Central Woodside Homes for Sale

Welcome to Central Woodside, a hidden gem nestled in the heart of San Mateo County, California. This enchanting neighborhood is renowned for its lush landscapes, expansive estates, and a serene atmosphere that offers the perfect escape from the hustle and bustle of city life. Central Woodside is characterized by its stunning natural beauty, with towering redwoods and rolling hills that provide a picturesque backdrop for outdoor enthusiasts and nature lovers alike.

As you wander through the tree-lined streets, you'll discover a charming community that is both welcoming and vibrant. Central Woodside boasts excellent schools, making it an ideal location for families seeking a nurturing environment for their children. Additionally, the neighborhood is home to a variety of parks, equestrian trails, and hiking paths, providing ample opportunities for recreation and relaxation.

For those in search of their dream home, Central Woodside offers a diverse selection of properties for sale, ranging from luxurious estates to cozy cottages. Each home showcases unique architectural styles, often featuring expansive yards and stunning views. Whether you desire a modern masterpiece or a classic retreat, you’ll find a residence that perfectly matches your lifestyle.

Living in Central Woodside means embracing a lifestyle of tranquility and elegance, all while being just a short drive away from the vibrant amenities of nearby cities. With its rich natural surroundings and a strong sense of community, Central Woodside is not just a place to live; it’s a place to thrive. Explore the homes for sale today and discover the enchanting lifestyle that awaits you in this idyllic neighborhood.

Newest Central Woodside Homes for Sale

$2,995,000

3 Beds ⋅ 3 Baths ⋅ ML82054634 MLS

Woodside Retreat "Beside The Woods in Woodside" Peaceful end-of-road privacy and a rustic, eclectic retreat once featured in the Almanac, cherished by one family for 50+ years. 4 sunny, wooded acres with sweeping hill and redwood views. Private gate opens directly onto the trails of 900+ acre Huddart Park. Close to town and Woodside schools. This rustic 3600+ ft 3 beds/2.5 bths home is a study in Vintage Tahoe-style craftsmanship. The living room anchors the house with wood and brick walls, an open stone fireplace, and terracotta tile underfoot. Wooden beams carry into the country kitchen with Subzero and stainless appliances, and the dining room flows onto an expansive view deck over the gardens and pool. A home office overlooks the gardens, and a skylit staircase leads down to a gallery hallway with a stained glass window and a private family room/bedroom. The showstopper: a dramatic Great Room "tavern," host to gatherings of 150, with 19' ceils and grand fireplace of original SF cobblestones. Custom bar built from salvaged San Carlos post office and pharmacy. A reclaimed-barn-siding full bath with steam shower. Large billiard room completes the tavern vibe. Decks and brick paths trace the contour of the land to the pool, framed by redwoods on all sides. Sep 2-car garage.

496 Raymundo DR, Woodside

Listed by Don DeFranco, 415-722-7259 from Compass
(If provided) CoList: Grayson Martin from Compass

$3,195,000

4 Beds ⋅ 2 Baths ⋅ ML82054316 MLS

Nestled on nearly two private acres in a coveted Woodside setting, this Mid-Century Modern home offers a rare blend of rustic charm, natural beauty, & breathtaking panoramic views. Thoughtfully designed to embrace its spectacular surroundings, the four-bedroom, two-bath residence features a sun-drenched living room framed by a dramatic wall of floor-to-ceiling windows that capture sweeping vistas & create an effortless connection to the outdoors. Adjacent to the living room, the open kitchen & dining area also flow seamlessly onto the expansive view deck which is an ideal setting for entertaining, sunset gatherings, or quiet mornings overlooking the horizon. The main level features the primary bedroom & a full bathroom, offering the ease and convenience of single-level living. Downstairs, three additional bedrooms, a full bath, dedicated laundry room, and a spacious bonus family room provides exceptional flexibility for a media lounge, home office, or recreation space. Set on 1.95 acres of serene grounds, the property offers a true sense of privacy and includes a charming barn, adding authentic Woodside character. Lots of possibilities! With access to acclaimed Woodside schools, this special property creates a lifestyle defined by tranquility, scenic beauty, and timeless appeal.

3635 Partition RD, Woodside

Listed by Jennifer Alfaro, 650-888-8338 from Compass
(If provided) CoList: Kimm Terpening from Compass

$3,895,000

4 Beds ⋅ 3 Baths ⋅ ML82053870 MLS

Central Woodside Opportunity on 1.11 Acres. Just over one mile from Woodside town center this 1.11-acre property presents an increasingly rare opportunity in a desirable Central Woodside setting. A seasonal creek at the rear of the property and stunning western hill views that may be further enhanced create a beautiful natural environment that reflects the scenic character for which Woodside is renowned. A secondary access point from Hillside Drive to the barn further enhances the property's flexibility and future potential. The mid-century ranch-style home has been recently refreshed with new paint inside and out, refinished hardwood floors, new carpet, and refreshed landscaping. Comfortable living spaces, flexible lower-level quarters with a bonus kitchen, and a detached two-stall barn with expansive upper-level space provide immediate enjoyment while offering numerous possibilities for the future. The true appeal extends beyond the home itself. Generous acreage, a close-in location, access to acclaimed Woodside Elementary School, and surrounding estate properties create an exceptional setting for renovation, expansion, or the creation of a significant new residence all while immediately enjoying the freshly updated home.

136 Jane DR, Woodside

Listed by Erika Demma, 650-740-2970 from Compass
(If provided) CoList: from

$3,825,000

3 Beds ⋅ 2 Baths ⋅ ML82050810 MLS

Set on nearly one-half acre of level land less than one-half mile from the Woodside town center, this classic mid-century home offers a special opportunity with a meaningful connection to the community's history. The property carries a legacy of beloved & highly respected figure whose contributions to local education helped shape generations of students. The home has been thoughtfully maintained over the years with refinished hardwood floors, numerous updates, & comfortable living spaces including 3 bedrooms & 2 baths. Freshly painted & ready to enjoy today, the home also presents wonderful possibilities for the future. The level grounds offer exceptional flexibility in a remarkably close-in location to the town center, acclaimed Woodside school, as well as hiking & biking trails that make Woodside such a treasured place to call home. Rich in local history & offering broad appeal for years ahead, this is an opportunity rarely found in one of the Peninsula's most treasured communities.

3270 Woodside RD, Woodside

Listed by Hugh Cornish, 650-619-6461 from Coldwell Banker Realty
(If provided) CoList: from

$3,950,000

3 Beds ⋅ 2 Baths ⋅ ML82050036 MLS

Set on 1.5 acres at the end of a quiet cul-de-sac in Central Woodside, the property offers a beautifully completely updated estimated 2,105 sq ft retreat in the highly regarded Woodside School District. The refreshed home features wide-plank oak hardwood floors, new dual-pane windows, LED lighting, and a new metal roof with added skylights. The renovated kitchen showcases shaker cabinetry, white marble countertops, a Wolf induction range, Sub-Zero refrigerator, dual Wolf ovens, a deep corner pantry with microwave, and an island with seating, plus a Dutch door to the spacious rear patio. Enjoy a cozy family room with wood-burning fireplace, large-screen TV, and articulating door to outdoor entertaining and dining. The primary suite includes an expansive sleeping area with French doors to the nearby native plant garden and majestic Redwoods, a Mitsubishi split A/C, and an upgraded and spectacular bath with marble counters, freestanding tub, new shower, and improved walk-in closet. Additional highlights: new central forced-air system with Nest controller, Level 2 EV charger, security cameras, new septic system and gated trail access to Teague Preserve.

855 Patrol RD, Woodside

Listed by Helen Miller, 650-400-1317 from Compass
(If provided) CoList: from

$34,995,000

6 Beds ⋅ 5 Baths ⋅ ML82038776 MLS

One of Woodside's premier estates, encompassing nearly 10,000 square feet across all structures, this property offers exceptional scale, quality, and lifestyle, highlighted by a classically styled main residence and a brand-new guest house crafted with authentic European detail. The main home is luxuriously appointed across two levels, with nearly every room opening to the outdoors. A state-of-the-art theatre and a temperature-controlled wine cellar are just two of many standout features. The newly completed guest house pairs handmade roof tiles and Genoise eaves inspired by the South of France with state-of-the-art smart home technology. Designed for entertaining, the guest house opens to a new saltwater pool and spa and expansive limestone terrace with a full outdoor kitchen and easy catering access. A 310-vine Cabernet vineyard anchors the south-facing gardens, while heritage olive trees and oaks, a fragrant parterre rose garden, bountiful orchard, and raised vegetable beds enhance the estates agrarian beauty. The result is a property where timeless elegance and refined European living are masterfully expressed in an extraordinary private setting of more than 3 acres with western hill views. Main Residence 6,485 | Guest House 1,505 | Garage One 560 | Garage Two 520 | Gym 560

307 Olive Hill LN, Woodside

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

$2,788,000

2 Beds ⋅ 1 Baths ⋅ ML82040350 MLS

Nestled in a highly sought-after Woodside neighborhood, this single-family home offers the rare combination of privacy, space, & future potential. Situated on an expansive ~0.340.37 acre lot (15,000+ sq. ft.), the property provides generous outdoor space ideal for entertaining, expansion, or the opportunity to build your custom dream home. The residence features a remodeled kitchen & an upgraded 150-amp electrical panel (completed in 2011), offering a solid foundation for comfortable living or further enhancements. Located in a low-density, established community, this home enjoys a serene, mature setting with exceptional privacy. Zoned for top-rated Woodside Elem., & Woodside High, its an excellent choice for those seeking both tranquility and access to quality education. Convenience meets location with just a 1015 minute drive to Downtown Redwood City, where youll find an array of dining, shopping, & everyday amenities. Commuters will appreciate the close proximity to Redwood City Caltrain Station and easy access to Highway 101 & I-280 via Woodside Road. A unique opportunity to own in one of Woodsides most desirable areas with endless potential.

4258 Jefferson, Woodside

Listed by Anson Ip, 408-221-7887 from Compass
(If provided) CoList: Marie Wang from Keller Williams Thrive

$3,998,000

4 Beds ⋅ 3 Baths ⋅ ML82039737 MLS

Tranquil Woodside Retreat Nestled within one of Woodside's most sought-after enclaves, this enchanting single-family residence offers a rare blend of privacy, natural beauty, and timeless appeal. Set on expansive, level to gently sloping grounds, the property is ideal for equestrian use, featuring serene open spaces framed by mature trees and lush, thoughtfully designed landscaping. Bathed in dappled sunlight, the home exudes warmth and charm throughout. The well-appointed floor plan includes 4 bedrooms and 2.5 bathrooms, with inviting living spaces that seamlessly connect to the outdoors perfect for both relaxed everyday living and elegant entertaining. Step outside to your own private oasis, complete with a pool, lush lawns, barn and meandering brick walkways. Whether enjoying quiet mornings or hosting gatherings, the setting offers unmatched serenity and beauty. Located within the boundaries of the highly acclaimed Woodside Elementary School, this exceptional property combines rural tranquility with convenient access to nearby amenities. A rare opportunity to experience the quintessential Woodside lifestyle.

425 Summit Springs RD, Woodside

Listed by Christienne Hadley, 650-533-3766 from Coldwell Banker Realty
(If provided) CoList: from

$12,800,000

2 Beds ⋅ 4 Baths ⋅ ML82039836 MLS

Discover an exceptional opportunity to create a dream home or reimagine the existing Neoclassical residence on one of central Woodsides most desirable streets. Spanning just over 3.4 acres, this expansive property showcases rare Bay views. There is an existing planning study for guidance in future opportunities. Positioned at the end of a private lane, the setting reflects the essence of Woodside country living, with lush perimeter trees and vast open land that offer a serene and private natural environment. The gated property includes an existing one-level home, a pool, and an original tennis court. Just one mile from Woodside Town Center and acclaimed Woodside Elementary School, and only minutes to Stanford University, Sand Hill Road venture capital firms, and the heart of Silicon Valley, this location offers both seclusion and convenience.

309 Olive Hill LN, Woodside

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

$10,988,000

5 Beds ⋅ 6 Baths ⋅ ML82037743 MLS

Set on more than 2.5 acres of quintessential Woodside grounds, this spectacular estate balances timeless elegance with easy comfort. Behind gates and surrounded by mature trees and lush foliage, it conveys a quiet sense of luxurious seclusion. Inside, more than 6,400 total SF includes a dramatic foyer with columns, expansive formal rooms, a chef's kitchen, private office, theater, and five bedrooms, including a sanctuary-like primary suite. Outdoors, resort-style grounds feature a pool, spa, pool house, patio with fireplace and grill, cascading waterfall with bridge, gardens, fruit trees, and a detached bonus studio for work or fitness. Tesla solar panels and 6 Powerwall batteries, a seamless Sonos sound system, and expert craftsmanship enhance every detail. Just minutes from Woodside, Sand Hill Road, Palo Alto, and top schools, it offers the rare blend of privacy, prestige, and proximity.

160 Phillip RD, Woodside

Listed by DeLeon Team, 650-900-7000 from Deleon Realty
(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 Fine Group Real Estate 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.