Portola Valley, CA Homes

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  $2,499,000

  • 3 Beds
  • 2 Baths
  • 1,560 Sq Ft

  108 Santa Maria Ave, Portola Valley, CA 94028

  Exceptional opportunity in Woodside Highlands on over half an acre of private, lush grounds. This light-filled 3-bedroom, 2-bath home is set on a quiet corner lot surrounded by mature trees, gardens, and fruit trees, offering a peaceful retreat in one of Portola Valleys most desirable neighborhoods. The main level features two bedrooms, one bath, hardwood floors, beautiful woodwork, and an

  Janeen Poutre Coldwell Banker Realty

  108 Santa Maria Ave, Portola Valley, CA 94028
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  /38

  $3,300,000 Sold Dec 01, 2025

  375 La Cuesta Dr, Portola Valley, CA 94028

  • 3 Beds
  • 2 Baths
  • 1,780 Sq Ft
  • Built 1954

  Last Sold Summary

  • 1% Below List Price
  • $1,854/SF
  • 9 Days On Market

  Last Listing Agent Rebecca Johnson Intero Real Estate Services

  375 La Cuesta Dr, Portola Valley, CA 94028
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  /39

  Est $4,152,570 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 3,015 Sq Ft

  45 Buckeye, Portola Valley, CA 94028

  45 Buckeye, Portola Valley, CA 94028
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  /36

  $3,687,500

  • 3 Beds
  • 2.5 Baths
  • 3,200 Sq Ft

  310 Old Spanish Trail, Portola Valley, CA 94028

  Welcome to this stunning 3-bedroom, 2.5 -bathrooms residence in the serene city of Portola Valley. This home boasts a spacious 3,200 sq. ft. layout situated on an expansive lot of over an acre. The heart of the home is the state-of-the-art kitchen, featuring granite countertops, dual fuel options, a built-in oven range, and an island with a sink. Enjoy meals in the eat-in kitchen or the formal

  Tim McKeegan Terrace Associates

  310 Old Spanish Trail, Portola Valley, CA 94028
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  /2

  $3,200,000 Sold Aug 27, 2025

  340 Canyon Dr, Portola Valley, CA 94028

  • 3 Beds
  • 2 Baths
  • 1,610 Sq Ft
  • Built 1980

  Last Sold Summary

  • 7% Above List Price
  • $1,988/SF
  • 3 Days On Market

  Current Estimated Value $3,068,040

  Last Listing Agent Karen Gunn Compass

  340 Canyon Dr, Portola Valley, CA 94028
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  /35

  Est $3,296,775 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,130 Sq Ft

  10 Foxtail, Portola Valley, CA 94028

  10 Foxtail, Portola Valley, CA 94028
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  /4

  $499,888 Under Contract

  • Land
  • 0.85 Acre
  • $588,104 per Acre

  00 Vista Verde Way, Portola Valley, CA 94028

  A RARE FINDING VACANT LAND IN BEAUTIFUL OLD SPANISH TRAIL OF PORTOLA VALLEY!

  Jenny Yang Compass

  00 Vista Verde Way, Portola Valley, CA 94028
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  /2

  $4,750,000 Sold Dec 23, 2025

  200 Cherokee Way, Portola Valley, CA 94028

  • 4 Beds
  • 3.5 Baths
  • 4,825 Sq Ft
  • Built 1986

  Last Sold Summary

  • 2% Below List Price
  • $984/SF
  • 7 Days On Market

  Last Listing Agent Ginny Kavanaugh Coldwell Banker Realty

  200 Cherokee Way, Portola Valley, CA 94028
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  /20

  Est $3,279,827 Not Listed For Sale

  • 5 Beds
  • 3 Baths
  • 2,670 Sq Ft

  371 Old Spanish Trail, Portola Valley, CA 94028

  371 Old Spanish Trail, Portola Valley, CA 94028
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  /11

  $750,000 Pending

  • Land
  • 0.16 Acre
  • $4,749,842 per Acre

  1050 Los Trancos Rd, Portola Valley, CA 94028

  A rare chance to bring your dream home to life in the heart of the coveted Portola Valley School District! Nestled on a serene, 6,878-square-foot forested lot, 1050 Los Trancos offers more than just land. It's a head start on creating something extraordinary. With San Mateo County Planning & Building Department approved plan, this property is truly shovel-ready for your vision. The plans include

  Ting Tan Compass

  1050 Los Trancos Rd, Portola Valley, CA 94028
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  /2

  $4,600,000 Sold Dec 15, 2025

  135 Wyndham Dr, Portola Valley, CA 94028

  • 4 Beds
  • 3.5 Baths
  • 4,110 Sq Ft
  • Built 1950

  Last Sold Summary

  • $1,119/SF
  • 17 Days On Market

  Last Listing Agent Hugh Cornish Coldwell Banker Realty

  135 Wyndham Dr, Portola Valley, CA 94028
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  /49

  Est $2,067,277 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,220 Sq Ft

  1183 Los Trancos Rd, Portola Valley, CA 94028

  1183 Los Trancos Rd, Portola Valley, CA 94028
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  /2

  $11,500,000 Pending

  • 4 Beds
  • 3 Baths
  • 3,421 Sq Ft

  640 Los Trancos Rd, Portola Valley, CA 94028

  Stunning vistas of the hills and bay in this once in a lifetime opportunity to own one of the largest lots in Palo Alto with 12.55 acres in Palo Alto Open Space with a Portola Valley mailing address. Located on an exclusive private road the property awaits a buyer wanting to create a new estate or remodel the existing mid-century style home with expansive hill views. Large living room with high

  Sue Crawford Coldwell Banker Realty

  640 Los Trancos Rd, Portola Valley, CA 94028
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  /2

  $1,600,000 Sold Jun 25, 2025

  102 Santa Maria Ave, Portola Valley, CA 94028

  • 2 Beds
  • 3 Baths
  • 2,000 Sq Ft
  • Built 1941

  Last Sold Summary

  • 18% Below List Price
  • $800/SF
  • 37 Days On Market

  Current Estimated Value $1,818,564

  Last Listing Agent Jean Isaacson Golden Gate Sotheby's International Realty

  102 Santa Maria Ave, Portola Valley, CA 94028
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  /34

  Est $1,351,137 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,030 Sq Ft

  103 El Nido Rd, Portola Valley, CA 94028

  103 El Nido Rd, Portola Valley, CA 94028
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  /20

  $1,849,000

  • 2 Beds
  • 2 Baths
  • 1,205 Sq Ft

  76 Old Spanish Trail, Portola Valley, CA 94028

  Sunlit Gem on Nearly One-Half Acre with Plans to Expand. Fresh, inviting, and completely sophisticated, this retreat has been transformed into a light-filled setting. Easily accessed via wide streets, the property spans nearly one-half acre of predominantly level grounds and includes approved plans for a future expansion. The current home, with 2 bedrooms and 2 baths, offers a streamlined scale

  Erika Demma Compass

  76 Old Spanish Trail, Portola Valley, CA 94028
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  /2

  $4,250,000 Sold Oct 08, 2025

  20 Bear Gulch Dr, Portola Valley, CA 94028

  • 4 Beds
  • 3 Baths
  • 2,310 Sq Ft
  • Built 1959

  Last Sold Summary

  • 1% Above List Price
  • $1,840/SF
  • 14 Days On Market

  Current Estimated Value $4,133,952

  Last Listing Agent Denise Welsh Compass

  20 Bear Gulch Dr, Portola Valley, CA 94028
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  /21

  Est $1,788,307 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,220 Sq Ft

  243 Bonita Rd, Portola Valley, CA 94028

  243 Bonita Rd, Portola Valley, CA 94028
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  /35

  $3,500,000

  • 4 Beds
  • 4 Baths
  • 2,960 Sq Ft

  176 Los Trancos Cir, Portola Valley, CA 94028

  A refined retreat in Los Trancos Woods, this thoughtfully reimagined estate blends natural light, privacy, and understated luxury. Set among forested hills yet offering rare level grounds and sun-filled interiors, the home is designed for both comfort and elegance. Cathedral ceilings with skylights, beautifully refinished hardwood floors, and clean, curated finishes create a warm, modern

  Treasure Molina Realty One Group Zoom

  176 Los Trancos Cir, Portola Valley, CA 94028
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  /71

  $8,750,000 Sold Oct 20, 2025

  5 Redberry Ridge, Portola Valley, CA 94028

  • 6 Beds
  • 9 Baths
  • 7,531 Sq Ft
  • Built 2002

  Last Sold Summary

  • 7% Below List Price
  • $1,162/SF
  • 115 Days On Market

  Current Estimated Value $8,701,656

  Last Listing Agent Omar M. Kinaan Golden Gate Sotheby's International Realty

  5 Redberry Ridge, Portola Valley, CA 94028
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  /2

  Est $1,951,209 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,010 Sq Ft

  66 Old Spanish Trail, Portola Valley, CA 94028

  66 Old Spanish Trail, Portola Valley, CA 94028
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  /2

  $11,500,000 Pending

  • Land
  • 12.55 Acres
  • $916,335 per Acre

  640 Los Trancos Rd, Portola Valley, CA 94028

  One of the largest lots in Palo Alto. Stunning vistas of the hills & bay in this once in a lifetime opportunity to own 12.55 acres in Palo Alto Open Space. This lot is located on an exclusive private road. Build a new estate or remodel the existing mid-century style home with expansive hill views. Sq ft allowed is based on a percentage of lot sq ft. Large living room with high ceilings and

  Sue Crawford Coldwell Banker Realty

  640 Los Trancos Rd, Portola Valley, CA 94028
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  /4

  $8,000,000 Sold Dec 01, 2025

  130 Meadowood Dr, Portola Valley, CA 94028

  • 4 Beds
  • 4.5 Baths
  • 3,750 Sq Ft
  • Built 2004

  Last Sold Summary

  • $2,133/SF
  • 0 Days On Market

  Last Listing Agent Michael Repka Deleon Realty

  130 Meadowood Dr, Portola Valley, CA 94028
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  /20

  Est $3,691,300 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,190 Sq Ft

  156 Brookside Dr, Portola Valley, CA 94028

  156 Brookside Dr, Portola Valley, CA 94028
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  /26

  $2,985,000 Pending

  • 3 Beds
  • 3 Baths
  • 3,320 Sq Ft

  40 Deer Path Dr, Portola Valley, CA 94028

  Nestled at the end of a private drive, this 3,320 square foot sits on almost 1.5 acres (per county) in tranquil Los Trancos Woods. Floor-to-ceiling and clerestory windows as well as skylights and sliding doors fill the 2-story home with natural light and provide views to the surrounding natural environment from every room. The top level includes an open-concept layout creating a seamless flow

  Ginny Kavanaugh Coldwell Banker Realty

  40 Deer Path Dr, Portola Valley, CA 94028
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  /2

  $4,200,000 Sold Apr 24, 2025

  20 Foxtail, Portola Valley, CA 94028

  • 4 Beds
  • 3 Baths
  • 2,650 Sq Ft
  • Built 1978

  Last Sold Summary

  • 17% Above List Price
  • $1,585/SF
  • 6 Days On Market

  Current Estimated Value $4,044,358

  Last Listing Agent Shelly Roberson Compass

  20 Foxtail, Portola Valley, CA 94028
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  /42

  Est $3,623,632 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,030 Sq Ft

  175 Los Trancos Rd, Portola Valley, CA 94028

  175 Los Trancos Rd, Portola Valley, CA 94028
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  /2

  $4,625,000 Sold May 12, 2025

  4 Franciscan Ridge, Portola Valley, CA 94028

  • 5 Beds
  • 3.5 Baths
  • 3,890 Sq Ft
  • Built 1981

  Last Sold Summary

  • 7% Below List Price
  • $1,189/SF
  • 52 Days On Market

  Current Estimated Value $4,553,997

  Last Listing Agent Scott Chase Intero Real Estate Services

  4 Franciscan Ridge, Portola Valley, CA 94028
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  /25

  Est $7,788,460 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 3,499 Sq Ft

  255 Golden Oak Dr, Portola Valley, CA 94028

  255 Golden Oak Dr, Portola Valley, CA 94028
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  /2

  $3,595,000 Sold Nov 13, 2025

  35 Bear Paw, Portola Valley, CA 94028

  • 3 Beds
  • 2.5 Baths
  • 2,615 Sq Ft
  • Built 1978

  Last Sold Summary

  • $1,375/SF
  • 16 Days On Market

  Current Estimated Value $3,597,572

  Last Listing Agent Colleen Foraker Compass

  35 Bear Paw, Portola Valley, CA 94028
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  /52

  Est $6,722,604 Not Listed For Sale

  • 4 Beds
  • 4.5 Baths
  • 4,140 Sq Ft

  43 Los Charros Ln, Portola Valley, CA 94028

  43 Los Charros Ln, Portola Valley, CA 94028
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  /55

  $3,350,000 Sold Apr 16, 2025

  240 Dedalera Dr, Portola Valley, CA 94028

  • 3 Beds
  • 2 Baths
  • 1,660 Sq Ft
  • Built 1960

  Last Sold Summary

  • 5% Above List Price
  • $2,018/SF
  • 8 Days On Market

  Current Estimated Value $3,156,488

  Last Listing Agent Chris Sabido eXp Realty of California Inc

  240 Dedalera Dr, Portola Valley, CA 94028
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  /37

  Est $5,499,242 Not Listed For Sale

  • 4 Beds
  • 4 Baths
  • 3,050 Sq Ft

  856 La Mesa Dr, Portola Valley, CA 94028

  856 La Mesa Dr, Portola Valley, CA 94028
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  /2

  $3,455,000 Sold Nov 13, 2025

  475 Cervantes Rd, Portola Valley, CA 94028

  • 3 Beds
  • 2.5 Baths
  • 2,550 Sq Ft
  • Built 1962

  Last Sold Summary

  • 8% Above List Price
  • $1,355/SF
  • 10 Days On Market

  Current Estimated Value $3,593,260

  Last Listing Agent Jennifer Alfaro Compass

  475 Cervantes Rd, Portola Valley, CA 94028
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  /29

  Est $7,078,977 Not Listed For Sale

  • 1 Bed
  • 2 Baths
  • 2,390 Sq Ft

  177 Alamos Rd, Portola Valley, CA 94028

  177 Alamos Rd, Portola Valley, CA 94028
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  $5,300,000 Sold Dec 19, 2025

  415 Golden Oak Dr, Portola Valley, CA 94028

  • 4 Beds
  • 3.5 Baths
  • 4,297 Sq Ft
  • Built 1961

  Last Sold Summary

  • 12% Below List Price
  • $1,233/SF
  • 208 Days On Market

  Last Listing Agent Scott Hayes Compass

  415 Golden Oak Dr, Portola Valley, CA 94028
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  /36

  Est $3,326,710 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,620 Sq Ft

  309 La Cuesta Dr, Portola Valley, CA 94028

  309 La Cuesta Dr, Portola Valley, CA 94028
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  /59

  $5,205,000 Sold Sep 12, 2025

  3 Oak Forest Ct, Portola Valley, CA 94028

  • 6 Beds
  • 5.5 Baths
  • 5,970 Sq Ft
  • Built 1991

  Last Sold Summary

  • 5% Below List Price
  • $872/SF
  • 46 Days On Market

  Current Estimated Value $5,233,991

  Last Listing Agent Hugh Cornish Coldwell Banker Realty

  3 Oak Forest Ct, Portola Valley, CA 94028
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  /55

  Est $9,226,716 Not Listed For Sale

  • 5 Beds
  • 7 Baths
  • 8,590 Sq Ft

  550 Westridge Dr, Portola Valley, CA 94028

  550 Westridge Dr, Portola Valley, CA 94028
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  /80

  $3,460,000 Sold Dec 17, 2025

  846 Portola Rd, Portola Valley, CA 94028

  • 3 Beds
  • 4.5 Baths
  • 3,497 Sq Ft
  • Built 2025

  Last Sold Summary

  • 19% Below List Price
  • $989/SF
  • 197 Days On Market

  Last Listing Agent Elena Licari Coldwell Banker Realty

  846 Portola Rd, Portola Valley, CA 94028

Showing Results 41 - 80, Page 2 of 18