Woodside Homes for Sale

Woodside Homes for Sale

Welcome to Woodside, California – a hidden gem nestled in the heart of San Mateo County. Known for its picturesque landscapes and serene atmosphere, Woodside offers a unique blend of rural charm and suburban sophistication. This enchanting town is characterized by its sprawling estates, lush greenery, and a strong sense of community, making it an ideal place for families, professionals, and nature lovers alike.

With a population of just over 5,000 residents, Woodside boasts a quaint, small-town feel while still being conveniently located near the bustling cities of San Francisco and Silicon Valley. The area is renowned for its excellent schools, making it a sought-after destination for families looking to provide their children with a top-tier education. Outdoor enthusiasts will appreciate the abundance of hiking and biking trails, including the stunning vistas of the nearby Huddart Park and the scenic beauty of the Woodside Trail.

For those considering a move to this idyllic locale, the real estate market in Woodside is vibrant and diverse. Homes for sale range from charming cottages to luxurious estates, each offering a unique character and style. Many properties feature expansive lots, providing ample space for gardens, outdoor entertaining, and even equestrian pursuits. With a strong sense of community and a commitment to preserving the natural beauty of the area, Woodside is more than just a place to live – it’s a lifestyle.

Explore the homes for sale in Woodside today, and discover the perfect sanctuary that awaits you in this enchanting California town. Your dream home is just a heartbeat away!

Newest Woodside Homes for Sale

$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 Lane, Woodside

Listing courtesy of Listing Agent: Steve Lessard (steve.lessard@compass.com) from Listing Office: Compass.
$2,995,000
4 Beds ⋅ 3 Baths ⋅ ML82060102 MLS
Set on approximately one-third acre in a serene Woodside setting, 232 Highland Terrace offers privacy, distinctive architecture, and exceptional indoor/outdoor living. Mature trees frame beautifully landscaped grounds with roses and fruit trees, while expansive patios and decks capture western hill views. The updated residence is rich in character, with wide-plank hardwood floors, a soaring paneled and skylit cathedral ceiling, hand-painted tilework, a distinctive pressed-metal ceiling, and French and Dutch doors opening outdoors. Just off the foyer is an office or playroom with multiple windows and mini-split ceiling HVAC. The primary suite features a steam shower and private deck with recessed spa. An authentic-style Japanese tea house, secluded koi pond, outdoor shower, and detached studio with bath provide flexible spaces for guests, work, wellness, or creative pursuits. Plans for an expansion of the main residence have been submitted to the Town of Woodside and remain active through approximately February 2027, offering the opportunity to further enhance the property. Just minutes from Woodside Town Center and acclaimed Woodside Elementary School, this distinctive property combines privacy, character, flexibility, and convenience.

232 Highland Terrace, Woodside

Listing courtesy of Listing Agent: Hugh Cornish (hcornish@cbnorcal.com) from Listing Office: Coldwell Banker Realty.
$6,880,000
5 Beds ⋅ 4 Baths ⋅ ML82056698 MLS
Welcome to this exquisite 5-bedroom, 3.5-bath home that combines elegance with an inviting, spacious floor plan. Step through the grand formal entry into a luxurious living room with a cozy fireplace, and into the adjoining formal dining room, perfect for gatherings. The gourmet eat-in kitchen is a chef's dream, featuring a central island, breakfast bar, and premium appliances. It connects to an expansive family room with soaring vaulted ceilings and a second fireplace. On the main level, you'll find three well-appointed bedrooms, including a breathtaking master suite featuring a private fireplace, a walk-in closet, and an opulent en-suite bath with dual sinks. The lower level offers two additional bedrooms, a huge recreation room, a charming wine cellar and tasting room, and a versatile exercise room. Unwind in the beautifully landscaped yard on a sprawling lot with a lovely patio and BBQ area. Located within the top-rated Las Lomitas School District, this home offers luxury, comfort, and convenience in one exceptional package. Don't miss the chance to experience this stunning property!

2120 Stockbridge Avenue, Woodside

Listing courtesy of Listing Agent: Jose Dos Ramos (jose.dosramos@bhhsdrysdale.com) from Listing Office: Berkshire Hathaway HomeServices DrysdaleProperties.
$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 Road, Woodside

Listing courtesy of Listing Agent: Scott Dancer (scott@scottdancer.com) from Listing Office: Compass.
$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 Avenue, Woodside

Listing courtesy of Listing Agent: Chris Iverson (c.iverson@ggsir.com) from Listing Office: Golden Gate Sotheby's International Realty.
$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 Road, Woodside

Listing courtesy of Listing Agent: Scott Hayes (scott@scottphayes.com) from Listing Office: Compass.
$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 Road, Woodside

Listing courtesy of Listing Agent: Erika Demma (erika@erikademma.com) from Listing Office: Compass.
$21,995,000
4 Beds ⋅ 5 Baths ⋅ ML82054839 MLS
Evoking the patina & permanence of a residence shaped over generations, this vineyard estate possesses an authenticity rarely achieved in contemporary construction. Completed in 2016 imbued with character of timeless European manor, it received the Julia Morgan Award for Classical Architecture, honoring its exceptional craftsmanship & architectural integrity. Hand-hewn beams, bespoke millwork, artisanal detailing, & imported Italian patterned terra cotta tile flooring define the interiors, while Mediterranean Revival influences create an atmosphere that is grand & welcoming. Arranged across two levels with elevator access, lower-level storage room with wine cellar potential, residence offers 4 bedrooms, dedicated office, & detached guest house. Formal & informal living spaces center around a chef's kitchen with a generous butlers pantry, while arched windows & French doors frame surrounding landscape. Set on approximately 4.33 acres in Woodsides coveted Hidden Valley, the estate enjoys sweeping views of Jasper Ridge, the Santa Cruz Mountains, the Western Hills, & Westridge. A pool, spa, rose gardens, crushed stone paths, dual-fuel backup generator, & professionally managed Pinot Noir vineyard producing up to 50 cases annually complete this extraordinary Silicon Valley retreat.

180 Farm Road, Woodside

Listing courtesy of Listing Agent: Hugh Cornish (hcornish@cbnorcal.com) from Listing Office: Coldwell Banker Realty.
$1,888,000
4 Beds ⋅ 4 Baths ⋅ ML82056831 MLS
An exceptional opportunity to own a premier property in the heart of Woodside, one of the Peninsula's most prestigious and sought-after communities. Located at 26 Big Tree Rd, this unique offering combines privacy, natural beauty, and convenient access to Silicon Valley, making it ideal for homeowners, investors, or those seeking a legacy property. Surrounded by mature trees and Woodside's renowned rural charm, it offers a peaceful retreat just minutes from downtown Woodside, Stanford University, Sand Hill Road, and major employment centers. Residents enjoy a rare balance of tranquility, open space, and access to world-class dining, shopping, and recreation. Whether creating a private estate, preserving a long-term investment, or capitalizing on one of the Bay Area's most desirable locations, 26 Big Tree Rd presents a rare opportunity in a market where exceptional properties are seldom available. Woodside remains one of Northern California's premier residential destinations, known for expansive estates, an equestrian lifestyle, enduring property values, and unmatched privacy, prestige, and long-term appreciation.

26 Big Tree Road, Woodside

Listing courtesy of Listing Agent: Matthew Dapolito (mdapolito@intero.com) from Listing Office: Intero Real Estate Services.
$4,750,000
4 Beds ⋅ 5 Baths ⋅ 41140473 MLS
Tucked at the end of a peaceful cul-de-sac in Woodside Hills, this beautifully reimagined single-level retreat pairs timeless ranch design with an unbeatable connection to nature. Panoramic views stretch across Hoover Tower, Moffett Field, the Dish, and Mount Hamilton — a backdrop that changes with the light throughout the day. Set on a full acre with a creekside property line, the grounds feel like a private nature escape. Deer and songbirds pass through regularly, while four terraced garden beds await your green thumb. Outdoor living is at the heart of this property, with a spacious private deck, a bocce ball court, horseshoes, a swing set, and even a chicken coop — space to entertain, play, and unwind in equal measure. A large paved driveway offers ample parking for hosting guests with ease. Inside, the open floor plan is anchored by a custom kitchen featuring a large center island, stainless steel appliances, and timeless leathered granite countertops, prized for their easy maintenance, complete with a pantry for extra storage — all flowing seamlessly into the home's entertaining spaces. The thoughtfully remodeled layout (2013) also offers true separation between private and social areas. Two en-suite bedrooms and a Jack-and-Jill bath provide flexibility for family or guests, and each of the three full bathrooms is finished with heated marble tile flooring — a quiet luxury that elevates the everyday. Finishes throughout were curated with a timeless sensibility that will feel just as fresh for years to come. This is indoor-outdoor living at its finest — a rare offering in one of the Peninsula's most sought-after enclaves.

140 Sheridan Way, Woodside

Listing courtesy of Listing Agent: Ella Naylor (ella.naylor@compass.com) from Listing Office: Compass.
$3,575,000
3 Beds ⋅ 2 Baths ⋅ ML82050810 MLS
Move in today, expand tomorrow. Nearly one-half acre of level land less than one-half mile from the Woodside town center. Fresh paint, refinished hardwood floors, and numerous updates make the home ready to enjoy, while the expansive property presents exceptional opportunities for future expansion or building new. The home has 3 bedrooms, 2 baths, an updated kitchen, living room with fireplace, attached 2-car garage, energy-efficient heat pump for heating and cooling, updated electrical service, and EV charging. Just down the street from renowned Woodside Elementary School (TK-8).

3270 Woodside Road, Woodside

Listing courtesy of Listing Agent: Hugh Cornish (hcornish@cbnorcal.com) from Listing Office: Coldwell Banker Realty.
$4,588,000
4 Beds ⋅ 4 Baths ⋅ ML82050181 MLS
Nestled among majestic oak trees on nearly 1.2 acres in Woodside Hills, this home is set well back from the street via a long paver driveway. Spanning 4,150 SF, the interiors feature wide-plank hardwood floors, soaring ceilings, and refined finishes that create a light-filled, airy atmosphere in harmony with its natural surroundings. Expansive formal rooms are complemented by multiple fireplaces, a well-appointed kitchen, and a walk-out family room that opens to the outdoors. The four-bedroom layout includes a primary suite with a spa-inspired bathroom designed for comfort and retreat. Outdoor living is equally compelling, with a generous deck and patio featuring an outdoor kitchen, all framed by a verdant, oak-studded backdrop that emphasizes the home's connection to nature. A three-car garage completes the property, while the setting balances privacy with convenience, just minutes to downtown Redwood City, nearby nature preserves and trailheads, and easy access to Highway 280.

61 Oak Haven Way, Woodside

Listing courtesy of Listing Agent: DeLeon Team (info@deleonrealty.com) from Listing Office: Deleon Realty.
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