bookshelves & opens to large entertaining deck with BBQ area. Primary suite offers a fireplace, walk-in closet, sumptuous bath w/ dual vanities, spa tub & separate shower. Bedrooms crowned w/ wood-beamed vaulted ceilings. Award-winning Woodside school district & steps away from the side gate to Wunderlich Park. Large driveway can hold approx. 10 vehicles. Square Footage discrepancy. Lawyer's Title - 3,670 Sq' for home, 219,281 Sq' for lot. Realist - 3,835 Sq' for home, 219,107 Sq' for lot. San Mateo County Assessor - 3,670 Sq' for home, 217,800 Sq' for lot. Lease option to purchase avail.

Competed in 2023, this contemporary Santa Barbara style sits on over 2 acres in Woodside. The house has approximately 4000 square feet of light filled living space with high ceilings and designer details and finishes. , The main level features a primary suite and two additional bedrooms, a large great room with kitchen, and dining and living areas that open to the patio. Upstairs is a family room with skylights and a large balcony, an additional bedroom, full bath and office. The guest house is 1000 sf and features a full kitchen, living/dining room and full bath.