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$3,695,000
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 Valley largely 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

$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

$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
$1,720,125
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

Sold listing courtesy of David Leland from J01975
$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
$3,350,000
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
$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
$2,500,000
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
$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
$2,225,000
2 Beds ⋅ 2 Baths ⋅ ML81955437 MLS
An excellent opportunity to create your dream home in the desirable Corte Madera area of Portola Valley. The lot is approximately 15,000 square feet of usable land, including views of the Santa Cruz Mountains, and an oasis garden. The neighborhood provides a community within a community, anchoring itself between Portola Road and Alpine Road. A short stroll to Corte Madera School, Roberts Market, Ace Hardware, and trails (including the hike to Windy Hill). Built in 1945, this property has not been available to the public in 55 years. The approximately 1,600 square foot home includes 2 bedrooms, 2 full bathrooms and a detached 1-car garage with entrance on Prado Court.

191 Corte Madera RD, Portola Valley

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

Sold listing courtesy of Hossein Jalali from CBR
$2,850,000
4 Beds ⋅ 2 Baths ⋅ ML81940061 MLS ⋅ Ladera BLDG.
This charming home embodies mid-century design with its flat planes, geometric lines & large picture windows that welcome the indoors with nature. Walls of windows flood the interior with natural light & frame the picturesque view of the backyard. The open-concept layout of the living & dining rooms provides a seamless flow, perfect for entertaining guests or relaxing with family. Classic galley kitchen with ample storage. Step outside into your own private paradise & live the quintessential indoor/outdoor California lifestyle. The beautifully landscaped yard is a quiet escape with two entertaining patios, & plenty of space for gardening, play, & leisure. The bedroom wing has a spacious primary suite + 3 more bedrooms. Attached 1-car garage + open carport for convenient covered parking. Convenient to the Ladera Rec., neighborhood paths & the Ladera Shopper. Only 3.5 miles to Stanford, easy access to Silicon Valley, commute routes & mid-way between SFO & SJC International airports.

285 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 Kari Chadwell from RFON

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