Woodside Homes with Guest House for Sale

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. Estate shows tremendous 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 parking trailers. Beautiful Western & Southern hills views. Award winning Las Lomitas Elementary Schools K-8. Nearby to town center, easy commute 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 separate driveway. Seller wants it sold.

389 Moore RD, Woodside

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

$38,800,000

6 Beds ⋅ 9 Baths ⋅ ML82045742 MLS

This extraordinary Woodside estate spans 6.4 level acres w/sun-swept vineyards & western hill views. The compound comprises multiple architecturally significant buildings, including the main residence, guest house, a multi-room wellness studio w/wine cellar & 6-car garages plus a working lab w/anti-static flooring. Designed for exceptional privacy & self-sufficiency, the property features a 35kW photovoltaic solar system, a 125kW whole-house backup generator, & a 1,600 amp electrical service. A comprehensive, enterprise-grade infrastructure includes a network w/fiber connectivity linking each building to the main racks, supported by a firewall, 26 ethernet switches, & 15 Wi-Fi access points. A whole-house audio system powered by advanced network amplifiers & Lutron-app controlled light further elevate the living experience. The grounds are equally compelling, with a well for irrigation, a clay tennis court, lighted sport court, & approximately 2 acres of Pinot Noir grafted aged vines. A whimsical designed 3-tree playhouse & fort adds a rare & enchanting element to the landscape. The result is a true sanctuary--where architectural beauty , advanced infrastructure and natural surroundings converge in one of Silicon Valley's most exceptional settings.

15 Hidden Valley LN, Woodside

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

$6,561,058

5 Beds ⋅ 5 Baths ⋅ ML82045206 MLS ⋅ Woodside Hills Association BLDG.

Set on a flat acre of gorgeously manicured grounds. This single story home borrows transitional architectural tones from the French countryside. The circular driveway leads up to a large 3 car garage. Five bedrooms that come with a separate guest house, sports court, large pool with covered grotto like spa, adjacent bath with changing room. Outdoor kitchen covered by a palapa, the perfect shade from natural elements while dining al fresco. Backyard is south facing and hosts the perfect weather all year long. The yard is an entertainers paradise. French oak engineered flooring throughout. Kitchen has an open layout with Thermador appliances and tuscan inspired limestone touches. Front living room has custom built shelving and cozy gas fireplace. Knotted Alderwood window and doors. Indoor surround sound. Generous master suite with walk in closet and wardrobes. Heated floors in bath and an oversized shower with tropical garden views. Enjoy the privacy this secluded subdivision provides. Hidden away, yet suburban enough hooked up to city sewer and close proximity to Sand Hill Road, Silicon Valley and San Francisco. Close to Menlo School, Sacred Heart Prep, Phillips Brooks, Woodside Priory amongst many other renown schools. Enjoy sunsets and the nature this lifestyle provides.

330 Ridgeway RD, Woodside

Listed by Mariana Pappalardo, 650-670-7888 from Compass
(If provided) CoList: from

Sold listing courtesy of Agnes Yu from BPRO

$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

$34,995,000

8 Beds ⋅ 7 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

$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

$12,750,000

4 Beds ⋅ 8 Baths ⋅ ML82041478 MLS

Extraordinary residence on 5 acres with opulence and European inspiration at every turn. Impeccably crafted by renowned builder Markay Johnson in 2014 on a private gated lane with gated driveway and sweeping views of San Francisco Bay. Lavish beauty throughout the home with hand-selected marble from Milan, elaborate millwork, Doric columns, intricate carvings, and gilded details. All-marble staircase with hand-forged railings leads to the upper level with formal living room, formal dining room, tremendous kitchen, family room, office, plus grand primary suite with 2 full baths. 3 luxurious bedroom suites plus large office and conference center make up the ground level. Breathtaking views from every room on both levels. Elevator in the main residence. 1-bedroom pool house and studio guest house, each with bath and full kitchen. Sparkling pool and spa plus fireplace terrace for idyllic entertaining in complete privacy.

490 Las Pulgas DR, Woodside

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

Sold listing courtesy of Scott Dancer from APR

$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

$12,988,000

6 Beds ⋅ 6 Baths ⋅ ML82032525 MLS

Discover this exceptional opportunity to own a generational estate spanning 7 acres across 3 separate parcels, each with its own APN. Through a private gate & down a long winding driveway, you're greeted by a circular motor court with incredible views of the Santa Cruz Mountains. The main residence offers 4,340 sqft featuring 6 beds & 5.5 baths, with exceptional upgrades throughout. On the east side of the property there is a large building pad; once the site of a horse stable, recently prepared for development. This pad is situated on the border of 2 of the 3 parcels & includes direct access from Moore Rd via a natural pathway. Nestled on the western edge of the property through via separate entrance is a 2k sqft guest house boasting high ceilings, 2 bed-1 bath, all opening out to an infinity-edge pool surrounded by lush landscaping. Winding pathways connect this serene retreat to the rest of the estate. This is a truly versatile offering with significant future upside through lot line adjustments, possible subdivision, or exploring SB9 opportunities. A unique & rare chance to create a lasting legacy in one of the most coveted zip codes in the country. Designated under the Las Lomitas school district with proximity to private institutions such as Sacred Heart & Woodside Priory.

1142 Moore RD, Woodside

Listed by Kia Amini, 408-694-7160 from Compass
(If provided) CoList: from

$2,050,000

3 Beds ⋅ 4 Baths ⋅ ML82032237 MLS

Step inside and step back in time to this to this stunning Henrik Bull-style home in Skywood Acres, where classic charm meets modern comfort. Nestled in a sunny tranquil setting, this architectural gem opens into a breathtaking great room with cathedral ceilings and walls of windows that frame sweeping treetop views. This seamless blend of indoor/outdoor living extends to an expansive deck offering a perfect retreat that harmonizes with nature. Reminiscent of a mountain ski lodge, this 2510 sqft private haven enjoys its own sunny microclimate and offers the ultimate escape, just 14 minutes to 280, 25 minutes to Stanford, minutes from Alices Restaurant, and private access to Wunderlick Park, Portola Valley schools. Main home features a primary bedroom that includes bathroom, dressing room and private office. Main level boasts a well-appointed kitchen, custom wood built-ins, opens to a grand living area. Downstairs 2 bedrooms and bath, 3 car garage with wine closet. Detached guest studio with sleeping loft. 1.5 acre lot includes a former sport court ready for new possibilities Make this getaway your private Shangri-La

45 Ranch RD, Woodside

Listed by James Milton, 650-868-1356 from Coldwell Banker Realty
(If provided) CoList: from

Sold listing courtesy of Shawnna Sullivan from CBR

$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

$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

$3,125,000

3 Beds ⋅ 2 Baths ⋅ ML82019083 MLS

A rare and private 15+ acre estate blending equestrian excellence, vineyard living, and natural beauty. Perfect for riders, vintners, or those seeking peaceful country living. The Barn Pros barn includes 4 matted stalls with Euro fronts, individual runs, a heated wash rack with hot/cold water, tack room, and enclosed feed/hay storage. Above, a spacious apartment with 2 sleeping areas, tall ceilings, and sweeping viewsideal for guests, caretakers, or rental income. Equestrian features include 2 fenced pastures with matted double run-ins, a paddock with a single matted shed, ~95x198 Olympia Footing arena (fenced with sand/rubber footing), and a ~60 round pen. The vintage 3BR, 1.5BA farmhouse offers rustic charm, storage, a cellar, and a relaxing front porch with serene views. A newer guest house (separately addressed) features 1BR + office/bonus roomideal for family, guests, or rental. Enjoy ~1 acre of Pinot Noir vines, fully fenced and producing excellent estate wineperfect for personal use or boutique winemaking. Mid Pen has plans to add a lot and access to the La Honda Open Space Perserve, that is right across the street. This is more than a propertyits a lifestyle sanctuary just ~20 mins to Hwy 280 and 30 mins to Half Moon Bay.

11120 La Honda RD, Woodside

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

Sold listing courtesy of David Cline from CBR

$7,500,000

4 Beds ⋅ 5 Baths ⋅ ML82017471 MLS

Set on a 3.1-acre, private and gated lot in one of Woodside's most scenic settings, this exceptional, newly-updated residence offers the perfect blend of refined luxury and modern comfort - just minutes from town. Flooded with natural light from expansive floor-to-ceiling windows, the main home spans 3 levels and offers 4 bedroom suites, a library with fireplace, an office, and grand public spaces in +/-5,555sf. The open-concept living room boasts 24-foot ceilings, massive curved windows, a striking fireplace, and flows seamlessly into the sun-filled dining room. The chef's kitchen opens to a huge family room with 10-foot ceilings, a dramatic fireplace, bar, and French doors opening to a patio-perfect for indoor/outdoor living. Designed for everyday comfort and entertainment, the home offers multiple terraces, temperature-controlled wine storage, and an expansive lower level replete with a gym, home theater, and full bath. Outdoor amenities include a pool with spa, tennis court, meandering paths that encircle the property, level lawns, and a vineyard. A detached 2BR/2BA, +/-1,135sf guest house is ideal for extended family or visitors. Access to the top-rated Woodside Elementary School completes this rare opportunity to experience a lifestyle of elegance, privacy, and convenience.

333 Raymundo DR, Woodside

Listed by Jim Arbeed, 650-558-4248 from Coldwell Banker Realty
(If provided) CoList: from

Sold listing courtesy of Jaswinder Gill from GILLJ

$9,600,000

5 Beds ⋅ 6 Baths ⋅ ML82013370 MLS

Set on more than 3.6 gated acres of quintessential Woodside grounds, this contemporary masterpiece is surrounded by towering oaks and lush greenery, offering a serene, woodsy retreat. The interiors reflect the natural setting with soaring cherry wood cathedral ceilings, cherry wood floors, and expansive picture windows that flood the home with light and invite the outdoors in. Designed for both entertaining and everyday living, the residence features grand formal rooms, multiple fireplaces, a chefs kitchen with sunny breakfast nook, a walk-out family room, and a stylish executive office. Four bedrooms include a luxurious primary suite with its own fireplace, balcony, and spa-inspired bath. Outside, sprawling grounds offer a center courtyard with covered deck and fire pit, built-in grill, a separate guest house, and two garages including one with a lift for car enthusiasts as well as an RC car racetrack. Minutes from Portola Valley, top schools, and Silicon Valley tech centers.

140 Farm RD, Woodside

Listed by DeLeon Team, 650-900-7000 from Deleon Realty
(If provided) CoList: from

Sold listing courtesy of David Weil from PACT

$2,100,000

4 Beds ⋅ 4 Baths ⋅ ML82006263 MLS

Discover the tranquility of Woodside living in this beautifully designed 4-bedroom, 3.5-bath home, nestled on 1.5 private acres with sweeping views of mountains and lush trees. Backing directly onto open space, this home offers unmatched peace and seclusionyet is just minutes from the heart of town. The spacious open floor plan is ideal for modern living, providing seamless flow between the living, dining, and kitchen areas. In addition to the main residence of 2 bed, 2 bath and loft , the property features a charming 2 bed, 1 bath guest unit and a versatile artists studio with half bath, offering two additional income-producing or creative spaces. Located within the award-winning Woodside Elementary School District (K8), this home is perfectly positioned for families seeking top-tier education and a strong sense of community. Enjoy the nearby outdoor treasures such as the scenic trails of Huddart Park, and explore the history of the area at the iconic Woodside Store. Dine at the legendary Bucks Restaurantfamous as the meeting place where many Silicon Valley startups were born. With convenient access to Highway 280, you're just a short drive from both Silicon Valley and San Francisco. Come experience the peaceful charm and timeless appeal of Woodside.

885 Patrol 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 Brendan Callahan from COMPS

$14,250,000

6 Beds ⋅ 8 Baths ⋅ ML82004065 MLS

Masterfully Renovated Bay-View Vineyard Estate. This extraordinary estate presents a masterfully executed whole-home renovation, captivating San Francisco Bay views, and resort-style amenities. Encompassing 1.8 acres of fully landscaped grounds, the property also includes a Chardonnay vineyard, two wine cellars, and expansive indoor and outdoor entertaining spaces designed for grand gatherings. The main residence was taken down to the studs with both levels reimagined with the ultimate in designer sophistication. Highlights include bespoke lighting, custom wall coverings, premium fixtures, exquisite finishes, and white oak floors throughout. The main residence has 6 bedrooms, 6 full baths, and 2 half-baths. As part of the renovation, an equally well-appointed 2-bedroom, 1-bath guest house was added along with a pool house with indoor barbecue center and ample space for entertaining.

140 Eleanor DR, Woodside

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

Sold listing courtesy of Pamela Culp from COMP32

$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

$5,750,000

4 Beds ⋅ 4 Baths ⋅ ML82002115 MLS

Welcome to a breathtaking estate crafted from heart redwood, where timeless elegance meets modern luxury. The beautifully updated main residence features four spacious bedrooms along with a renovated kitchen and baths, designed for both comfort and style. Two inviting guest houses provide flexible living options, while a third guest unit serves as a bright, inspiring studio/gym. Soak up the sun by the luxurious pool, unwind in the private spa just off the primary suite, or find serenity on one of the many garden patios. Skylights throughout the home flood the interiors with natural light, creating a warm and welcoming ambiance. For outdoor entertainment, enjoy friendly competition on the bocce ball court or stroll through the storybook grounds, complete with sweeping lawns and majestic oaks. Set on fully fenced, gated, and alarm-secured acreage with garage parking for three, this rare retreat offers privacy, beauty, and convenienceall within the acclaimed Portola Valley school district. A truly magical and one-of-a-kind offering.

1477 Portola RD, Woodside

Listed by Kristin Cashin, 650-387-2603 from Christie's International Real Estate Sereno
(If provided) CoList: from

Sold listing courtesy of Ankur Luthra from CATAPULT

$4,200,000

4 Beds ⋅ 3 Baths ⋅ ML82000241 MLS

Best Value in Woodside! 3 SUNNY acres- all usable. Spacious and expansive, the classically simple and refreshed one-level home is designed for effortless indoor/outdoor living. Highlights include a dramatic great room, extra-large kitchen, 4 bedrooms, and seamless access to the pool and enchanting outdoor living spaces. Enhancing the appeal is a separate guest cottage or ADU, equestrian facilities with direct trail access to 973-acre Huddart Park, plus access to acclaimed Woodside Schools. 3 sunny acres, all usable and ready for planting/farming and/or horses Spacious, refurbished one-level home with a design for indoor/outdoor living ( approx 3340 square feet) 4 bedrooms and 3 baths; approximately 3,340 square feet Guest cottage or ADU with full kitchen, bath, and large deck( approx 640 square feet) 3-car garage with workshop ( approx 970 square feet) Pool plus expansive entertaining patios and decks ( approx storage rooms 215 sq ft, dressing rm 90 sq ft,) Equestrian facilities with two barns ( approx 1175 and 190 sq ft) riding arena ( approx 50x100), and fully fenced horse pastures Woodside Elementary (K-8) School (total structure approximate square feet 6620)

252 Raymundo DR, Woodside

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

Sold listing courtesy of Michael Warren from APR

$4,170,000

4 Beds ⋅ 4 Baths ⋅ ML81997614 MLS

Welcome to 277 Grandview Drive, a contemporary Craftsman style haven in Woodside, CA offering privacy near Silicon Valley. The 4-bed, 4-bath main house with 2 offices spans 4920 sq ft on a 10+ acre lot. A 996 sq ft guest house, with an additional 1 bedroom and 1 bath, adds versatility (currently used as a music studio). The gated entrance reveals a welcoming design which includes an 8.4 kW solar system with battery backup. Inside, discover radiant heating, a chef's kitchen and two living rooms with surround sound. Outside, a fireplace, porch and deck offer relaxation and entertainment spaces, not to mention ultimate privacy. Adjacent to Thornewood Open Space, and built in 2008, this residence seamlessly combines modern amenities with eco-conscious features. Explore the harmonious blend of modern living and natural beauty.

277 Grandview DR, Woodside

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

Sold listing courtesy of Eddie Oberoi from NTERO

$10,495,000

4 Beds ⋅ 4 Baths ⋅ ML81981937 MLS

Just-completed one-level vineyard estate with San Francisco Bay views. Built with natural stone walls inside and out and vaulted all-wood ceilings in every room. Nearly every room has French limestone floors, cabinetry is waterfall-wrapped in natural quartzite, and handcrafted iron doors are inspired by Tiffanys in New York. Unique see-through wine cellar upon entry, formal dining room opens to a waterfall wall, and stunning great room for entertaining. The primary suite has a couture closet room and spa-inspired bath. There are 4 bedrooms and 3.5 baths in the main home plus 2 bedrooms and 1 bath in the updated original guest house with full kitchen. Outdoor living spaces are spectacular with a zero-edge pool and spa, kitchen/dining lounge with pizza oven, vast eco-friendly lawn, fire pit terrace, and bocce court in the vineyard. Exceptional dog run and custom tortoise enclosure for the animal lover. Square Footage Breakdown: Main Residence: 4,887 | Garage: 782 | Guest House: 1,184 | Total: 6,853. Buyer to verify.

2195 Greenways DR, Woodside

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

Sold listing courtesy of Joe Kwan from JODI

$4,600,000

4 Beds ⋅ 4 Baths ⋅ ML81981262 MLS

Opportunity abounds on over one acre just a mile from town center and with access to acclaimed Woodside Elementary School. Move in and enjoy, renovate, or build new. The sprawling mid-century ranch home is bright and light and has been freshly updated with all new paint while preserving its vintage charm in the kitchen and bathrooms. There are 4 bedrooms and 3 baths plus a 1-bedroom, 1-bath ADU with full kitchen for guest accommodations, rental potential, or a comfortable space while designing a future estate. Vast level grounds, separately fenced pool, and equestrian zoning.

155 Ravine DR, Woodside

Listed by Judy Byrnes, 650-208-2388 from Coldwell Banker Realty
(If provided) CoList: from

Sold listing courtesy of Christienne Hadley from CBR

$5,200,000

5 Beds ⋅ 6 Baths ⋅ ML81966423 MLS

Rare new-build contemporary in Woodside! Designed by Steve Simpson/SDG Architecture and built by Milne Design and Build, both know for attention to detail, this spectacular dream home provides your own private sanctuary. Its total livable area of 3,875 sf, is comprised of a two story 4 BR / 4.5 BA Main Home (approx 3,175 sf) with an artful blend of wood finishes, large windows and dark steel beams. Its main level open floor plan has a large chefs kitchen connected to a light-filled living room and dining area and also features a separate office which can double as the fourth bedroom. A lower level boasts three additional bedrooms, including a large primary suite, walk-in closet, soaking tub, shower and dual sinks and a spacious laundry room. The main home also has a coveted attached two-car garage (approx 465 sf) along with several additional off street parking areas. An adjacent detached two level 1 BR/1BA Guest House (approx 700 sf) has a full kitchen and guest suite, lower bedroom and covered exercise patio, providing perfect optionality for a remote office, hosting visitors or indoor/outdoor exercising. The property is situated on a less traveled one way street within walking distance to Town Center shops, restaurants and the acclaimed Woodside School (pre-K to 8th)

327 Hillside DR, Woodside

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

Sold listing courtesy of Helen Miller from APR

$5,500,000

4 Beds ⋅ 5 Baths ⋅ ML81959261 MLS

3 acres in a superb close-in location with a wonderful combination of mid-century aesthetics and country amenities. Sleek and expanded main home has tile and hardwood floors, grand main living room, formal dining room, and eat-in kitchen with high-end Wolf and Sub-Zero appliances. 3 bedroom suites on the main level including primary suite with private office, plus lower-level suite with outside entrance and 2-bedroom, 1-bath Accessory Dwelling Unit with full kitchen and private garage. Pool, poolside recreation room, changing room with bath, large barn, solar-powered electricity, and beautiful serene grounds. Less than one mile from acclaimed Woodside School (K-8) and from trailhead access to 974-acre Huddart Park with miles of horse and walking trails.

259 Kings Mountain RD, Woodside

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

Sold listing courtesy of Dana Cappiello from SIR

$16,800,000

4 Beds ⋅ 6 Baths ⋅ ML81947147 MLS

New Price! This magnificent contemporary farmhouse is situated on 3+ flat acres with spectacular views of the Western Hills and is within easy walking distance to the Woodside School (preK-8th grade) and Town Center. A testament to timeless architecture, meticulous craftsmanship and designer details, the main home and guest house were newly constructed in 2012 by renowned builder, Pacific Peninsula Group. Nothing short of exceptional, the 4 bedroom main home has high end finishes and white oak floors throughout, a state-of-the-art chefs kitchen and a eye catching two-story great room with rustic wooden beams and a honed limestone two-sided gas-fed fireplace. This estate's flat 3+ acres, which include a detached 1,255 sf elegant one-bedroom guest house, are elegantly fully utilized between the natural front equestrian pasture, the rear pool, spa and large entertaining terrace, the wisteria-framed fire pit, a 6-raised bed vegetable garden, chicken coop, dog run and fenced corrals. Privacy, entertainment options and enviable location, this property has it all!

140 Olive Hill LN, Woodside

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

Sold listing courtesy of Liz Daschbach from COMPS

$12,099,888

5 Beds ⋅ 6 Baths ⋅ ML81933807 MLS

Originally owned by socialite Adelaide Kirkbride, Canardia is a majestic 7+ acre Woodside equestrian estate. This special home has been extensively remodeled and reimagined to fit today's contemporary lifestyle. The main home features abundant light, high ceilings, energy efficient metal roof, dual pane windows and doors, hardwood flooring, remodeled bathrooms, and a gourmet chef's kitchen that features a huge center island, sub zero refrigerator, and 2 La Cornue stoves. This entertainer's paradise has hosted many gatherings, charities, fundraisers and weddings on its bountiful grounds with over 500 guests at a time. Other features of the property include a long scenic winding driveway, private lake with sand beach, a 6 stall remodeled stable, an outdoor kitchen, pool, pool house, multiple fountains, 3 wells, fire pits, a bocce ball court, a rose garden and large grassy areas. Only a short drive to Sand Hill Road, 280 and everything that San Francisco and Silicon Valley have to offer.

1550 Portola RD, Woodside

Listed by Monique Anton, 650-380-5512 from Modern Homes Realty
(If provided) CoList: from

Sold listing courtesy of Min Hui from ABAC

View All Woodside CA Home Listings - With Guest House