Woodside CA Gated Community Real Estate | Woodside Gated Community Homes for Sale

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

$12,995,000

7 Beds ⋅ 9 Baths ⋅ ML82045810 MLS

Lowest price per square foot @ $956 in Woodside, Atherton or Portola Valley. Spectacular Monterey Colonial home on 6+ private acres. Long gated driveway & large motor court. 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

$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

$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

$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

$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

$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

$10,988,000

5 Beds ⋅ 6 Baths ⋅ ML82037743 MLS

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

160 Phillip RD, Woodside

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

$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

$16,250,000

5 Beds ⋅ 8 Baths ⋅ ML82031334 MLS

Completed in 2021 following a 5-year design and construction process, this extraordinary residence showcases the work of renowned professionals in architecture, interior design, and landscape architecture. Located on a gated corner lot of approximately 0.9 acres surrounded by award-winning heritage oaks, the home has been featured in Luxe and California Homes magazines and honored with awards. Every inch reflects a masterful level of craftsmanship and a meticulous eye for detail. Interiors reveal a refined yet livable luxury, where traditional elements are balanced with a modern aesthetic across three beautifully curated levels. Signature materials, custom finishes, and seamless indoor/outdoor connections define the living experience. With 5 bedrooms, 5 full baths, and 3 half-baths, the home offers exceptional accommodations for a variety of lifestyle needs. A true architectural statement in the heart of Woodside, designed to endure and impress for generations to come.

3490 Tripp RD, Woodside

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

Sold listing courtesy of Scott Dancer from APR

$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

$18,900,000

7 Beds ⋅ 9 Baths ⋅ ML82019556 MLS

A magnificent transformation has redefined this 1929 French chateau into a modern estate of extraordinary light and sophistication. Once known for its European formality and ornate detail, the home has been renewed from top to bottom with the highest level of design, cabinetry, and finishes. Original millwork and moldings were meticulously preserved, now presented in a palette of light tones that elevate rather than overshadow the architecture. Exceptional lighting and carefully curated finishes bring contemporary elegance to every room, creating a residence that feels entirely new while honoring its historic character. The result is a home that stands among the finest expressions of luxury living today. Equally compelling are the dual-gated five acres of formal grounds that frame the estate. Vast lawns, parterre gardens, and farm-to-table gardens accompany resort amenities of a pool, spa, and tennis court, with multiple terraces providing an unparalleled setting for entertaining or private retreat. All of this unfolds within easy reach of Silicon Valley and San Francisco, establishing a rare estate property where history and modern vision meet at the highest level. among the finest expressions of luxury living today.

320 Harcross RD, Woodside

Listed by Michael Warren, 650-315-0224 from Compass
(If provided) CoList: from

Sold listing courtesy of Charles Liu from COMPS

$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

$2,037,000

4 Beds ⋅ 2 Baths ⋅ ML82008982 MLS

Perched on a peaceful mountain with breathtaking views of the Pacific Ocean, this updated 4-bedroom, 2-bath home offers the perfect blend of privacy and convenience. Just minutes from Half Moon Bay and San Mateo, this gated property is tucked within the cozy Kings Mountain community and designed for flexible living. With two spacious living rooms, two kitchens, and a bonus room, the home has excellent potential for separate living spaces; ideal for multigenerational living or guest quarters. The main kitchen features sleek Bosch appliances and modern finishes, while large windows throughout the primary living space capture breathtaking ocean vistas. Enjoy outdoor entertaining and evening sunsets on the deck, soak in the hot tub under the stars, and embrace the quiet, coastal mountain lifestyle. Whether you're looking for a serene full-time residence or a versatile retreat with income potential, this home offers comfort, flexibility, and unmatched views in a truly special setting. Just steps from Purisima Creek Redwoods Open Space Preserve and minutes to local favorites like The Mountain House and Alice's Restaurant, this home offers nature, charm, and versatility in one stunning package.

12960 Skyline BLVD, Woodside

Listed by David Skokan, 650-200-7420 from RE/MAX Gold Redwood Shores.
(If provided) CoList: from

Sold listing courtesy of Emily Baratzadeh from CBR

$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

$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

$13,500,000

5 Beds ⋅ 6 Baths ⋅ ML82001314 MLS

Panoramic Western Hills views set the stage for this stunning Central Woodside estate, nestled on approximately 3.2 flat, fully usable acres just moments from downtown shops, dining, and top-rated Woodside Elementary. Designed for both comfort and function, the primarily single-level layout includes a spacious primary suite, multiple living areas, and a bright eat-in kitchen opening to a large deck overlooking a sprawling lawn, pool, and spa. Work or unwind in the detached office near a private chipping and putting green, while the beautifully crafted barn features a 4-stall stable, tack room, hay storage, riding ring, and fenced turnouts surrounded by peaceful pastures. This estate is brimming with amenities: a rose garden, fountains, sports court, horseshoe area, hidden redwood trails, and vibrant landscaping throughout. The expansive ~2,700 sq ft basement offers incredible storage, along with a wine cellar. Separate guest quarters complete with a second kitchen and private entrance. A rare combination of luxury, land, and locationthis is Central Woodside living at its finest.

258 Kings Mountain RD, Woodside

Listed by David Bergman, 650-948-1100 from Intero Real Estate Services
(If provided) CoList: Angela Bergman from Intero Real Estate Services

Sold listing courtesy of Nicholas French from SGP

$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

$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

$6,710,000

5 Beds ⋅ 5 Baths ⋅ ML81989774 MLS ⋅ Buck Estate Home Owners Assoc BLDG.

This charming home is tucked away on a private cul-de-sac,within the prestigious gated community of Buck Estates. Built in 2001, this home exudes the artistic allure of Carmel, w/unique architectural details throughout. Boasting a spacious office (or additional bedroom) and 1 bd/1 ba guest house w/granite kitchen and large entertaining area. Newly refinished mahogany floors in the main living areas of the main house with multiple French doors to professionally landscaped yard. Open-concept kitchen connects the family room w/gas fireplace and soaring wood-beamed cathedral ceilings. The kitchen offers 2 Bosch dishwashers, built-in Miele coffee system, wine refrigerator, and breakfast bar. Luxurious primary suite on main level has cozy seating area w/fireplace, French doors to private terrace, spa-like bath w/heated floors, dual shower heads, and soaking tub. Both the main house and guest house have 2-car garages, 4 total spaces. Expansive yard w/multiple terraces, Jacuzzi, saltwater pool, and beautiful lanai w/custom bluestone patio among a vibrant mix of fruit trees and florals. Infrared heaters, stone fireplace w/seating hearth, and ceiling fan, make it the perfect space for year-round enjoyment. Great access to commuter routes, Menlo Country Club, Stanford, Menlo Park, and more.

50 Buck CT, Woodside

Listed by Bogard-Tanigami Team, 650-924-8365 from The Agency
(If provided) CoList: from

Sold listing courtesy of Michelle Englert from COMP

$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

$2,520,000

3 Beds ⋅ 3 Baths ⋅ ML81977802 MLS

Stylish retreat nestled on 1.35 acres in the serene Kings Mountain neighborhood of Woodside boasts an idyllic setting surrounded by natural beauty and a convenient location near myriad amenities such as open space trails, acclaimed restaurants & the top-rated Kings Mountain Elementary School. Picture windows and an expansive deck offer breathtaking views of the mountains, valleys, redwoods & Pacific Ocean, while multiple outdoor seating areas and a custom-built pergola are poised for soaking in the enchanting panoply of native plants, trees & colorful blooms. Impeccably renovated with high quality craftsmanship evident throughout, the two-story design features 3 bedrms & 2.5 baths, including a private primary suite with beautifully remodeled spa-like bath. Highlights include an updated open-concept kitchen w/new quartz counter tops & designer light fixtures, view-facing dining room, living room with dramatic stucco-clad fireplace, family room w/direct access to the mostly level backyard, and a charming artist studio/office. High ceilings, multiple skylights, newly refinished oak flooring, brand new siding and a newer roof are just a few of the attributes that make this home so appealing. Within a short drive to Half Moon Bay & downtown Woodside, plus easy access to Hwy 92 & 280.

108 Ware RD, Woodside

Listed by Deborah Elowson, 650-867-2217 from Compass
(If provided) CoList: from

Sold listing courtesy of Glen Mitchell Group from KWPEN

$7,800,000

4 Beds ⋅ 5 Baths ⋅ ML81958693 MLS

Location, location! This lush jewel estate is located along central Woodside's most exclusive Mountain Home Road corridor. A rarely available opportunity to own a 1.25 flat acre property in the heart of the town's most prestigious neighborhood, discover an effortless blend of fine craftsmanship with luxurious elements and a touch of Hollywood style: 4(+1) brs, 4.5 ba plus an array of multi-functional spaces: a main-level suite easily converts to lounge/5th bedroom, the primary suite is enhanced by a private library/office/ walk-in closet, nursery or 2nd bedroom. Venture to the wine cellar with its own tasting room through a potential home theatre. An entertainer's dream for elegant al fresco afternoons by the pool and easy indoor/outdoor living, and the expansive grassed yard is framed for utmost privacy by pristine mature landscaping, a romantic rose garden, olive and fruit orchards. A short walk to town and the Woodside Elementary School, this garden estate balances peaceful seclusion with close proximity to all commuter routes and less than 20 minute drive to SFO Airport.

290 Winding WAY, Woodside

Listed by Linda Hymes, 415-377-6061 from Intero Real Estate Services
(If provided) CoList: from

Sold listing courtesy of Josh Rubin from COMPS

$5,200,000

4 Beds ⋅ 6 Baths ⋅ ML81960173 MLS

Welcome to Woodside Whisper, a fully gated property stands as an epitome of refined luxury & tranquil living.This distinguished single-family home spans across 4050 square feet of meticulously crafted living space on a 1 acre parcel. Boasting 4 spacious beds & 4.5 baths, this residence offers ample room for both relaxation & entertainment. Upon entering, guests are greeted by an inviting formal entrance characterized by abundant natural light & tasteful finishes. The gourmet kitchen, equipped w/high-end appliances & custom cabinetry, serves as the heart of the home, inspiring culinary creativity & gatherings. The primary suite exudes sophistication & serenity, featuring a luxurious en-suite bath w/huge walk-in closet. Additional bedrooms offer comfort & privacy, each thoughtfully appointed to ensure restful nights & rejuvenating mornings. Get your game on at the on-site sports court, perfect for basketball, pickleball, or tennis. Post-match, plunge into the saltwater pool or jacuzzi, or detox in the outdoor sauna it's wellness on your doorstep. The outdoor space is a dreamy landscape for enjoying the Californian sunshine. Chill on the vast patios, gather around the fire pit under the stars, or wander through the lush gardens it's all about serene outdoor living.

165 Woodside DR, Woodside

Listed by Alan Canas, 415-298-8940 from Engel & Voelkers San Francisco
(If provided) CoList: from

Sold listing courtesy of Syed Baqar from MXR

$8,498,000

4 Beds ⋅ 5 Baths ⋅ ML81955662 MLS

Through the private driveway at 11 Southgate Drive, something extraordinary awaits. Youre greeted by hand crafted iron gates which open to an expansive front courtyard, meticulously landscaped grounds, and an astounding, Ernest Coxhead designed 5,790-square foot Spanish Colonial home. The classic estate, built in 1929 as the original owners summer retreat, combines timeless design and luxury in a private, California setting with unmatched views of the Woodside hills, the sparkling Bay Area and beyond. Inside, youll find dramatic architecture, spacious living & entertaining areas, and distinct treatments throughout, with four bedrooms and bathrooms for family and guests. Outside, inspired by nearby historic Filoli gardens, youll enjoy the unique trees, plants, and flowers, as well as the resort-like backyard with large pool and entertainment areas. This is an extremely rare opportunity to enjoy the lifestyle of a more refined era all in the heart of world-renowned Silicon Valley. A world away, yet close to everything.

11 Southgate DR, Woodside

Listed by Granoski,Weil Assoc., 650-269-8556 from Compass
(If provided) CoList: from

Sold listing courtesy of Keri Nicholas from PARCA

$6,035,000

4 Beds ⋅ 6 Baths ⋅ ML81950242 MLS

Fantastic property! At 1.6 acres and at the end of the cul-de-sac, this 4 bed 6 full bath home has views of the Bay and East Bay mountain range. On the property there is a long private driveway, heated pool with pool house (full bathroom, kitchenette and changing room), tennis court, detached 3 car garage with attached workroom, and ample parking around the property. The home was originally built in the 50s, but a large addition in the early '90s increased the square footage, which totals roughly 5640 square feet (buyer to verify). There are 3 fireplaces - 2 of them wood burning. Each bedroom (2 on each side of the house) has its own full bathroom. There is a large laundry room that has area for crafting and workout equipment. The property is very private and quiet with wonderful views, which gives it an estate feel. New, high-end appliances in the expansive kitchen, upgraded lighting throughout and new flooring create a property that you can call home!

2195 Ward WAY, Woodside

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

Sold listing courtesy of Dennis Phan from EXPCA

$8,850,000

5 Beds ⋅ 4 Baths ⋅ ML81939228 MLS

Custom rebuilt Hidden Valley / Farm Rd estate will not disappoint! On just over 3.25-acres, this 5,253 sq ft estate home was taken down to the studs, remodeled, expanded and structurally retrofitted over the years. The main residence has a spacious office loft and 4 bedrooms, including a main-level primary suite with 2 couture closet rooms and sumptuous marble bath. The large, detached building with executive office and overhead studio guest house, each with bath and kitchenette. Spacious terrace, pool, and vast stretches of lawn intertwined with walking paths encircling the entire property. Also suitable for up to 6 horses. This magical Woodside area is just minutes to 280, Sand Hill Road, Stanford University, and excellent Portola Valley schools. Luxurious livability, acreage, privacy, and every amenity needed for today.

165 Farm RD, Woodside

Listed by Sean Foley, 650-207-6005 from Compass
(If provided) CoList: from

Sold listing courtesy of Derek Timm from DTIMM

$3,020,000

3 Beds ⋅ 4 Baths ⋅ ML81940521 MLS

Fantastic cumulative price reduction by $855,000! A Game Changer! Home is on PUBLIC SEWER SYSTEM-not on septic system, Endless Potential for updating or perfect the way it is! 2,820 sq. ft. MOL, it is unknown if listed SF includes the big down stairs laundry room and recreation room, building plans show a rec room downstairs. Home w/high ceilings, big rooms, 3 massive & attractive fireplaces, downslope lot w/view of hills, peaceful/secluded. Big 3 car garage, downstairs recreation room staged as 2nd family room, possible 4th BR, big laundry room + bathroom, could be in-law suite for guests or home schooling, what's your pleasure? Entry level boasts big living room, dining room, family kitchen w/grand fire place, 2 baths & Powder Rm & 3 Bedrooms, Original Owner. Roof is 12 years old MOL & there are fire protection sprinklers atop the roof, Decks provide views of the hills, front wrap around patio could be changed to lawn, garden or play area. The home has been lovingly cared for & now ready for your TLC. Surrounded by more expensive Pride of Ownership Homes, ##### MATTERPORT FLOOR PLAN SHOWS MAIN FLOOR AS 2,732 SF & LOWER LEVEL @ 1,431 SF & "GROSS INTERNAL AREA" @ 4.163 ST EXLUDING garage area of 1,281 SF, BUYERS TO RELY ON THEIR OWN APPRAISAL FOR HOME'S SQUARE FEET #####

41 Oak Haven WAY, Woodside

Listed by David Blewett, 650-867-4389 from Intero Real Estate Services
(If provided) CoList: from

Sold listing courtesy of Benjamin Wang from LEXI

$10,055,000

4 Beds ⋅ 5 Baths ⋅ ML81934420 MLS

Set on 3.4 acres in central Woodside bordering the 75-acre Fleishhacker Estate Conservancy this home was designed by renowned architect Goodwin Steinberg. Organic appointments that include copper chandeliers by Albert Guibara, stained glass windows by Hermann Lirk, and walls in clear vertical grain cedar and stone. Exceptional spaces for entertaining plus two separate offices for remote work. 4 bedrooms include a luxurious main-level primary suite + lower level w/3-bedrooms, including an en suite, central play area, large storage area or potential fitness room, & wine cellar. Upgraded 400 amp service including Tesla charger. Beautifully landscaped grounds, originally designed by Thomas Church, with enchanting gardens, inviting courtyards, open meadows, and a wraparound deck overlooking the sun-drenched pool. A private nature trail winds around the inside perimeter of the fenced property. Just over a mile from the Town Center. Highly-regarded Woodside School (K-8).

301 Olive Hill LN, Woodside

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

Sold listing courtesy of Julie Baumann from APR

$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

$20,750,000

5 Beds ⋅ 8 Baths ⋅ ML81925551 MLS

Stately Italian villa sitting on roughly 7.7 acres on one of Woodsides most sought after cul-de-sac locations is now available. Incredible attention to detail and rare, highest end, European finishes makes this home a rare treasure and true sight to behold. Venetian plaster walls, brick barrel ceiling with oak beams, herringbone terra cotta flooring, and 300-year-old terracotta roof tiles imported from Italy to name a few. Majestic park-like grounds offer the ultimate private escape. Resort like amenities include pool, hot tub, tennis court, gym, vast lawns. Have dinner under the stars in your private redwood grove with tranquil creekside setting. Incredible guest house, additional gatehouse. This is one of Woodsides finest. Highly sought after Portola Valley schools.

30 Trail LN, Woodside

Listed by Zachary Trailer, 650-906-8008 from Compass
(If provided) CoList: from

Sold listing courtesy of DeLeon Team from DLRPA

$2,230,000

4 Beds ⋅ 5 Baths ⋅ ML81899491 MLS

On the hunt for the ultimate Woodside getaway where you can leave behind the hustle and bustle of everyday life? Set on a majestic 2 acres, this spectacular residence provides an ideal blend of luxury and tranquility, all just moments from everything San Francisco has to offer. A long driveway, lush redwoods, and a contemporary façade greet you. Inside, discover a bright, welcoming layout with crisp white tones, soaring ceilings, and fine finishes throughout. Warm up in front of the stately fireplace in your well-sized living room or take advantage of one of the extensive decks framing verdant vistas. Your gourmet kitchen comes fitted with modern appliances, ample cabinetry, and an eat-in bar. Dine in your adjacent dining room where tray ceilings add to the captivating ambiance. At the end of a tiring day, rejuvenate in your secluded retreats, or savor a nightcap outdoors with 360 degrees of pure nature. As a bonus, you'll have a private library and an attached 7 garage.

35 Echo LN, Woodside

Listed by Douglas Heydon, 408-373-7844 from Century 21 Real Estate Alliance
(If provided) CoList: from

Sold listing courtesy of Douglas Heydon from ALNC

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