Woodside and Portola Valley Luxury Homes

Curated by Sophia Rosenberg. Last updated April 16
a view of a building with a yard
Sold 9/9/25Virtual Tour

$8,000,000

5
Bedrooms
4,645
Square Feet
1.26
Acres

45 Bear Gulch Drive, Portola Valley, CA 94028

$5,765,000 | 4 Buck Meadow Drive, Portola Valley, CA 94028
Sold 9/19/25

$5,765,000

4
Bedrooms
4,420
Square Feet
1.96
Acres

4 Buck Meadow Drive, Portola Valley, CA 94028

a front view of a house with garden
a view of a patio with couches table and chairs
a view of a house with a yard
a view of a porch
a outdoor space with patio couch and glass windows
a living room with furniture and a potted plant
a living room with a couch and a large window
a view of a dining room with furniture window and wooden floor
a dining room with furniture and window
a kitchen with a table and chairs in it
a view of a dining room with furniture window and outside view
a living room with furniture and a large window
a kitchen with stainless steel appliances granite countertop a sink a stove and a wooden floors
a bedroom with bed and large window
a living room with furniture a flat screen tv and a large window
a bathroom with a double vanity sink and a mirror
a view of entryway
a bedroom with a bed and painting on the wall
a bedroom with a large bed and a window
a bathroom with a double vanity sink and a mirror
a bedroom with a bed and a mirror
a bedroom with a bed and a window
a living room with furniture a flat screen tv and a floor to ceiling window
a view of a balcony with wooden floor and outdoor space
a terrace with outdoor seating and wooden floor
a view of a patio with table and chairs with wooden floor and fence
a view of a yard
a view of a yard with plants and trees
a view of a patio with iron fence
a view of a garden with lawn chairs
a garden with lots of flowers and trees
a view of a patio with couches table and chairs and potted plants
a view of a yard with plants and large trees
a living room with furniture and a table
a living room with furniture and a fireplace
a view of couches with wooden floor and city view
a view of a outdoor space
$6,550,000 | 30 Cheyenne Point, Portola Valley, CA 94028
1/38
Sold 6/18/25

$6,550,000

4
Bedrooms
2,860
Square Feet
1.00
Acres

30 Cheyenne Point, Portola Valley, CA 94028

$13,500,000 | 258 Kings Mountain Road, Woodside, CA 94062
Sold 5/30/25Virtual Tour

$13,500,000

5
Bedrooms
6,135
Square Feet
3.23
Acres

258 Kings Mountain Road, Woodside, CA 94062

an aerial view of residential houses with outdoor space and swimming pool
an aerial view of multiple house
an aerial view of houses covered in trees
a view of a lush green forest with a mountain
a view of a city
an aerial view of a forest with mountain
a view of a green field with lots of bushes
a view of a forest with a tree
an aerial view of a city
an aerial view of a house with a yard
a front view of a house with a yard
a view of a house with a yard
a view of an entryway and livingroom in right side
a living room with furniture and a rug
a living room with furniture and a large window
a living room with furniture and a large window
a view of a dining room with furniture window and outside view
a kitchen with stainless steel appliances kitchen island granite countertop a table chairs in it and a window
a living room with furniture a book shelf and a book shelf
a view of a swimming pool with a yard
a view of a house with a tree
a view of an outdoor space and a yard
an aerial view of residential houses with outdoor space
an aerial view of residential houses with outdoor space and trees
a view of outdoor space and street view
$11,500,000 | 640 Los Trancos Road, Palo Alto, CA 94028
$11,500,000 | 640 Los Trancos Road, Palo Alto, CA 94028
$11,500,000 | 640 Los Trancos Road, Palo Alto, CA 94028
$11,500,000 | 640 Los Trancos Road, Palo Alto, CA 94028
1/29

$11,500,000

4
Bedrooms
3,421
Square Feet
12.55
Acres

640 Los Trancos Road, Palo Alto, CA 94028

a view of a house with swimming pool and sitting area
Sold 3/27/25

$4,995,000

4
Bedrooms
2,540
Square Feet
1.02
Acres

1365 Westridge Drive, Portola Valley, CA 94028

a view of a yard with plants and trees
a view of backyard with green space
a view of a yard
a big yard with lots of green space and deers
a view of a forest with trees
a view of a dry yard with trees and stairs
a view of outdoor space and yard
a view of a forest
a view of a yard of snow
a view of outdoor space and yard
a view of a yard with plants and large trees
a view of a yard with a tree
a view of a forest with trees
a view of a forest with trees in the background
a view of a yard with plants and trees
a big yard with flowing stream of water in middle
a view of a yard with plants and large trees
a view of a yard with a tree
a view of a yard with plants and trees
a view of a yard with plants and trees
a view of a yard with a tree
a view of a forest with trees in the background
a view of a forest with trees in the background
a view of a pathway both side of yard
a view of a garden with plants and a bench
a view of a yard with a plant
a view of a forest with a street
a backyard of a house with lots of green space
a view of a flower in a garden
a view of a garden with plants
a picture of a tree
view of a lush green forest
a picture of flowers
a view of a tree with lots of flowers
a backyard of a house with lots of plants and trees
a picture of flowers
a view of a plant
a picture of trees
a plant with lots of trees
a view of a forest with a street
a view of a green field
$2,500,000 | 12 Montecito Road, Woodside, CA 94062
$2,500,000 | 12 Montecito Road, Woodside, CA 94062
1/43

$2,500,000

Unavailable
Bedrooms
Unavailable
Bathrooms
Unavailable
Square Feet
3.66
Acres

12 Montecito Road, Woodside, CA 94062

a view of a house with a yard and garden
Sold 5/20/25

$6,820,000

5
Bedrooms
6,200
Square Feet
2.18
Acres

7 Oak Haven Way, Woodside, CA 94062

a front view of a house with a garden and plants
an aerial view of a house with swimming pool outdoor seating and yard
a view of a house with swimming pool and sitting area
a front view of a house with a yard and garage
a front view of a house with a yard
a front view of a house with a yard
a bathroom with a white tub shower and sink
a view of entryway and hall
a kitchen with a table chairs refrigerator and cabinets
a kitchen with a table chairs and a dining table
a view of outdoor space with seating area
a view of entryway
a bathroom with a shower
a view of work space with windows
a bathroom with a sink a toilet and shower
a living room with furniture a rug and a white wall
a bathroom with a bathtub and a sink
a bathroom with a bathtub and a shower
a bathroom with a shower
a living room with furniture and a window
a bathroom with a double vanity sink and mirror
a backyard of a house with barbeque oven and tree
a view of dirt field with large trees
a view of outdoor space and yard
a view of a forest with a house
a view of a yard with plants and flowers
a view of a yard with plants
view of building
an aerial view of a forest with houses
a view of a city with lush green forest
a view of a yard with plants and tree
an aerial view of multiple house
an aerial view of a houses with a yard
$5,995,000 | 3343 Alpine Road, Portola Valley, CA 94028
$5,995,000 | 3343 Alpine Road, Portola Valley, CA 94028
$5,995,000 | 3343 Alpine Road, Portola Valley, CA 94028
1/36
Listed By Compass

$5,995,000

6
Bedrooms
6,800
Square Feet
4.15
Acres

3343 Alpine Road, Portola Valley, CA 94028

a front view of a house with a yard
an aerial view of a house with a yard
a view of a city with lush green forest
a view of a kitchen with furniture and a window
a living room with furniture and a window
a living room with furniture and a large window
a view of an ocean
a living room with furniture and a floor to ceiling window
a view of a balcony with chairs and wooden floor
a living room with furniture
a view of a balcony
a view of a dining room with furniture window and outside view
a view of a dining room with furniture and wooden floor
a living room with furniture and a fireplace
a view of a dining room with furniture and wooden floor
a table and chairs in a patio
a view of entryway and hall
a living room with furniture and floor to ceiling windows
a living room with furniture and a large window
a living room with furniture and a flat screen tv
a living room with furniture and a window
a bathroom with a double vanity sink a toilet a mirror and a window
a view of balcony with wooden floor
a view of a back yard of the house
a backyard of a house with lots of green space
a kitchen with a table chairs microwave and cabinets
a front view of a house with a porch
a view of swimming pool with outdoor seating and plants
a view of a house with a tree in the background
a view of a small house with a yard bed and a patio
a view of an outdoor space
a view of staircase with railing and white walls
$2,950,000 | 33 Bear Glen Drive, Woodside, CA 94062
1/33
Sold 7/9/25

$2,950,000

4
Bedrooms
3,725
Square Feet
6.44
Acres

33 Bear Glen Drive, Woodside, CA 94062

a view of a house with large windows and a small yard
Sold 9/18/25

$2,977,000

3
Bedrooms
2,890
Square Feet
0.31
Acres

625 West Glen Way, Woodside, CA 94062

a front view of a house with a garden and plants
an aerial view of a house with garden space and sitting area
a view of a house with swimming pool and sitting area
a front view of a house with a yard and garage
a front view of a house with a yard
a front view of a house with a yard
a bathroom with a white tub shower and sink
a view of entryway and hall
a kitchen with a table chairs refrigerator and cabinets
a kitchen with a table chairs and a dining table
a view of outdoor space with seating area
a view of entryway
a bathroom with a shower
a view of work space with windows
a bathroom with a sink a toilet and shower
a living room with furniture a rug and a white wall
a bathroom with a bathtub and a sink
a bathroom with a bathtub and a shower
a bathroom with a shower
a living room with furniture and a window
a bathroom with a double vanity sink and mirror
a backyard of a house with barbeque oven and tree
a view of dirt field with large trees
a view of outdoor space and yard
a view of a forest with a house
a view of a yard with plants and flowers
a view of a yard with plants
view of building
an aerial view of a forest with houses
a view of a city with lush green forest
a view of a yard with plants and tree
an aerial view of multiple house
an aerial view of a houses with a yard
$5,995,000 | 3343 Alpine Road, Portola Valley, CA 94028
$5,995,000 | 3343 Alpine Road, Portola Valley, CA 94028
$5,995,000 | 3343 Alpine Road, Portola Valley, CA 94028
1/36
Listed By Compass

$5,995,000

Unavailable
Bedrooms
Unavailable
Bathrooms
Unavailable
Square Feet
4.15
Acres

3343 Alpine Road, Portola Valley, CA 94028

a view of a lounge chair and tables in the patio
a view of a swimming pool with sitting area
a view of a house with a large window and plants
a view of living room filled with furniture and potted plants
a view of an entryway
a potted plant sitting in front of a door
a view of a swimming pool and sitting area
a front view of a house with a garden
a flower garden is sitting in a backyard
a room with a table chairs and a kitchen view
a view of a dining room with furniture a chandelier and wooden floor
a view of a house with yard and staircase
view of city and mountain
an aerial view of residential houses with outdoor space
an aerial view of residential house with parking space
a view of a yard with a mountain
a view of street with shops
a view of an outdoor space
a close up of a street sign
a view of a brick house
a front view of a building with lot of cars and trees
a view of a chair and a fire pit
$3,999,999 | 387 Moore Road, Atherton, CA 94027
$3,999,999 | 387 Moore Road, Atherton, CA 94027
$3,999,999 | 387 Moore Road, Atherton, CA 94027
1/25
Contingent - ShowVirtual Tour

$3,999,999

Unavailable
Bedrooms
Unavailable
Bathrooms
Unavailable
Square Feet
6.94
Acres

387 Moore Road, Atherton, CA 94027

a kitchen with stove and cabinets
a living room with furniture and a large window
a living room with furniture and a large window
a view of a park with large trees
a view of a house with a tree in front
a living room with furniture and a large window
a view of entryway with a white wall
a living room with fireplace furniture and a flat screen tv
a living room with furniture and a large window
a living room with furniture and walk in closet
a view of a dining room with furniture window and glass windows
a living room with furniture and a large window
a kitchen that has a sink and a stove with wooden floor
a kitchen with a sink appliances and cabinets
a close view of tap
a kitchen with stainless steel appliances a refrigerator a stove and white cabinets with wooden floor
a view of entryway
a kitchen with stainless steel appliances granite countertop a stove refrigerator and a sink
a stove top oven sitting inside of a kitchen
a dining room with large window
a view of a patio with a table and chairs
a bedroom with a bed and a large window
a bedroom with furniture and a large window
a bedroom with a bed and a large window
a view of an empty room
a bedroom with a large bed and a chandelier
a bedroom with a bed and a mirror
a view of walk in closet with empty racks
a bathroom with a glass shower door and a sink
a bed room with a bed and a television
a bedroom with a large bed and a window
a bathroom with a sink toilet tub and shower
a living room with furniture and a window
a view of balcony with wooden floor and fence
a view of outdoor space with garden
a view of a garden with a tree
a view of a yard with plants and large trees
a view of a yard with plants and large trees
a view of a house with a yard and tree s
a view of a backyard with patio
a view of a large building with a large tree
a view of balcony with wooden floor and fence
a outdoor view with a sitting space
a view of entryway
a view of balcony with chairs and wooden fence
an aerial view of a residential houses with outdoor space
a view of a city
a view of a yard with plants and wooden fence
a view of a tree with a flower
a picture of a bench in front of a window
$4,100,000 | 250 Hardwick Road, Woodside, CA 94062
$4,100,000 | 250 Hardwick Road, Woodside, CA 94062
$4,100,000 | 250 Hardwick Road, Woodside, CA 94062
$4,100,000 | 250 Hardwick Road, Woodside, CA 94062
$4,100,000 | 250 Hardwick Road, Woodside, CA 94062
$4,100,000 | 250 Hardwick Road, Woodside, CA 94062
$4,100,000 | 250 Hardwick Road, Woodside, CA 94062
$4,100,000 | 250 Hardwick Road, Woodside, CA 94062
$4,100,000 | 250 Hardwick Road, Woodside, CA 94062
$4,100,000 | 250 Hardwick Road, Woodside, CA 94062
$4,100,000 | 250 Hardwick Road, Woodside, CA 94062
$4,100,000 | 250 Hardwick Road, Woodside, CA 94062
$4,100,000 | 250 Hardwick Road, Woodside, CA 94062
$4,100,000 | 250 Hardwick Road, Woodside, CA 94062
$4,100,000 | 250 Hardwick Road, Woodside, CA 94062
1/65
Sold 9/8/25

$4,100,000

4
Bedrooms
2,960
Square Feet
1.64
Acres

250 Hardwick Road, Woodside, CA 94062

a view of a patio with table and chairs and potted plants
Sold 6/3/25

$2,900,000

4
Bedrooms
2,490
Square Feet
1.51
Acres

1 Hayfields Road, Portola Valley, CA 94028

$15,500,000 | 5660 Alpine Road, Portola Valley, CA 94028
$15,500,000 | 5660 Alpine Road, Portola Valley, CA 94028
$15,500,000 | 5660 Alpine Road, Portola Valley, CA 94028
$15,500,000 | 5660 Alpine Road, Portola Valley, CA 94028
$15,500,000 | 5660 Alpine Road, Portola Valley, CA 94028
$15,500,000 | 5660 Alpine Road, Portola Valley, CA 94028
$15,500,000 | 5660 Alpine Road, Portola Valley, CA 94028
$15,500,000 | 5660 Alpine Road, Portola Valley, CA 94028
1/8
Virtual Tour

$15,500,000

Unavailable
Bedrooms
Unavailable
Bathrooms
Unavailable
Square Feet
41.72
Acres

5660 Alpine Road, Portola Valley, CA 94028

$4,625,000 | 4 Franciscan Ridge, Portola Valley, CA 94028
Sold 5/12/25Virtual Tour

$4,625,000

5
Bedrooms
3,890
Square Feet
0.5
Acres

4 Franciscan Ridge, Portola Valley, CA 94028

a view of a lush green field
a view of a yard with a tree
a view of a trees with a tree
a view of a forest with trees in the background
a view of a city
an aerial view of a houses with yard
a view of a yard with a tree
a view of a yard
a view of a yard with plants and trees
a view of a yard with plants and trees
a view of a forest with trees
a view of a wooden fence
a view of a green field
a view of a yard with wooden fence
a view of a field
a view of a dry yard with trees in the background
a view of a dry yard with trees
a view of outdoor space with trees all around
a view of a yard with a tree
a front view of a house with a yard
a front view of a house with garden
a picture of a floor plan
$4,995,000 | 941 High Road, Woodside, CA 94062
1/23
Listed By Compass

$4,995,000

Unavailable
Bedrooms
Unavailable
Bathrooms
Unavailable
Square Feet
2.84
Acres

941 High Road, Woodside, CA 94062

an aerial view of a house
a room with furniture and a chandelier
a living room with fireplace furniture and a rug
a view of a dining room with furniture window and outside view
a view of a dining room with furniture window and wooden floor
a view of a balcony with table and chairs with wooden floor
a bathroom with a granite countertop tub and a large window
a wooden bench sitting in front of a building
a view of a building with stairs
an aerial view of a house with a yard
$8,750,000 | 16351 Skyline Boulevard, Woodside, CA 94062
1/11
Listed By Compass

$8,750,000

6
Bedrooms
14,270
Square Feet
17.79
Acres

16351 Skyline Boulevard, Woodside, CA 94062

a house view with sitting space and garden space
Sold 4/17/25

$25,000,000

7
Bedrooms
11,185
Square Feet
6.68
Acres

40 Firethorn Way, Portola Valley, CA 94028

an aerial view of a house with a yard
a view of lake and mountain
an aerial view of house with yard swimming pool and mountains
a view of a chairs and table in the terrace
a backyard of a house with yard and outdoor seating
a porch with a table and chairs under an umbrella
a living room with furniture a fireplace and a chandelier
a living room with furniture and a large window
a living room with furniture and a view of kitchen
a view of a dining room with furniture a chandelier and wooden floor
a kitchen with a sink and cabinets
a kitchen with stainless steel appliances kitchen island granite countertop a sink cabinets and wooden floor
a bedroom with a bed and wooden floor
a bedroom with a bed and a large window
a bedroom with two beds and a large window
a bedroom with a bed and window
a view of swimming pool with outdoor seating
a view of a chairs and table on the terrace
a view of outdoor space with lounge chairs
an aerial view of a house
unknown
$7,998,000 | 600 Westridge Drive, Portola Valley, CA 94028
1/22
Listed By CompassVirtual Tour

$7,998,000

4
Bedrooms
2,630
Square Feet
2.5
Acres

600 Westridge Drive, Portola Valley, CA 94028

a view of a lake with a house
Sold 9/16/25

$85,000,000

34
Bedrooms
23,900
Square Feet
74.04
Acres

329 Albion Avenue, Woodside, CA 94062

a front view of a house with garden
Sold 6/13/25Virtual Tour

$15,750,000

6
Bedrooms
8,470
Square Feet
1.5
Acres

961 High Road, Woodside, CA 94062

$15,500,000 | 5660 Alpine Road, Portola Valley, CA 94028
$15,500,000 | 5660 Alpine Road, Portola Valley, CA 94028
$15,500,000 | 5660 Alpine Road, Portola Valley, CA 94028
$15,500,000 | 5660 Alpine Road, Portola Valley, CA 94028
$15,500,000 | 5660 Alpine Road, Portola Valley, CA 94028
$15,500,000 | 5660 Alpine Road, Portola Valley, CA 94028
$15,500,000 | 5660 Alpine Road, Portola Valley, CA 94028
$15,500,000 | 5660 Alpine Road, Portola Valley, CA 94028
$15,500,000 | 5660 Alpine Road, Portola Valley, CA 94028
$15,500,000 | 5660 Alpine Road, Portola Valley, CA 94028
$15,500,000 | 5660 Alpine Road, Portola Valley, CA 94028
$15,500,000 | 5660 Alpine Road, Portola Valley, CA 94028
$15,500,000 | 5660 Alpine Road, Portola Valley, CA 94028
$15,500,000 | 5660 Alpine Road, Portola Valley, CA 94028
$15,500,000 | 5660 Alpine Road, Portola Valley, CA 94028
$15,500,000 | 5660 Alpine Road, Portola Valley, CA 94028
$15,500,000 | 5660 Alpine Road, Portola Valley, CA 94028
$15,500,000 | 5660 Alpine Road, Portola Valley, CA 94028
$15,500,000 | 5660 Alpine Road, Portola Valley, CA 94028
$15,500,000 | 5660 Alpine Road, Portola Valley, CA 94028
$15,500,000 | 5660 Alpine Road, Portola Valley, CA 94028
$15,500,000 | 5660 Alpine Road, Portola Valley, CA 94028
$15,500,000 | 5660 Alpine Road, Portola Valley, CA 94028
$15,500,000 | 5660 Alpine Road, Portola Valley, CA 94028
$15,500,000 | 5660 Alpine Road, Portola Valley, CA 94028
$15,500,000 | 5660 Alpine Road, Portola Valley, CA 94028
$15,500,000 | 5660 Alpine Road, Portola Valley, CA 94028
$15,500,000 | 5660 Alpine Road, Portola Valley, CA 94028
$15,500,000 | 5660 Alpine Road, Portola Valley, CA 94028
$15,500,000 | 5660 Alpine Road, Portola Valley, CA 94028
$15,500,000 | 5660 Alpine Road, Portola Valley, CA 94028
$15,500,000 | 5660 Alpine Road, Portola Valley, CA 94028
$15,500,000 | 5660 Alpine Road, Portola Valley, CA 94028
$15,500,000 | 5660 Alpine Road, Portola Valley, CA 94028
$15,500,000 | 5660 Alpine Road, Portola Valley, CA 94028
$15,500,000 | 5660 Alpine Road, Portola Valley, CA 94028
$15,500,000 | 5660 Alpine Road, Portola Valley, CA 94028
$15,500,000 | 5660 Alpine Road, Portola Valley, CA 94028
$15,500,000 | 5660 Alpine Road, Portola Valley, CA 94028
1/39
Virtual Tour

$15,500,000

6
Bedrooms
14,500
Square Feet
41.72
Acres

5660 Alpine Road, Portola Valley, CA 94028

a front view of a house with a garden
Sold 11/14/25Virtual Tour

$56,000,000

6
Bedrooms
12,305
Square Feet
11.8
Acres

20 Meadow Lane, Portola Valley, CA 94028

Sophia Rosenberg

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