$5,995,000 - 50 Bear Gulch Drive, Portola Valley

  • 5Beds
  • 4Baths
  • 3,718SQ. Feet
  • 1.12Acres

Portola Valley Home For Sale

With 5 bed /4 baths, this home has space & options. The 1.14+/- ac. gated prop. enjoys level lawn, pool & mature privacy trees. The home is welcomingthey say the kitchen is the heart of the home & this space embodies that. Amenities include quality appliances & extras: 6-burner Wolf range, 2 ovens, microwave & warming drawers, 2 dishwashers-one for dishes/one for pots & pans. Exceptional storage with pull out shelving, custom corner cabinets & and an appliance lift. The island provides workspace & seating. An adjacent family room has light, a fireplace, & access to the large deck. French doors open to incorporate the formal dining/living rooms into this space. Beamed ceilings, a fireplace, hardwood floors, a wall of windows & doors allow you to access the deck, to enjoy the view & host large gatherings. With a private entry a flexible, bookshelf-lined space could be an office, au pair or guest suite. There are 2 primary suites: 3 additional bedrooms + an office. The upper-level has the second primary & includes a bonus room for an office/nursery/or workout space. There is a bedroom off the family room (ideal for guests). Great Portola Valley location: close to local shopping, Alpine Hills Swim & Tennis club, The Alpine Inn, excellent PV schools, & just 4 min. to Hwy. 280.

Sales Agent

Sam Smith
  • Sam Smith
  • San Clemente Realtor ®
  • Phone: 949-204-5110
  • Cell: 949-204-5110
  • Contact Agent Now

Amenities

  • Parking Spaces2
  • # of Garages2
  • Has PoolYes
  • PoolIn Ground, Above Ground

School Information

  • DistrictOther

Essential Information

  • MLS® #ML82039321
  • Price$5,995,000
  • Bedrooms5
  • Bathrooms4.00
  • Full Baths4
  • Square Footage3,718
  • Acres1.12
  • Year Built1955
  • TypeResidential
  • Sub-TypeSingle Family Residence
  • StatusActive
  • Listing AgentPeter Cowperthwaite
  • Listing OfficeGolden Gate Sotheby's International Realty

Exterior

  • RoofComposition
  • FoundationConcrete Perimeter

Additional Information

  • Date ListedMarch 19th, 2026
  • Days on Market34
  • ZoningR1001A
  • Short SaleN
  • RE / Bank OwnedN

Community Information

  • Address50 Bear Gulch Drive
  • Area699 - Not Defined
  • CityPortola Valley
  • CountySan Mateo
  • Zip Code94028

Interior

  • CoolingCentral Air
  • FireplaceYes
  • FireplacesFamily Room, Living Room, Wood Burning
  • # of Stories1

Price Change History for 50 Bear Gulch Drive, Portola Valley, (MLS® #ML82039321)

Date Details Price Change
Price Reduced (from $6,395,000) $5,995,000 $400,000 (6.25%)

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  • City:
    Portola Valley
  • Price Range:
    $1,649,000 - $15,500,000
  • Current Listings:
    26
  • HOA Dues:
    $181
  • Average Price per Square Foot:
    $1,410

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Based on information from California Regional Multiple Listing Service, Inc. as of April 22nd, 2026 at 3:16pm PDT. This information is for your personal, non-commercial use and may not be used for any purpose other than to identify prospective properties you may be interested in purchasing. Display of MLS data is usually deemed reliable but is NOT guaranteed accurate by the MLS. Buyers are responsible for verifying the accuracy of all information and should investigate the data themselves or retain appropriate professionals. Information from sources other than the Listing Agent may have been included in the MLS data. Unless otherwise specified in writing, Broker/Agent has not and will not verify any information obtained from other sources. The Broker/Agent providing the information contained herein may or may not have been the Listing and/or Selling Agent.