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Set on a private acre in Woodside Hills, this exceptional midcentury residence offers more than 4,600 square feet of living space, spectacular Bay views, and a wonderful connection between indoors and out. Walls of glass, hardwood floors, and expansive living areas create a distinctive setting, complemented by two fireplaces and a stylish kitchen with black granite and appliances from top brands. The family room provides a comfortable gathering space, while five bedrooms plus an office offer flexibility for family, guests, and work. Multi-level grounds showcase the views with a large deck, inviting pool, and broad lawn, creating an ideal setting for entertaining and everyday enjoyment. Conveniently located near shops, restaurants, parks, nature preserves, and Interstate 280, the home is also just five minutes from acclaimed Woodside High School (buyer to verify eligibility).

5 Beds ⋅ 4 Baths ⋅ ML82062056 MLS

Set on a private acre in Woodside Hills, this exceptional midcentury residence offers more than 4,600 square feet of living space, spectacular Bay views, and a wonderful connection between indoors and out. Walls of glass, hardwood floors, and expansive living areas create a distinctive setting, complemented by two fireplaces and a stylish kitchen with black granite and appliances from top brands. The family room provides a comfortable gathering space, while five bedrooms plus an office offer flexibility for family, guests, and work. Multi-level grounds showcase the views with a large deck, inviting pool, and broad lawn, creating an ideal setting for entertaining and everyday enjoyment. Conveniently located near shops, restaurants, parks, nature preserves, and Interstate 280, the home is also just five minutes from acclaimed Woodside High School (buyer to verify eligibility).

160 Crest RD, Woodside

Listed by DeLeon Team, 650-407-0160 from Deleon Realty
(If provided) CoList: from

$3,495,000

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.

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 BLVD, Woodside

Listed by Scott Dancer, 650-888-8199 from Compass
(If provided) CoList: from

$3,195,000

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.

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 RD, Woodside

Listed by Scott Dancer, 650-888-8199 from Compass
(If provided) CoList: from

$3,088,000

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.

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 RD, Woodside

Listed by Geoffrey Nelson, 650-455-3735 from Coldwell Banker Realty
(If provided) CoList: from

$2,750,000

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.

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 RD, Woodside

Listed by Chris Iverson, 650-450-0450 from Golden Gate Sotheby's International Realty
(If provided) CoList: from

$2,195,000

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.

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 BLVD, Woodside

Listed by Jennifer Paulson, 650-996-7147 from Christie's International Real Estate Sereno
(If provided) CoList: from

$2,100,000

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.

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 BLVD, Woodside

Listed by Scott Hayes, 650-245-5044 from Compass
(If provided) CoList: from

$1,888,000

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.

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 RD, Woodside

Listed by Matthew Dapolito, 408-202-9202 from Intero Real Estate Services
(If provided) CoList: Scott Bishop from Intero Commercial

$599,999

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.

2 Beds ⋅ 1 Baths ⋅ ML82061335 MLS ⋅ Kings Mountain Association BLDG.

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 BLVD 3, Woodside

Listed by M&W Collective, 559-681-5477 from Ocean Element Real Estate
(If provided) CoList: from

$550,000

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!

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 RD, Woodside

Listed by Kimberly Hansen, 415-806-8230 from Golden Gate Sotheby's International Realty
(If provided) CoList: from

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