50 Bear Paw, Portola Valley | $4,950,000
Windy Hill Views, Level Grounds, Huge Deck, Open Space, and a Stunning Whole-Home Transformation
50 Bear Paw
This extraordinary Portola Valley Ranch property combines rare level land, breathtaking Windy Hill views from every floor, and a comprehensive whole-home remodel – all on just over one-half acre. The home’s thoughtful expansion and renovation, along with just completed interior and exterior painting and completely redone bamboo and hickory floors throughout, present a beautiful ambiance. With large windows enhanced by skylights in almost every room, the house is filled with natural light. Formal living and dining rooms extend to expansive decks at both the front and rear, perfect for fresh air entertaining AND outdoor play — hard to find features in the Ranch. At the heart of it all is a beautifully remodeled kitchen appointed with custom cabinetry and high-end appliances.
There are 4 bedrooms and 4 baths, including 2 full baths in the primary suite with walk-in closets, plus a large upstairs office that could also serve as a fitness center. A recreation room, craft room, laundry room, and temperature-controlled wine cellar are found on the lower level along with a private bedroom and bath ideal for guests. An attached 2-car garage is complemented by rare abundant guest parking on a flat road adjacent to the house. Rounding out the appeal is a five-minute easy walk to all Ranch amenities, including two pools, tennis courts, a clubhouse, community vineyard, and hiking trails, and a two-minute walk across the street to Corte Madera school with its playing fields, playground, and basketball courts making this the perfect place to call home midway between Silicon Valley and San Francisco.
Summary of the Home
- 4 bedrooms, office, and 4 baths on multiple levels.
- Approximately 4,025 square feet of living space (per floor plan).
- Over one-half acre (approximately 22,547 square feet).
- Exceptional direct Windy Hill views from each level.
- Built in 1978, fully remodeled and expanded in 1993, whole-home renovation and expansion in 2006, and freshly painted interiors, exteriors, and renovated floors in 2025.
- A gentle flight of steps leads to the front entrance where the front door is set beside a sidelight and beneath a large transom.
- The two-story skylit foyer introduces bamboo floors that continue on the main and upper levels; refinished hickory floors span the lower level; a split-level staircase leads up to the office and down to the main level with living areas.
- Spacious living room with paneled and beamed cathedral ceiling, gas-log fireplace, and wall of windows with sliding glass door to the front deck and Windy Hill views.
- Formal, but open, dining room with 8-light chandelier from the paneled cathedral ceiling, built-in cabinetry with serving counter and custom bar storage, plus sliding glass door to the very private rear deck.
- Stunning remodeled kitchen features custom wood cabinetry, including island with seating, topped in granite with full-height backsplashes; skylight, customized walk-in pantry, and sliding glass door to the rear deck.
- Appliances include: new Mueller 8-burner gas range with 2 ovens; microwave oven and warming drawer; Miele dishwasher; Fisher & Paykel dishwasher drawer; built-in new KitchenAid refrigerator.
- Primary bedroom suite with two full baths features sliding glass door to the front deck and Windy Hill views, vaulted skylights, and custom shutters; each bath has a customized walk-in closet, travertine finishes, skylight, single-sink vanity, and large shower.
- Two main-level bedrooms, one with sliding glass door to the rear yard, are served by a hallway bath with frameless-glass shower.
- Upper-level flexible-use room ideal for an office or gym with windows on three sides and Windy Hill views.
- Lower-level recreation room with built-in media center, elevated front windows with Windy Hill views, and adjoining temperature-controlled wine cellar.
- Lower-level bedroom and bath with frameless-glass shower and private commode room.
- Temperature controlled walk-in wine cellar.
- Other features:
- Lower-level laundry room with new Electrolux washer and dryer.
- Crafts/hobbies room with sink.
- Attached 2-car garage plus 2 driveway spots and 10 nearby guest parking spots all on a flat cul-de-sac.
- Whole house audio system with distributed speakers.
- Custom organizers in all closets.
- Stairless walkway around the house.
- Three built-in safes.
- Large finished storage area off the garage of approximately 162 square feet.
- Community amenities including two seasonally heated pools, clubhouse, tennis courts, community vineyard, as well as hiking trails and beautiful open spaces right off the back deck.
- Acclaimed Portola Valley schools: Ormondale Elementary K-3, Corte Madera 4-8 (across the street), and Woodside High 9-12 (buyer to verify).
Floor Plans

Floor Plan

Floor Plan
Location
Contact
Kavanaugh Real Estate Group
415.377.2924 john.kavanaugh@cbnorcal.com
116 Portola Road, Portola Valley, CA 94028