Woodside CA Real Estate & Homes for Sale

Escape to this peaceful and picturesque property with old world charm and modern updates. The elevated lot of approximately 2.41 acres offers sweeping views of the surrounding natural beauty with beautiful 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!

Experience contemporary luxury with awe-inspiring San Francisco Bay views in a retreat setting with pool and hilltop yoga/meditation area. This fully renovated home exudes designer sophistication from a whole-home renovation blending wood, natural stone, and glass to create an organic ambiance. Sustainability shines behind the scenes with newly added solar power, 5 backup batteries and synthetic front lawn plus a dedicated farm area for crops or animals. The interior boasts European white oak floors, ultra-smooth walls, and premium finishes like Dolomite and Italian statuary marble. The open floor plan spans two levels with every room, even the primary suite's closet and bathroom, opening to a deck for fresh-air enjoyment and captivating Bay or western hill views. Located off a private road on more than 2.5 acres, this homes location is superb just 4 minutes from the town center, renowned Woodside School, and Highway 280 with access to Silicon Valley and San Francisco.

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.

The perfect combination of heritage redwoods and open sunny meadow provide the ideal backdrop for the authentic barn-style home. Although rustic on the outside, it is truly modern inside. This country home lives in the present, with high-end appliances, beautiful appointed bathrooms with great attention to the use of space. Features include a large family kitchen with both dining and sitting areas, a separate living room and huge multi-purpose room. The private, spaciouse master suite features rustic rough beam trusses and Australian cypress floors. The Modern Treehouse was built by Dustin Feider and his team at O2 Treehouse who have installed bespoke treehouse creations all over the world and has been featured on NBC Nightly News, Weird Homes and Australian channel 7 and features 12V lighting, a pull-out sofa bed with a queen-size memory foam mattress, and a composting toilet. There is also an additional ~1700 sq ft barn/workshop, a playhouse and chicken coop.

Presiding over a glorious 1.36 +/- acre parcel with panoramic vistas, this quintessential Woodside Hills property provides an exciting opportunity to remodel and expand the existing 3 bed/2.5 bath residence, or design and build a sophisticated new estate in one of the most desired communities on the Peninsula. Rising gently from the street, the property climbs to a virtually flat building pad, allowing for privacy and the ability to maximize the sweeping bay, bridge, and hill views. The home is primely positioned to take advantage of the lots topography and is imbued with a sense of scale and volume, from the exposed beam vaulted ceiling and wall of windows in the living room, to the large bathrooms and closets in the two primary suites. While the neighborhood maintains a rural and genteel ambiance, the property enjoys proximity to downtown Menlo Park and Redwood City, acclaimed public and private schools, and commute routes to major employers. Realize your dream here!

Woodside Hills home has always been connected to PUBLIC SEWER SYSTEM-was never on septic system), Endless Potential for updating or perfect the way it is! 2,820 sq. ft. MOL, & building plans show a recreation room downstairs. Home has high ceilings, big rooms, 3 massive fireplaces, downslope property w/view of rolling hills, peaceful/secluded. Big 3 car garage + workshop, downstairs, recreation 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 or imagination? Entry level boasts big living room, dining el, kitchen/family kitchen, w/grand fire place, 2 baths & Powder Rm & 3 bdrms, Original Owner selling it, 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.

PRICE REDUCED...Enjoy the relaxing ambiance of this custom home located in the redwoods above Woodside. This beautiful residence and its' surrounding garden is a perfect place for tranquility. Tastefully updated, home rests on .88 acres. Natural illumination from large windows & skylights flood the home in beautiful light. An open concept main level floor plan creates gathering areas that connect seamlessly to the chef-inspired kitchen featuring a suite of stainless appliances including a 48" Thermador range. Harwood floors run throughout the 2 level home & high, open beam ceilings accentuate this outstanding residence. There is an en-suite bedroom on the main floor, 3 additional bedrooms on the 2nd floor along with a stunning bath. A spacious family room, separate mudroom, laundry & surrounding decks are all additional features of this hi end home that is surrounded by a beautiful garden. Charming separate Artist studio, large decks, basement, storage sheds too. Seller is the Agent.

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.

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. Originally designed by Architect John "Jack" Kruse, this unique mid-century modern home was built to high specifications. 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.

Beautiful mountain home on private 5 acre parcel with partial bay views. Great room with vaulted open beam ceiling & fireplace. Bright gourmet kitchen with top of the line stainless steel appliances, skylights & beverage coolers. The adjoining dining room is large & has a fireplace. Huge downstairs family room with bathroom & exterior door to the patio. 3 nice large bedrooms with exterior doors. Laundry room has work areas & lots of storage. There are hardwood & tile floors & beautiful natural wood paneling throughout. Generous mix of trees & hiking trails on the property. Parks & open space is nearby & abundant. Located within the top rated Portola Valley School District with local bus service & Woodside High School. Several outdoor decks & patios surrounded by the serene greenbelt. Too many nice features to list. Short walk to Wunderlich Park, Alice's Restaurant, & Skywood Trading Post. 10 minutes to Robert's Market & 280. 15 minutes to the ocean. Owner may consider well behaved pets

Nestled on 2.6 gentle sloping acres w/meadows & big sky view! This beautiful architecturally stunning home with contemporary features like walls of windows and soaring exposed beam ceilings faces west and the pacific ocean in the distance. Lots of sunlight fills not only the home but the 2.6 acres are a delight and very usable. Solar makes this another reason to keep this home at the top of your "must see" houses while looking. The open floor plan is defined by soaring exposed beam ceilings, walls of glass & gleaming hardwood floors. Bottom floor boasts a home office, wine/tech rm and another living room and full bath. Also 1440 Sf finished barn/work with 240V wiring, 3 horse stalls & room for multiple cars... bring your passion... this is the place!

Welcome to this craftsman style oasis just 10 minutes from hwy 280! This quality owner/architect well built home is nestled among the redwood trees offering a tranquil retreat from everyday living. Vaulted Ceilings, hardwood and tile floors throughout w/ 9 zones of hydronic heat and 2 wood burning fireplaces. The primary suite has a steam shower, whirlpool tub & 2 walk-in closets. This home comes complete with an Endless pool swim spa, using electricity for heat so you can enjoy it year round! Plus, this fairly flat lot that is nearly one acre provides plenty of outdoor space to explore your very own slice of nature. Large ADU over garage, with separate entrance, & a full bath was permitted as an architect's studio/office. This house has a fire sprinkler system, a security system and whole house automatic backup generator. With proper permits this home could be converted to a 5 bedroom. Don't miss out on this incredible opportunity. Call today for a showing!

New Price! 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, and still be able to quickly access the flats - only 3.9 miles from 280. PV schools.

Welcome to The Barrel House. This distinctive property was built in 1973 and designed by Sidney Hoover, a distinguished local architect that was influenced by Frank Llyod Wright. The private two-story home boasts three bedrooms and two and a half baths along with an ADU which is attached to a two-car garage. The inspiration for this home came from the beauty of four enormous redwood water barrels that were used as the cornerstones of the residence. The abundant natural light is drawn through massive windows and skylights throughout to give you the feeling of living in the forest. An abundance of trees are scattered across the beautiful 1+acre parcel. The quiet serenity of the property is enhanced by the location which is accessed by a flag lot lane. The home is within a short distance to Woodside Elementary School and the Town Center for upmost convenience. If you have ever envisioned living in nature The Barrel House could be your dream come true!

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.

Enjoy a peaceful oasis nestled among redwood/Douglas fir forests, with hiking trails along Skyline and to the coast. Enjoy views of the hills and Half Moon Bay while you cook in the remodeled kitchen with granite cabinet tops, gas stove, big windows & and a skylight, or relax in the living room by a wood burning stove. The open floor plan flows from entry to kitchen or living room into an additional office/bedroom, all anchored by a balcony that spans the entire width of the home. A full art deco style bathroom completes this level. The lower level opens to a work/office area that leads to a 28 x 14 primary bedroom with a gas fireplace at one end and doors to a full width, wrop around deck at the other. A large walk-in closet and custom bathroom with heated floor complete the lower level. A 3rd, lower balcony provides a large storage shed and additional storage space. Kings Mountain Elementary School, a California Distinguished School, is just down the Road at 11 Swett Road.

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.

Nestled among oak trees, this Woodside Glens home is tucked away on nearly half an acre at the end of a quiet cul-de-sac. This move-in ready home features abundant natural light and forest views from every room. The main level has three bedrooms and two bathrooms. The lower level includes rooms for an office, fitness/play space and laundry. Highlights include hardwood floors, updated kitchen with stainless steel appliances, dedicated off-street parking and sunny spaces for flower/vegetable gardens. Enjoy the relaxed California indoor-outdoor lifestyle with a spacious deck off the main living area, with views of the propertys seasonal creek and trail access to Joan Olson Natural Preserve. This magical woodland retreat is conveniently located within walking distance to Woodside Village and the award-winning Woodside Elementary K-8. It is excellently positioned for commutes to SF and Silicon Valley, with I-280 just minutes away.

First time on the market! On Woodside's most prestigious street, a stone's throw to town and school. This home is at the highest point on Olive Hill Lane offering bay views. This French Provincial inspired home is firmly rooted in natural California aesthetics. Perfectly situated in complete privacy on over 3 acres in an extraordinary setting. **more interior photos coming soon

Price Improvement! Amazing Opportunity to Own Your Private Estate! This property offers almost 5 acres to build your dream home, agricultural project, or explore the many other possibilities that a Resource Management zoned property provides. It includes paved road access and is surrounded by other spacious estates that are bordered on all sides by Open Space and Heacox Road. If you are looking for serenity, you will find it here! It's located near Skyline and approx. 20 minutes from Highway 280. Buyer to confirm all remarks and usability with the San Mateo County Building and Planning Department.