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$11,000,000
2 Beds ⋅ 4 Baths ⋅ ML82039836 MLS
Discover an exceptional opportunity to create a dream home or reimagine the existing Neoclassical residence on one of central Woodsides most desirable streets. Spanning just over 3.4 acres, this expansive property showcases rare Bay views. There is an existing planning study for guidance in future opportunities. Positioned at the end of a private lane, the setting reflects the essence of Woodside country living, with lush perimeter trees and vast open land that offer a serene and private natural environment. The gated property includes an existing one-level home, a pool, and an original tennis court. Just one mile from Woodside Town Center and acclaimed Woodside Elementary School, and only minutes to Stanford University, Sand Hill Road venture capital firms, and the heart of Silicon Valley, this location offers both seclusion and convenience.

309 Olive Hill LN, Woodside

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

$5,800,000
2 Beds ⋅ 1 Baths ⋅ ML82039615 MLS
Nestled in a prime location in the prestigious town of Woodside, this exceptional property offers a rare opportunity to create something truly extraordinary. Set on an expansive 58,893 square foot (1.35-acre) lot, the setting is both private & picturesque - surrounded by beautiful estates that define the areas renowned character and enduring appeal. Here, the possibilities are truly limitless, offering an ideal canvas to design and build your dream estate in one of the Peninsulas most sought-after communities. The property includes a quaint 2 bed/1 bath cottage, detached garage, plus a pool. Offered for the first time in over 75 years, this is a once-in-a-generation opportunity to secure a premier parcel in a location known for its elegance, natural beauty, and long-held generational ownership. Just minutes from Woodside Town Center (Roberts Market, acclaimed local restaurants, etc.) you'll enjoy a seamless balance of peaceful seclusion and close-to-town living. Outstanding Woodside TK-8 School and proximity to Highway 280 further enhance the property's exceptional livability and convenience. A truly rare offering in a coveted location, framed by distinguished neighboring estates - this is your opportunity to create a legacy property in the heart of Woodside.

391 Mountain Home RD, Woodside

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

Sold listing courtesy of Brad Miller from APR
$800,000
2 Beds ⋅ 2 Baths ⋅ ML82033018 MLS
This property scores high on the unique scale! Just 5 minutes drive from Alice's Restaurant, nestled in a sorrel, fern and redwood gorge, this two bedroom, two bath home is an engineering feat to behold. Outstanding vehicular accessibility as the .87 acre property enjoys a horse-shoe looped driveway off Highway 84 which would be ideal for heavy equipment operators, or motorcycle enthusiasts. There is a large shop and multiple outbuildings. 20 minutes drive to Palo Alto yet a world away; think clubhouse, weekend get-a-way, or create your own Dwell Magazine worthy abode.

121 La Honda RD, Woodside

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

Sold listing courtesy of Dante Razzini from NTERO
$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
$699,000
2 Beds ⋅ 1 Baths ⋅ ML82018470 MLS ⋅ Kings Mountain Association BLDG.
Tucked along Skyline Boulevard, this 2-bedroom, 1-bath Woodside condo with its own private one car garage and laundry offers a lifestyle thats becoming increasingly hard to find: quiet, privacy, and nature; without giving up proximity to Silicon Valley and the Peninsula. Only 10-15 minutes to hwy 280 and set among towering redwoods, open sky, an ocean view and steps away from trails. This home features a spacious, light-filled layout with comfortable living areas that feel both grounded and welcoming. Whether youre starting your morning surrounded by nature or coming home after a long day below the hill, this property delivers a sense of retreat that most condos simply cant. This is Woodside living at an attainable level; ideal for a first-time buyer, down-sizer, or anyone craving a peaceful escape with real long-term value. Inventory in this area is limited, and opportunities like this dont come along often. If youve been waiting for the right way into Woodside; this is it.

14826 Skyline BLVD 3, Woodside

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

$1,099,900
2 Beds ⋅ 1 Baths ⋅ ML81980445 MLS
Welcome to this charming Woodside home, cradled amongst a cathedral of Redwood trees, and loaded with character. Enjoy the relaxing ambiance of this home, featuring Pella windows, vaulted wood ceilings, skylights, and pine wainscoting. With the perfect balance of updated convenience and country charm, this lovely home boasts an open kitchen with an adjacent dining nook, a loft perfect for storage, guests, or office, and a living room with vaulted ceiling, perfect for curling up by the wood burning stove. Outdoor eating area, flagstone patio w/arbor, built-in benches, large shed, extra storage, detached garage

144 Creek TRL, Woodside

Listed by Ed Gory, 650-743-7645 from Intero Real Estate Services
(If provided) CoList: from

Sold listing courtesy of Michael Mendenhall from KWSV
$1,688,000
2 Beds ⋅ 3 Baths ⋅ ML81966261 MLS
Experience country living just 30 minutes from the heart of Silicon Valley. Nestled in California's majestic Redwood Forest, this horse-zoned property blends natural beauty and equestrian potential. Set on a 2-acre lot with a HUGE open grass field, this home offers ample space for just about every lifestyle. Surrounded by lush greenery and open skies, it's a perfect retreat for those seeking a serene, private lifestyle. The expansive grounds provide endless possibilities for gardening, recreation, or creating your own outdoor oasis. Despite its secluded feel, youre close to top-rated schools and the 280 freeway, ensuring easy access to everything you need. The property is fenced, gated, and obscured by trees. The well-designed home features a fully equipped kitchen, spacious living room, high ceilings, and a welcoming family room, ideal for daily living and entertaining. Inside, cozy bedrooms offer a perfect haven after a long day. Tall windows and glass doors flood the floor plan with natural light. A bonus room under the house is perfect as a gym, recreation room, or playroom. Outside, a huge patio and wraparound deck overlook the expansive lot. Come live the life you deserve in this peaceful retreat.

161 Ware RD, Woodside

Listed by Stanley Lo, 650-373-0007 from Green Banker Realty
(If provided) CoList: from

Sold listing courtesy of Michael Pierce from PPGRP
$1,285,000
2 Beds ⋅ 1 Baths ⋅ ML81965709 MLS

13714 Skyline BLVD, Woodside

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

Sold listing courtesy of Joakim Bye from HAUG
$2,675,000
2 Beds ⋅ 2 Baths ⋅ ML81953706 MLS
This was a private sale. This listing is for Comp Purposes only.

506 Eastview WAY, Woodside

Listed by Mark Palermo, 650-218-6400 from Compass
(If provided) CoList: from

Sold listing courtesy of Mark Palermo from APR
$1,600,000
2 Beds ⋅ 1 Baths ⋅ ML81947067 MLS
Open house for Sunday, Nov. 19 canceled due to weather. Open house will b scheduled for weekend after Thanksgiving. Your own private, secluded resort on 11000+ lot in prestigious Woodside. Completely fenced property with secure gate to driveway. Like new home. lovingly rebuilt and renovated by licensed, contractor homeowner. Beautiful, newer kitchen and spa like bath. Bonus room could be third bedroom and includes a 3piece 2nd bathroom in garage. Attic/loft space in garage offers extra flexible space possibilities. Large two car garage with extra 3-4 vehicle parking on driveway. Views of the Redwoods and canyon off the large deck and kitchen. Wide plank, light woods floors and Integrity by Marvin windows throughout. 1500 gallon septic tank.

126 Filbert RD, Woodside

Listed by Samuel Young, 650-576-5566 from Corcoran Icon Properties
(If provided) CoList: from

Sold listing courtesy of Yvette Stout from ILLU
$1,725,000
2 Beds ⋅ 1 Baths ⋅ ML81944381 MLS
Best value in Woodside! This move-in ready 2 bedroom, 1 bath home boasts approx 1,570 sq feet on an almost 14,000 sq ft level lot. Many updates have been made over the years including fresh interior and exterior paint, new carpets and new light fixtures in preparation for sale. Centrally located near Hwy 280 , just 2 miles from downtown Woodside and don't forget the top rated Woodside Schools!

807 Canada RD, Woodside

Listed by Joyce and Tatum Real Estate, 650-888-4366 from Christie's International Real Estate Sereno
(If provided) CoList: from

Sold listing courtesy of Raylene Khan from SGP
$1,275,000
2 Beds ⋅ 2 Baths ⋅ ML81933855 MLS
Must See! Views are incredible! Magnificent Redwood Trees in your own Back yard! Home is located in the Phleger Estate Area. You are in the forest, yet approximately 7 miles from Interstate 280 and Hwy 92. 2 lots together for a combined 3/4 of an acre. Plenty of room for parking, outdoor living spaces and the ability to make your home even larger. Currently configured with 2 bedrooms and 2 baths.

13503 Skyline BLVD, Woodside

Listed by James Light, 650-341-8193 from Bay Area Real Estate Services
(If provided) CoList: from

Sold listing courtesy of Rebecca Navarro from KWPA

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