Refine Search
Map
Sort by
20421 Skyline Boulevard, Woodside
$2,100,000
3 Beds ⋅ 3 Baths ⋅ ML82056662 MLS ⋅ Active Status
Perched high along Skyline Boulevard on 2.67 acres, this exceptional mountain retreat offers sweeping 180-degree views stretching from San Francisco to San Jose. Surrounded by the natural beauty and serenity of the Santa Cruz Mountains, its an ideal sanctuary for remote work, writing, creative projects, or simply escaping the everyday. Built in 2007, the 2,180-square-foot home features 3 bedrooms and 2.5 baths, with expansive walls of glass that flood the living spaces with natural light. Warm straight-grain fir trim and custom baseboards add timeless character throughout. The open floor plan flows onto a spacious view deck with hot tubperfect for sunset relaxation or casual entertaining. An outdoor shower makes returning from a morning hike or gardening especially refreshing. Practical amenities include a private well, backup generator, and attached 2-car garage with covered breezeway. Enjoy exceptional privacy and mountain tranquility while remaining connected to the Peninsula, with Stanford roughly 20 minutes away and easy access to Woodside, Portola Valley, and beyond.

20421 Skyline Boulevard, Woodside
140 Sheridan Way, Woodside
$4,750,000
4 Beds ⋅ 5 Baths ⋅ 41140473 MLS ⋅ Active Status
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, and each of the three full bathrooms is finished with heated marble tile flooring — a quiet luxury that elevates the everyday. Finishes throughout were curated with a timeless sensibility that will feel just as fresh for years to come. This is indoor-outdoor living at its finest — a rare offering in one of the Peninsula's most sought-after enclaves.

140 Sheridan Way, Woodside
309 Olive Hill Lane, Woodside
$11,000,000
2 Beds ⋅ 4 Baths ⋅ ML82039836 MLS ⋅ Active Status
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 Lane, Woodside
941 High Road, Woodside
$4,499,000
ML82042331 MLS ⋅ Active Status
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 Road, Woodside

Based on information from California Regional Multiple Listing Service, Inc. as of . This information is for your personal, non-commercial use and may not be used for any purpose other than to identify prospective properties you may be interested in purchasing. Display of MLS data is usually deemed reliable but is NOT guaranteed accurate by the MLS. Buyers are responsible for verifying the accuracy of all information and should investigate the data themselves or retain appropriate professionals. Information from sources other than the Listing Agent may have been included in the MLS data. Unless otherwise specified in writing, Broker/Agent has not and will not verify any information obtained from other sources. The Broker/Agent providing the information contained herein may or may not have been the Listing and/or Selling Agent.