Woodside Real Estate

Nestled in the heart of San Mateo County, Woodside, California, is a hidden gem that embodies the essence of serene suburban living while remaining just a stone's throw away from the bustling energy of the Bay Area. With its lush landscapes, towering redwoods, and charming equestrian properties, Woodside offers a unique blend of natural beauty and sophisticated living.

Known for its affluent community and stunning estates, Woodside boasts a rich history that dates back to the 19th century. The town's commitment to preserving its rural character is evident in its expansive open spaces and scenic trails, making it a paradise for outdoor enthusiasts. Whether you're hiking through the picturesque Huddart Park or enjoying a leisurely ride along the renowned Woodside Trail, the area invites you to immerse yourself in nature.

The community is also home to a vibrant arts scene, with local galleries and cultural events that celebrate creativity and craftsmanship. Residents enjoy a tight-knit atmosphere, where friendly neighbors and community gatherings foster a sense of belonging.

Education is a top priority in Woodside, with highly-rated schools that provide exceptional learning opportunities for children. The town's proximity to Silicon Valley makes it an ideal location for professionals who seek a tranquil retreat without sacrificing access to career opportunities.

In Woodside, you’ll discover not just a place to live, but a lifestyle that values tranquility, community, and the great outdoors. Experience the charm of Woodside, where every day feels like a getaway in your own backyard.

Newest Listings in Woodside

$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

$2,870,000

7 Beds ⋅ 6 Baths ⋅ ML82039818 MLS

A rare opportunity to own an expansive estate with breathtaking panoramic views, exceptional square footage, and incredible potential in a private hillside setting. From the moment you arrive, the home commands attention with its grand entry and impressive scale. Inside, soaring ceilings, dramatic open spaces, and walls of windows flood the home with natural light while showcasing sweeping valley views. The main level is built for both everyday living and entertaining, featuring a spacious living room, multiple gathering areas, and seamless access to a wraparound deckperfect for true indoor-outdoor living. The kitchen offers a large island, ample cabinetry, and a functional layout ready to be elevated into a stunning chefs space. Generous bedrooms and flexible living areas include a primary suite with scenic windows, dual vanities, and a soaking tub, creating a peaceful retreat with beautiful natural surroundings. The lower level offers an expansive bonus/game room with bar area and endless possibilities for entertaining, recreation, or extended living. A dedicated wine cellar adds a rare and desirable touch. Expansive decking and usable outdoor space complete this exceptional offering, blending privacy, scale, and opportunity in a truly unique setting.

245 Heacox RD, Woodside

Listed by Aaron Derbacher, 408-828-8114 from KW Bay Area Estates
(If provided) CoList: Benjamin Frieden from KW Bay Area Estates

$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

$4,750,000

4 Beds ⋅ 5 Baths ⋅ BE41140473 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,

140 Sheridan Way, Woodside

Listed by Ella Naylor, (650) 520-9864 from Compass
(If provided) CoList: Daniel Boot from Compass

$4,795,000

4 Beds ⋅ 4 Baths ⋅ ML82051662 MLS

Inspired by traditional Norwegian farmstead architecture, this home was extensively rebuilt and expanded in 2002 with views of the western hills and Kite Hill Wildflower Preserve across the street. The home showcases exceptional craftsmanship with solid cedar siding, windows, doors, and screens, a slate roof, old-growth redwood trim, wide-plank Tennessee longleaf pine floors, soapstone countertops, Venetian plaster around the fireplace, and salvaged Douglas fir beams. The flexible 3-level floor plan includes lower-level quarters with kitchenette and private bath, two main-level bedrooms and a bath, plus upstairs primary suite and second suite. Beautifully landscaped grounds feature winding paths, specimen plantings, numerous fruit trees, a rare bamboo grove, pond, flagstone terrace with fireplace, spa, and large chicken coop. Additional features include dual-zone air conditioning, EcoFlow battery backup system and generator, distributed sound, EV charging for 2, and a detached garage. Minutes to Town Center, miles of trails, and acclaimed Woodside Elementary School (K-8).

144 Alta Mesa RD, Woodside

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

$3,725,000

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

$4,788,000

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

Listed by DeLeon Team, 650-407-0160 from Deleon 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

$12,995,000

7 Beds ⋅ 9 Baths ⋅ ML82045810 MLS

Lowest price per square foot @ $956 in Woodside, Atherton or Portola Valley. Spectacular Monterey colonial home on 6+ private acres. Long gated driveway & large motor court the estate shows tremendous original character and beauty. Improvements include a stunning primary bath, a complete new roof & gutters & Exterior paint 2025. 3 expansive levels with grand public rooms, large eat-in kitchen, English Pub bar, recreation/media room and fitness room with sauna, wine room for approx. 1,000 bottles. Seven large bedrooms, including two primary suites, a full two bedroom attached apartment, a separate 1 bedroom guest house privately located on the grounds with a separate 2 car garage and parking. Additionally, attached 4 car garage, large swim pool, tennis court and Stable for 5 horses & riding arena, Hay storage, wash rack, multiple areas for trailers & RV parking. Beautiful Western & Southern hills views. Award winning Las Lomitas Elementary Schools K-8. Nearby to town center, easy commute routes to SF or Silicon Valley. Main house 13,590 sf per county records, 5,560 sf main level , 4,300 sf 2nd level, 3,730 sf lower level includes home theater, wine room, workout/ sauna. Not including guest house, extra 2 car garage, shop & Horse stable. Corral & stable have a separate driveway.

389 Moore RD, Woodside

Listed by Steve Lessard, 650-704-5308 from Compass
(If provided) CoList: from

$750,000

ML82048576 MLS

*6.02 acres of land ready to develop *Secluded, quiet: mature redwoods, huge oaks, ocean view *flat parking turnaround meets county permit requirements *continuous paved road from Hwy 35 *PG&E electricity at street *cellphone signal *water well exceeds requirements *perc test for septic meets requirements *Surveyed topographic map available *Open space, preserve trails nearby Gorgeous, unique acreage in the redwoods off Skyline Blvd (Hwy 35): Kings Mountain area, north of Alices Restaurant on SF Peninsula. Close to Redwood City, Woodside. Big trees, ocean views, quiet and private. Paved road, PG&E wired electricity, cellphone signal. Ready for full-time living, remote work, or retirement. Water well exceeds production requirements: perc test approved for septic. Current owner has an initial design, calculations and drawings. Close to extensive trails, parks and open spaces, King's Mountain school. Unique opportunity, with lots of the leg work done, submit your plans to the county and go.

0000 Native Sons RD, Woodside

Listed by Frank Vento, 650-888-9900 from Intero Real Estate Services
(If provided) CoList: from

$3,695,000

3 Beds ⋅ 3 Baths ⋅ ML82047690 MLS

Classic architecture & timeless interior finishes define this exceptional home in the Central Woodside, tucked away at the end of a peaceful cul-de-sac just one mile from the Woodside town center. The property offers a distinctive presence with an added sense of privacy & refinement. Freshly painted interiors & hardwood floors introduce warm, inviting spaces filled with natural light. Traditional character is 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. The flexible floor plan includes 3 bedrooms, a dedicated office, & 2.5 baths, including a 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 yards offer expansive areas for entertaining & relaxation with level lawn, expansive deck, paver stone terrace, & large spa, all in a tranquil park-like setting. Access to the excellent Woodside Elementary School (TK-8) further enhances the appeal of this special offering.

63 Ridgecourt, Woodside

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

$5,495,000

4 Beds ⋅ 4 Baths ⋅ ML82046648 MLS

Classic architecture & beautifully curated grounds define this inviting Woodside home set on more than one-third acre moments from the town center. Stone-clad exteriors, newly planted lawns, & a picture-perfect approach introduce interiors that are warm, welcoming, & thoughtfully designed for everyday living. Natural light fills the home through expansive windows, hardwood floors, detailed millwork, & a floor plan that offers both openness & comfortable separation of spaces. Main living areas transition easily from formal rooms to casual gathering spaces, welcoming family room & well-appointed kitchen designed for both function & connection. Lower-level recreation/media room adds flexibility for entertainment or office use. Privately located primary suite with jetted tub & steam shower, bedroom with its own outside entrance & adjacent bath ideal for guest quarters. Outdoor living is a central focus, with a large arbor-covered deck extending from the home & terraced grounds below featuring a play area & garden spaces, all enhanced by refreshed landscaping. Located on a cul-de-sac street in the Woodside Glens neighborhood, with acclaimed Woodside School & offers a combination of traditional appeal, updated comfort, & an exceptionally convenient setting with a true sense of retreat.

103 Toyon CT, Woodside

Listed by Hugh Cornish, 650-619-6461 from Coldwell Banker 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 RE/MAX CAPITAL 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.