Woodside Real Estate

Woodside: A Serene Escape in San Mateo County, California

Nestled in the picturesque San Mateo County, California, lies the charming town of Woodside. Known for its tranquil ambiance and natural beauty, Woodside offers a serene escape from the hustle and bustle of city life. With its close proximity to Silicon Valley and San Francisco, this hidden gem provides the perfect balance between a peaceful retreat and convenient access to urban amenities.

Woodside boasts a rich history, dating back to the mid-19th century when it was established as a logging community. Today, the town embraces its heritage with a blend of historic architecture and modern amenities. The community takes pride in preserving its rural character, with strict zoning regulations that ensure the preservation of the town's natural landscapes and open spaces.

Nature enthusiasts will find themselves at home in Woodside, as the town is surrounded by breathtaking natural beauty. The nearby redwood forests, rolling hills, and scenic trails offer endless opportunities for hiking, biking, and horseback riding. The iconic Wunderlich County Park is a local favorite, offering over 1,900 acres of pristine wilderness to explore.

Woodside also boasts a vibrant equestrian culture, with numerous horse trails and equestrian facilities. The town is home to prestigious equestrian events, attracting riders and enthusiasts from all over the country. Whether you're an avid rider or simply appreciate the grace and beauty of horses, Woodside is the perfect place to indulge your equestrian passions.

In addition to its natural wonders, Woodside offers a range of cultural and recreational activities. The town features a variety of art galleries, boutique shops, and gourmet restaurants, providing residents with a diverse array of experiences. The local community center hosts regular events and classes, fostering a strong sense of community and camaraderie among residents.

With its idyllic setting, strong sense of community, and convenient location, Woodside is a highly sought-after destination for those seeking a peaceful and luxurious lifestyle. Whether you're looking for a weekend getaway or a permanent residence, Woodside offers the perfect blend of tranquility and accessibility.

Newest Listings in Woodside

$1,475,000

3 Beds ⋅ 2 Baths ⋅ ML81982613 MLS

Mountain Retreat with Valley Views, Ultimate Privacy, and Open-Concept Living! This 3-bedroom, 2-bath home offers the best of both worldsclose enough for a quick Silicon Valley commute, yet it feels like a secluded mountain escape. The open-concept design connects the kitchen, dining, and living spaces, creating an airy flow perfect for relaxing and entertaining. Enjoy stunning valley views from the kitchen, living room, upstairs bedroom, and spacious decks. The largest bedroom, with a private entrance, offers ADU potentialideal for a guest suite, rental, or a teens private space.The sun-drenched backyard features mature oaks, fruit trees, berry bushes, a greenhouse, and irrigated planting beds. The front yard, with a redwood ring and native plants, enhances the peaceful retreat feel. Inside, the home boasts updated bathrooms, wood floors upstairs, and heated tiles in the downstairs bedroom and bath. Skylights and double-pane windows fill the home with light, while fresh paint and newer decks make it move-in ready. Walking distance to Skywood Trading Post and Alices Restaurant, this home has a small-town vibe. With top-rated Portola Valley schools and nearby trails, and only 25 minutes from the beach, its a perfect blend of nature and convenience.

12 Skylonda DR, Woodside

Listed by Scott Hayes, 650-245-5044 from Compass
(If provided) CoList: from

$490,000

ML81981105 MLS

Nestled amidst the estate-like homes of Woodside, this nearly 4-acre parcel offers a serene, secluded retreat. The location is incredible - less than 10 minutes away from Hwy 280 and the business world along Sand Hill Road and only 10 minutes from the hilltop restaraunt - Alices Restraunt. The property is accessed via a private shared road that brings you into the core of this gently sloped land, surrounded by towering redwoods and a tranquil seasonal creek. With ample potential for your own Retreat, Glamping / Campsite, Mountain Biking / Off Road Trails, RV Getaway, an Artists haven or just creating a peaceful weekend getaway - this land offers endless possibilities. With Silicon Valleys tech hubs, Stanford University, & premier shopping within minutes, this location is ideal. The property also falls within the coveted Portola Valley School District & Woodside High School. This rare opportunity invites a visionary buyer to bring their creativity to life in one of San Mateo Countys most secluded yet reasonably distanced areas. Text Joseph Suarez for video tour of property.

446 Old La Honda RD, Woodside

Listed by Joseph Suarez, 650-678-7056 from Christie's International Real Estate Sereno
(If provided) CoList: Philip Watson from Christie's International Real Estate Sereno

$10,495,000

4 Beds ⋅ 4 Baths ⋅ ML81981937 MLS

Just-completed one-level vineyard estate with San Francisco Bay views. Built with natural stone walls inside and out and vaulted all-wood ceilings in every room. Nearly every room has French limestone floors, cabinetry is waterfall-wrapped in natural quartzite, and handcrafted iron doors are inspired by Tiffanys in New York. Unique see-through wine cellar upon entry, formal dining room opens to a waterfall wall, and stunning great room for entertaining. The primary suite has a couture closet room and spa-inspired bath. There are 4 bedrooms and 3.5 baths in the main home plus 2 bedrooms and 1 bath in the updated original guest house with full kitchen. Outdoor living spaces are spectacular with a zero-edge pool and spa, kitchen/dining lounge with pizza oven, vast eco-friendly lawn, fire pit terrace, and bocce court in the vineyard. Exceptional dog run and custom tortoise enclosure for the animal lover. Square Footage Breakdown: Main Residence: 4,887 | Garage: 782 | Guest House: 1,184 | Total: 6,853. Buyer to verify.

2195 Greenways DR, Woodside

Listed by Mary & Brent Gullixson, 650-888-0860 from Compass
(If provided) CoList: from

$1,650,000

ML81981635 MLS

Ideal setting to build your dream home. Large 3000 sq. ft metal shop on site. Building sites for house, guest house, and barn. The most spectacular views in all directions and total privacy. Minutes to Skylonda center and Alices restaurant. Quiet setting off highway 84 on a quiet country lane. These sites rarely come available in this premium location with views and privacy.

12725 Old La Honda RD, Woodside

Listed by Scott Dancer, 650-888-8199 from Compass
(If provided) CoList: from

$759,845

ML81981564 MLS

Excellent opportunity to build on this peaceful parcel. Artist's rendering of home. 4000 ft2 home deemed possible by Lea and Braze engineers; price includes feasibility study, survey and septic perc test results. 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. You to dig a well (plentiful water here) and add septic system. Seasonal creek and temperate climate.

0-250 Heacox RD, Woodside

Listed by Kimberly Hansen, 415-806-8230 from Golden Gate Sotheby's International Realty
(If provided) CoList: from

$799,845

ML81981563 MLS

Excellent opportunity to build on this peaceful, sun-drenched parcel that has nice flat area for development. Artist's rendering of home. 3800 ft2 home plus 1000 ft2 ADU deemed possible by Lea and Braze engineers; price includes feasibility study, survey and septic perc test results. 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. Old well on-site (plentiful water here), you add septic system. Invest in your future!

0-220 Heacox RD, Woodside

Listed by Kimberly Hansen, 415-806-8230 from Golden Gate Sotheby's International Realty
(If provided) CoList: from

$2,100,000

3 Beds ⋅ 4 Baths ⋅ ML81973577 MLS

"Discover this rustic log cabin-style home nestled among the towering redwoods. Spread across two levels, this enchanting property features three bedrooms and 3.5 baths. Skylights flood the interior with natural light, while wood floors and a grand stone fireplace create a warm and inviting ambiance. Step out onto the beautiful deck with forest views, establishing a cozy and private retreat. The .85 acre lot, comprising 3 merged parcels(075-092-040, 075-092-050, 075-092-0600 slopes down to a tranquil creek. The great outdoors beckons with multiple usable areas, perfect for relaxation or entertaining. And with numerous open space trailheads accessible off Skyline Boulevard, you'll have plenty of opportunities to explore natures beauty. Conveniently located near Alices Restaurant, its just a 13-minute drive to Highway 280, 20 minutes to Stanford University or the San Mateo coast. Dont forget the excellent Portola Valley Schools!"

139 Redland RD, Woodside

Listed by James Milton, 650-868-1356 from Coldwell Banker Realty
(If provided) CoList: from

$18,500,000

5 Beds ⋅ 6 Baths ⋅ ML81981274 MLS

Stunning Custom Built 3 Level Home with Guest Cottage and Pool on 4.37+/- Acres with Stables and Riding Ring on Private Cul-de-Sac in Central Woodside. 5 Bedrooms. 5.5 Bathrooms. Living Room Features Vaulted Ceilings, Wood Floors, and Floor-to-Ceiling Windows. Spacious Kitchen with Large Island, Peninsula and Views of the Pool and a Pond. Intimate Family Room with Sliding Glass Doors to Pool. Library with Fireplace. Wine Room, 3 Laundry Rooms, and Large Fitness Area with Sauna and Steam Room. Outdoor Cold Plunge. Three-Car Garage. Ipe Decking, Pool, Large Pool House, and Outdoor Kitchen. Guest Cottage. Sand Riding Arena and Horse Stables with 8 Stalls and Loft. Situated Hillside for Amazing Views.

3 Vintage CT, Woodside

Listed by Keri Nicholas, 650-533-7373 from Parc Agency Corporation
(If provided) CoList: from

$1,199,000

2 Beds ⋅ 1 Baths ⋅ ML81980445 MLS

Welcome to this charming Woodside home, cradled amongst a cathedral of Redwood trees, and loaded with character. Enjoy the relaxing ambiance of this home, featuring Pella windows, vaulted wood ceilings, skylights, and pine wainscoting. With the perfect balance of updated convenience and country charm, this lovely home boasts an open kitchen with an adjacent dining nook, a loft perfect for storage, guests, or office, and a living room with vaulted ceiling, perfect for curling up by the wood burning stove. Outdoor eating area, flagstone patio w/arbor, built-in benches, large shed, extra storage, detached garage

144 Creek TRL, Woodside

Listed by Ed Gory, 650-743-7645 from Intero Real Estate Services
(If provided) CoList: from

$1,988,888

4 Beds ⋅ 3 Baths ⋅ ML81979968 MLS

Nestled in a serene redwood grove in the hills above Woodside, this 4-bedroom, 2.5-bath home offers a tranquil retreat with modern convenience. Set on a spacious mostly level 1/2-acre, this property blends the beauty of nature with sophisticated living. The open concept living area features vaulted ceilings, large windows, & a cozy fireplace, filling the space with natural light and framing breathtaking views of the towering redwoods. The kitchen boasts stainless steel appliances with granite countertops. The primary suite offers a private sanctuary with two story cathedral windows looking out onto the private back yard. Adjacent to it is an enclosed downstairs porch with a built-in hot tub with 3 additional bedrooms providing ample space for guests, or a home office. Outside, the half-acre lot offers endless opportunities for relaxation & recreation, with pathways, fruit trees a garden area and plenty of space to create your vision. Located just a short drive from the city, this home provides the perfect balance of seclusion and convenience, offering a unique lifestyle for those who value nature and privacy without sacrificing proximity to urban amenities. A rare find in the Bay Area, this home invites you to experience the perfect blend of rustic charm and modern luxury.

8 Big Tree WAY, Woodside

Listed by Brian Dakin, 650-483-5760 from Compass
(If provided) CoList: from

$159,000

ML81979482 MLS

This is it! Your meditation getaway retreat is waiting with a vision! Approximately 2 acres of Peacefulness and Tranquility describe this unique location on Kings Mt in Woodside. Refresh your inner senses among glorious redwoods, spectacular views, and serene moments that can capture the feel of being in a remote mountain area while being a short distance from the hustle and bustle of everyday life. A pathway leads to a deck overlooking the Purisima Canyon. The trail extends past the deck, through the redwood forest to an amazing rock outcropping, onward to a higher clearing, and then to your own Heritage tree that is over 500 years old! A short walk down the road takes you into miles of Open Space trails through an entrance that is for designated locals use. Perfect for the hiker and/or biker, that is a place to enjoy the summer weather. The views of the coast are breathtaking! Such a great location comes with a caveat. This is currently an unbuildable residential parcel, however stairs, a small deck, and trails already exist. You cannot drive up into the property, but parking is at the base of property .If you use your imagination, it's a hideaway that is yours to keep !!!!

000 Purisima RD, Woodside

Listed by Dante Razzini, 650-868-2593 from Intero Real Estate Services
(If provided) CoList: from

$2,699,000

4 Beds ⋅ 2 Baths ⋅ ML81978313 MLS

Situated in a tranquil yet accessible location, this Woodside home seamlessly combines comfort with modern design. Gleaming hardwood floors and fully remodeled features add a contemporary flair, while expansive windows and glass doors capture breathtaking views of the surrounding landscape. The large deck is ideal for entertaining, enhanced by the calming sounds of a nearby seasonal creek, creating a serene escape. Located in a charming country setting, the property offers direct trail access to Woodside Village, just over a mile away, and falls within the highly regarded Woodside Elementary School district. Ideally positioned between San Francisco and Silicon Valley, this home provides a truly exceptional living experience.

136 Otis AVE, Woodside

Listed by Chris Budelli, 650-714-4167 from Christie's International Real Estate Sereno
(If provided) CoList: from

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The data relating to real estate for sale on this display comes in part from the Internet Data Exchange program of the MLSListingsTM MLS system. Real estate listings held by brokerage firms other than Intero Real Estate Service are marked with the Internet Data Exchange and detailed information about them includes the names of the listing brokers and listing agents.
Based on information from MLSListings MLS as of . All data, including all measurements and calculations of area, is obtained from various sources and has not been, and will not be, verified by broker or MLS. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.