Portola Valley Single Story Homes for Sale

4 Beds ⋅ ML82056611 MLS

Located in Portola Valley, this spacious 2,960 sq. ft. home sits on a sizable 17,623 sq. ft. lot. The kitchen is equipped with modern amenities including a built-in gas oven range, microwave, island, hood over range, and garbage disposal, offering both functionality and convenience for everyday cooking. The home features central forced air gas heating and central air conditioning to maintain comfort year-round. This property does not include a garage. It is part of the Portola Valley Elementary School District. This residence combines ample living space with essential features in a desirable town setting.

176 Los Trancos CIR, Portola Valley

Listed by Tim Gilmartin, 650-348-2020 from Gilmartin Group
(If provided) CoList: from

$3,500,000

4 Beds ⋅ 4 Baths ⋅ ML82056610 MLS

Located in Portola Valley, this spacious 2,960 sq ft home features four bedrooms and four full bathrooms. The kitchen is equipped with built-in gas oven range, microwave, hood over range, island, and garbage disposal, opening to a combined kitchen and family room area. Enjoy two fireplaces, one in the living room and another in the primary bedroom, providing warmth and ambiance. The home includes a dining area with a breakfast bar, central forced air gas heating, and central AC for comfort. Laundry facilities are conveniently located inside the home. The property sits on a 17,623 sq ft lot and falls within the Portola Valley Elementary school district.

176 Los Trancos CIR, Portola Valley

Listed by Tim Gilmartin, 650-348-2020 from Gilmartin Group
(If provided) CoList: from

$2,595,000

2 Beds ⋅ 1 Baths ⋅ ML82052857 MLS

Beautiful (Bonita!) very large property in upper Los Trancos Woods. Over 1.6 AC of mostly flat land with old, mostly not habitable House, Cottage, Garage and Carport, comfortably spread throughout the property. In Feb 2026, San Mateo County approved a 2 lot subdivision, and work is ongoing to complete the final map recording. The house is available prior to recording of the subdivision as a single lot for buyers who might want more flexibility in what they do with the property. Extensive geological, geotechnical, arborist, historical, biological and civil reports and plans come with the property.

245 Bonita RD, Portola Valley

Listed by Mike Sokolsky, 650-465-2573 from Coldwell Banker Realty
(If provided) CoList: from

$5,600,000

3 Beds ⋅ 2 Baths ⋅ ML82047359 MLS ⋅ Westridge Arch. Supervis. Comm. BLDG.

Nestled along coveted Alamos Road in the prestigious Westridge area, this extraordinary property was refurbished top to bottom; presenting a rare opportunity to own a private retreat in one of the Peninsula's most exclusive neighborhoods. Set on nearly 2.75 acres of serene, country-like grounds, this exceptional estate offers unmatched privacy, tranquility, & breathtaking panoramic bay views; all just minutes from Highway 280 & Stanford Shopping Center & Campus. Beautifully & fully renovated, this move-in ready home features 3 bedrooms & 2 bathrooms, thoughtfully designed to capture stunning vistas from nearly every room. Expansive windows & outdoor spaces invite the natural beauty indoors, creating a peaceful sanctuary surrounded by lush greenery & rolling landscapes. Whether you choose to enjoy the home exactly as it is or envision expanding it into a larger custom estate, the possibilities are endless. Add a second story, subterranean garage, ADU, tennis court, lap pool, tranquil pond, an RV or other personalized amenities to create your dream compound. Opportunities like this are exceptionally rare - a timeless setting w/ forever views, exclusive privacy, & unlimited potential. Experience your own private piece of heaven & make this remarkable property yours before its gone!

365 Alamos RD, Portola Valley

Listed by Jeanette Cook, 650-344-3447 from Cook Properties
(If provided) CoList: from

Sold listing courtesy of Ken Glidewell from COMP29

$3,050,000

3 Beds ⋅ 2 Baths ⋅ ML82047659 MLS ⋅ Ladera BLDG.

Welcome to Portola Valley! Situated on a lovely, quiet & cul-de-sac & situated in the highly desirable Ladera community! This home has1,560 +/- sq ft. of living space & sits on a 9,600 +/- sft. flat lot w/views & within the highly rated Las Lomitas Elementary school district. The residence offers three bedrooms and two full bathrooms, including a primary bedroom with a walk-in closet and a stall shower. The living room / dining combo features a wood-burning fireplace and open beam ceilings & wood flooring & a slider leading to a lovely expansive backyard with views! The kitchen is equipped with a gas cooktop, built-in oven range, refrigerator, dishwasher, garbage disposal & an eat-in breakfast nook. Heating is provided by central forced air with gas. Laundry facilities are located in the utility room. The home includes a two-car garage and access to community amenities such as an in-ground pool, child's pool, tennis courts, children's playground, Bocce ball, trails & more through the Ladera Recreation Center. A little TLC or a major redo we leave that to you! Professionally cleaned & freshly painted interior await you, a must see!

221 W Floresta WAY, Portola Valley

Listed by Steve Coan, 408-234-8700 from Coldwell Banker Realty
(If provided) CoList: from

Sold listing courtesy of Jessica Heredia from RPSNT

$1,749,000

2 Beds ⋅ 2 Baths ⋅ ML82047556 MLS

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 plans for a future expansion. The current home, with 2 bedrooms and 2 baths, offers a streamlined scale yet the open concept design lends an unexpected sense of expansiveness. A crisp palette of whites defines the interiors, from the all-white kitchen with quartz countertops and subway tile backsplashes to the remodeled baths finished in marble and tile. Vaulted ceilings with skylights and exposed beams enhance the airy atmosphere, while wood-like luxury vinyl floors provide continuity throughout. Multiple sets of glass doors open to wraparound flagstone patios and expansive land, where limited tree canopies allow brilliant sunlight to fill both the interiors and outdoor gathering spaces. Finishing touches include a separate laundry room, an outdoor storage shed, and a two-car carport. Portola Valleys acclaimed schools and miles of scenic trails are just moments away, making this a remarkable opportunity to enjoy contemporary style and comfort today with the option to expand in the future.

76 Old Spanish TRL, Portola Valley

Listed by Erika Demma, 650-740-2970 from Compass
(If provided) CoList: from

$5,950,000

4 Beds ⋅ 3 Baths ⋅ ML82045714 MLS

Located in the highly desirable Westridge subdivision of Portola Valley, this approximately 3.9-acre property presents an exceptional opportunity to remodel or create a new legacy estate. The superb setting is defined by privacy and sweeping western hill views, including Windy Hill. The expansive parcel offers broad open space, mature oaks, and gently terraced grounds providing a remarkable canvas for a future vision. The existing circa 1967 single-level Ranch style home spans approximately 3,300 square feet with 4 bedrooms, an office, and 3 full baths. Freshly painted interiors and exterior enhance its character, which includes walls in fine wood paneling, floors in terra cotta tile and hardwood, cathedral ceilings, and numerous sliding glass doors oriented to the western hill views. Located within the highly regarded Portola Valley school system and moments from Stanford University and key Silicon Valley tech centers, this property offers rare scale, views, and opportunity in a premier location.

747 Westridge DR, Portola Valley

Listed by Hugh Cornish, 650-619-6461 from Coldwell Banker Realty
(If provided) CoList: from

Sold listing courtesy of Keri Nicholas from PARCA

$3,080,000

4 Beds ⋅ 2 Baths ⋅ ML82044409 MLS ⋅ Ladera BLDG.

Nestled on one of Ladera's most sought-after streets, this delightful ranch-style home blends timeless charm with everyday comfort. A cozy living room with a fireplace and an expansive picture window invites natural light and serene views of the lush, private backyard. The eat-in kitchen features granite countertops, stainless steel appliances, and seamless access to the patio, perfect for indoor-outdoor living. The thoughtfully designed bedroom wing includes four bedrooms, two of which are connected by a Jack-and-Jill pocket door, ideal for shared living or added privacy. The primary suite offers its own en-suite bath and direct patio access. Enjoy a prime location near the Ladera Recreation Center, school bus stop, and Ladera walking paths, with easy access to Stanford, major commute routes, and top Silicon Valley employers. This charming home provides the perfect canvas to add your personal touch and make it your own!

130 Erica WAY, Portola Valley

Listed by Rebecca & Karen, 650-281-8752 from Intero Real Estate Services
(If provided) CoList: from

Sold listing courtesy of Sanit Bordeianu from CBR

$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

$1,760,000

2 Beds ⋅ 1 Baths ⋅ ML82042381 MLS

Vintage home, circa 1956, situated on a 1/3 acre parcel in a quiet corner of Portola Valley. This cozy, uncomplicated home could become your haven away from the hustle and bustle of Silicon Valley life -- or, it could become the site of your dream home. Reimage this cottage or create something completely new! Nearby is Robert's Market (groceries,etc.) a hardware store, the fire department, a full-service (gas and repairs) station. This area is favored by cyclists and hikers. And it's a quick distance to Freeway 280 for commutes north and south.

208 Canyon DR, Portola Valley

Listed by Nancy Goldcamp, 650-400-5800 from Coldwell Banker Realty
(If provided) CoList: from

Sold listing courtesy of Samie Goodman from CBR

$2,850,000

3 Beds ⋅ 2 Baths ⋅ ML82041743 MLS

Peaceful Updated Country Living on Nearly 1.5 Acres . Beautifully updated and framed by sun-swept open meadows and majestic trees, this property spans nearly 1.5 acres at the end of a lane. An inviting front porch takes in the tranquil surroundings and sounds of nature. Stepping inside, the ambiance is bright and inviting with refinished hardwood floors, crisp white woodwork, and expansive windows and glass doors. The designer all- white kitchen has Carrara marble counters and stainless steel appliances, including a quality Viking gas range. A separate wing comprises 2 full-size bedrooms and one small bedroom, plus 2 full baths. Perfect for exercise, art, and/or office needs is a detached 2-room studio plus a Nordic-inspired newly added second studio. Tying it all together are many beautiful and versatile outdoor living spaces plus a fully fenced vegetable garden, small orchard, and a chicken coop.

377 Wayside RD, Portola Valley

Listed by Janis F. Grube, 650-346-8690 from Friedenberg Grube Real Estate
(If provided) CoList: from

Sold listing courtesy of Angela K. Galatolo from AGNC

$5,712,500

5 Beds ⋅ 4 Baths ⋅ ML82039321 MLS

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.

50 Bear Gulch DR, Portola Valley

Listed by Peter Cowperthwaite, 650-207-4101 from Golden Gate Sotheby's International Realty
(If provided) CoList: from

Sold listing courtesy of Jennifer Alfaro from COMPS

$3,800,000

3 Beds ⋅ 2 Baths ⋅ ML82037272 MLS

Located in prime central Portola Valley, discover the potential of this single-level home & spectacular property. With 3 bdrms, 2 bthrms, & 2,210 sq. ft. of living space on an expansive 42,575 sq. ft. lot, this home offers a rare opportunity to create your dream lifestyle. The front door leads you into a spacious living room w/ a cozy fireplace, stunning floor-to-ceiling windows & a dining area. The kitchen & adjoining family room flow seamlessly to the private backyardfeaturing a large deck and sparkling pool. On clear days, enjoy stunning views of the South Bay both while inside the home and from the backyard. The freshly painted interior and brand-new carpet provide a clean slate, ready for your personal touch. The primary suite includes two walk-in closets and a private bathroom, while the two additional bedrooms share a convenient hall bath. Functional amenities like a dedicated laundry room and attached 2-car garage add to the home's overall comfort and practicality. Ideally situated for easy access to PV schools, Stanford, Highway 280, local shopping, and scenic hiking trails, this property combines convenience and natural beauty. First time on the market, this home presents a unique opportunity to customize and enjoy a peaceful retreat in a very desirable location.

285 Golden Oak DR, Portola Valley

Listed by Kimm Terpening, 650-867-4880 from Compass
(If provided) CoList: Jennifer Alfaro from Compass

Sold listing courtesy of Lisa Dippel from NTERO

$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

$8,100,000

5 Beds ⋅ 5 Baths ⋅ ML82033403 MLS

Contemporary single-level main residence with attached two-story ADU on 1.1+ private acres finished in 2021, offering direct Windy Hill views and walking distance to Portola Valley Town Center, library, restaurants, farmers market, and trailheads. Striking modern architecture features walls of glass, soaring ceilings, skylights, and white oak floors throughout. The dramatic great room opens to covered and open terraces and a level lawn just off the living room patio, with rear grounds anchored by a heritage oak. The designer kitchen showcases Calacatta marble surfaces, a waterfall island, and high-end appliances. The main residence includes a dedicated office, four bedrooms, and three and a half baths, highlighted by a serene primary suite with Windy Hill views and a Zen-inspired bath with private garden. A privately located bedroom suite is ideal for guests or an au pair. The attached ADU offers one bedroom, one bath, a full kitchen, and a living room with fireplace, with finishes matching the main home. Gated entry, custom pavers, cedar entry door, fountains, mature landscaping, level synthetic lawn, raised garden beds, and fully fenced grounds complete this desirable property. Total Finished square footage: 4,390 sq. ft. (main house: 3,520 sq. ft. and ADU: 870 sq. ft.)

1390 Westridge DR, Portola Valley

Listed by Hugh Cornish, 650-619-6461 from Coldwell Banker Realty
(If provided) CoList: from

Sold listing courtesy of John Kavanaugh from CBR

$4,600,000

4 Beds ⋅ 4 Baths ⋅ ML82025987 MLS

Beautifully updated & remodeled for contemporary living, this home enjoys a rare setting on a circular street in central Portola Valley. Framed by towering redwoods & mature oaks, the property enjoys exceptional privacy with a sunlit deck & spa plus a seasonal creek that traces the rear border. Home open & light filled design, featuring reconfigured living areas, designer kitchen, & perfectly hued refinished hardwood floors. Main living areas are designed with flexibility for formal or everyday living. Great room that encompasses the kitchen, family room, & formal dining space, while an adjoining library also offers the option of use as a formal dining room. All of the spaces open to the enchanting rear grounds including a large office off the living room. Tranquil main-level primary suite with remodeled bath & direct access to the spa deck. Second bedroom & bath on this level are ideal for guests plus a dedicated office. Upper level features a spacious recreation room with fireplace & refreshment center, plus two additional bedrooms, each opening to a rear deck with stairs to the yard, & remodeled bath. Completing this inviting retreat is its close-in location just minutes from Portola Valley Town Center, Windy Hill hiking trails, & acclaimed Portola Valley schools.

135 Wyndham DR, Portola Valley

Listed by Hugh Cornish, 650-619-6461 from Coldwell Banker Realty
(If provided) CoList: from

Sold listing courtesy of Courtney Charney from PARCA

$5,850,000

3 Beds ⋅ 3 Baths ⋅ ML82025817 MLS

On an expansive, level acre, this single-level residence captures the essence of relaxed California living where indoor and outdoor spaces flow effortlessly and every detail invites connection with nature. A welcoming front patio opens to the home's bright and spacious interiors, where generous living and dining areas are anchored by broad windows and warm hardwood floors. The open-concept kitchen and breakfast area overlook the pool and gardens, blending casual comfort with an easy elegance that defines the homes spirit. Three bedrooms, three baths, and two dedicated offices create flexibility for family life, guests, and work-from-home needs. The expansive primary suite enjoys garden views, large walk-in closet, and a spa-like bath. Outside, the property unfolds like a private oasis, complete with a sparkling pool and spa, multiple entertaining terraces, lush lawn, and a dedicated pickleball court. Additional features include a large recreation room, laundry/mud room, carport, and three storage sheds. Perfectly located within one of Portola Valleys most desirable neighborhoods, this home is moments from scenic hiking trails, top-rated schools, and the conveniences of nearby Sand Hill Road, Menlo Park, and Stanford University.

135 Meadowood DR, Portola Valley

Listed by Kavanaugh Group, 650-400-8076 from Coldwell Banker Realty
(If provided) CoList: from

Sold listing courtesy of Evan Kohen from APR

$3,300,000

3 Beds ⋅ 2 Baths ⋅ ML82025326 MLS ⋅ Ladera BLDG.

Experience serene, modern living in this beautifully updated 3-bedroom, 2-bath ranch home infused with Japanese-inspired design, with a harmonious connection to the outdoors, creating an atmosphere of calm and balance throughout. Light-filled living spaces flow seamlessly to a private backyard oasis, creating the perfect setting for both relaxation and entertaining. Spacious living room featuring a built-in bookcase and gas fireplace. Modern kitchen with granite and stainless steel counters, breakfast bar, and updated cabinetry. Separate family room with easy access to the backyard. Private backyard retreat with black-bottom pool, pergola, with space for gatherings. Close to the Ladera Shopper and Ladera Recreation Center, near the bus stop and Woodland School, just 3.5 miles to Stanford University, easy access to commute routes, Silicon Valley, and mid-way between San Francisco and San Jose International Airports. Optional membership to the Ladera Recreation Center provides year-round tennis, pickleball & fitness programs, a seasonal aquatics program, and a variety of community events and activities.

375 La Cuesta DR, Portola Valley

Listed by Rebecca & Karen, 650-281-8752 from Intero Real Estate Services
(If provided) CoList: from

Sold listing courtesy of Josh Rubin from COMPS

$4,275,000

4 Beds ⋅ 3 Baths ⋅ ML82024644 MLS ⋅ Ladera BLDG.

Experience the charm and comfort of this beautifully maintained Ladera home, offering generous living spaces, an open floor plan, and seamless indoor-outdoor flow ideal for gatherings and everyday living. The inviting living room features a wall of windows, a wood-burning fireplace, and wide-plank hardwood floors throughout. The open floor plan of the kitchen, featuring a large center island, dining area, and adjoining family room, is the true heart of this home. A convenient full bath is located near the family room for guests or access from the backyard. En-suite primary bedroom with direct access to the backyard for a peaceful morning coffee or evening relaxation. Three spacious bedrooms share a newly updated bathroom. Enjoy California living in a spacious, level backyard with deck, paver patio, built-in BBQ, and inviting gas firepit. Convenient to the Ladera Recreation Center, school bus stop, local shopping, restaurants, Stanford, and commute routes.

630 La Mesa DR, Portola Valley

Listed by Rebecca & Karen, 650-281-8752 from Intero Real Estate Services
(If provided) CoList: from

Sold listing courtesy of Loveless Team from NTERO

$1,800,000

3 Beds ⋅ 2 Baths ⋅ ML82024365 MLS

Discover the perfect blend of nature and modern convenience at 1019 Los Trancos Road in the peaceful Los Trancos Woods neighborhood. This charming home, built in 1930, offers 1,770 SF of versatile living space (per the Seller) in two buildings with freshly painted exteriors. The 1,225 SF main house features three bedrooms and two baths, with vaulted ceilings and skylights that invite abundant natural light. The airy living room, featuring exposed beams, seamlessly transitions to a large deck and patio, ideal for indoor-outdoor entertainment. The galley kitchen is a chef's delight, featuring stainless steel appliances and ample cabinetry that overlooks the garden. A 545 SF studio is situated behind the one-car garage. While not reflected in the County records, the studio is a flexible space with a kitchen, stacked washer/dryer, full bathroom, new wall-to-wall carpeting, and a private deck - ideal for multi-generational living, working from home, or generating rental income. Positioned on a generous 9,360 SF parcel, you'll enjoy peaceful views and easy access to Portola Valley's lively Town Center and Highway 280 for easy commuting.

1019 Los Trancos RD, Portola Valley

Listed by Robert Parish, 650-400-1011 from Compass
(If provided) CoList: from

$6,200,000

5 Beds ⋅ 4 Baths ⋅ ML82022890 MLS

Remodeled and expanded on 1.3 level acres with tennis court, views, and beautiful grounds in central Portola Valley. Custom craftsmanship and artistic detail showcase cathedral ceilings with industrial lighting and windmill-style fans, numerous skylights, and reclaimed wood accents creating rustic sophistication. Two dramatic works by a Post Ranch Inn artist a sculptural stainless-steel fireplace surround and a custom steel hot tub on the elevated deck merge art and function. Gourmet kitchen with French Lacanche range and rolling ladder to upper storage. Primary suite couture closet designed for nearly 500 pairs of shoes also has a rolling ladder plus a spa like bath with open shower. Natural landscaping, pollinator gardens, and impressive variety of fruit trees. Private tennis court enhances the rear grounds. Moments from the town center and Windy Hill trails for the ultimate Portola Valley lifestyle. Excellent Portola Valley schools.

70 Stonegate RD, Portola Valley

Listed by Ciana Megan Tierney, 650-954-8642 from Compass
(If provided) CoList: from

Sold listing courtesy of Erika Demma from APR

$3,455,000

3 Beds ⋅ 3 Baths ⋅ ML82022989 MLS

Discover the potential at 475 Cervantes Rd, nestled in the heart of Portola Valley, where opportunity meets prime location. Situated on a lovely 1 acre lot, this property presents a remarkable canvas for those looking to build or remodel in order to create their optimal living space. The home boasts 2,550 feet of living space, featuring 3 bedrooms, 2.5 bathrooms. The primary bedroom is a retreat in itself, complete with an ensuite bathroom that includes a separate tub and shower. The additional two bedrooms share a convenient and spacious hall bath. The heart of this home is its open-concept kitchen and family room, perfect for gatherings and entertaining. The kitchen comes equipped with a center island and a cozy eating area, while the family room offers built-in bookcases and fireplace. For more formal occasions, enjoy the separate dining room and large living room. To enhance the thoughtful flow of the home, all common areas lead to the serene backyard. Additional amenities include a dedicated laundry room, a detached 2-car garage, a screened patio and a deck overlooking the private yard while offering a peaceful retreat and space for outdoor enjoyment. This home already offers fabulous spaces and a thoughtful floor plan; it just needs the creativity of its next owner.

475 Cervantes RD, Portola Valley

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

Sold listing courtesy of Eric Ruxton from TERA

$5,500,000

4 Beds ⋅ 3 Baths ⋅ ML82011438 MLS

Fabulous views at this 3800 sf home plus 1200 sf ADU , greenhouse and pool on nearly 2 acres in prime Portola Valley. Gorgeous property with sublime views on nearly 2 acres in the prime Westridge neighborhood of Portola Valley. The gorgeous updated ranch-style home has sublime views of the hills and a formal entry, living room with fireplace and built-ins, large eat-in kitchen with Viking range, and two subzero refrigerators, bright pantry with skylight; full bath off kitchen, large office with built-in file drawers and fireplace. The 1,000-sf sunroom accommodates living, dining and work areas and has Bosch dishwasher, Thermador grill and a wine cooler. Four distinct bedrooms; primary has doors to patio, walk-in closet, bathroom with steam shower and heated floors. Large office in main home + in converted garage bay. Outside there is a gorgeous garden in full bloom, pool, hot tub, greenhouse, ample extra storage and beautiful views to the coastal mountains. Separate private well-appointed two+ bedroom ADU. Loads of built-in bookcases, and cabinets. You won't want to miss this distinctive property on almost two acres. Solar panels provide electricity throughout the property.

1175 Westridge DR, Portola Valley

Listed by Monica & Mandy Group, 650-823-8212 from Compass
(If provided) CoList: from

Sold listing courtesy of Cindy Hung from NTERO

$4,250,000

4 Beds ⋅ 3 Baths ⋅ ML82019049 MLS

Welcome to this beautiful home located in central Portola Valley. This spacious 4-bedroom, 3-bathroom residence offers comfortable living with generous amenities. A secluded fourth bedroom and full bath provide a comfortable solution for guests or extended family. The kitchen is well-positioned with an electric cooktop, double oven, refrigerator, and opens to the rear patio. The living room boasts vaulted ceilings, providing an open and airy feel enhanced by a wall of windows overlooking the patio area. The bedrooms are well-sized with ample closet space. Recently painted in a neutral tone with complementary carpets, this home is turn-key and one can move right in and enjoy the holidays! Ideally positioned on 1.6 acres. with two level tiers and a downslope, the oak studded lot is both private and accessible. The property features a solar-heated in-ground pool, and a convenient pool house complete with a full bath - perfect for relaxation and entertaining. The Portola Valley Elementary School District serves the area. With additional structures like a lighted pergola, and large storage shed, this home is a perfect blend of comfort and functionality.

20 Bear Gulch DR, Portola Valley

Listed by Denise Welsh, 415-999-0727 from Compass
(If provided) CoList: from

Sold listing courtesy of Ashu Chadha from COMPS

$7,257,000

4 Beds ⋅ 4 Baths ⋅ ML82019615 MLS

Nearly every room of this ±1-acre property captures sweeping views of nature, gardens, a sparkling pool, and the iconic Windy Hill backdrop. Completely and thoughtfully remodeled, the home blends modern comfort with exceptional attention to detail. The single -level floor plan features 4 bedrooms (one currently used as an office) and 3.5 beautifully updated baths. The layout includes both a living room and a separate family room, while the kitchen shines with high-end appliances, a large island with seating, and a coffee/serving bar with sink and storageperfect for entertaining. The kitchen and dining areas flow together seamlessly, easily accommodating large gatherings. The primary suite opens directly to the pool and spa, with a spa-inspired bath that includes a free-standing tub, oversized shower, dual vanities with designer cabinetry, custom tile and hardware, and a walk-in custom closet. A private ADU provides an additional bedroom and bath, along with its own entrance, soaring ceilings, oversized windows, and a full kitchenideal for guests, extended family, or flexible use. In the heart of Portola Valley, close proximity Alpine Hills Swim & Tennis Club, the historic Alpine Inn, and top-rated PV schools minutes to Highway 280 for easy access to Silicon Valley and SF.

415 Cervantes RD, Portola Valley

Listed by Peter Cowperthwaite, 650-207-4101 from Golden Gate Sotheby's International Realty
(If provided) CoList: from

Sold listing courtesy of Erika Demma from APR

$6,950,000

4 Beds ⋅ 3 Baths ⋅ ML82019602 MLS

Located in the desirable WESTRIDGE Neighborhood, this impressive 2.62+/- ac. property offers views, room for expansion, a vineyard, separate ADU, and a freshly updated home with 4 bedrooms & 3 remodeled baths. The kitchen has new appliances, & flows into a family living space. The large dining area sets the stage for entertaining. The Primary Suite has tall beamed ceiling, 3 closets, & deck that overlooks the property & Windy Hill views. Additional bedrooms enjoy a private wing that centers around a flexible space This space is served by a separate entrance for flexibility. A lower level is a blank slate. Finishedit has a work-shop, lots of storage, 2 rooms with sliding glass doors, a large well-lit space thats ideal as a game room or exercise center. Potential for a wine cellar. And there is a full bath. The ADU is 1 bed. 1 bath & has an open living/dining/kitchenette space, + private deck & entrance. There is a small upper pasture or a large area at the front of the property that could be used for horses or pool, possibly a tennis court or just let nature share its beauty with you. Central Portola Valley location, convenient to shopping, Alpine Hills Swim & Tennis club, The Alpine Inn, excellent PV schools, & just 5+/- min. to Hwy. 280.

15 Naranja WAY, Portola Valley

Listed by Peter Cowperthwaite, 650-544-8968 from Golden Gate Sotheby's International Realty
(If provided) CoList: from

Sold listing courtesy of Peter Cowperthwaite from DP

$4,600,000

4 Beds ⋅ 3 Baths ⋅ ML82017822 MLS

Single-level ranch home set on a private acre in a forest-like oasis with majestic redwoods. This renovated 4-bedroom, 2.5-bath residence features a cozy family room and a spacious living room with cathedral ceilings and a wall of windows that fill the home with natural light while showcasing the serene yard. A half-moon driveway provides a welcoming approach, complemented by a separate driveway leading to a large garage. The kitchen is designed for both beauty and function, with custom cabinetry, interior lighting, double sinks, built-in Thermador refrigerator, La CornuFe' range with an elegant exhaust. The bathrooms are thoughtfully updated, offering a soaking tub and walk-in shower. Portola Valley Trails are right outside your door!

240 Willowbrook DR, Portola Valley

Listed by Roberto Ruiz, 408-234-7249 from Intero Real Estate Services
(If provided) CoList: from

Sold listing courtesy of Samira Amid-Hozour from SGP

$2,500,000

4 Beds ⋅ 2 Baths ⋅ ML82016089 MLS ⋅ Ladera BLDG.

Mid-century modern diamond in the rough. Unlock the full potential of this 4-bedroom, 2-bath mid-century modern gem nestled in the desirable Ladera neighborhood. Set on a private and spacious corner lot with mature landscaping, this home is brimming with opportunity for the savvy buyer to renovate and restore its original charm or build your dream home from the ground up. Convenient to the Ladera Shopper, Ladera Rec, school bus stop, Stanford 3.5 miles, easy access to Silicon Valley, commute routes & mid-way between SFO & SJC International airports. This is your chance to create your dream home in one of the Peninsula's most sought-after communities.

291 La Mesa DR, Portola Valley

Listed by Rebecca & Karen, 650-281-8752 from Intero Real Estate Services
(If provided) CoList: from

Sold listing courtesy of Sonia Maiello from NTERO

$3,380,000

3 Beds ⋅ 2 Baths ⋅ ML82014861 MLS

VALUE VALUE VALUE! Nestled in the heart of one of Silicon Valleys most sought-after communities, 10 Bear Gulch Drive in Portola Valley presents a rare and exciting opportunity. This timeless Craftsman-style home sits on a sprawling 1.25-acre parcel and offers a 3-bedroom, 2-bath main residence plus a detached guest cottageideal for extended family, home office, or rental potential. Priced to sell due to its current condition, this property is the ultimate blank canvas for those seeking to remodel, rebuild, or even explore lot-split potential (buyer to verify with city). Whether youre dreaming of a serene family retreat or a visionary development project, the possibilities are endless. Living in Portola Valley means being surrounded by nature while remaining remarkably close to everything. Just moments from local favorites like Rossottis Alpine Inn and the Portola Valley Town Center, you'll also enjoy access to the scenic Windy Hill Open Space Preserve, miles of biking and hiking trails, and beloved community events like the summer concert series and farmers market. With top-rated schools, a welcoming small-town atmosphere, and a laid-back commute to Stanford, Sand Hill Road, and Highway 280, this location blends peaceful living with everyday convenience. Make this yours!

10 Bear Gulch DR, Portola Valley

Listed by Danny Burgess, 650-665-0922 from eXp Realty of California Inc
(If provided) CoList: from

Sold listing courtesy of Heidi Tang from VINE

$6,020,000

3 Beds ⋅ 3 Baths ⋅ ML82012718 MLS

Modern Luxury on 2+ Acres with Windy Hill Views || Striking modern design, total privacy, and chic designer interiors define this exceptional property in the heart of central Portola Valley. Gated at the end of a long driveway and spanning over 2 acres, the setting offers expansive grounds with views toward Windy Hill and a layout designed for effortless indoor/outdoor living. Every detail of the home has been meticulously curated, with radiant-heated concrete and white oak floors, soaring ceilings, and floor-to-ceiling walls of glass stretching the entire length of the home. The sleek white kitchen is finished with Carrara marble and anchored by two large islands part of a dramatic great room that includes formal and casual living spaces, dining area, and seamless access to the outdoors, pool, and views. The multi-level floor plan features a luxurious primary suite with spa-inspired bath and an enormous skylit dressing room, two additional bedrooms with a shared luxe bath, and a striking hallway bath. Outdoor amenities include a solar-heated pool, spa, fire pits, crushed stone walking paths, an elevated pavilion, and expansive Ipe deck. All just minutes from trails, town conveniences, and top-rated Portola Valley schools.

22 Grove DR, Portola Valley

Listed by Erika Demma, 650-740-2970 from Compass
(If provided) CoList: from

Sold listing courtesy of Judy Citron from COMPS

$8,750,000

6 Beds ⋅ 9 Baths ⋅ ML82011147 MLS ⋅ Blue Oaks BLDG.

Prominently perched on the Portola Valley hillside, this contemporary home has been upgraded with the finest materials and craftsmanship providing glorious panoramic views of rolling hills with Silicon Valley and the Bay in the distance. This home is elegant, sophisticated and secluded and just a short drive to Silicon Valley with easy freeway access. The flexible floor plan includes six bedroom suites, dedicated office/den with fireplace, living room with soaring ceilings, fireplace, adjacent balcony and forever views, great room with access to the outdoor kitchen and spa plus a gathering spot and an in-home theater on the lower level. The kitchen is appointed with high-end appliances, butlers pantry, island and breakfast bar, all open to the casual dining/family room--perfect for intimate gatherings and sufficient for hosting formal dinner parties or large events. The garden boasts wrap around balconies and patios, views, beautiful plantings in front and sunny, enclosed fruit/vegetable beds below. Solar power system with robust Tesla battery support, 5 zone heat & A/C, full property security system, two laundry facilities, two two-car garages and community pool/spa complete this move-in ready home. Top rated Portola Valley schools. Close by hiking/biking/equestrian trails.

5 Redberry RDG, Portola Valley

Listed by Omar M. Kinaan, 650-776-2828 from Golden Gate Sotheby's International Realty
(If provided) CoList: Ellen Ashley from Golden Gate Sotheby's International Realty

Sold listing courtesy of Kavanaugh Group from CBR

$2,950,000

3 Beds ⋅ 2 Baths ⋅ ML82009816 MLS

On the market for the first time in nearly 50 years, this classic ranch home is set on a lushly planted corner lot of approximately one-third acre. Gardens are the soul of this property - loving tended & richly layered with heritage roses, wisetria, towering redwoods, & a soothing water feature. Brick walkway winds through the front gardens, while the private rear grounds invite outdoor living with a large patio, an arbor-covered lounge, a deck built around a majestic oak tree, & a seasonal creek along the edge of the property. This home offers timeless comfort with three bedrooms & two full baths, including a spacious primary suite with French doors to the gardens. Cathedral wood-paneled ceiling in the living room, numerous skylights throughout the home, & generously sized windows bring natural light into every space. Kitchen & casual dining area open directly to the rear yard, as well as to the family room with fireplace. Located close to Portola Valley's town center & Windy Hill trailhead, & with access to top-rated schools, this cherished home offers a wonderful opportunity to enjoy peaceful surroundings & exceptional gardens in a close-in location.

3 Wyndham DR, Portola Valley

Listed by Hugh Cornish, 650-619-6461 from Coldwell Banker Realty
(If provided) CoList: from

Sold listing courtesy of Lynn Roberts from COMP52

$5,300,000

4 Beds ⋅ 4 Baths ⋅ ML82006455 MLS

You wake up one morning on the deck of 415 Golden Oak Drive, coffee in hand, gazing at a view that makes time stand still. From this elevated perch in central Portola Valley, the South Bay unfolds rolling hills, morning mist, and the quiet promise of a perfect day. This beautifully updated 4-bedroom, 3.5-bath home offers approximately ~4,300 sq. ft. of refined living space, blending clean architectural lines, natural light, and sweeping sightlines. Set on just under two acres with lawn, pool, mature trees, and expansive decks the property is both functional and breathtaking. Inside, vaulted ceilings and large windows frame the views. The open living and dining areas flow into a thoughtfully designed kitchen with high-end appliances, custom cabinetry, and a spacious island ideal for entertaining or quiet mornings. The ~600 sq. ft. primary suite is a private retreat with a spa-like bath, walk-in closet, and a balcony perfect for stargazing or late-night talks. A separate bonus room with full bath offers flexible space for guests, work, or play. Located in the heart of Portola Valley, minutes from top-rated schools, scenic trails, and local shops, this isn't just a home its a vantage point. A place where space, calm, and style come together.

415 Golden Oak DR, Portola Valley

Listed by Scott Hayes, 650-245-5044 from Compass
(If provided) CoList: from

Sold listing courtesy of Josh Rubin from COMPS

$3,800,000

3 Beds ⋅ 2 Baths ⋅ ML81999778 MLS

Located in tranquil Portola Valley, this single-level, 3-bedroom, 2-bath home with pool and spa sits on an oak tree studded 1.2-acre lot (per county). Ample skylights, sliding doors and picture windows create rooms filled with natural light and peaceful views of the surrounding landscape. The spacious living room and dining area flow seamlessly into the large, modern kitchen and family room. Easy access to the rear yard from these spaces make them ideal for indoor and outdoor entertaining. The bedroom wing includes the primary suite with remodeled ensuite bath, two additional bedrooms, a second remodeled full bath with new LG washer/dryer, and a hall linen closet. A two-story structure adjacent to the main house offers a range of possibilities. The upper level includes new flooring, a closet and remodeled 1/2 bath, ideal for use as a guest room, office, artist studio or game room. The lower level includes a wine cellar, workshop and storage space. This convenient location is just minutes to local hiking trails, shopping and restaurants, major commute routes, Stanford University and the excellent Portola Valley schools.

90 Bear Gulch DR, Portola Valley

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

Sold listing courtesy of Camille Eder from CBR

$9,000,000

4 Beds ⋅ 4 Baths ⋅ ML82003847 MLS

In Portola Valleys most coveted Westridge corridor, this striking property captures iconic Windy Hill views from its setting on more than 2 acres. The grounds unfold with California splendor sweeping level lawns, meandering garden paths amid native plantings, and a resort-style pool and spa perfectly oriented to Windy Hill. Inside, the home stuns with cathedral ceilings richly paneled in wood and white oak floors that span the open, multi-level floor plan designed for flow and functionality. Expanses of glass at every turn bring in the light, the landscape, and the views, creating a seamless connection to the outdoors. The living, dining, and family rooms flow off the chefs kitchen, which is highlighted by a commercial-quality AGA range. The primary suite is privately located, three bedrooms and two baths are in a separate wing, plus there is a gym with outside sauna. A rare and captivating retreat in one of Portola Valleys most exclusive locations.

130 Deer Meadow LN, Portola Valley

Listed by Peter Cowperthwaite, 650-207-4101 from Golden Gate Sotheby's International Realty
(If provided) CoList: Helen Miller from Compass

Sold listing courtesy of Vincent O'Shea, from ALREB

$5,000,000

3 Beds ⋅ 4 Baths ⋅ ML82003366 MLS ⋅ Ladera BLDG.

Step into this stunning single-level remodeled modern home nestled in the desirable Ladera neighborhood. Blending contemporary design with everyday comfort, this thoughtfully renovated home is the ultimate expression of California living. Dream chef's kitchen featuring a large center island, high-end appliances, custom cabinetry, & a walk-in pantry. This home has radiant heating, custom concrete floors, & large picture windows that flood the space with natural light, seamlessly blending indoor & outdoor living. Two spacious bedrooms share a Jack & Jill bathroom. A versatile bonus room perfect for a media room, home office, or even a fourth bedroom. Your own private resort awaits outside. Relax or entertain in the lush backyard, complete with a sparkling pool, mature landscaping, and multiple outdoor living areas. Convenienty located to the Ladera Rec Center, 5 miles to Stanford, near Silicon Valley, commute routes, and midway between San Francisco & San Jose international airports.

831 La Mesa DR, Portola Valley

Listed by Rebecca & Karen, 650-281-8752 from Intero Real Estate Services
(If provided) CoList: from

Sold listing courtesy of Mark Cohan from COMPS

$6,550,000

4 Beds ⋅ 4 Baths ⋅ ML82001354 MLS

Transformed with a whole-home renovation, this exquisite home offers luxurious designer style and wellness-focused amenities in a prime Central Portola Valley location. Every detail has been elevated, with stunning interiors featuring heated tiled floors in every room. Expansive retractable glass doors create a seamless indoor/outdoor connection in the living and dining room plus there is a spacious kitchen and family room combination with built-in casual dining area. A spa-like ambiance defines this 4-bedroom, 3.5-bath home, anchored by a sumptuous primary suite with steam shower. A private wellness retreat continues outside on the tremendous rear deck which feels like living space, including a recessed spa, cold plunge tub, and cedar-lined sauna. A lower deck with linear gas fireplace invites gatherings, sanded walking paths encourage quiet reflection beside the creek, and a vast synthetic lawn awaits recreation. Designed for effortless living and exceptional comfort, this home also has a wonderfully converted garage bay with the perfect space for a remote office.

30 Cheyenne PT, Portola Valley

Listed by Erika Demma, 650-740-2970 from Compass
(If provided) CoList: from

Sold listing courtesy of Bryan Jacobs from RWH

$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

$3,350,000

3 Beds ⋅ 2 Baths ⋅ ML81998188 MLS

Location is everything in real estate, & this charmer on an expansive lot could not be more ideal in the highly desirable Ladera neighborhood! Featuring 3 bedrooms, 2 full bathrooms, & a bonus room all on one level. Recent interior paint, updated floors & kitchen w/ granite countertops, double pane windows & custom sliders, & fresh landscaping. Expansive wrap around yard w/ potential & ideal for entertaining & gatherings. Close proximity to an award winning school district, Stanford University, Ladera Shopping Center, Ladera Recreation Center, horseback riding at Webb Ranch, Highway 280, hiking & biking trails, & so much more!

240 Dedalera DR, Portola Valley

Listed by Chris A. Sabido, 650-922-8888 from eXp Realty of California Inc
(If provided) CoList: from

Sold listing courtesy of Camilo Perez from RWH

$1,850,000

2 Beds ⋅ 1 Baths ⋅ ML81988410 MLS

Luxury Silicon Valley Getaway in Portola Valley with Views, updated single family /rustic modern interior, move-in ready and personal retreat on a large 11,500 square foot lot, surrounded by natural beauty, a network of trails. Open floor plan with natural light throughout, skylights, hardwood floors, built in bookshelves, new kitchen and appliances, eat-in kitchen and sliding glass doors to the expansive deck from living room and primary bedroom, outdoor Jacuzzi, bonus room below can be used for guests, entertainment, media room, hobbies, workshop or possible JDU, Room to expand on large lot. Less than 5 miles without getting on the freeway to Stanford University. Enjoy the Sunrise trail steps away from your private sanctuary with access to 650+ acres open space and trails. Also, direct access to Arastradero Preserve and Los Trancos Open Space with over 1500 acres of more hiking trails.

1023 Los Trancos RD, Portola Valley

Listed by Karen Gunn, 650-888-9457 from Compass
(If provided) CoList: from

Sold listing courtesy of JJ Team:Jones/Cassel from NTERO

$2,450,000

3 Beds ⋅ 1 Baths ⋅ ML81997941 MLS

Welcome to this charming single-story home ideally located in central Portola Valley. Scenic trails, open space preserves, and popular biking routes are right outside the door. Town Center's library, tennis courts, playing fields, and weekly Farmers Market are just a short stroll away. Coveted preschools in addition to Portola Valley's highly acclaimed elementary and middle schools provide exceptional educational opportunities. Expansive windows fill the house with sunlight and create inviting interior space. Three large bedrooms, beautiful oak hardwood floors, and a newly updated kitchen and bathroom make this home move-in ready. Enjoy it as is or plan for expansion - renderings from 2016 for a proposed expansion are available for review. The sunny backyard is lightly shaded by Redwood trees and provides exceptional space for entertaining or to unwind and enjoy the outdoors. Wyndham Drive, a circular street of approximately 29 homes, hosts annual block parties and provides a multigenerational neighborhood reminiscent of days gone by. With so much to offer, this home is not to be missed. Come see the best of Portola Valley living.

319 Wyndham DR, Portola Valley

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

Sold listing courtesy of Leslie Woods from SGP

$2,325,000

3 Beds ⋅ 1 Baths ⋅ ML81996192 MLS

Beautiful 3 Bedroom Home in Award Winning Portola Valley School District. Elegant Living Room with Fireplace. Formal Dining Area. Stunning Kitchen with Quartz Countertops and Skylight. 3 Bedrooms. Updated Bathroom with Double Sinks, Separate Shower, and Skylight. Spacious Patio with Outdoor TV and Trellis. Lovely Landscaped Yard. Award Winning Portola Valley School District. Best Value for Central Portola Valley

322 Wyndham DR, Portola Valley

Listed by Keri Nicholas, 650-533-7373 from Parc Agency Corporation
(If provided) CoList: from

Sold listing courtesy of Denise Crosetti Schaul from DCBR

$4,995,000

4 Beds ⋅ 3 Baths ⋅ ML81996063 MLS

Freshly Updated on a Beautiful 1+ Acre Level Lot. This stunning level one-acre property offers a rare opportunity to embrace the essence of Portola Valley living, whether enjoying today with its fresh updates or transforming for the future. Just blocks from Town Center and Windy Hill trails, the location is ideal. The main residence features random plank hardwood floors in the living areas, an updated kitchen and baths, and numerous glass doors opening to the wraparound grounds with privacy afforded from its set-back location. With 4 bedrooms and 3 baths, there is also ample space for the addition of an ADU, plus there is a 2-stall vintage barn with tack room and hay room, and large storage shed. Completing the appeal is access to top-rated Portola Valley schools, with the elementary school just minutes away. A rare opportunity to create your dream lifestyle in a premier location.

1365 Westridge DR, Portola Valley

Listed by Erika Demma, 650-740-2970 from Compass
(If provided) CoList: from

Sold listing courtesy of Erika Demma from APR

$3,025,000

4 Beds ⋅ 3 Baths ⋅ ML81995172 MLS

A rare gem in the heart of Portola Valley! Nestled on a serene 1/3-acre lot, this beautifully maintained property offers two charming homesperfect for multi-generational living, guests, or rental income. The main residence boasts 3 beds, 2 baths, a formal living and dining area, an inviting family room, and a luxurious primary suite. High ceilings, abundant natural light, and thoughtful updates enhance the warm, welcoming ambiance. The detached 1-bed, 1-bath guest cottage (approx. 600 sq. ft.) has a private entrance, ideal for extended stays or potential rental income. Outside, enjoy the asphalted sports court, lush landscaping, and ample parking, including a spacious oversized garage. Connected to the sewer, this home is move-in ready with top-rated Portola Valley schools nearby. Access to hiking trails. Located minutes from Alpine Rd., this peaceful retreat offers both tranquility and convenience. Don't miss this exceptional opportunity!

111 Carmel WAY, Portola Valley

Listed by Josh Rubin, 650-575-5981 from Compass
(If provided) CoList: from

Sold listing courtesy of Kimm Terpening from COMPS

$4,350,000

3 Beds ⋅ 3 Baths ⋅ ML81994941 MLS

Formal entry. Elegant living room with fireplace. Chefs kitchen with center island and dining area. Open family room with fireplace. Spacious yard with pool and spa. 3 bedrooms, 3 bathrooms, 2-car garage and extras off-street parking. Over 19,300 square foot lot. A must see!

441 La Mesa DR, Portola Valley

Listed by Loren Dakin, 650-714-8662 from Parc Agency Corporation
(If provided) CoList: from

Sold listing courtesy of Keri Nicholas from PARCA

$56,000,000

6 Beds ⋅ 13 Baths ⋅ ML81978361 MLS

Villa del Prato is a singular gem among Silicon Valley estates. Nestled in the woodlands of Portola Valley on nearly 12 acres of tranquil, private, flat land, the estate comprises three structures: a main house (12,000 sf); an entertainment or business building (6,500 sf); and a pool house (2,000 sf). Inspired by classic Palladian Italian architecture, each structure is reminiscent of a Tuscan villa, featuring soaring arches, 20-foot ceilings, dramatic skylights, solid stone columns direct from Italy, and the finest-quality finishes. The main home, built on two levels, features a one-of-a-kind 900-square-foot dressing suite that doubles as a safe room. Unseen are advanced systems for the comfort and security of residents and guests. The entertainment/business building provides an opportunity for customization. With its towering columns, airy loggia, and spacious ballroom, it could be utilized for entertaining, as a home office, conference center, staff housing, or a home for your next startup. Electrical, plumbing, HVAC, and other key systems are fully fitted out. This grand estate is centrally located close to Hwy 280 mid-way between San Francisco and San Jose, with easy access to major airports and technology and business centers. (All sf info per plans).

20 Meadow LN, Portola Valley

Listed by Chris Iverson, 650-450-0450 from Golden Gate Sotheby's International Realty
(If provided) CoList: from

Sold listing courtesy of Leslie Bauer from CTYRE

$4,990,000

4 Beds ⋅ 6 Baths ⋅ ML81990000 MLS

Nestled on more than 1.5 acres, this exquisite home has been thoughtfully transformed to deliver an unparalleled living experience. With more than 4,200 sf, the home exudes luxury, from its soaring ceilings and impeccable finishes to the dramatic use of glass. Expansive living areas, multiple fireplaces, a gourmet kitchen, and an executive office offer both comfort and style. Four bedrooms are highlighted by a private, retreat-like primary suite, complete with a spa-inspired bathroom. Outside, multi-level grounds provide the perfect venues for enjoying the idyllic setting, and this home also includes air conditioning, and a 3-car garage. Located just moments from trails, nature preserves, and Roberts Market, this home offers tranquility and convenience, while easy access to Interstate 280 ensures the entirety of the Bay Area is within easy reach. Plus, children may attend acclaimed schools such as Ormondale Elementary and Corte Madera Middle (buyer to verify eligibility).

5 Oak Forest CT, Portola Valley

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

Sold listing courtesy of Loren Dakin from PARCA

$2,900,000

4 Beds ⋅ 2 Baths ⋅ ML81990121 MLS

Welcome to 1 Hayfields Road! Motivated Seller - best price on the flats of Portola Valley!!! Nestled in a serene and peaceful country setting, this inviting rancher offers the perfect balance of privacy and convenience. With stunning access to nearby trails, you can enjoy the natural beauty right outside your doorstep, whether you're hiking, biking, or simply soaking in the outdoors. Inside, this lovely, updated home are multiple living areas, including 4 bedrooms and 2 bathrooms. Featuring soaring cathedral ceilings, skylights, and expansive windows, the home is filled with natural light, creating a bright, open atmosphere. Updated kitchen with stainless appliances. Separate laundry with top of the line LG washer and dryer. Solar panels and 240 outlet in garage for EV charging. The yard offers a natural retreat with seating and dining areas, and is partially fenced for either a dog run or a child's playground. Located just 3 miles from 280, and close to the Portola Valley Schools, and local amenities, you won't have to sacrifice accessibility for country living.

1 Hayfields RD, Portola Valley

Listed by Debora Smith, 650-580-8286 from Sotheby's Intl Rlty
(If provided) CoList: from

Sold listing courtesy of Chris Iverson from GGSIR

$7,998,000

4 Beds ⋅ 4 Baths ⋅ ML81990081 MLS

This rare offering truly has it all 2.5 acres in the prestigious Westridge area with complete privacy set back from the street, San Francisco and foothill views, a regulation-size tennis court, resort-style pool with elevated spa and waterfall, and a poolside sauna with an outdoor shower. The well-appointed classic ranch home features bright and light interiors with fine hardwood floors throughout its effortless single-level design. Recent updates, including crisp white paint, refinished floors, new lighting, and newer appliances, make this home move-in ready while also presenting an excellent opportunity to further transform it into your dream vision. Four spacious bedrooms, each with an en suite bath, include one that is privately located and perfect for guests or a home office. In a premier location, with 2.5-acre minimum parcels, and access to top-rated Portola Valley schools, this property offers an unparalleled lifestyle of sophistication, serenity, and endless potential.

600 Westridge DR, Portola Valley

Listed by Dean Asborno, 650-255-2147 from Compass
(If provided) CoList: from

Sold listing courtesy of Hugh Cornish from CBR

$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

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