Woodside Real Estate

Welcome to Woodside, California, a picturesque gem nestled in the heart of San Mateo County. Known for its stunning natural beauty and serene atmosphere, Woodside offers an idyllic retreat from the hustle and bustle of city life while still being conveniently located just a short drive from the vibrant urban centers of Silicon Valley and San Francisco.

With its sprawling estates, lush forests, and rolling hills, Woodside is a haven for nature lovers and outdoor enthusiasts. The area boasts an extensive network of hiking and biking trails, including the scenic Woodside Trail, where residents can immerse themselves in the breathtaking landscapes and enjoy the tranquility of the great outdoors. The town is also home to a variety of parks, such as the beautiful Huddart Park, which features picnic areas, horseback riding trails, and stunning redwood groves.

Woodside is not just about natural beauty; it also has a rich cultural heritage. The town is known for its historic architecture and charming downtown area, where you can find delightful boutiques, gourmet restaurants, and local art galleries. The community is tight-knit and friendly, making it an ideal place for families and individuals looking to settle down in a welcoming environment.

Education is a priority in Woodside, with access to top-rated schools that provide students with a strong foundation for their future. Whether you’re seeking a peaceful place to raise a family or a serene escape from the fast-paced world, Woodside, CA, offers the perfect blend of luxury, nature, and community spirit. Explore the possibilities of calling Woodside home, and experience the magic of this enchanting town for yourself!

Newest Listings in Woodside

$3,489,000

4 Beds ⋅ 3 Baths ⋅ ML82062642 MLS

Beautifully updated interiors & striking architectural character define this exceptional home in the Glens newly built in 2007. Tucked away at the end of a peaceful cul-de-sac just one mile from the Woodside town shopping & acclaimed restaurants as well as the highly rated TK-8 Woodside Elementary school. Framed by custom Corten-style fencing, terraced gardens, & underground utilities rarely found in this neighborhood, the property presents an added sense of privacy & refinement. Freshly painted interiors & hardwood floors introduce warm, inviting spaces filled with natural light. Original architectural details are complemented by contemporary finishes, custom cabinetry, granite surfaces, & expansive windows & sliding glass doors opening to the outdoor living areas. Cathedral ceilings enhance the open-concept design, creating wonderful scale for everyday living & entertaining. Flexible floor plan, spacious primary suite with fireplace, customized walk-in closet, & newly finished bath. There is also expansion & ADU potential (subject to Town approval & applicable development standards). Fully fenced front & rear yard offer expansive areas for entertaining & relaxation with a level rear lawn, expansive deck, paver stone terrace, & large spa, all in a tranquil park-like setting.

63 Ridge CT, Woodside

$5,690,000

2 Beds ⋅ 2 Baths ⋅ ML82062379 MLS

This beautifully appointed residence blends warm natural materials with abundant windows and effortless indoor/outdoor living, on one of Woodsides most desired streets/locations. Expansive decks provide multiple areas for dining, entertaining & relaxing while overlooking the Cabernet Sauvignon vineyard. Stunning living room with vaulted wood beam ceilings, wood burning fireplace & wall of glass overlooking the vineyard. Separate family room features recessed lighting & gorgeous built-ins. Kitchen features Miele built in oven, Thermador gas cooktop, dishwasher drawers, & a glass door refrigerator. The serene primary suite features custom built-ins, a window seat, walk-in closet, private deck access w/hot tub & a beautifully detailed bath with dual vanities and freestanding soaking tub.Additional bedroom features a built-in desk and a sliding glass door to the deck. Separate den, office or wine room with wet bar & sliding doors to the back deck.Terraced gardens, level side and rear lawns, and raised beds for vegetables bring forth ultimate usability throughout the grounds.Mature landscaping and a striking outdoor water feature complete this extraordinarily peaceful setting.A rare opportunity to experience the privacy & natural beauty that define Woodside living in an A+ location.

1100 Mountain Home RD, Woodside

$7,295,000

5 Beds ⋅ 4 Baths ⋅ ML82062065 MLS

An extensive remodel completed in 2023 transformed this classic New England Colonial with designer style and a fresh approach to modern living. The remodeling went well beyond new finishes, with the floor plan reconfigured to add a main-level bedroom and full bath for a total of 5 bedrooms and 4 baths. The kitchen and dining area were completely transformed with an open design and commercial-quality appliances, while all new windows, glass doors, and recessed lighting enhance the ambiance and connections to the surrounding three-acre grounds. Significant infrastructure improvements were completed as well, including upgraded electrical, new HVAC, a tankless water heater, earthquake retrofitting, and new irrigation.The setting is equally impressive with mostly level grounds, a 5-stall -1700 square foot barn, with hayloft and tack room, vast stretches of lawn, a newly fenced yard, and expansive brick terraces for outdoor living and entertaining. There is also a separately fenced and newly resurfaced pool featuring a 75-foot lap lane, elevated spa, and new owned solar heating system, plus equestrian facilities that include a 5-stall barn with paddocks. A detached 2-car garage with 2 EV charging outlets adds further convenience. Wonderful location close to Woodside and PV Town Centers

1543 Portola RD, Woodside

$5,988,000

5 Beds ⋅ 4 Baths ⋅ ML82062056 MLS

Set on a private acre in Woodside Hills, this exceptional midcentury residence offers more than 4,600 square feet of living space, spectacular Bay views, and a wonderful connection between indoors and out. Walls of glass, hardwood floors, and expansive living areas create a distinctive setting, complemented by two fireplaces and a stylish kitchen with black granite and appliances from top brands. The family room provides a comfortable gathering space, while five bedrooms plus an office offer flexibility for family, guests, and work. Multi-level grounds showcase the views with a large deck, inviting pool, and broad lawn, creating an ideal setting for entertaining and everyday enjoyment. Conveniently located near shops, restaurants, parks, nature preserves, and Interstate 280, the home is also just five minutes from acclaimed Woodside High School (buyer to verify eligibility).

160 Crest RD, Woodside

$2,100,000

3 Beds ⋅ 3 Baths ⋅ ML82056662 MLS

Perched high along Skyline Boulevard on 2.67 acres, this exceptional mountain retreat offers sweeping 180-degree views stretching from San Francisco to San Jose. Surrounded by the natural beauty and serenity of the Santa Cruz Mountains, its an ideal sanctuary for remote work, writing, creative projects, or simply escaping the everyday. Built in 2007, the 2,180-square-foot home features 3 bedrooms and 2.5 baths, with expansive walls of glass that flood the living spaces with natural light. Warm straight-grain fir trim and custom baseboards add timeless character throughout. The open floor plan flows onto a spacious view deck with hot tubperfect for sunset relaxation or casual entertaining. An outdoor shower makes returning from a morning hike or gardening especially refreshing. Practical amenities include a private well, backup generator, and attached 2-car garage with covered breezeway. Enjoy exceptional privacy and mountain tranquility while remaining connected to the Peninsula, with Stanford roughly 20 minutes away and easy access to Woodside, Portola Valley, and beyond.

20421 Skyline BLVD, Woodside

$599,999

2 Beds ⋅ 1 Baths ⋅ ML82061335 MLS ⋅ Kings Mountain Association BLDG.

This 2-bedroom, 1-bath home in Woodside offers 1,110 square feet of comfortable living space. The updated bathroom features a stall shower and tile finishes. The kitchen includes an electric oven range, dishwasher, refrigerator, and a 220-volt outlet, with an eat-in area for casual dining. Flooring throughout combines hardwood and carpet for a balanced look. A separate family room provides additional living space. Additional features include a skylight that brings natural light into the living areas. A one-car garage adds to the functionality. This property falls within the Cabrillo Unified elementary school district. HOA is in the process of putting on a new roof, so home is under contruction. This is a shortsale home and will take a minimum of 3 to 6 months(minimum) for bank approval. This purchase is not for a buyer who might be in a hurry as we have two loans to get short-sale approval. Inspections will need to be done by buyers. Bank will NOT have any inspections.

14826 Skyline BLVD 3, Woodside

$65,000,000

5 Beds ⋅ 6 Baths ⋅ ML82032838 MLS

Completed in 2023 on Woodside's most premier central corridor, a Cul De Sac off Mountain Home Road. This 3 acre Tuscan inspired estate property is a masterpiece of design that blends the finest materials from around the globe. Breathtaking displays of quartzite evoke artful elegance, while floors of marble and French oak exude timeless sophistication. Every detail is crafted with precision- French oak cabinetry, ceilings, and trim, coupled with Venetian plastered walls in the grand public rooms, softly illuminated by chandeliers from Spain. Designed to perfection for today's lifestyle, the great room serves as the heart of the home, offering a magnificent kitchen with a seamless flow to the loggia and vast private grounds. Five bedroom suites, including both main and upper level primary suites, provide ultimate flexibility and privacy. The guest house mirrors the main residence's impeccable standards, complete with a full kitchen, bedroom, two baths, and sauna. The estate's grandeur extends outdoors with a wrap around loggia with fireplace, 60 foot pool and spa with canopy jets, fully fenced tennis court, expansive lawns and meadows. Located in one of the country's most exclusive Silicon Valley zip codes, nearby Venture Capital hub Sandhill Road, Stanford Univ. & Silicon Valley.

7 Blue Ridge LN, Woodside

$6,880,000

5 Beds ⋅ 4 Baths ⋅ ML82056698 MLS

Elegant Woodside living in an exceptionally spacious and versatile 5-bedroom, 3.5-bath residence bordering Atherton. A gracious formal entry opens to the inviting living room with a fireplace and adjoining formal dining room, creating an ideal setting for entertaining. The gourmet eat-in kitchen features a generous center island, breakfast bar, premium appliances, and abundant workspace, and opens to a spectacular family room with soaring vaulted ceilings and a second fireplace. Three bedrooms are located on the main level, including a luxurious primary suite with a private fireplace, a walk-in closet, and a beautifully appointed en-suite bath with dual vanities. The lower level offers two additional bedrooms, an office/den, a large recreation room, a wine cellar and tasting room, and a flexible exercise space. Beautifully landscaped grounds extend the living experience outdoors, with a sprawling lot, an inviting patio, and a BBQ area, perfect for relaxed gatherings and outdoor entertaining. This exceptional residence offers a rare combination of elegance, scale, versatility, and indoor-outdoor living. Bordering Atherton, a coveted location, close to shopping, parks, great schools, and near commute routes. Welcome Home!

2120 Stockbridge AVE, Woodside

$1,950,000

3 Beds ⋅ 3 Baths ⋅ ML82059245 MLS

Skyline corridor on nearly one-half acre with spectacular unobstructed ocean views and easy access to both the Peninsula and the coast. The two-story floor plan features vaulted beamed ceilings, angled transom windows, and abundant natural light. The main level has a spacious living room with fireplace, dining area opening to the view deck, an updated eat-in kitchen, plus the primary suite, two additional bedrooms, and a bath. The lower level includes a large family room with fireplace and wet bar, full bath, laundry room, and access to the 2-car garage. Detached bonus studio with wet bar and bath provides flexible space for guests, office, or hobbies. Expansive wraparound deck with ocean views plus covered and open patios extend the living space outdoors. Just one-half mile from a trailhead to Purisima Creek Redwoods Preserve with miles of hiking and equestrian trails, 5 miles to Highways 92 and 8 miles to Highway 84 for access throughout the Peninsula and to the coast. Excellent Kings Mountain Elementary School.

115 Forest View RD, Woodside

$3,389,000

3 Beds ⋅ 2 Baths ⋅ ML82059026 MLS

There is a particular quiet at 411 Glenwood Avenue. Stand on the main level and look through walls of glass. The first thing you notice is the treetops. The second is what you do not see: neighbors. The Oak canopy and the open expanse of the Joan Olson Preserve fill the windows instead. Friends who visit call it the Treehouse. Built in 1959, the home keeps its mid-century bones: mahogany paneling, a brick fireplace, and warm cork and hardwood floors. The kitchen opens to the great room, with stone counters and a gas cooktop. Walls of glass open onto a broad deck for slow dinners, the preserve as backdrop. Upstairs, the bedrooms share that same treetop view. Downstairs adds real flexibility: an open room with a slider to a flat, green yard, suited to an office or playroom, an en suite bedroom with its own patio, plus laundry and storage. Cross the street and you are on a trailhead into the preserve, a shortcut into downtown Woodside on foot, coffee in hand, oaks the whole way. Downtown, with the Village Bakery, Buck's, and Highway 280, is minutes out. The home sits within the highly rated Woodside Elementary School District, TK - 8. 411 Glenwood does not ask you to choose between nature and convenience. It offers both, as the best Woodside properties do.

411 Glenwood AVE, Woodside

$2,299,000

4 Beds ⋅ 3 Baths ⋅ ML82058136 MLS

Panoramic Views, Absolute Privacy Perched high above the valley on over six acres, this rare 4-bedroom, 3-bath mountain sanctuary pairs total seclusion with sweeping, unobstructed views stretching clear across the Bayfrom vibrant sunrises over the water to shimmering city lights at night. Inside, three thoughtfully designed levels of living space are anchored by soaring ceilings, expansive glass, and two cozy wood-burning fireplaces. The main floor centers around a functional kitchen with a central island and walk-in pantry, opening directly to a multi-level wraparound deck designed for effortless indoor-outdoor living and scenic dining. The layout includes a primary suite positioned to capture morning light, complete with an oversized bath and walk-in closet. Three additional bedrooms feature a built-in loft, a walk-in closet, and a ground-floor room with private outdoor entry ideal for a peaceful home office. Sprawling level lawn areas, mature trees, and a hot tub set for stargazing complete the grounds. Extras include an attached 2-car garage, large utility room, ample parking, Jackery backup battery, and a Tesla EV charger. Located minutes from trailheads, preserves, central Woodside, and I-280-a high-elevation retreat moments from Silicon Valley.

255 Allen RD, Woodside

$14,900,000

7 Beds ⋅ 9 Baths ⋅ ML82057953 MLS

A rare, fully realized legacy compound offering the soul of a European retreat in the heart of Woodside. Hidden within 3.2 acres of curated gardens and ancient oaks, this meticulously renovated sanctuary blends old-world artistry, artisan tile, and beamed ceilings with the peace of mind of enterprise-grade infrastructure. The grounds are a private resort masterpiece designed for serene living, anchored by a rare clay tennis court, a waterfall grotto, a pool and spa, a pitch-and-putt green, and a bocce court. The main residence features four refined suites, a professional grade kitchen, a magnificent wine cellar,and a private executive office. Multi-generational living is perfected with a 2-bedroom family cottage, a 1-bedroom guest house, and a detached fitness center with sauna and Tonal strength training equipment.Beyond the charm, the estate offers total autonomy with redundant internet access, a backup generator, and advanced surveillance. This is the ultimate turnkey acquisition: an impossible-to-replicate blend of character and modern high-performance living, perfectly positioned minutes away from Silicon Valleys entrepreneurial eco-systems most iconic hubs.

600 Moore RD, Woodside

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