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$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

$2,300,000
3 Beds ⋅ 1 Baths ⋅ ML82053963 MLS
Welcome to your own private retreat where modern comfort meets the beauty of nature. Set on a picturesque property surrounded by towering trees and breathtaking valley and ocean views, this beautifully updated home offers the perfect blend of tranquility and style. Inside, you'll find light-filled living spaces and quality finishes throughout. Large windows frame the natural landscape, creating a seamless connection between indoors and out. Step outside to discover thoughtfully designed grounds featuring lush landscaping, expansive lawns, inviting patios, and multiple areas for entertaining or relaxing. Wander along a charming walking path that winds through the property to a secret garden, an enchanting sanctuary with mature trees, unique sculptures, and peaceful spaces to unwind. Whether enjoying morning coffee overlooking the hills, hosting gatherings under the stars, or exploring your own private woodland retreat, every corner of this property offers something special. A detached garage provides room for vehicles, hobbies, or future expansion. This is more than a home it's a lifestyle where privacy, nature, and refined living come together in perfect harmony. Just minutes from Highways 92 and 280, for an easy commute to Silicon Valley, SFO, San Francisco, and the Peninsula.

12180 Skyline BLVD, Woodside

$2,275,000
4 Beds ⋅ 4 Baths ⋅ ML82036766 MLS
A very special home among the trees with peekaboo views towards the ocean. An ideal escape from the bustle just down the hill. The chefs kitchen with center island is open to the spacious family room and breakfast nook. Just outside is an extensive deck and your eyes are drawn out to the natural beauty around. The formal dining room and adjacent living room are light filled with large windows and gracious views. Completing the main floor is a convenient bedroom and nearby full bathroom. Upstairs, the massive primary bedroom has double suite bathrooms, yes, TWO bathrooms attached to the primary. Two additional bedrooms, one decorated as an office/media room, a convenient bathroom with dual sinks, plus the adjacent laundry area with storage round out the second floor. Whether awakening to the mist drifting through the trees or falling asleep listening to the sounds of owls, nature is ever present.

6 Megans LN, Woodside

$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

$2,199,000
3 Beds ⋅ 3 Baths ⋅ ML82019950 MLS
Nestled among the redwoods, 13630 Skyline Blvd offers the perfect Woodside retreat. Recently refreshed with a brand-new roof, new decks, refinished hardwood floors, and new carpet, this 3,270 sq ft home is move-in ready. The floorplan includes 3 bedrooms plus a dedicated office, a huge main suite, and spacious living areas that balance privacy with flow. A 2-car garage provides convenience, while the 0.56-acre lot delivers peace and room to grow. Located in the Kings Mountain Elementary boundary, this home offers the serenity of mountain living with the accessibility buyers wantjust 15 minutes to Hwy 280 at 92 and 45 minutes to SFO. Whether youre seeking a full-time residence or a weekend retreat, this property combines natural beauty, thoughtful updates, and everyday practicality in one of the Peninsulas most desirable settings.

13630 Skyline BLVD, Woodside

$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

$2,000,000
3 Beds ⋅ 3 Baths ⋅ ML82035391 MLS
Spanning 2,670 square feet of living space, this home envelopes you with warmth and charm from the moment you enter. Sunlight filters through towering redwoods, creating a serene atmosphere throughout. Refinished hardwood floors and thoughtful modern updates blend timeless quality with everyday comfort. The spacious floor plan flows seamlessly, ideal for both daily living and entertaining. The main floor features a gourmet kitchen with high-end appliances, sleek finishes, dining area, family room and dedicated home office offers the perfect space for remote work or creative pursuits. Upstairs, the bedrooms provide privacy and tranquility. A large, bright family room stands out as a favorite space, filled with natural light and a cozy, welcoming ambiance. Multiple large decks extend the living space outdoors, offering peaceful spots for relaxing, entertaining, or enjoying the majestic redwood surroundings. Additional features include a wine cellar and ample storage. Tucked just off the scenic Skyline Corridor with easy access to Hwy 92, 280/101, SFO, open space trails, restaurants, and award-winning Kings Mtn Elementary, this home offers a rare blend of privacy, convenience, and a strong sense of community fostered by friendly neighbors and the Kings Mtn Volunteer Art Fair.

13872 Silver Sky WAY, Woodside

$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

$1,150,000
ML82019754 MLS
Exceptional Development Opportunity in Woodside, with panoramic views. Discover a rare and versatile opportunity in the heart of the Santa Cruz Mountains. This 2.55-acre vacant lot offers breathtaking views of the rolling hills, coastal mountains, and on clear days, sweeping vistas of the Pacific Ocean. Located in the town of Woodside, this property is ideal for visionary buyers seeking a private estate, a high-end residential development, or a unique commercial venture. Multiple Potential Building Sites, Ideal for a luxury home with expansive square footage and unobstructed views. New 3,000 Sq Ft Warehouse Featuring three 12'x16' roll-up doors, perfect for storage, workshop, or staging future development. Upgraded Infrastructure, including PG&E, propane gas, private well with water storage tanks, and a septic system already in place. Zoned Resource Management (RM), allowing for a variety of uses including residential, agricultural, and limited commercial. Whether you're envisioning a private retreat, a multi-use compound, or a strategic investment, this property offers the flexibility and infrastructure to bring your vision to life. Located minutes from Silicon Valley, yet worlds away in serenity and natural beauty.

12725 Old La Honda RD, Woodside

$950,000
ML81989854 MLS
THIS 21 ACRE COUNTRY ESTATE IS AN OASIS OF CALM PARADISE SET IN A PARK OF OAK, FIR & REDWOODS IN UNINCORPORATED SM COUNTY; AN EXPANSIVE FEELING OF TOP OF THE WORLD OVERLOOKING SOOTHING GREEN VISTAS IN THE ULTIMATE FAIRYTALE SETTING; A RARE OPPORTUNITY TO BUILD ON THE LARGEST & LAST REMAINING BUILDABLE LOT ON ALLEN RD BUILD A MOUNTAINTOP CASTLE ON EXPANSIVE GROUNDS W/TOTAL PRIVACY & SECLUSION IN AN ENVIRONMENT WHOSE NATURAL BEAUTY IS UNDUPLICATED; THE SILICON VALLEY VIEWS ARE CENTER STAGE & TAKE YOUR BREATH AWAY IN THIS SHANGRI-LA SPOT; DRAMATIC ROCK FORMATIONS ON THIS PRISTINE WOODLAND PICTURE POSTCARD SETTING OF ALMOST ALL USABLE LAND; THERE ARE MANY POSSIBLE BUILDING SITES AT THIS HEAVEN-ON-EARTH PROPERTY OF A LIFETIME W/SPECTACULAR SUNRISES & MOONRISES; WOODSIDE IS THE AREAS MOST DESIRABLE LOCATION; THE PARCEL IS SITUATED ON A SECLUDED COUNTRY RD SET AMONG BEAUTIFUL RUSTIC HIGH END HOMES; THE PARCEL IS IN THE MOST ACCESSIBLE PART OF SKYLINE; CLOSE TO WOODSIDE RD & CA-92 STEP BACK IN TIME TO A SIMPLER WAY OF LIVING WHEN YOU KNOW YOUR NEIGHBORS & HAD A HEALTHY RESPECT FOR PRIVACY & UNSPOILED ENVIRONMENT; HIKING TRAILS & NATURE WALKS ARE CLOSE BY; THE CURRENT FOREST TIMBERLAND PRESERVE ZONING(TPZ) STIPULATES CURRENT PROPERTY TAXES OF $209/YR UNTIL A RESIDENCE IS BUILT & COMPLETED

0 Allen, Woodside

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