Woodside 2 Car Garage Real Estate, Homes for Sale

2 Beds ⋅ 3 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 RD, Woodside

Listed by Matthew Dapolito, 408-202-9202 from Intero Real Estate Services
(If provided) CoList: Scott Bishop from Intero Commercial

$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

$3,725,000

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 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

$4,075,000

4 Beds ⋅ 4 Baths ⋅ ML82050010 MLS

One Acre with Sweeping Bay Views in Woodside Hills! Sweeping San Francisco Bay views take center stage at this exceptional Woodside Hills property with fresh updates throughout. Spanning one acre, the elevated corner lot is positioned to capture the expansive views while also providing generous level areas for outdoor living. Enhancing the setting is the gentle sound of a meandering creek and strolling paths that create a distinctly parklike ambiance. Fresh interior updates include new paint, refinished hardwood floors, and new carpet, all complementing the living rooms signature vaulted ceiling, handcrafted with layered redwood cedar rising to a dramatic center peak. Multiple fireplaces add warmth and character, while glass doors open to several outdoor spaces oriented to enjoy the Bay views. The formal living room and dining room each have Bay views, plus there is a large open kitchen and family room for everyday gatherings. Four bedrooms, an office, and 3.5 baths are well arranged, featuring a main-level primary suite and a second suite comprising the entire lower-level with outside access and flexibility for future ADU conversion. An attached two-car garage and abundant off-street parking complete this inviting retreat with close-in convenience.

199 Brookwood RD, Woodside

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

Sold listing courtesy of Erika Demma from APR

$3,645,000

3 Beds ⋅ 3 Baths ⋅ ML82047690 MLS

Access to renowned Woodside Elementary School, an end of cul-de-sac location with underground utilities, and just one mile from the Woodside town center set this home apart. Newly built in 2007, the home has soaring cathedral ceilings, hardwood floors, expansive windows, and an open floor plan that flows to generous outdoor living spaces. The flexible layout includes 3 bedrooms and a dedicated office, including a spacious primary suite with fireplace, customized walk-in closet, and newly remodeled bath. The open kitchen features custom cabinetry, granite slab counters, a BlueStar gas range, Liebherr wine cooler, and counter seating at a center island. A large deck, level lawn, paver stone terrace, and spa create exceptional outdoor living on fully fenced grounds. Additional features include central air conditioning, wiring for EV charging, plus expansion and ADU potential (subject to Town approval & applicable development standards).

63 Ridge CT, Woodside

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

$4,300,000

3 Beds ⋅ 2 Baths ⋅ ML82047585 MLS

For Comp Purposes Only

180 Phillip RD, Woodside

Listed by Costantini Team, 650-430-8425 from Compass
(If provided) CoList: from

Sold listing courtesy of Costantini Team from APR

$5,495,000

4 Beds ⋅ 4 Baths ⋅ ML82046648 MLS

More than one-third acre creates an exceptional setting for this spacious home with 4 bedrooms, 3.5 baths, and multiple living areas designed for today. There are formal living and dining rooms, a designer kitchen with Carrara marble finishes and wine bar, a welcoming family room, a lower-level recreation and media room, and a private bedroom with its own entrance and adjacent bath that is ideal for guests or office use. The primary suite is privately located and features a steam shower and jetted tub. Outdoor living is equally inviting with an arbor-covered deck, newly planted lawns, terraced gardens, play area, and raised vegetable beds. Located on a cul-de-sac street less than one mile from the Woodside town center and served by renowned Woodside Elementary School (TK-8). Additional highlights include abundant storage, optional RV parking with hookups, and refreshed landscaping throughout.

103 Toyon CT, Woodside

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

$3,195,000

3 Beds ⋅ 3 Baths ⋅ ML82045702 MLS

Luxury retreat offers a serene escape on 9+ acres, secured by an electronic gate. Under 2 miles and just minutes to Alices restarant. Stunning style on one level, the home features dramatic light-filled interiors with an open-concept design, SOARING CEILINGS, and abundant sliding glass doors and skylights. Bamboo floors, vertical grain cabinetry, and polished concrete counters. The main rooms revolve around a central patio with a stunning heritage oak tree, while an expansive rear deck with a large spa beneath the redwoods and a sunswept front yard for gardening enhance the outdoor experience. Three privately located bedrooms, each with its own bath, ensure comfort and flexibility. An equally well-appointed ADU above the garage includes a kitchen, bath, and laundry. Total privacy directly adjacent to MidPen open space. Flat useable grounds with large vegetable garden, ample of paved parking, large ground level deck and heritage oak entertainment area for large parties. Open sunny side toward views and beauty of Redwood forest on the oposite side of the house with heated spa under the redwoods. Main house 2870 sq.ft, plus ADU 550 sq.ft., plus attached garage 525 sq.ft for total of 3945 sq.ft.

1100 Old La Honda RD, Woodside

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

$3,650,000

3 Beds ⋅ 3 Baths ⋅ ML82045699 MLS

A setting of extraordinary natural beauty defines this distinctive redwood retreat, where architecture and environment exist in quiet harmony. Designed by renowned builder Jerry Ellis, the home is masterfully engineered above a seasonal creek, where the gentle movement of water enhances the serene surroundings of more than 2 acres. Dramatic ceilings and expansive walls of glass create a seamless connection to the landscape. Sunlight filters through the trees and skylights above, casting an ever-changing interplay of light and shadow throughout the day. Spacious decks and winding paths extend the living experience outdoors. The result is a home with a rare sense of place, offering a living experience that feels both peaceful and architecturally compelling while being just minutes from the Town Center, acclaimed Woodside School, and all of Silicon Valley.

573 Patrol RD, Woodside

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

Sold listing courtesy of Scott Dancer from APR

$8,700,000

4 Beds ⋅ 5 Baths ⋅ ML82044880 MLS ⋅ Woodside Hills BLDG.

A rare opportunity to own an earthy modern estate set in the esteemed Woodside Hills with breathtaking sweeping Bay views. The residence was reimagined with uncompromising attention to detail, offering a truly like-new experience that has never been lived in. Situated on 0.98 acres, the 6,809 sq ft home blends dramatic scale with warm, livable sophistication for true California Living. The thoughtfully designed floor plan includes 4 well-appointed bedrooms, 4 designer bathrooms, 1 powder room, dedicated office, flex studio, media room, laundry/mud room, and luxurious rec room. The designer kitchen serves as both a functional showpiece and an entertainers dream, featuring open steel & beam vaulted ceiling, natural light, custom white oak cabinetry, top-of-the-line appliances, wet bar, pantry, temperature controlled wine cellar, and designer finishes. The grounds include a stunning chefs kitchen, fire pit lounge, abundance of areas to entertain, view decks, and a refreshing pool. Surrounded by other distinguished estates, 150 Brookwood Rd is an iconic offering, combining design-forward architecture, extraordinary views, exceptional outdoor living, and an unparalleled Woodside setting to create a one-of-a-kind luxury retreat. Buyer to verify.

150 Brookwood RD, Woodside

Listed by QL Realty Group, 831-566-0006 from Coldwell Banker Realty
(If provided) CoList: from

Sold listing courtesy of Susan Ferguson from COLD02

$7,495,000

4 Beds ⋅ 6 Baths ⋅ ML82044344 MLS

New Price! Set at the end of a private, gated country lane on approximately 1.11 fully usable acres, this elegant estate with French country architecture offers an exceptional blend of refined living and natural beauty, with sweeping views of the Western Hills and stunning sunsets. The main residence features 4 BR and 5.5 BA and a dedicated office/library with inspiring views. A recently updated chefs kitchen with a sunny breakfast area, main-level primary suite with connecting recreation room, patterned oak hardwood floors, and dual-paned windows throughout create a warm yet sophisticated ambiance. Designed for indoor/outdoor entertaining with expansive terraces and beautifully landscaped gardens this is a one of a kind home. A detached 1 BR 1 BA guest house has a full kitchen, wood-burning fireplace, and high ceilings, perfect for guests, extended family, or independent work space. An additional 520 square feet of garage space and 795 square feet of basement storage provide functionality alongside luxury. Ideally located within walking distance to Woodside Town Centers shops and restaurants, and close to Woodside School (Pre-K8th), Interstate 280, Sand Hill Road, and Stanford University, this home exemplifies the best of serene, convenient, and elegant Woodside living

55 Mission Trail RD, Woodside

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

Sold listing courtesy of Victoria Yang Surles from CBR

$5,450,000

5 Beds ⋅ 4 Baths ⋅ ML82044125 MLS

Tucked away on a private, gated cul-de-sac, 200 Todo El Mundo in Woodside offers the perfect balance of privacy, convenience, and natural beauty. Situated on approximately 1.5 acres of flat, usable land bordered by a seasonal creek, the property features expansive front and back irrigated lawns and a peaceful, park-like setting. The European-influenced traditional 4,885-square-foot main residence is designed for effortless indoor-outdoor entertaining, with several rooms opening through French doors to two sunny decks. A dramatic living room with soaring two-story ceilings and fireplace anchors the home, complemented by a spacious family room with its own fireplace and wet bar, a cozy kitchen and a private dining room ideal for intimate gatherings. The thoughtful five-bedroom, three-and-a-half-bath layout includes a serene upper-level Primary Suite with a full bath, sauna, fireplace and walk-in closet, two additional upstairs bedrooms and two main-level bedrooms with a full bath and tub. With its proximity to Woodside Town Center, Woodside Plaza shopping, Sand Hill Road, Stanford University, and nearby freeway access to major Silicon Valley destinations, this exceptional property offers a rare opportunity to enjoy the Woodside lifestylequiet, connected, and surrounded by nature

200 Todo El Mundo, Woodside

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

Sold listing courtesy of Larry Liu from APR

$5,350,000

4 Beds ⋅ 4 Baths ⋅ ML82043727 MLS

Set at the end of a private lane on more than one acre, this stylish contemporary retreat offers a rare sense of privacy just moments from downtown Woodside. Refreshed landscaping & a spacious, partially covered front deck introduce interiors defined by clean lines, hardwood floors, vaulted ceilings, & expansive walls of glass that fill the home with natural light. The flexible two-level floor plan features 4 bedrooms, an office, & 4 full baths, including a main-level primary suite. A dramatic living room with a fossilized limestone fireplace, formal dining room, & streamlined maple kitchen with honed black granite & butcher block surfaces create a modern yet inviting backdrop for everyday living & entertaining. Sliding glass doors open to a wraparound deck for seamless indoor-outdoor flow. The lower level expands the living space with a large recreation room with a built-in workstation for two, plus 2 additional bedrooms, one with an en suite bath. Terraced rear grounds include a free-form pool, barn with potential equestrian use, zip line, & refreshed landscaping, along with additional usable outdoor areas suited for recreation, play, or future possibilities. Just one-half mile from downtown Woodside & within the acclaimed Woodside School District.

35 Neuman LN, Woodside

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

Sold listing courtesy of Erika Demma from APR

$5,080,000

3 Beds ⋅ 4 Baths ⋅ ML82041730 MLS

This is the forever home everyone hopes for! Exceptionally quiet and private, this gated single-level ranch home spans approximately 3,000 sq ft on over one acre of rare, level land in a prestigious Woodside Hills cul-de-sac. Offering a unique combination of serenity and convenience, the property is just minutes from Highway 280 for easy commuting. A gated entry opens to an expansive front yard with ample parking and a spacious motor court. This lot is ready for a pool, lawn games or an ADU. The home features a well-designed floor plan highlighted by a grand-scale living room, a separate formal dining room, and a sun-filled kitchen with wraparound windows overlooking the backyard. The kitchen flows seamlessly into the family room, creating an open-concept great room ideal for everyday living and entertaining. The bedroom wing includes three generously sized bedrooms, each with its own connected bathroom, including a primary suite. The grounds are park-like, featuring a large, flat lawn, mature trees, and partial view-an uncommon offering in this area. An exceptional opportunity to enjoy a peaceful setting with easy access to commute routes and nearby amenities.

140 Northridge, Woodside

Listed by Costantini Team, 650-430-8425 from Compass
(If provided) CoList: from

Sold listing courtesy of Linda Wang from AGNC

$4,500,000

4 Beds ⋅ 4 Baths ⋅ ML82041987 MLS

Known as the High Hilltop home, you will be surprised by this move-in-ready gems breathtaking views of the Western Hills, portions of the SF Bay and colorful sunsets. Closely adjacent to Kite Hill open space trail network and within easy and safe walking distance to the acclaimed Woodside School (pre-K to 8th) and Town Center restaurants and shops, this wonderful two-story home, situated in a quiet part of the sought-after Woodside Glens neighborhood, features a host of thoughtful upgrades by long time owners. They created a floor plan which showcases views from nearly every room and which, with its ipe hardwood spacious rear decks, presents a host of seamlessly flowing indoor/outdoor entertainment options. All new appliances were added in the chefs kitchen, the hardwood floors were recently refinished, new dual paned windows installed, high end finishes and touches were made throughout and the outside grounds sport attractive low maintenance, water-conserving plantings. Designed around light and nature, the home currently has three bedrooms on the main level and a lower level with an expansive family room and adjacent primary suite, all of which provide a range of configuration alternatives for home office, workout or entertainment setups. Come see this amazing home!

175 Alta Mesa RD, Woodside

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

Sold listing courtesy of Lucy Goldenshteyn from RDFIN

$16,000,000

5 Beds ⋅ 6 Baths ⋅ ML82041798 MLS

In one of the best locations in Central Woodside, easy walking distance to Town Center and acclaimed Woodside School (pre-K to 8th); this home captures California Country with East Coast Elegance with its breathtaking views of the Western Hills from the flat one-acre parcel. The open floor plan flows seamlessly for indoor/outdoor entertaining featuring a rear dining patio, built-in BBQ, 50 foot saltwater pool, bocce court, shaded pergola sitting area, spacious rear grass lawn and surrounding array of colorful gardens. Gorgeous oak hardwood floors unify the two-story home, with a comfortable family room adjacent to the chefs kitchen and large combined dining and living room, all with French Doors opening out to the sunny rear entertaining patio. The home has 5 spacious bedrooms, each with its own bath and ideally arranged for a variety of lifestyle needs. The main-level also has a separate home office. Upstairs a primary suite plus 3 additional en-suite bedrooms provide a perfect living area layout. This location offers it all: a private home and property on one of the best country lanes in Woodside while also being within walking distance to Woodside School, Town Center shops and restaurants, and all of the hiking, biking and horseback trails that make Woodside special.

180 Romero RD, Woodside

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

Sold listing courtesy of Katy Thielke Straser from COMPS

$6,500,000

3 Beds ⋅ 2 Baths ⋅ ML82041776 MLS

This is an idyllic Woodside property on over 1 level acre, where open land, equestrian facilities, and close-in convenience come together just one-half mile from the Town Center and highly acclaimed Woodside School. The expansive, level grounds set the tone complete with a 1 bedroom and 1.5 bath guest house, barn, fenced paddocks, pool, and broad stretches of lawn that capture the true spirit of country living. The home has been beautifully remodeled with a fresh, cohesive design that includes all-new lighting, a fully renovated kitchen, and beautifully updated bathroom. The interiors feel bright, current, and immediately livable, and a remodeled 1 bedroom guest house adds valuable flexibility for extended stays, office use, or possible rental. Beyond what is already in place, the scale and level nature of the property presents outstanding opportunity. Expansion, further personalization, or even the creation of a new estate can all be envisioned here, making this property as compelling for today as it is for the future.

3362 Woodside RD, Woodside

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

Sold listing courtesy of Michael Warren from APR

$2,150,000

3 Beds ⋅ 2 Baths ⋅ ML82032924 MLS

BEST VALUE IN WOODSIDE!! Nestled under Woodside's heritage oaks, this 1929 Woodside Glens retreat offers a rare blend of vintage character, privacy, and views. The nearly 0.5 acre lot features abundant, verdant scenery and a wrap-around deck to take it all in. The main level boasts a large, open-beam living room anchored by a cozy wood-burning stove, and is surrounded by windows which bring the natural beauty of the Glens inside. The floor plan includes a vintage kitchen, a dining area overlooking the oaks, and two bedrooms -- one featuring its own fireplace. Central air-conditioning provides year-round comfort. Upstairs is a versatile loft with a storage area. The lower level features a large bedroom with a bathroom and shower, an oversize 2-car garage, plus driveway space for 2 additional vehicles. With the large lot, an ADU is possible (buyer to confirm with the town). Located in the district for top-rated Woodside Elementary (K-8) and Woodside High, this home is moments from Woodside Village and offers a convenient commute to the entire Bay Area via Hwy 280. Experience the quintessential Woodside lifestyle in this timeless woodland sanctuary.

235 Hillside DR, Woodside

Listed by Steve Rumberg, 408-981-2383 from Keller Williams Realty-Silicon Valley
(If provided) CoList: from

$5,388,000

4 Beds ⋅ 4 Baths ⋅ ML82041471 MLS ⋅ Woodside Hills Home Association BLDG.

Set on beautifully landscaped grounds with sweeping Bay views, this impeccably maintained Woodside residence offers privacy, scale, and resort-inspired living. Light-filled interiors feature soaring ceilings, refined millwork, and an elegant flow designed for both entertaining and everyday living. Formal living and dining rooms provide distinct gathering spaces, while the well-appointed kitchen with custom cabinetry, stone countertops, and a center island opens seamlessly to the adjacent family room and surrounding outdoor spaces for effortless indoor outdoor living. The spacious primary suite is a private retreat with a view deck and spa-inspired bath. Three additional bedrooms offer flexibility for guests, office space, fitness, or extended living. Resort-style grounds include expansive patios, a pool, covered lounge area, mature landscaping, and multiple vantage points capturing sweeping Bay views and natural beauty throughout. Conveniently located near downtown Woodside and Redwood City, Highway 280, and major Silicon Valley employers. Nearby private schools include Menlo School, Phillips Brooks School, Sacred Heart Schools, and Woodside Priory.

140 Ridgeway RD, Woodside

Listed by Caroline Dinsmore, 650-773-2226 from The Agency
(If provided) CoList: from

Sold listing courtesy of Jennifer Bitter from GGSIR

$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 Foundation Real Estate
(If provided) CoList: from

$11,000,000

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

$5,800,000

2 Beds ⋅ 1 Baths ⋅ ML82039615 MLS

Nestled in a prime location in the prestigious town of Woodside, this exceptional property offers a rare opportunity to create something truly extraordinary. Set on an expansive 58,893 square foot (1.35-acre) lot, the setting is both private & picturesque - surrounded by beautiful estates that define the areas renowned character and enduring appeal. Here, the possibilities are truly limitless, offering an ideal canvas to design and build your dream estate in one of the Peninsulas most sought-after communities. The property includes a quaint 2 bed/1 bath cottage, detached garage, plus a pool. Offered for the first time in over 75 years, this is a once-in-a-generation opportunity to secure a premier parcel in a location known for its elegance, natural beauty, and long-held generational ownership. Just minutes from Woodside Town Center (Roberts Market, acclaimed local restaurants, etc.) you'll enjoy a seamless balance of peaceful seclusion and close-to-town living. Outstanding Woodside TK-8 School and proximity to Highway 280 further enhance the property's exceptional livability and convenience. A truly rare offering in a coveted location, framed by distinguished neighboring estates - this is your opportunity to create a legacy property in the heart of Woodside.

391 Mountain Home RD, Woodside

Listed by Greg Celotti, 650-740-1580 from Compass
(If provided) CoList: Katherine Celotti from Compass

Sold listing courtesy of Brad Miller from APR

$800,000

2 Beds ⋅ 2 Baths ⋅ ML82033018 MLS

This property scores high on the unique scale! Just 5 minutes drive from Alice's Restaurant, nestled in a sorrel, fern and redwood gorge, this two bedroom, two bath home is an engineering feat to behold. Outstanding vehicular accessibility as the .87 acre property enjoys a horse-shoe looped driveway off Highway 84 which would be ideal for heavy equipment operators, or motorcycle enthusiasts. There is a large shop and multiple outbuildings. 20 minutes drive to Palo Alto yet a world away; think clubhouse, weekend get-a-way, or create your own Dwell Magazine worthy abode.

121 La Honda RD, Woodside

Listed by Mollie Whipp, 415-741-4012 from Coldwell Banker Realty
(If provided) CoList: Cameron Jeffs from Coldwell Banker Realty

Sold listing courtesy of Dante Razzini from NTERO

$4,295,000

4 Beds ⋅ 4 Baths ⋅ ML82037717 MLS

Stunning views of Stanford, San Francisco Bay, and the East Bay, just 10 minutes from downtown Woodside and 4 minutes to Alices Restaurant. Custom-built in 2004 on 1.4 acres with INCREDIBLE QUALITY AND SEISMIC INTEGRITY, this home exudes quality features including walnut floors, 12-foot ceilings, and fireplaces in the living and dining rooms. The large kitchen features Carrara marble and zinc countertops. Every bedroom and main living area opens to wraparound decks with sweeping views. Dedicated office for remote work, and a large 2-car garage. Level yard for entertaining, with room for pickle ball court, plus a sunny pool area. Direct walking distance access to scenic hiking on Mid-Pen Open Space trails. Convenient door-to-door bus to top-rated Portola Valley schools.

950 Espinosa RD, Woodside

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

$4,000,000

4 Beds ⋅ 3 Baths ⋅ ML82037542 MLS ⋅ Skywood Acres BLDG.

Significant Mid-Century Modern Architecture with Bay Views! Mid-century modern architecture of exceptional pedigree defines this Skywood Acres property designed by renowned furniture maker John Kapel as his own home. Recognized for embodying the distinctive characteristics of mid-century modern design with remarkable artistic value and integrity of workmanship, the home has been featured in numerous publications and described as a masterpiece of artful craftsmanship. A recent renovation honors his original vision while enhancing comfort and energy efficiency for today, including an all-new kitchen and baths, solar panels, three Tesla Powerwalls, and SPAN energy management panels. The home spans 3.16 acres with Bay views and a multi-level floor plan that includes 4 bedrooms, an art studio or playroom, plus a high-end theater and car collectors garage. A separate studio guest house with bath and full kitchen provides added flexibility. Outdoor living spaces are plentiful with a soothing hot tub, heated lounges, and wraparound Bay view decks. This serene location is just one mile from famed Alices Restaurant, 5.5 miles from Woodside town center, and has access to excellent Portola Valley schools.

80 Skywood WAY, Woodside

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

Sold listing courtesy of Sternsmith Group from APR

$10,500,000

5 Beds ⋅ 6 Baths ⋅ ML82035970 MLS

Nestled in prime central Woodside, this remarkable estate was designed by Charlie Barnett and includes a modern farmhouse main home accompanied by a guest house and a charming log cabin, all harmonizing beautifully with the areas rural ambiance. Positioned on a level lot with majestic oaks, the estate features a refined, timeless palette with warm gray concrete floors, oak cabinetry, and limestone tile baths that create a sophisticated yet natural feel. French doors open onto surrounding terraces, inviting in soft, filtered light from the surrounding trees, while the perfect Woodside location places you just moments from Woodside Elementary, the library, and nearby shops and restaurants. This is an exceptional opportunity to enjoy life on one of central Woodside's most coveted streets.

222 Albion AVE, Woodside

Listed by Thomas Werbe, 650-207-9168 from Breakwater Properties, Inc.
(If provided) CoList: from

Sold listing courtesy of Brent Gullixson from COMPS

$2,000,000

3 Beds ⋅ 3 Baths ⋅ ML82035391 MLS

Spanning 2,670 square feet of living space, this home envelopes you with warmth and charm from the moment you enter. Sunlight filters through towering redwoods, creating a serene atmosphere throughout. Refinished hardwood floors and thoughtful modern updates blend timeless quality with everyday comfort. The spacious floor plan flows seamlessly, ideal for both daily living and entertaining. The main floor features a gourmet kitchen with high-end appliances, sleek finishes, dining area, family room and dedicated home office offers the perfect space for remote work or creative pursuits. Upstairs, the bedrooms provide privacy and tranquility. A large, bright family room stands out as a favorite space, filled with natural light and a cozy, welcoming ambiance. Multiple large decks extend the living space outdoors, offering peaceful spots for relaxing, entertaining, or enjoying the majestic redwood surroundings. Additional features include a wine cellar and ample storage. Tucked just off the scenic Skyline Corridor with easy access to Hwy 92, 280/101, SFO, open space trails, restaurants, and award-winning Kings Mtn Elementary, this home offers a rare blend of privacy, convenience, and a strong sense of community fostered by friendly neighbors and the Kings Mtn Volunteer Art Fair.

13872 Silver Sky WAY, Woodside

Listed by Joakim Bye, 650-284-2080 from Ocean Element Real Estate
(If provided) CoList: from

Sold listing courtesy of Evan Walsh from EXPCA

$4,200,000

3 Beds ⋅ 2 Baths ⋅ ML82034218 MLS

Set on approximately 1.65 acres in Woodside Hills, this rare single-story property presents an exceptional opportunity to create a custom estate in one of Silicon Valleys most coveted settings. The existing 3-bedroom, 2-bath residence built in 1955, features a classic footprint, swimming pool, and expansive groundsoffering endless potential for renovation, expansion, or a complete reimagining. Surrounded by mature trees and natural beauty, the property delivers privacy, scale, and a premier canvas for builders, developers, or visionaries seeking to craft something truly extraordinary. Whether restoring the homes mid-century character or designing a brand-new architectural statement, this is a rare chance to secure a sizable parcel in a prestigious enclave where world-class estates define the landscape.

135 Harcross RD, Woodside

Listed by David Kelsey, 650-388-2086 from Compass
(If provided) CoList: from

Sold listing courtesy of Jasmine Lee from CBR

$11,706,000

4 Beds ⋅ 6 Baths ⋅ ML82033323 MLS

151 Eleanor DR, Woodside

Listed by Billy McNair, 650-862-3266 from Coldwell Banker Realty
(If provided) CoList: Andrea Schultz from Coldwell Banker Realty

Sold listing courtesy of Julie Hadidi from COMPS

$23,500,000

6 Beds ⋅ 8 Baths ⋅ ML82031620 MLS

Walking distance to all that the Woodside Village has to offer, this just completed masterpiece showcases the brilliant, organic design of architect Steve Simpson and builder Gilson Development, perfectly in tune with the natural setting. The spacious three-story home, connected by elevator, presents cathedral ceilings, custom Portella steel windows and glass doors, and hydronic-heated white oak floors that span all levels. Four bedrooms and five and one-half baths in the main home are complemented by a detached office with bath and a separate one-bedroom guest house with full kitchen. The lower level featuring a sculptural stainless-steel slide that serves as both art and function, along with a theater, fitness center, steam shower, wine cellar, fully loaded HD Golf simulator, and a bunk room. Resort-style amenities unfold outdoors with a fully tiled saltwater pool and therapeutic spa, fire pit, heated terrace, and full outdoor kitchen surrounded by vast synthetic lawn and professionally landscaped gardens with exceptional lighting. Solar power, four Tesla Powerwalls, and home automation. Acclaimed Woodside Elementary School. Habitable footage: 9,406; Main house: 8,261; ADU: 799; Detached office: 346 Plus garage 550. Total all buildings: 9,956 per Seller architect drawings

6 Cedar LN, Woodside

Listed by Scott Dancer, 650-888-8199 from Compass
(If provided) CoList: Jenn Gilson from Golden Gate Sotheby's International Realty

Sold listing courtesy of RECIP from RCIP

$3,325,000

4 Beds ⋅ 3 Baths ⋅ ML82030869 MLS

OPEN HOUSE SAT. 1/17 & SUN. 1/18 2-4PM. SET ON A ONE-ACRE PARCEL IN DESIRABLE WOODSIDE, THIS 4-BEDROOM, 3-BATHROOM HORSE PROPERTY OFFERS EXCEPTIONAL SPACE, PRIVACY, AND OPPORTUNITY. SUN-FILLED INTERIORS SHOWCASE GLEAMING HARDWOOD FLOORS AND A FLEXIBLE FLOOR PLAN THATS IDEAL FOR EVERYDAY LIVING. THE EXPANSIVE DECK SITS OFF THE MAIN LIVING AREAS AND OFFERS INDOOR/OUTDOOR ENTERTAINING VERSATILITY. THE LUSH GROUNDS INVITE ENDLESS POSSIBILITIESEQUESTRIAN USE, GARDEN OASIS, EXPANSION, OR CUSTOM ESTATE VISIONMAKING THIS AN IDEAL CANVAS FOR BUYERS SEEKING TO CREATE SOMETHING TRULY SPECIAL. AN OVERSIZED GARAGE PROVIDES AMPLE ROOM FOR VEHICLES, STORAGE, OR WORKSHOP NEEDS, AND AN UNFINISHED LOWER-LEVEL AREA OFFERS EVEN MORE ROOM FOR STORAGE. WHETHER ENJOYED AS-IS OR REIMAGINED, THIS PROPERTY PRESENTS POTENTIAL GALORE IN ONE OF THE PENINSULAS MOST SOUGHT-AFTER COMMUNITIES, WITH EASY ACCESS TO TOP SCHOOLS, SCENIC TRAILS, WOODSIDE SHOPPING & RESTAURANTS, AND ALL MAJOR SILICON VALLEY CONVENIENCES.

112 JANE DR, Woodside

Listed by Maxine & Michelle Dumas, 650-591-8000 from Dumas & Company
(If provided) CoList: from

Sold listing courtesy of Angie Wolff from NTERO

$1,650,000

3 Beds ⋅ 2 Baths ⋅ ML82024935 MLS

Handcrafted California adobe-style home nestled among towering redwoods with sweeping Bay views. Built in the mid-century era, this residence blends timeless craftsmanship with natural tranquility. Exposed beam ceilings, brick and adobe walls, and terracotta tile floors create warmth and authentic character throughout. The open living and dining areas feature expansive windows and French doors that frame panoramic vistas and open to patios for seamless indoor-outdoor living. The original kitchen showcases artisan tile counters and solid wood cabinetry with easy flow to the main living areaideal for entertaining or everyday comfort. The spacious primary suite enjoys stunning Bay views and direct patio accessperfect for morning coffee or evening sunsets. Set on a private, fenced lot just minutes from downtown Woodside, this property offers architectural integrity, peaceful surroundings, and exceptional potential to update or expand while preserving its handcrafted charm.

205 Grandview DR, Woodside

Listed by Stephanie Nash, 650-995-3820 from Compass
(If provided) CoList: from

Sold listing courtesy of Lucy Goldenshteyn from RDFIN

$4,049,000

3 Beds ⋅ 3 Baths ⋅ ML82024793 MLS

Refined Country Luxury on a Gated Level Lot Set beyond a gate on a spacious level lot, this newer home offers luxurious quality with an open and bright floor plan. Bamboo floors with a hewn finish, coved crown moldings, solid wood doors, and up-lit tray ceilings exemplify the quality details found throughout. The open design revolves around a spacious foyer with a formal living room, dining area, chefs kitchen with breakfast bar, and family room. There is a dedicated office, perfect for todays work-from-home needs, plus 3 upstairs bedrooms, including the primary suite with Western hill views and marble bath. Outside, the newly landscaped grounds unfold as a private retreat with mature trees and an expansive lawn, all with newly added lighting for evening enjoyment. A vibrant rose garden adds color, a welcoming patio invites effortless al fresco dining and entertaining, plus there is a raised bed succulent garden. Adding to the appeal is the homes close-in convenience just over 2 miles from the Woodside Village and with access to acclaimed Woodside Elementary School.

750 W California WAY, Woodside

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

Sold listing courtesy of Costantini Team from APR

$2,390,000

2 Beds ⋅ 2 Baths ⋅ ML82024519 MLS

Peaceful Woodside Retreat with Sweeping Bay Views Welcome to 168 Sunrise Drive, a serene retreat in the heart of Skywood Acres where you'll enjoy breathtaking panoramic views of the Bay, stretching from San Carlos to San Jose. Set on a spacious 53,577Â± sq. ft. lot, this home offers both privacy and connection to nature. A long driveway leads you to the inviting residence, surrounded by mature landscaping, lush foliage and the quiet beauty of Woodside's countryside. Inside, the home features 2 bedrooms, 2 baths, and a versatile bonus room perfect as an office, studio, or guest space. Vaulted ceilings and floor-to-ceiling windows fill the open living areas with sunlight, creating a warm, inviting space with stunning views from nearly every room. Step outside to a sunny deck and sparkling pool, the perfect place to relax, entertain, or take in the peaceful surroundings. Experience the best of Woodside living - privacy, natural beauty, and views that truly take your breath away. Just minutes from Menlo Park, Palo Alto, and top schools, it offers the rare blend of privacy, prestige and convenience.

168 Sunrise DR, Woodside

Listed by Deanna Reudy, 650-759-2986 from Compass
(If provided) CoList: from

Sold listing courtesy of Sam Habib from C21MM

$2,900,000

5 Beds ⋅ 5 Baths ⋅ ML82023275 MLS

Perched a top of Skyline Ridge, this gated custom estate offers spectacular views of the San Francisco South Bay, including Mt. Diablo, Stanford, and San Jose. Nestled on a private 5+ acre east-facing parcel near the 942-acre Wunderlich Park, the home features 5 bedrooms, 4.5 bathrooms, 4 large decks, and a 2-car garage. The gourmet kitchen with center island, dining room, and large pantry opens to the great room with vaulted ceiling, skylights, and 3 French doors. Upstairs showcases imported slate floors, a central family/activity room, a guest half bath, a library/office, and a spacious primary suite with a walk-in shower, a 2-person jetted spa, a private deck, double sinks, a bidet, and a walk-in closet. A nearby flexible room could serve as a bedroom, nursery, or den. The laundry area opens to a flat yard suitable for a future pool, tennis court, or stables. Downstairs includes 2 bedrooms, a large bath, a sitting room, and a fully self-contained ADU with private entry and a deck. In the coveted Portola Valley/Woodside School District, the estate feels private yet is minutes from Alice's Restaurant, Fogarty Winery, central Woodside, Stanford, and the Coast.

16501 Skyline BLVD, Woodside

Listed by Hebe Li, 650-889-6649 from The Agency
(If provided) CoList: from

Sold listing courtesy of Alexandra Gilmartin from GILM

$4,262,500

4 Beds ⋅ 3 Baths ⋅ ML82023027 MLS

Absolutely the BEST VIEW of the Bay. Wake up early and catch the stunning panoramic view of the sun rising from this 4 bed/3 Mid-Century Modern home in Woodside Hills. Sit back relax and enjoy expansive views of the San Francisco Bay. On a clear day looking a bit Northwest youll catch a glimpse of the Bay Bridge as well as Treasure Island. One of the iconic features of a Mid-Century Modern home is their floor to ceilings windows that provide one with scenic views as well as bringing in an abundance of natural light. As the day transitions from day to night your view will be filled with lights from the bay that can leave you breathless. This 2,430 sq. ft. home on a mostly flat one-acre lot provides an excellent opportunity for one to remodel or design/build the home of your dreams with spectacular priceless views in one the most desired locations on the Peninsula. It's just 35 miles from The City and only 26 miles from Silicon Valley. A short drive from downtown Woodside shops and restaurants. Fine dine at The Pub or enjoy a meal at Bucs of Woodside a fixture of Silicon Valley. Nature lovers can explore the nearby vast open spaces,parks and preserves which provide an abundance of hiking and biking trails. Don't miss your opportunity to make this your forever home. Virtually Staged

170 Hardwick RD, Woodside

Listed by Eliot Beja, 408-506-3788 from Intero Real Estate Services
(If provided) CoList: from

Sold listing courtesy of Matthew Rogers from ELI

$5,525,000

4 Beds ⋅ 4 Baths ⋅ ML82021333 MLS ⋅ Woodside Hills Home Association BLDG.

Set on approximately 1.4 acres with views stretching out to the Bay, this beautifully remodeled 4-bedroom, 3.5-bathroom home offers timeless traditional style with elevated designer finishes. The 3339 sq ft interior features oak hardwood floors with inlaid borders, decorative moldings, and three fireplaces, creating a refined yet comfortable ambiance throughout. The floor plan is ideal for everyday living and entertaining, with formal and casual living spaces, a spacious kitchen, and light-filled rooms that open to the outdoors. Each bedroom offers privacy and flexibility, including options for a home office or guest accommodations. Outside, enjoy the peaceful setting with a sparkling pool, a charming pool house, and beautifully landscaped grounds framed by mature trees. A rare opportunity for style, space, and serenity just a short drive from town and local conveniences.

155 Normandy LN, Woodside

Listed by Tim Kerns, 650-430-4052 from Coldwell Banker Realty
(If provided) CoList: Kyle Katz from Coldwell Banker Realty

Sold listing courtesy of JJ Team:Jones/Cassel from NTERO

$6,495,000

3 Beds ⋅ 3 Baths ⋅ ML82016045 MLS

Mid-Century Modern Style on 1.3 Acres Blocks from Town Center. Classic mid-century modern architecture is showcased on beautiful grounds of approximately 1.3 level acres just blocks from Town Center. Complete privacy is offered behind gates, where a long driveway leads past a fenced tennis court to the home and detached garage. Inside, the ambiance is airy and light-filled with soaring wood-paneled ceilings, skylights, and an entire wall of glass that frames the natural surroundings. Beautifully appointed throughout, the home has hardwood floors, dazzling modern lighting, and a sleek open layout with 3 bedrooms, an office, and 2.5 baths. The formal living & dining rooms as well as the kitchen share a dramatic wood-paneled cathedral ceiling and the wall of glass. A fireplace plus floor-to-ceiling library shelves with moveable ladder access are highlights. A separate family room anchors one wing with two bedrooms and a bath, while the primary suite and office are privately positioned in a separate wing, which has access to a patio with large spa. The grounds are a true retreat with redwood groves, creekside sitting areas, raised vegetable beds, tennis court, plus expansive areas for outdoor entertaining. Access to acclaimed Woodside Elementary School (K8) adds the finishing touch.

3323 Woodside RD, Woodside

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

Sold listing courtesy of Michael Warren from APR

$2,199,000

3 Beds ⋅ 3 Baths ⋅ ML82019950 MLS

Nestled among the redwoods, 13630 Skyline Blvd offers the perfect Woodside retreat. Recently refreshed with a brand-new roof, new decks, refinished hardwood floors, and new carpet, this 3,270 sq ft home is move-in ready. The floorplan includes 3 bedrooms plus a dedicated office, a huge main suite, and spacious living areas that balance privacy with flow. A 2-car garage provides convenience, while the 0.56-acre lot delivers peace and room to grow. Located in the Kings Mountain Elementary boundary, this home offers the serenity of mountain living with the accessibility buyers wantjust 15 minutes to Hwy 280 at 92 and 45 minutes to SFO. Whether youre seeking a full-time residence or a weekend retreat, this property combines natural beauty, thoughtful updates, and everyday practicality in one of the Peninsulas most desirable settings.

13630 Skyline BLVD, Woodside

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

Sold listing courtesy of David Skokan from RMXSP

$2,425,000

4 Beds ⋅ 3 Baths ⋅ ML82019227 MLS

Discover the perfect blend of space, comfort, and natural beauty in this Woodside retreat. A scenic meadow highlights the property, plus a flat, usable acreideal for recreation, gardening, or expansion. The log cabin exterior with river rock accents evokes timeless curb appeal and a true Tahoe-inspired feel. Inside, the open floor plan, formal dining, breakfast room, and large bonus room provide flexibility for entertaining and everyday living. With 3 bedrooms upstairs and 1 downstairs with separate entry, the layout is perfect for families, guests, or multigenerational living. Enjoy top-of-the-mountain living in a park-like setting with redwoods, meadows, and direct access to hiking and equestrian trails in nearby Huddart Park. Sunset views from the expansive deck, a wood-burning stove, hardwood floors, and spa tub in the primary suite add charm and comfort. Amenities include central AC with dual zones, Generac whole-house generator with propane hookup, RV parking, ADT security, gutter guard filters, and a tranquil fenced yard. Just 6 miles from Hwys 92 and 84, youre minutes from the Peninsula or coast while enjoying the privacy and community spirit of Kings Mountain.

13890 Skyline BLVD, Woodside

Listed by Teri Rossetto Shaughnessy, 650-504-4016 from Christie's International Real Estate Sereno
(If provided) CoList: from

Sold listing courtesy of Gina Nibbi from COMP12

$3,800,000

4 Beds ⋅ 3 Baths ⋅ ML82019068 MLS

Great cul-de-sac location, this sunny, designer-updated home is as charming as it is comfortable. Just minutes from downtown Woodside and top-rated K-8 Woodside School, this location in the Glens is coveted. Step inside to discover the main level, featuring three bedrooms, including two with en-suite baths. The primary suite is a peaceful sanctuary with a generous footprint, sitting area, and direct access to the deck. A third full bath accommodates guests and the third bedroom. The heart of the home is open-concept, with a family room that flows seamlessly into an updated kitchen. Flow into the formal dining room and the inviting living room, where picture windows, custom built-ins, and one of two elegant stone fireplaces create a welcoming atmosphere. Step outside onto the expansive deck for effortless indoor-outdoor living and entertaining. Downstairs, discover a flexible fourth bedroom that can also serve as a home office or bonus room. With exposed beam ceilings, French doors leading to a private patio and fire pit, this may become your favorite space. A separate laundry room and two-car garage add functionality. The landscaped, tiered, and fenced backyard is perfect for entertaining, playing, or enjoying the serene natural surroundings.

115 Toyon CT, Woodside

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

Sold listing courtesy of Ginna Lazar from LHG

$4,000,000

5 Beds ⋅ 5 Baths ⋅ ML82018950 MLS

Private ~half-acre property is prime for redevelopment with an existing 3,365+/- sf house and ADU* with 5BDs and 5BAs, a carriage house with studio, paddock, two access gates and multiple outbuildings. This highly coveted location is within 0.5 mile of Woodside Village with Roberts Market, Bucks, the library, The Village Pub (Michelin starred), Village Hub and Village Bakery and Cafe, and near top rated schools, miles of hiking, biking and horseback riding trails and surrounding open space preserves. Nestled in the foothills of the Santa Cruz Mountains between the Pacific Ocean and SF Bay, Woodside is one of the wealthiest communities in Silicon Valley and the U.S. It is renowned for its natural beauty, redwood forests, equestrian culture, sprawling estates, high-profile residents and proximity to Stanford, venture capital firms and tech hubs like Palo Alto and Menlo Park. It is about 30 minutes from San Francisco and the coast, 1.5 hours from Napa Valley and located between two international airports and private jet centers. Affluent, private and understated, this scenic rural town of about 5,100 residents offers a low-key lifestyle and tranquil retreat within easy reach of thriving epicenters. *Some structures may have been built without permits; buyer to investigate.

120 Miramontes RD, Woodside

Listed by Michael Silva, 650-515-2388 from Compass
(If provided) CoList: from

Sold listing courtesy of Josh Rubin from COMPS

$3,000,000

6 Beds ⋅ 4 Baths ⋅ ML82013538 MLS

Perched on 1.5 acres of beautiful land, this spacious 6-bedroom, 3.5-bathroom home offers panoramic views and room to grow. With generously sized rooms and views from nearly every window, this property combines comfort, versatility, and endless potential. A formal entry leads to a grand living room featuring soaring ceilings, a cozy fireplace, and access to an expansive entertaining deckperfect for indoor-outdoor living. The family-style kitchen includes a charming eat-in area, a second fireplace, and plenty of space for gathering. The main level also offers a formal dining room and a functional laundry room with ample storage, conveniently connected to a 2-car garage. Upstairs, youll find four spacious bedrooms, while the lower level has been thoughtfully converted into an ADU, featuring two bedrooms, a full kitchen, bathroom, and its own separate entry and dedicated parking areaideal for extended family, guests, or rental income. This solidly built home is ready for your personal touch and updates. Dont miss the opportunity to make this property your own retreat in a truly special setting.

495 Summit Springs RD, Woodside

Listed by Margot Lockwood, 650-400-2528 from Golden Gate Sotheby's International Realty
(If provided) CoList: Ricky Flores from Golden Gate Sotheby's International Realty

Sold listing courtesy of Ginna Lazar from LHG

$4,900,000

4 Beds ⋅ 3 Baths ⋅ ML82011671 MLS

Surrounded by natures beauty... on 5.4 acres on a private street yet just 3 miles from Sand Hill Road venture capital centers this home offers complete privacy, organic architecture, and spa-like amenities. Oaks and wildflower-strewn meadows create a serene setting deeply connected to the natural landscape with enchanting walking paths. Inside, warm wood finishes, soaring paneled ceilings, and walls of glass establish a tranquil, Zen-like atmosphere that invites the outdoors in at every turn. The layout unfolds with multiple stone fireplaces, outdoor access from nearly every room, and refined materials that reflect the homes high-end craftsmanship. A spa-inspired primary suite features an all-marble bath with cedar-lined sauna and sliding glass doors to the outdoor spa. The flexible floor plan includes one bedroom with a fireplace, en suite bath, and private entrance making it ideal for guest quarters or a possible family room. There is also a detached studio and a lower-level wine cellar with outside access. Outdoor living is equally well considered with a spacious deck overlooking the natural landscape. This one-of-a-kind property offers a close-in location just minutes to miles of hiking and biking trails, town centers, and access to excellent Portola Valley schools.

19 Preston RD, Woodside

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

Sold listing courtesy of Kemper Ray from COMPS

$7,125,000

4 Beds ⋅ 4 Baths ⋅ ML82008127 MLS

Located in the desirable Woodside Heights neighborhood adjacent to Atherton, this dramatic Mid-Century Modern home on 1.05-acres showcases a top-to-bottom designer transformation that elevates every aspect of the home's features. Single-level floor plan offers 4 bedrooms & 4 baths, 2 spacious bedroom suites (one with its own separate office) positioned at opposite ends of the home for optimal privacy with guests or extended family. High-end Walker-Zanger Italian porcelain tile floors throughout provide the look of hardwood with the superior durability & easy maintenance of porcelain. Outdoor designed for entertaining & everyday enjoyment & landscaped to enhance privacy. Sparkling pool, expansive lawn, flagstone terrace with firepit, & separate-level flagstone terrace with fireplace for gatherings. Large poolside cabana open on three sides with its own stone fireplace adds architectural interest & functionality, while the vast undeveloped space at the bottom of the property extends the sense of space & privacy & provides great potential for additional use. Private front courtyard includes an antique marble fountain & a large, wisteria-covered arbor. Complete privacy, a close-in location, & access to top-rated Las Lomitas schools further elevate this one-of-a-kind designer home.

275 Eleanor DR, Woodside

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

Sold listing courtesy of Sanaz Khalili Malek from CBR

$1,875,000

3 Beds ⋅ 2 Baths ⋅ ML82008056 MLS

Morning light pours through redwoods onto white oak floors at this 3BR/2BA retreat on 2.44 private acres. Updated kitchen and marble baths blend comfort and style. A bright barn office and workshop offer flexible use easily converted for equestrian needs with an existing corral. A fenced dog run adds convenience. Enjoy sunrises on the expansive deck or quiet moments on a meditation deck tucked in a redwood fairy ring. Just 10 minutes to Roberts Market, 15 to Stanford, and close to Facebook (20 min), Google (25 min), and Apple (25 min). Top Portola Valley schools and Woodside High.

350 Grandview DR, Woodside

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

Sold listing courtesy of Jennifer Pollock from COMPS

$3,500,000

4 Beds ⋅ 4 Baths ⋅ ML82006889 MLS

Bring your builder and architect!! First time on the market in 50 years - incredible value, priced to sell. Four beds and 4 baths in original ranch home plus more recent addition and ADU above garage. Beautiful in ground pool. Horses allowable and close to Woodside trails. Almost three acres!!!! Close to all Central Woodside has to offer including highly desirable Woodside elementary school.

380 La Questa WAY, Woodside

Listed by Andrea Ivarsson, 949-933-0219 from Coldwell Banker Realty
(If provided) CoList: from

Sold listing courtesy of Andrea Ivarsson from CBR

$1,924,911

3 Beds ⋅ 2 Baths ⋅ ML82002229 MLS

Welcome to this charming updated 3-bedroom, 2-bathroom home located in the beautiful city of Woodside. This inviting residence sits on a spacious 15,400 sq ft lot, offering plenty of room to enjoy the outdoors. Inside, the well-appointed updated kitchen features modern amenities including a gas cooktop, dishwasher, microwave, oven range, and refrigerator, making meal preparation a breeze. The dining area, conveniently situated in the living room, creates a cozy atmosphere perfect for entertaining. Updated ADU with additional 3rd bathroom separate entrance. Large barn-like 2 car garage with extra room for storage workshop/office or more. This home is located within the Woodside Elementary School District. Lush and serene grounds with quiet and privacy inside this beautifully done home. Easy access to HWY 280 and downtown Woodside, close proximity to the Filoli Historic House and Garden. Don't miss the opportunity to make this lovely Woodside home your own. Large price reduction..Motivated Sellers!

789 Canada RD, Woodside

Listed by Tammy T-Cole, 650-683-0426 from Compass
(If provided) CoList: from

Sold listing courtesy of Sharad Gupta from LY55V

$12,600,000

4 Beds ⋅ 5 Baths ⋅ ML82003378 MLS

Striking Modern Retreat near Town Center. In the heart of central Woodside, this modern home retains secluded privacywith convenience to shopping & dining just down the road. On a private country lane off the main road, the just over 1-acre setting presents sweeping western hill views from its gentle knoll beyond custom gates. Sophisticated architecturalelements define the home, from Ann Sacks tiles and radiant-heated French oak and marble floors to dazzling designerlighting and Fleetwood doors and windows. The open floor plan balances spacious gathering areas with options for privacyand flexibility plus indoor/outdoor living all around. A dramatic fireplace is shared by the family room with the living anddining room, all oriented to the majestic views. The open kitchen is a hallmark of the design, blending warm wood toneswith French limestone and designer tiles, while an adjacent den/study center offers versatility. There are 4 bedrooms and4.5 baths plus an equally well-appointed 1-bed, 1-bath guest house with full kitchen and laundry, perfect as an ADU orpoolside entertaining. At the center, a sparkling infinity-edge pool is surrounded by level lawn and sun-drenched terraces.A rare combination of modern luxury, a premier location, plus access to Woodside School (K-8).

1491 Canada LN, Woodside

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

Sold listing courtesy of Michael Warren from APR

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