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$21,995,000
4 Beds 5 Baths ML82054839 MLS
Evoking the patina & permanence of a residence shaped over generations, this vineyard estate possesses an authenticity rarely achieved in contemporary construction. Completed in 2016 imbued with character of timeless European manor, it received the Julia Morgan Award for Classical Architecture, honoring its exceptional craftsmanship & architectural integrity. Hand-hewn beams, bespoke millwork, artisanal detailing, & imported Italian patterned terra cotta tile flooring define the interiors, while Mediterranean Revival influences create an atmosphere that is grand & welcoming. Arranged across two levels with elevator access, lower-level storage room with wine cellar potential, residence offers 4 bedrooms, dedicated office, & detached guest house. Formal & informal living spaces center around a chef's kitchen with a generous butlers pantry, while arched windows & French doors frame surrounding landscape. Set on approximately 4.33 acres in Woodsides coveted Hidden Valley, the estate enjoys sweeping views of Jasper Ridge, the Santa Cruz Mountains, the Western Hills, & Westridge. A pool, spa, rose gardens, crushed stone paths, dual-fuel backup generator, & professionally managed Pinot Noir vineyard producing up to 50 cases annually complete this extraordinary Silicon Valley retreat.

180 Farm RD, Woodside

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

$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

$12,995,000
7 Beds 9 Baths ML82045810 MLS
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. Easy to show.

389 Moore RD, Woodside

Listed by Steve Lessard, 650-704-5308 from Compass
(If provided) CoList: from

$34,995,000
8 Beds 7 Baths ML82038776 MLS
This exceptional property spans more than 3 acres with sweeping western hill views and 9,880 square feet of total living space. The main home was completely rebuilt in 2000, and in 2025, an entirely new guest house and entertainment complex was added to the estate. The classically styled main residence features nearly every room opening to the views and includes a state-of-the-art theater and temperature-controlled wine cellar. The newly completed guest house showcases authentic European detail with roof tiles handmade in Provence and Genoise eaves, complemented with modern construction and smart home technology. A new saltwater pool and spa, nearly 60 feet in length, is surrounded by an expansive terrace with sound system, outdoor kitchen, pizza oven, and easy catering access. The south-facing grounds are equally impressive, with a 310-vine Cabernet vineyard, heritage olive trees and oaks, a parterre rose garden, bountiful orchard, and raised vegetable beds. Reflecting timeless European elegance and exceptional craftsmanship, the estate is remarkably private, with far-reaching views enhancing the entire setting and all midway between Silicon Valley and San Francisco.

307 Olive Hill LN, Woodside

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

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