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1543 Portola Road, Woodside
$6,995,000
5 Beds ⋅ 4 Baths ⋅ ML82065045 MLS
An extensive remodel completed in 2023 transformed this classic New England Colonial with designer style and a fresh approach to modern living. The remodeling went well beyond new finishes, with the floor plan reconfigured to add a main-level bedroom and full bath for a total of 5 bedrooms and 4 baths. The kitchen and dining area were completely transformed with an open design and commercial-quality appliances, while all new windows, glass doors, and recessed lighting enhance the ambiance and connections to the surrounding three-acre grounds. Significant infrastructure improvements were completed as well, including upgraded electrical, new HVAC, a tankless water heater, earthquake retrofitting, and new irrigation.The setting is equally impressive with mostly level grounds, a 5-stall -1700 square foot barn, with hayloft and tack room, vast stretches of lawn, a newly fenced yard, and expansive brick terraces for outdoor living and entertaining. There is also a separately fenced and newly resurfaced pool featuring a 75-foot lap lane, elevated spa, and new owned solar heating system, plus equestrian facilities that include a 5-stall barn with paddocks. A detached 2-car garage with 2 EV charging outlets adds further convenience. Wonderful location close to Woodside and PV Town Centers

1543 Portola Road, Woodside

Listing courtesy of Erika Demma from Compass. 650-740-2970

12520 Skyline Boulevard, Woodside
$3,495,000
3 Beds ⋅ 4 Baths ⋅ ML82064329 MLS
Spectacular views of the Pacific Ocean, Half Moon Bay, and San Francisco highlight this exceptionally private property just 3 miles from Highway 92. On the market for the first time in 50 years the home is set well back from the road on more than 11 acres with vast level areas and potential for additional structures like an ADU or equestrian facilities. The spacious one-story home is ready to enjoy. Vaulted natural wood ceilings, hardwood floors, and a two-sided brick fireplace enhance the main living areas. The eat-in kitchen has stainless steel appliances and a breakfast room plus there is a separate family room. 3 bedrooms include the primary suite, a second suite, and bedroom with dual-entry bath plus there is a privately located spacious room for an office or gym. An expansive deck spans the home and looks out to the views. Additional amenities include a 3-car garage, central air conditioning, a fenced vegetable garden, and greenhouse. Just 8 miles from downtown Half Moon Bay and a 24-minute drive to SFO. Kings Mountain Elementary School.

12520 Skyline Boulevard, Woodside

Listing courtesy of Scott Dancer from Compass. 650-888-8199

160 Redland Road, Woodside
$2,750,000
4 Beds ⋅ 3 Baths ⋅ ML82063276 MLS
Some houses announce themselves, this one settles quietly into the redwoods of Skylonda, a 1967 mid-century modern by architect Edwin Wadsworth where the light comes first, then the trees, and only after that the house itself. High wood ceilings and heavy beams carry the eye through walls of glass to the forest beyond, the sunken living room feels sheltered beside a stone fireplace, and the dining room opens to the decks through floor to ceiling windows and a sliding door, with a pass through to the island kitchen and a sunny breakfast area warmed by a freestanding wood-fired stove. Upstairs, the primary suite sits in the canopy like a separate apartment, with its own outside entrance, walk-in closet, and balconies on either side. The recreation room has its own entrance from the gravel courtyard, and a small detached office offers a quiet place to work. Approximately 3,420 square feet, 4 bedrooms, 3 baths, and approximately 0.91 acres, expanded in 1989 and refreshed with new flooring through much of the home, interior paint, updated lighting, and deck repairs, with Alice's, the Skywood Trading Post, and County Fire Station 58 close by.

160 Redland Road, Woodside

Listing courtesy of Chris Iverson from Golden Gate Sotheby's International Realty. 650-450-0450

20421 Skyline Boulevard, Woodside
$2,100,000
3 Beds ⋅ 3 Baths ⋅ ML82056662 MLS
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

Listing courtesy of Scott Hayes from Compass. 650-245-5044

14826 Skyline Boulevard Unit #3, Woodside
$599,999
2 Beds ⋅ 1 Baths ⋅ ML82061335 MLS
This 2-bedroom, 1-bath home in Woodside offers 1,110 square feet of comfortable living space. The updated bathroom features a stall shower and tile finishes. The kitchen includes an electric oven range, dishwasher, refrigerator, and a 220-volt outlet, with an eat-in area for casual dining. Flooring throughout combines hardwood and carpet for a balanced look. A separate family room provides additional living space. Additional features include a skylight that brings natural light into the living areas. A one-car garage adds to the functionality. This property falls within the Cabrillo Unified elementary school district. HOA is in the process of putting on a new roof, so home is under contruction. This is a shortsale home and will take a minimum of 3 to 6 months(minimum) for bank approval. This purchase is not for a buyer who might be in a hurry as we have two loans to get short-sale approval. Inspections will need to be done by buyers. Bank will NOT have any inspections.

14826 Skyline Boulevard Unit #3, Woodside

Listing courtesy of from Ocean Element Real Estate. 559-681-5477

180 Farm Road, Woodside
$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 Road, Woodside

Listing courtesy of Hugh Cornish from Coldwell Banker Realty. 650-619-6461

26 Big Tree Road, Woodside
$1,888,000
4 Beds ⋅ 4 Baths ⋅ ML82056831 MLS
An exceptional opportunity to own a premier property in the heart of Woodside, one of the Peninsula's most prestigious and sought-after communities. Located at 26 Big Tree Rd, this unique offering combines privacy, natural beauty, and convenient access to Silicon Valley, making it ideal for homeowners, investors, or those seeking a legacy property. Surrounded by mature trees and Woodside's renowned rural charm, it offers a peaceful retreat just minutes from downtown Woodside, Stanford University, Sand Hill Road, and major employment centers. Residents enjoy a rare balance of tranquility, open space, and access to world-class dining, shopping, and recreation. Whether creating a private estate, preserving a long-term investment, or capitalizing on one of the Bay Area's most desirable locations, 26 Big Tree Rd presents a rare opportunity in a market where exceptional properties are seldom available. Woodside remains one of Northern California's premier residential destinations, known for expansive estates, an equestrian lifestyle, enduring property values, and unmatched privacy, prestige, and long-term appreciation.

26 Big Tree Road, Woodside

Listing courtesy of Matthew Dapolito from Intero Real Estate Services. 408-202-9202

103 Toyon Court, Woodside
$4,950,000
4 Beds ⋅ 4 Baths ⋅ ML82046648 MLS
More than one-third acre creates an exceptional setting for this spacious home with 4 bedrooms, 3.5 baths, and multiple living areas designed for today. There are formal living and dining rooms, a designer kitchen with Carrara marble finishes and wine bar, a welcoming family room, a lower-level recreation and media room, and a private bedroom with its own entrance and adjacent bath that is ideal for guests or office use. The primary suite is privately located and features a steam shower and jetted tub. Outdoor living is equally inviting with an arbor-covered deck, newly planted lawns, terraced gardens, play area, and raised vegetable beds. Located on a cul-de-sac street less than one mile from the Woodside town center and served by renowned Woodside Elementary School (TK-8). Additional highlights include abundant storage, optional RV parking with hookups, and refreshed landscaping throughout.

103 Toyon Court, Woodside

Listing courtesy of Hugh Cornish from Coldwell Banker Realty. 650-619-6461

1100 Old La Honda Road, Woodside
$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 Road, Woodside

Listing courtesy of Scott Dancer from Compass. 650-888-8199

20255 Skyline Boulevard, Woodside
$2,195,000
3 Beds ⋅ 3 Baths ⋅ ML82042155 MLS
Spanning approximately 2.92 usable acres of gently rolling meadows with picture-postcard views, this classic horse property offers miles-away tranquility just 20 minutes from Highway 280. A palatial driveway leads to a two-story, 3-bedroom, 3-bath, open-plan residence with walls of windows capturing the rolling hill and city-light views. Almost every room has glass doors to the long, view balcony. Lawn and mini orchard. A separate charming barn captures the Old West Woodside feel with a wood-beamed ceiling, full-sized bar, and French doors to a veranda with flowering vines. Just a mile to the Thomas Fogarty Winery and 8 minutes to Alice's Restaurant.

20255 Skyline Boulevard, Woodside

Listing courtesy of Jennifer Paulson from Christie's International Real Estate Sereno. 650-996-7147

235 Hillside Drive, Woodside
$2,150,000
3 Beds ⋅ 2 Baths ⋅ ML82032924 MLS
BEST VALUE IN WOODSIDE!! Nestled under Woodside's heritage oaks, this 1929 Woodside Glens retreat offers a rare blend of vintage character, privacy, and views. The nearly 0.5 acre lot features abundant, verdant scenery and a wrap-around deck to take it all in. The main level boasts a large, open-beam living room anchored by a cozy wood-burning stove, and is surrounded by windows which bring the natural beauty of the Glens inside. The floor plan includes a vintage kitchen, a dining area overlooking the oaks, and two bedrooms -- one featuring its own fireplace. Central air-conditioning provides year-round comfort. Upstairs is a versatile loft with a storage area. The lower level features a large bedroom with a bathroom and shower, an oversize 2-car garage, plus driveway space for 2 additional vehicles. With the large lot, an ADU is possible (buyer to confirm with the town). Located in the district for top-rated Woodside Elementary (K-8) and Woodside High, this home is moments from Woodside Village and offers a convenient commute to the entire Bay Area via Hwy 280. Experience the quintessential Woodside lifestyle in this timeless woodland sanctuary.

235 Hillside Drive, Woodside

Listing courtesy of Steve Rumberg from Keller Williams Realty-Silicon Valley. 408-723-5200

0-220 Heacox Road, Woodside
$550,000
ML82033274 MLS
Tranquil land. Excellent opportunity to build or ? on this sun-drenched parcel that has gentle grade for development. 3800 ft2 home plus 1000 ft2 ADU deemed possible by Lea and Braze engineers; price includes feasibility study, survey and septic perc test results. This land could be a great location for your estate home or quiet get-away. Plenty of room for horses, animals and/or hobby farm, you'll find that you are conveniently located to access the hiking and riding trails that abound in the area's open space. Seller has 2 lots for sale (0-220 and 0-250 Heacox); the actual address is not yet determined. Electric pole on site. Old well on-site (plentiful water here), you add septic system. Invest in your future!

0-220 Heacox Road, Woodside

Listing courtesy of Kimberly Hansen from Golden Gate Sotheby's International Realty. 415-806-8230

1 Reids Roost Road, Woodside
$3,088,000
4 Beds ⋅ 8 Baths ⋅ ML82017325 MLS
SKY VILLA: RE-IMAGINE ROYALTY IN THE WOODS. Sky Villa is an opportunity to dream big with unmatched grandeur & privacy. This is a bank-owned, non-livable development opportunity, approximately 70% complete, with expired permits. Buyer to verify with County of San Mateo the existence and status of any past permits and the ability to resume construction towards completion. Grand scale luxury features such as: 2-Story Lobby with Imperial Staircase | 4 levels of destinations inspire your finishing details | Library off the lobby | Two Enormous Primary Suites (one main level, one upstairs) | Multiple Offices | Immense walk-in closets | Unfinished lower levels of Rec Room, Wine Vault, Grand Loggia, & dreamy Mezzanine facing majestic Sequoia Forest | Flat rear grounds inspire a future pool & ADU | Off-street parking for the most grand events, plus 2 separate attached garages: a daily 3-car at the motor court, plus a lower level 2-car attached garage | Long the bastion for Silicon Valley founders and CEO's, Woodside blurs the line between timeless province and epicenter of wealth and innovation. SKY VILLA, prepare to take flight in one of California's most prestigious communities.

1 Reids Roost Road, Woodside

Listing courtesy of Geoffrey Nelson from Coldwell Banker Realty. 650-455-3735

Bay East © 2026. CCAR © 2026. BridgeMLS © 2026. Information Deemed Reliable But Not Guaranteed. This information is being provided by the Bay East MLS, or CCAR MLS, or bridgeMLS. The listings presented here may or may not be listed by the Broker/Agent operating this website. This information is intended for the personal use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated on:

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