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$2,870,000
7 Beds ⋅ 6 Baths ⋅ ML82039818 MLS
A rare opportunity to own an expansive estate with breathtaking panoramic views, exceptional square footage, and incredible potential in a private hillside setting. From the moment you arrive, the home commands attention with its grand entry and impressive scale. Inside, soaring ceilings, dramatic open spaces, and walls of windows flood the home with natural light while showcasing sweeping valley views. The main level is built for both everyday living and entertaining, featuring a spacious living room, multiple gathering areas, and seamless access to a wraparound deckperfect for true indoor-outdoor living. The kitchen offers a large island, ample cabinetry, and a functional layout ready to be elevated into a stunning chefs space. Generous bedrooms and flexible living areas include a primary suite with scenic windows, dual vanities, and a soaking tub, creating a peaceful retreat with beautiful natural surroundings. The lower level offers an expansive bonus/game room with bar area and endless possibilities for entertaining, recreation, or extended living. A dedicated wine cellar adds a rare and desirable touch. Expansive decking and usable outdoor space complete this exceptional offering, blending privacy, scale, and opportunity in a truly unique setting.

245 Heacox RD, Woodside

Listed by Aaron Derbacher, 408-828-8114 from KW Bay Area Estates
(If provided) CoList: Benjamin Frieden from KW Bay Area Estates
$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
$3,150,000
4 Beds ⋅ 3 Baths ⋅ ML82049733 MLS
Truly extraordinary 10+ acre retreat offers a rare combination of privacy, usability, and natural beauty. Tastefully updated home sits on an elevated, level setting surrounded by mature trees and abundant sunshine, creating a peaceful sanctuary that feels far removed from the pace of everyday life. A private road winds down through the property, crossing a seasonal creek before opening to a spectacular sunny meadow below & connects to Horse and Hiking trails. This expansive area presents endless possibilities, from horses, barns, and riding facilities to orchards, gardens, recreational uses, or simply enjoying the open space. Outdoor enthusiasts will appreciate direct access to miles of nearby trails for hiking, horseback riding, and mountain biking right from the property. Combining turnkey living with exceptional land, tremendous sun exposure, remarkable privacy, and a setting that inspires exploration and relaxation, this is a truly special opportunity to own one of Skylines most compelling lifestyle properties

17001 Skyline, Woodside

Listed by Nino Gaetano, 650-207-1986 from The Agency
(If provided) CoList: from

Sold listing courtesy of Greg Damelio from SGP
$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
$2,715,000
4 Beds ⋅ 4 Baths ⋅ ML82048252 MLS

320 Grandview DR, Woodside

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

Sold listing courtesy of Julie Hadidi from COMPS
$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
$4,499,000
ML82042331 MLS
2.8 Acres of Buildable Land Next to Menlo Country Club. This exceptional nearly 3 acre vacant parcel presents an extraordinary opportunity in a prestigious setting, offering endless possibilities for building. The vacant land, bordering the Menlo Country Club, offers gently rolling terrain with open meadows, wildflowers, perimeter trees, and views of the East Bay hills. With a serene landscape and conceptual plans for a custom residence and accessory structures, this lot offers a unique chance to establish an exceptional property in a sought-after location.

941 High RD, Woodside

Listed by Erika Demma, 650-740-2970 from Compass
(If provided) CoList: Michael Dreyfus from Golden Gate Sotheby's International Realty
$2,195,000
3 Beds ⋅ 3 Baths ⋅ ML82042155 MLS
Spanning approximately 2.92 usable acres of gently rolling meadows with picture-postcard views, this classic horse property offers miles-away tranquility just 20 minutes from Highway 280. A palatial driveway leads to a two-story, 3-bedroom, 3-bath, open-plan residence with walls of windows capturing the rolling hill and city-light views. Almost every room has glass doors to the long, view balcony. Lawn and mini orchard. A separate charming barn captures the Old West Woodside feel with a wood-beamed ceiling, full-sized bar, and French doors to a veranda with flowering vines. Just a mile to the Thomas Fogarty Winery and 8 minutes to Alice's Restaurant.

20255 Skyline BLVD, Woodside

Listed by Jennifer Paulson, 650-996-7147 from Christie's International Real Estate Sereno
(If provided) CoList: from

$2,250,000
4 Beds ⋅ 4 Baths ⋅ ML82041849 MLS
Set on 2.6+ wooded acres in the hills, this warm & beautifully renovated home offers something genuinely rare on the Peninsula: complete privacy amid towering redwood trees, a profound sense of forest immersion, and less than 15 minutes to Sand Hill & 280. The updated & open floor plan kitchen flows into generous dining and living spaces, all oriented towards sweeping forest views. Natural light fills the space, and wraparound decks extend living outdoors, with a hot tub just off the primary suite. A flexible two bedroom wing can accommodate children, teens, guest rooms, or office and studio space. An independent 1-bdrm ADU with its own kitchen / bath is ideal for rental income, an au pair, or an aging parent. The kitchen, secondary bathrooms, finishes, HVAC, roof, and water heater - have all been recently renovated, and pre-sale inspections were completed with virtually all items addressed. Hiking, cycling & equestrian trails connect directly to the property, and the land is zoned for horses. Stanford's campus is a short, predictable 25 min commute away. Zoned for Portola Valley El / Mid schools and Woodside HS, with several excellent private schools nearby. Soaring redwoods, architectural warmth & effortless access to the heart of Silicon Valley - come see it for yourself.

12 Summit RD, Woodside

Listed by Alexander Nichols, 650-575-4069 from eXp Realty of California Inc
(If provided) CoList: from

Sold listing courtesy of Susanne Bohl from RDFIN
$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
$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
$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

$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
$5,750,000
4 Beds ⋅ 3 Baths ⋅ ML82037292 MLS
Gorgeous, unobstructed views of the bay and mid-century styling in a private setting in Woodside Hills. Situated on a 1.12-acre lot with 4 spacious bedrooms plus an office and 3 bathrooms, this single level home offers a terrific floor plan. Designed to embrace natural light with dramatic floor-to-ceiling windows and high ceilings that create an airy, open atmosphere while seamlessly connecting indoor and outdoor spaces. The large patio, seen through walls of glass throughout the home, overlooks the views and is the ideal spot for entertaining. The gardens feature mature fruit trees, charming landscaping, spaces for children to play, and a sparkling pool and spa. The 2-car attached garage and additional detached 1-car garage and a generous circular driveway provide ample parking.

51 Cragmont WAY, Woodside

Listed by Monica & Mandy Group, 650-823-8212 from Compass
(If provided) CoList: from

Sold listing courtesy of Judy Citron from COMPS
$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
$4,850,000
4 Beds ⋅ 4 Baths ⋅ ML82024655 MLS
Sweeping views across the San Francisco Bay take center stage at this beautifully remodeled home on more than 3 acres of predominantly level land. Minute to downtown Woodside and Stanford. Designed for entertaining and recreation, the property features a large pool and separate spa framed in Connecticut bluestone, an expansive synthetic lawn for recreation and play, and broad decks with built-in seating and cable-strung railings. A brick-walled garden courtyard with Art Deco metal and glass front doors introduces the interiors highlighted by soaring ceilings and skylights. Wall-to-wall windows capture the panorama of the glorious views immediately upon entering. Multiple gathering spaces include a dramatic living room with stone-clad fireplace, a remodeled kitchen and dining area, and a family room with full bar and fireplace. A flexible use room between the foyer and kitchen offers versatility for a home office or playroom. Four bedrooms in a separate wing include a spacious primary suite with Bay views and steam shower, three bedrooms and a remodeled bath, plus there are two half-baths. Solar power with four Tesla Powerwalls, reclaimed San Francisco cobblestone paths, and a three-car garage are added features. Highly Rated Portola Valley Schools. Minutes to Woodside Village.

6 Friars LN, Woodside

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

Sold listing courtesy of Elena Tsukanova 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 53,577± 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
$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
$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
$1,790,000
3 Beds ⋅ 3 Baths ⋅ ML82011144 MLS
Welcome to Five Acre Woods - A Magical Retreat in Woodside! Nestled on 5.6 private acres, this enchanting property offers sweeping Bay views framed by majestic redwoods. Combining seclusion with convenience, its just minutes from Hwy 280 and the town center of Woodside. Originally built in 1915, this 3-bed,3-bath home has been thoughtfully updated for modern living. With approx. 2,300 SF of single floor space, recent upgrades include a new metal roof, fresh paint, & flooring. The open kitchen flows into a great room that leads to a wrap-around deck, perfect for entertaining or enjoying the serene setting. 2 en-suite bedrooms are off the great room, while a 3rd bedroom & bath open directly to the deck. An office/bonus room offers inspiring redwood views, and the lower level features large, partially finished spaces ideal for a workshop, gym, or studio. Outside, explore your own stream, swing, and private trail connecting to the Thornewood Open Space Preserve. The ppty enjoys a mostly fog-free climate, making outdoor living a year-round pleasure. Located just 2 minutes from Four Corners, home to Alices Restaurant, gas station, and Skywood Trading Post -this home is also in the PV Sch Dist. Offering charm, privacy, and potential, this classic Woodside retreat is a rare find.

125 Grandview DR, Woodside

Listed by Lisa Keith, 650-703-8644 from Golden Gate Sotheby's International Realty
(If provided) CoList: from

Sold listing courtesy of Disen Cai RE Group from KWPEN
$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
$4,850,000
5 Beds ⋅ 4 Baths ⋅ ML82004201 MLS
Completely transformed with sophisticated designer style, this home showcases luxury living at every turn, elevated by panoramic views that stretch from the San Francisco Bay & East Bay hills to the western hills. A striking front entrance, reimagined with cable-strung railings & beautiful landscaping, sets the tone for the more contemporary interiors. Located on just over one-half acre, the setting offers exceptional privacy along with expansive outdoor space designed for both relaxation & play, with vast level lawn, custom treehouse & playground, & expansive view-facing decks. A crisp white palette & refinished hardwood floors are complemented by sleek modern lighting & a reimagined kitchen. Multiple fireplaces enhance the ambiance, while vaulted ceilings & skylights infuse the home with natural light. Open-concept floor plan is designed for formal & casual living, including a lower-level family room & separate recreation room with fitness zone & rock climbing wall, plus a full kitchenette, all with direct access to outdoor play & entertaining space. Adding the finishing touch is a close-in location just minutes from town center & within the highly sought-after Woodside Elementary School District.

83 Tum Suden WAY, Woodside

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

Sold listing courtesy of Lynne Mercer, CRS from APR
$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
$2,700,000
3 Beds ⋅ 3 Baths ⋅ ML82003150 MLS
Lakeview Lodge: A Storybook Sanctuary with Iconic Views and a Surprisingly Convenient Location. Every now and then, a property comes along that feels pulled from the pages of a storybook. Lakeview Lodge is one of those rare places, loved and nurtured by its owners for 29 years for the simplest reason: its just that special. Perched above the treetops with sweeping views of Stanfords Jasper Ridge, and originally named for its view of Searsville Lake, this peaceful retreat offers a front-row seat to natures changing beauty. From golden sunrises to dusky twilight, the vistas inspire reflection. Located near the bottom of Old La Honda Rd at Portola Rd, your minutes from Stanford, top schools, commute routes, and dining - seclusion without sacrifice. Nearby Dennis Martin Creek trails offer tranquil walks under the redwoods. The main home features 2BD/2BA, and a private-entry suite below with kitchen, living area, bedroom, and bathideal for guests or a home office. With high-speed internet, you can Zoom by day and stargaze by night. Lakeview Lodge is more than a home, its a soulful escape with a country feel and unbeatable convenience.

171 Old La Honda RD, Woodside

Listed by Kavanaugh Group, 650-850-1046 from Coldwell Banker Realty
(If provided) CoList: Steven Gray from Coldwell Banker Realty

Sold listing courtesy of Alexander Nichols from EXPCA
$15,750,000
6 Beds ⋅ 7 Baths ⋅ ML81992668 MLS
Completely Renovated inside and out! This architectural Jewel with Dazzling Views! Originally imagined by the visionary architect Gardner Dailey in 1934, this exceptional estate is a testament to his architectural brilliance updated with a complete comprehensive renovation. The classic style of a country manor is presented, creating a visual symphony from the slate tile roof to the leaded glass windows and exceptional gardens. The views offered are nothing short of dazzling, encompassing verdant views of the bordering Menlo Country Club golf course, the sweeping panorama of San Francisco Bay, and the majestic silhouette of the East Bay hills. Set within a gated sanctuary of 1.5 acres, the home is adjacent to a 2.8 acre lot available for separate acquisition, enhancing the promise of exclusivity or with potential for further development. The palatial home spans more than 10,000 square feet of grace and sophistication. The journey into the home begins with a unique entrance a pedestrian gate beyond the gated driveway opens into a vast front courtyard with a magnificent heritage oak tree, lawns and patios, and pool, creating an enchanting space for grand celebrations or private relaxation. This is a once-in-a-lifetime property! Gorgeous Gardner Daley Home.

961 High RD, Woodside

Listed by Erika Demma, 650-704-7928 from Compass
(If provided) CoList: The Dreyfus Group from Golden Gate Sotheby's International Realty

Sold listing courtesy of Steve Lessard from APR
$1,775,000
3 Beds ⋅ 3 Baths ⋅ ML81993016 MLS
Welcome to 55 Bigtree, a charming retreat nestled among the towering redwoods of Woodside. This historic cabin has been beautifully remodeled and expanded, blending rustic charm with modern comfort. The original structure has been thoughtfully updated with a spacious addition, giving you more room to relax while keeping its timeless character intact. The heart of the home is the stunning great room, featuring soaring ceilings, tons of natural light, and amazing views of the surrounding redwoods. The new kitchen is a dream for any cook, with top-of-the-line appliances, custom cabinetry, and a large center island perfect for meal prep or gathering with friends. Right next to it, the cozy family room is an ideal spot to unwind, with easy access to outdoor living spaces. Step outside and take in the peaceful setting, complete with a partial bay view that adds even more charm to this woodland escape. Sitting on nearly half an acre, theres plenty of space to garden, entertain, or simply soak in the beauty of nature. Plus, you get the benefit of top-rated Portola Valley schools! If youve been looking for a tranquil retreat with modern amenities, this is your chance to call it home. Don't miss out!

55 Big Tree RD, Woodside

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

Sold listing courtesy of Wayne Rivas from AGNC
$1,335,000
3 Beds ⋅ 2 Baths ⋅ ML81991484 MLS
Mountain Retreat with Valley Views, Ultimate Privacy, and Open-Concept Living! This 3-bedroom, 2-bath home offers the best of both worldsclose enough for a quick Silicon Valley commute, yet it feels like a secluded mountain escape. The open-concept design connects the kitchen, dining, and living spaces, creating an airy flow perfect for relaxing and entertaining. Enjoy stunning valley views from the kitchen, living room, upstairs bedroom, and spacious decks. The largest bedroom, with a private entrance, offers ADU potentialideal for a guest suite, rental, or a teens private space.The sun-drenched backyard features mature oaks, fruit trees, berry bushes, a greenhouse, and irrigated planting beds. The front yard, with a redwood ring and native plants, enhances the peaceful retreat feel. Inside, the home boasts updated bathrooms, wood floors upstairs, and heated tiles in the downstairs bedroom and bath. Skylights and double-pane windows fill the home with light, while fresh paint and newer decks make it move-in ready. Walking distance to Skywood Trading Post and Alices Restaurant, this home has a small-town vibe. With top-rated Portola Valley schools and nearby trails, and only 25 minutes from the beach, its a perfect blend of nature and convenience.

12 Skylonda DR, Woodside

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

Sold listing courtesy of Kelsey Takaha from COMPS
$2,950,000
4 Beds ⋅ 4 Baths ⋅ ML81989328 MLS
ARCHITECTURAL DIGEST MODERN OF ULTIMATE VIEWS! EXCLUSIVE GATED COMMUNITY, WOODSIDE SCHOOLS, HEART OF SILICON VALLEY LIFESTYLE! Bespoke architecturally singificant modern overlooking the Bay. Private natural wonderland with the Peninsula's best Bay vistas. Custom designed in 1991 by celebrated architect Paul Gilger, it's no wonder this home takes on cinematic qualities: around the same time Gilger was crafting this modern opus, he was masterminding the film studio of George Lucas, the legendary Industrial Light and Magic in San Rafael. *3 bed/3 ba in main house + ADU with bed area, office area, kitchen & full bath. *Lower level of main home makes a Zen Office, Lounge, or Family Room * Bold Open Concept * Unobstructed water views * Extensive new landscaping of handpicked native plants and organic design *2-story staircase nearly 30 feet high as work of art * Indoor/Outdoor w/ view dining decks and flat pad to rear * Immersive privacy beyond circular motor court * Tons of Sunlight * New Fountain Courtyard * Backup Generator, Tesla Charger in huge 3-car garage *Architecturally significant bespoke caliber, served by two gates: one at Central Woodside's Bear Gulch/Woodside Road, and upper gate at Skyline, not far from Mountain House Restaurant and easy Highway 92 connection

33 Bear Glen DR, Woodside

Listed by Geoffrey Nelson, 650-455-3735 from Coldwell Banker Realty
(If provided) CoList: from

Sold listing courtesy of Kavanaugh Group from CBR
$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

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