Woodside Highlands Real Estate, Homes, Condos for Sale in Portola Valley, CA

3 Beds ⋅ 3 Baths ⋅ ML82056981 MLS

Some homes are simply built. Others are cared for, collected, and shaped over time. Set among mature trees and thoughtfully designed gardens, this distinctive Portola Valley farmhouse reflects years of careful stewardship. Reclaimed wide-plank North Carolina pine floors, plaster walls and ceilings, painted millwork, marble, handmade tile, exposed beams and French doors give the home its character. The kitchen features a La Cornue range, original farmhouse sink, marble countertops, generous island, butler's pantry and cozy dining nook. The dining room is suited to everyday meals and larger gatherings, while the living room centers on a marble wood-burning fireplace and opens through two sets of French doors to a covered porch overlooking the gardens. The primary suite includes a walk-in closet and marble bath with mosaic tile and imported European brass fixtures. Upstairs are two additional bedrooms, a claw-foot bath and flexible spaces for study, work, hobbies or storage. A spacious family room is located downstairs. Originally designed by landscape artist Cevan Forristt, the grounds are rare for Portola Valleylargely flat and usable, with mature trees, fruit trees, grapevines, water features and multiple areas for outdoor gathering.

133 Russell AVE, Portola Valley

Listed by Carrie Davis, 650-269-4768 from Coldwell Banker Realty
(If provided) CoList: from

$1,750,000

2 Beds ⋅ 2 Baths ⋅ ML82042559 MLS

Tucked among mature oaks in the coveted Woodside Highlands, 9 Russell Avenue offers a rare blend of privacy, character, and opportunity on nearly one-third of an acre in prestigious Portola Valley. The main level features a generous living room anchored by a remarkable stone fireplace crafted from historic ship ballast, along with a separate family room, two bedrooms, and a full bath. Downstairs, bonus room, second bath, and laundry/storage area provide flexibility for guests, a home office, or future customization, with direct access to the 2 car garage. The main level is approximately 1440 sq. ft, with another 900 sq. of finished basement. The private grounds include a pool and multiple outdoor shaded gathering spaces beneath the oaks to relax or reimagine. Portola Valley is known for its top-rated schools, including Ormondale and Corte Madera, its vibrant Town Center, and miles of scenic trails at Windy Hill Preserve. Whether you envision a thoughtful renovation or a custom rebuild, this property delivers exceptional upside in a premier location.

9 Russell AVE, Portola Valley

Listed by James Gardner, 408-202-9602 from Intero Real Estate Services
(If provided) CoList: from

Sold listing courtesy of Esther Wang from ASPR

$2,700,000

3 Beds ⋅ 2 Baths ⋅ ML82032072 MLS

Just up the hill off of Portola Valley Road is this beautifully maintained 3-bedroom, 2-bath home which offers the perfect blend of comfort and functionality. A welcoming formal entry sets the tone, with stairs leading to the main open living area. The spacious living room with vaulted ceilings, floor to ceiling windows opens effortlessly to a back deck and large lush backyard with a designer playhouse. The updated gourmet kitchen features a center island, beautiful wood cabinetry, and tranquil views of the surrounding natural landscape of the backyard. There is a cozy loft with a full bathroom and walk-in closet, plus a deck, thats perfect for a home office, playroom, or additional bedroom/ living space.The expansive attached garage/ basement provide an exceptional amount of bonus space, laundry area and storage, offering flexibility for a variety of needs. The driveway has been expanded. Highly ranked, Portola Valley School District This home is just minutes from the town center, Highway 280, and scenic hiking and biking trails, tennis facilities and more. This is a must See!

16 Tynan WAY, Portola Valley

Listed by Sue Nystrom-Walsh, 408-482-9343 from Compass
(If provided) CoList: Silke Stearns from Compass

Sold listing courtesy of Michele Harkov from APR

$2,250,000

3 Beds ⋅ 2 Baths ⋅ ML82034150 MLS

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 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 oversized kitchen that opens to a sunny deckideal for indoor-outdoor living and entertaining. The lower level offers a flexible layout with a private bedroom or primary suite, full bath, and separate exterior entrance, perfect for guests, home office, or additional living space. Bonus room above the garage provides added versatility. Expansive multi-level grounds include wraparound patios, private garden areas, and tranquil natural surroundings. Elevated views overlook Portola Valley toward the East Bay Hills, offering stunning sunrises and full-moon views. Property offers excellent potential. Conveniently located near Town Center, Highway 280, scenic trails, and local favorites including the Alpine Inn. Served by top-rated Portola Valley schools, including Ormondale and Corte Madera.

108 Santa Maria AVE, Portola Valley

Listed by Janeen Poutre, 408-209-6640 from Coldwell Banker Realty
(If provided) CoList: from

Sold listing courtesy of James Steele from COMPS

$1,900,000

2 Beds ⋅ 2 Baths ⋅ ML82024776 MLS

Exceptional Portola Valley bungalow located in Woodside Highlands. This charming 2-bedroom, 2-bath home with a den offers 1,430± sqft of living space on a generous 13,507± sqft lot surrounded by nature. The home features an inviting floor plan with open-beam ceilings and a large wood-burning fireplace that creates a warm and welcoming atmosphere. Upstairs, find the primary suite with a walk-in closet and sliding doors that open to the deck. The den provides flexibility for a home office or creative space. Upstairs is finished with an updated bathroom and a kitchen with stainless steel appliances. A striking spiral staircase leads to the lower living area, where you'll find a spacious family room with a cozy fireplace perfect for relaxing or entertaining. Downstairs find a bedroom and a modern bathroom. Enjoy the seamless connection to the outdoors with private patios and garden areas offering peaceful views of the natural landscape. Additional highlights include a carport with a large storage room underneath. Enjoy easy access to Hwy 280 for all your Bay Area commutes. Located in a tranquil, sought-after neighborhood near scenic trails, local shops, and top-rated Portola Valley schools, this home captures the best of California living.

57 Santa Maria AVE, Portola Valley

Listed by Kulda Group, 650-560-8663 from KW Advisors
(If provided) CoList: from

Sold listing courtesy of Andy Tse from NTERO

$3,566,750

5 Beds ⋅ 4 Baths ⋅ ML82007268 MLS

Secluded in complete privacy above the street, this contemporary home embodies a true connection to nature through its vast expanses of glass and warm, organic finishes. Designed with a modernist spirit, and award-winning for green design, the home showcases soaring vaulted ceilings, open concept living spaces, and entire walls of glass that frame the surrounding greenery. Bamboo floors, cherry cabinetry, slate accents, and terrazzo countertops combine to create a sophisticated yet welcoming ambiance that harmonizes beautifully with the natural setting. Sustainable living unfolds behind the scenes with four Powerwall's, two EV charging stations, tankless hot water, and 11-zone radiant heat. The home's versatile layout offers ideal flexibility for recreation, entertaining, or even private living quarters, plus a separate office with half-bath. Indoor-outdoor flow is seamless with multiple decks, an atrium-style entry, and numerous sliding glass doors opening to fresh-air living spaces. Set on an expansive lot of approximately 30,040 square feet, comprised of three separate parcels, the property offers rare space and serenity while still being close to everything. Access is easy from a convenient driveway on Wayside Road, leading to carport parking with EV charging.

1005 Portola RD, Portola Valley

Listed by Kavanaugh Group, 650-400-5312 from Coldwell Banker Realty
(If provided) CoList: from

Sold listing courtesy of Lena Gustafsson from COMPS

$1,600,000

2 Beds ⋅ 3 Baths ⋅ ML82001310 MLS

Welcome to a remaining piece of Portola Valley history, full of possibilities! The charming and rustic original structure, with its tall brick fireplace, high ceiling, and exposed rafters, rests on a sunny, gently sloped, half acre lot. Later additions include a very large primary bedroom and bath. A wide veranda wraps around two sides of the house, perfect for relaxing while taking in the expansive view over Portola Valley and on to the East Bay hills. Colorful sunrises, full moons, and an occasional complete rainbow are yours to enjoy. An additional deck provides another viewing spot, with access from both the primary bedroom and the dining room. Nestled in the Woodside Highlands neighborhood, this location offers Portola Valley's excellent schools and provides nearby access to Portola Valley's hiking trails and to the popular Town Center with its library, children's playground, tennis and pickle ball courts, playing field, a redwood grove, and farmers' market. The half acre lot is all usable. Old stonework lines paths and a pond, and off street parking is plentiful. Bring your imagination and make this lovely space your own!

102 Santa Maria AVE, Portola Valley

Listed by Jean Isaacson, 650-387-8427 from Golden Gate Sotheby's International Realty
(If provided) CoList: from

Sold listing courtesy of Jean Isaacson from GGSIR

$2,500,000

3 Beds ⋅ 2 Baths ⋅ ML81989993 MLS

Nestled in a serene location, this beautifully maintained 3 bedroom, 2 bath home offers the perfect blend of comfort and functionality. Step inside to discover the welcoming formal entry way. Charming stairs lead you to the main living space which showcases dramatic high ceilings and an open-concept floor plan that creates a bright & airy ambiance. The living room perfectly opens up to a front balcony while also seamlessly opening up to a large flat backyard creating a space that is perfect for everyday living & entertaining. The updated kitchen features a center island, lots of cabinet space and peaceful views to the surrounding nature. In addition, this home boasts 3 bedrooms on the main level plus a cozy loft ideal for a home office, playroom or additional living space. A few additional features include beautiful hardwood floors throughout, views, lots of natural light, a wonderful landscaped flat yard featuring a rose garden and a darling functional playhouse. The very large attached garage/basement area provides a huge amount of bonus space and additional storage offering plenty of room for all your needs. With top rated PV schools, being minutes from town center, 280 and hiking trails this unique property presents an incredible opportunity for a lucky buyer.

16 Tynan WAY, Portola Valley

Listed by Jennifer Alfaro, 650-888-8338 from Compass
(If provided) CoList: Kimm Terpening from Compass

Sold listing courtesy of Susan Nystrom-Walsh from COMPS

$2,800,000

3 Beds ⋅ 3 Baths ⋅ ML81978529 MLS

Architecturally stunning home w/vaulted ceilings, skylights & oversized windows convey the feeling of living among nature. The rustic stacked stone fireplace, hardwood floors & heavy cross-beamed ceilings blend effortlessly w/sophistication of modern life demands: wide open floor plan, lofty ceilings, recessed lighting, built-in speakers, beautiful wall of windows & wide open connection to outdoor decks. Spacious kitchen features top appliances, generous skylight, picture window over the sink, peninsula breakfast bar, framed glass cabinetry & day desk. Very private primary bedroom suite has vaulted ceilings & is large enough to accommodate a desk area. Second bedroom & full bath are located on the main level. The lower level boasts yet another large bedroom w/ample room for desk area, adjacent full bath, & private access to an outdoor deck (could be a perfect au pair suite or home office). Lush landscaping surrounds the home w/multiple sitting, dining, & play areas. Woodside Highlands neighborhood is a place you will enjoy calling home gaining access to the Town's wonderful trail network is just a few doors away! Close by: Portola Valley's Town Center tennis courts, playing fields, library, & weekly farmers' market, Windmill preschool, Parkside Grill, and just 6 min to 280.

114 Russell AVE, Portola Valley

Listed by Dulcy Freeman, 650-804-8884 from Golden Gate Sotheby's International Realty
(If provided) CoList: from

Sold listing courtesy of Terri Lin from BHGJF

$3,995,000

5 Beds ⋅ 4 Baths ⋅ ML81970104 MLS

Price Improvement! Estate home situated in a quiet & serene park like setting tucked away from the street. This gated property is located in the heart of Portola Valley, a short stroll to Town center, Famers market, Summer concerts, Just a few minutes drive to 280 & Sand Hill Venture Row. 5 bedrooms/3.5 fully remodeled baths with a unique welcoming feeling. Primary suite with a freshly remodeled bathroom & walk-in closet. Located on a wooded yet sunny 1.3 acre's. The 3,600 s.f. Home has a gourmet Chef's kitchen, Calcutta marble, custom cabinets, commercial grade appliances, gas range/oven, Liebherr refrigerator, breakfast bar, and bench seat storage. Large formal living room with high ceilings and slider to outdoor entertaining area. Separate family room/library with high ceilings. hardwood floors throughout. Double pane windows throughout. Inside laundry and abundance of storage cabinets. Two outdoor living rooms for entertaining. Raised planters for a vegetable & herb garden, Space ideal for a chicken coop, Tons of usable lawn space, On cooler nights, there is a spacious theater that insures many hours of entertainment. Wonderfully high ceilings & high end custom finishes throughout. No detail was ignored This home speaks of quality Come home to style and comfortable elegance.

1077 Portola RD, Portola Valley

Listed by William Lister, 408-892-9300 from Coldwell Banker Realty
(If provided) CoList: from

Sold listing courtesy of Jennifer Alfaro from COMPS

$2,100,000

2 Beds ⋅ 1 Baths ⋅ ML81968272 MLS

Nestled in serene Portola Valley, this property offers stunning western hill views and three separate parcels totaling almost half an acre of mostly level yard space. In addition to the main residence, a thoughtfully designed guest house awaits, complete with its own address and separate access, offering the perfect opportunity for rental income or accommodating guests in comfort and style. Both the main house and guest house have been recently renovated, ensuring modern amenities and tasteful finishes at every turn. With over 1,000 square feet of deck space, the outdoor areas offer an ideal setting for hosting gatherings while enjoying a California sunset over the Western Hills. The allure continues outside with a thriving garden including vegetables, fruit and citrus trees, providing a serene retreat for gardening enthusiasts or those seeking a connection to nature. Conveniently close to Highway 280, Stanford, and local amenities, this private oasis presents a rare opportunity for tranquil and private living in a wonderful neighborhood. Top rated Portola Valley schools.

140 Santa Maria AVE, Portola Valley

Listed by Michael Warren, 650-315-0224 from Compass
(If provided) CoList: from

Sold listing courtesy of Evan Kohen from APR

$2,430,000

3 Beds ⋅ 2 Baths ⋅ ML81964277 MLS

This stunning Portola Valley gem is set back from the street on almost one-third acre. Beautifully updated, this move-in ready home boasts one-level living with a level yard in the front and a private terrace in the back. Inside, newly refinished hardwood floors, an updated kitchen, and bathrooms with designer touches throughout provide elegance and style throughout the tastefully appointed country home. Expansive windows provide abundant natural light into the living spaces. The finished garage offers additional play & storage space with potential for a family room. The gated front motor court provides plenty of parking. The level yard, fresh landscaping & new pavers make it perfect for entertaining & outdoor activities. Additionally, the home's sizeable lot provides various expansion options. Conveniently located near Hwy 280 and Sand Hill Rd venture capital centers, this home is perfect for commuters. Walkable to PV schools, Village Square, the library, the Farmer's Market, and trails on the Woodside/Portola Valley loop, it is a true Portola Valley gem!

975 Portola RD, Portola Valley

Listed by Jennifer Gilson, 650-642-6957 from Golden Gate Sotheby's International Realty
(If provided) CoList: from

Sold listing courtesy of George Chopoff from REMS

$4,000,000

3 Beds ⋅ 3 Baths ⋅ ML81953983 MLS

Nearly 1.4 AC plays host to this inviting 3-bedroom home. Enveloped by lush greenery, this home offers a serene retreat, featuring over 3,300 sf of living space and a light-filled ambiance. Stylish appointments such as beamed ceilings, refinished hardwood floors, and beautiful woodwork adorn this home. The expansive floorplan encompasses generous gathering areas, a cozy fireplace, a kitchen equipped with a professional-grade Thermador range, a dedicated office, and a spectacular Hinoki soaking tub in the primary suite that provides a spa-like experience. Enjoy an indoor/outdoor lifestyle that only Portola Valley can provide on sprawling, multi-level grounds that feature a pool, numerous fruit trees, and a delightful tea room. And though this home offers incredible privacy, you will still be a short drive from amenities such as the iconic Alpine Inn, Interstate 280, vibrant parks and nature preserves, and top schools including Ormondale and Corte Madera (buyer to verify eligibility).

40 Santa Maria AVE, Portola Valley

Listed by DeLeon Team, 650-900-7000 from Deleon Realty
(If provided) CoList: from

Sold listing courtesy of Mini Kalkat from NTERO

$1,865,000

2 Beds ⋅ ML81950966 MLS

Welcome to Woodside Highlands, just a stone's throw to Village Square, library, Farmer's Market, top schools, Larry Lane Trail, and much more. This charming 2 bedroom home with 2 full bathrooms offers the very best of California living. A bright kitchen with center island, stainless steel appliances including gas range, and generous breakfast nook. Adorned by a free-standing, wood-burning stove, the spacious living room's french doors open to a large refinished deck that overlooks the beautiful backyard with mature landscaping, rope swing, gathering area, and views. Oversized laundry room lends itself perfectly for a bathroom/laundry conversion (rendering available). This meticulously maintained home has refinished hardwood, new carpet, and fresh paint inside. Large, accessible basement for additional storage. Parking is a plentiful in the wide, flat driveway. A Silicon Valley oasis: all the benefits of a tranquil, country setting while also conveniently located mere minutes from 280.

6 Leroy WAY, Portola Valley

Listed by Bob Johnston, 650-400-5039 from Coldwell Banker Realty
(If provided) CoList: Francesca Lampert from Coldwell Banker Realty

Sold listing courtesy of Rigo Campos from EORE

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