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55 Vista Verde WAY, Portola Valley
$4,450,000
3 Beds ⋅ 5 Baths ⋅ ML82060715 MLS
Set within 2.77 acres, this remarkable residence is enveloped by gardens, mature trees, and the kind of natural stillness that feels increasingly rare in Silicon Valley. Though close to the amenities of Portola Valley, the property has the character of a private retreat. A long, tiled staircase moves through layers of lush planting, creating a sense of anticipation before the architecture comes into view. Inside, the house reveals soaring 10- and 12-foot ceilings, fine millwork, oak floors, and an abundance of natural light. The main level unfolds naturally. A generous kitchen and family room form the heart of the home, with a substantial pantry designed for effortless entertaining. Beyond, the dining and living rooms are framed by graceful arch-top windows, their wooded outlooks becoming an ever-changing part of the interior. The primary suite is conceived as a sanctuary of its own. Two private balconies open toward the surrounding landscape, while a fireside sitting area offers a quiet place to retreat. An expansive walk-in closet and beautifully appointed marble bath complete the suite with a sense of understated luxury. Two additional bedrooms, one is en-suite. Sweeping views, multi-level deck and pergola extend into the gardens, with a built-in outdoor kitchen and barbecue.

55 Vista Verde WAY, Portola Valley

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

Sold listing courtesy of Michele Harkov from APR

289 Ramona RD, Portola Valley
$4,100,000
3 Beds ⋅ 3 Baths ⋅ ML82024513 MLS
Embraced by the serene beauty of Foothills Park and Los Trancos Open Space Preserve, this stunning home is neatly perched. Its hard to improve on Mother Nature, but this ~1.2-acre property certainly complements her work. Peaceful surroundings and sweeping ridgeline views create an astounding backdrop, enjoyed from the expansive deck and patio each extending the homes living space outdoors. The 3 bed, 2.5 bath residence offers a warm blend of elegance and comfort. The dramatic foyer opens to a formal living and dining area with custom built-ins and tall arched windows framing the view. The spacious, eat-in kitchen features high-end appliances, generous storage, and a large island that flows seamlessly into the inviting family room with custom cabinetry, perfect for everyday living or entertaining. The upper level hosts the primary suite which includes a private balcony, multiple closets, and an elegant bath, while a full bath serves the additional bedrooms. A detached guest apartment with its own address, kitchen, laundry and bath; a 2-car garage with 60 linear feet of storage; solar panels with dual Enphase IQ batteries; high-speed internet; and excellent schools.

289 Ramona RD, Portola Valley

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

Sold listing courtesy of Peter Cowperthwaite from DP

76 Vista Verde WAY, Portola Valley
$4,000,000
5 Beds ⋅ 6 Baths ⋅ ML82025339 MLS
Come right in. Enjoy the view. This stunning remodel completed in 2025 offers space, views, and peace of mind. With completely new high-end finishes throughout, this Mid-Century Modern masterpiece sits atop a private, lush acre, seamlessly blending modern luxury with nature's tranquility. Designed for those who appreciate both serenity and grand entertaining, a true retreat where hawks glide above. The expansive open-concept living space flows into a gourmet kitchen, featuring Bertazzoni five-burner gas stove, refrigerator and dishwasher plus gorgeous brass fixtures. Floor-to-ceiling windows showcase panoramic views of rolling hills & twinkling city lights, creating an awe-inspiring backdrop. A grand two-story entryway leads to an elegant dining area, warmed by a glass-enclosed gas fireplace. Step onto the rooftop deck, where alfresco dining meets unparalleled stargazing & sunset views. The primary suite is a private sanctuary, complete with a spa-like soaking tub and a bed perfectly positioned for breathtaking sunset views. Four additional bedrooms offer luxury & privacy for all, each has its own full bath. This is more than a home. It's an experience of modern elegance, timeless design, & natures embrace.

76 Vista Verde WAY, Portola Valley

Listed by Deniece Watkins Smith, 650-744-0888 from Compass
(If provided) CoList: from

Sold listing courtesy of Ruth Mistry from CBR

141 Lake RD, Portola Valley
$3,700,000
4 Beds ⋅ 5 Baths ⋅ ML82043726 MLS
Bay views and cutting-edge smart house design come together in this newly built retreat by the lake. Surrounded by nature, the contemporary home is on a quiet cul-de-sac, leading to acres of open space and hiking trails, The home is designed to embrace its setting with expansive windows, skylights, multiple outdoor spaces, and views stretching to the Bay. At the heart of the home is a light-filled, open-concept living space anchored by a striking chef's kitchen, complete with an oversized island, wet bar, wine fridge, and high-tech appliances. The kitchen flows seamlessly into generous living and entertaining areas, a potential home office, and out to expansive decks, creating an effortless connection between indoors and the surrounding landscape. The multi-level design offers flexibility, including a permitted attached ADU that could alternatively function as an auxiliary family room with second kitchen for guests, a media room or fitness space. Privately situated bedrooms provide peaceful retreats, while the primary suite and rooftop deck offer elevated views of the surrounding greenery to the Bay. State-of-the-art technology is integrated throughout, including Wi-Fi-enabled appliances, solar, Tesla Powerwall, and a dumbwaiter connecting the garage to the main level.

141 Lake RD, Portola Valley

Listed by Kavanaugh Group, 415-377-2924 from Coldwell Banker Realty
(If provided) CoList: from

Sold listing courtesy of Hoi Wing Ng from NTERO

310 Old Spanish TRL, Portola Valley
$3,670,000
4 Beds ⋅ 3 Baths ⋅ ML82049530 MLS
Welcome to 310 Old Spanish Trail in Portola Valley, a beautifully maintained custom home built in 2006 and lovingly cared for by its original owner. With gleaming floors, soaring ceilings, and expansive windows framing the natural landscape, the home feels remarkably fresh and almost brand new. Set in one of the Bay Area's most desirable communities, this property offers a rare combination of privacy, tranquility, and value. The scenic drive through Portola Valley's rolling hills leads to a setting that feels secluded, yet is minutes from restaurants, shops, and conveniences. Designed for modern living, every room is generously sized with high ceilings and abundant natural light. Expansive decks stretch across the rear of the home, creating seamless indoor/outdoor living with peaceful tree views. The decks connect directly to a high-end gourmet kitchen, making the home ideal for entertaining. The living, family, and dining rooms are stunning, featuring dramatic windows, beautiful finishes, and an exceptional open layout. In addition to four bedrooms, including a spacious primary suite, the home offers a dedicated office and a huge unfinished bonus room not included in the stated square footage (450 sq ft), providing excellent potential for expansion, recreation, or storage.

310 Old Spanish TRL, Portola Valley

Listed by Costantini Team, 650-430-8425 from Compass
(If provided) CoList: from

Sold listing courtesy of Alexander Nichols from EXPCA

124 Foxwood RD, Portola Valley
$3,100,000
4 Beds ⋅ 4 Baths ⋅ ML82044193 MLS
Imagine life at this exceptional Portola Valley residence: an elevated lifestyle in one of the areas most coveted settings. Close-in to Alpine Rd and Hwy 280, this private sanctuary is surrounded by natural beauty while close to every convenience. A dramatic arrival begins with a sculptural stone waterfall and a grand entry flanked by flexible living spaces: a private office or fifth bedroom with1/2 bath on one side, and a guest retreat with kitchenette & full bath on the other. This sets the tone for the homes sleek design and exceptional craftsmanship. Upstairs, soaring ceilings define the expansive living area, where walls of glass invite the outdoors in. Designed for entertaining and everyday living, the great room with modern fireplace opens through telescoping glass doors to an expansive terrace and resort-inspired grounds with a spa. The adjoining kitchen features bespoke counters, rich walnut cabinetry, generous pantry, and top-tier appliances. The luxurious primary suite offers a private terrace, walk-in wardrobe, and serene bath with skylit shower and rainfall fixture. Addt'l spaces include two more bedrooms, a library with fireplace, wine room, and mudroom. Owned solar and EV charging (240V) add efficiency. 12,400 sq. ft. lot within the Portola Valley Sch. District.

124 Foxwood RD, Portola Valley

Listed by Lisa Keith, 650-703-8644 from Golden Gate Sotheby's International Realty
(If provided) CoList: Liz Daschbach from Compass

Sold listing courtesy of Lisa Keith from GGSIR

40 Deer Path DR, Portola Valley
$2,550,000
3 Beds ⋅ 3 Baths ⋅ ML82007263 MLS
Nestled at the end of a private drive, this 3,320 square foot sits on almost 1.5 acres (per county) in tranquil Los Trancos Woods. Floor-to-ceiling and clerestory windows as well as skylights and sliding doors fill the 2-story home with natural light and provide views to the surrounding natural environment from every room. The top level includes an open-concept layout creating a seamless flow between the living room, dining area and kitchen. The expansive living room includes a wood burning fireplace surrounded by a sunken, built-in circular sofa, a wet bar and an additional large area ideal for a game table. The dining area flows seamlessly to the large kitchen, complete with island and walk in pantry. Access to the connecting deck from all three areas creates a large space ideal for indoor/outdoor entertaining. Completing the level is a spacious bedroom, a full bath. The lower level accommodates the primary suite and the third spacious bedroom, both with en suite baths, walk-in closets and outside access. The conveniently placed large laundry room includes ample cabinetry, a sink and an attached large storage room.

40 Deer Path DR, Portola Valley

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

Sold listing courtesy of Andy Pham from FIHI

1019 Los Trancos RD, Portola Valley
$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

244 Bonita RD, Portola Valley
$1,650,000
3 Beds ⋅ 2 Baths ⋅ ML82038783 MLS
Nestled among the scenic hills of Portola Valley, this 3-bedroom, 2-bathroom home offers a rare opportunity to enjoy peaceful living surrounded by nature. Set on a generous lot, the property presents endless possibilities to remodel, expand, or build your dream home in one of the Peninsulas most desirable communities. Inside, the family room features vaulted ceilings with natural wood detail, creating a warm and inviting space filled with character. Windows frame beautiful hillside views, bringing the surrounding greenery indoors and enhancing the tranquil atmosphere. The updated kitchen showcases exposed wood cabinetry, blending rustic charm with modern functionality. Throughout the home, lush green scenery is visible from nearly every angle. The expansive lot provides ample space for outdoor living, gardening, or future expansion, offering exceptional potential. First time available in approximately 55 years. Ideally located just 10 minutes from Portola Valley Town Center, the historic Alpine Inn, Highway 280, and Webb Ranch, with easy access to renowned hiking trails, parks, and open space preserves, allowing you to fully embrace the Portola Valley lifestyle.

244 Bonita RD, Portola Valley

Listed by Talia Citron, 650-465-4814 from Compass
(If provided) CoList: Judy Citron from Compass

Sold listing courtesy of Josh Felder from RDFIN

128 Los Trancos CIR, Portola Valley
$1,650,000
2 Beds ⋅ 2 Baths ⋅ ML82002420 MLS
Come see this modern marvel. With a variety of recent updates, this spacious two bedroom bungalow is a wonderful country living retreat. Views of open space hills and near to Coal Mine Open Space Preserve and a host of scenic hiking trails. Situated on a 7,440 sf lot with ample off street parking on newly paved driveway, the home features a new roof, a main floor living room with high ceilings, hardwood floors, large wood white-washed beams, large glass picture windows and a scenic deck for having your morning coffee. The recently updated kitchen is conveniently located near a sunny series of rear decks, framed with gardens, mature oak trees and a sloping backyard, making a picturesque setting for outdoor entertaining. The primary suite is on the main level and includes space for a small office set up and an updated bathroom with dual sinks and a spa tub. A second bedroom upstairs has views of the nearby open space hills and features another recently updated bathroom. Los Trancos Woods neighborhood is only minutes from a host of amenities which include Roberts Market, Windy Hill Open Space Preserve, Rossottis Alpine Inn, Stanford University and Hospital and Silicon Valley business activities. It is in the acclaimed Portola Valley School District. This is your next home!

128 Los Trancos CIR, Portola Valley

Listed by Helen Miller, 650-400-1317 from Compass
(If provided) CoList: from

Sold listing courtesy of RECIP from RCIP

161 Los Trancos CIR, Portola Valley
$850,000
ML82016029 MLS
Perched in the peaceful Los Trancos Woods neighborhood of Portola Valley, 161 Los Trancos Road is a rare opportunity to bring your vision to life. This vacant 6,685 square foot lot comes with a full set of architectural plans- permit-ready- for a thoughtfully designed, two-story modern residence over a finished basement. The approved plans feature a 4-bedroom, 5-bathroom home with over 3,100 square feet of living space, including a grand primary suite, open-concept main level, and bonus flex space in the basement. An additional 400 square foot attached ADU offers income potential, multigenerational living, or a spacious guest retreat, in addition to an attached 2-car garage. Surrounded by natural beauty, the proposed home captures the essence of Portola Valley living- privacy, serenity, and a deep connection to nature- all just minutes from Alpine Road and local amenities. Whether you're a builder, investor, or future homeowner, this is your chance to build a bespoke residence in one of the Peninsulas most coveted communities. Plans and reports available upon request.

161 Los Trancos CIR, 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 Domarina Beitpoulice from 1STC

1050 Los Trancos RD, Portola Valley
$550,000
ML82033730 MLS
A rare chance to bring your dream home to life in the heart of the coveted Portola Valley School District! Nestled on a serene, 6,878-square-foot forested lot, 1050 Los Trancos offers more than just land. It's a head start on creating something extraordinary. With San Mateo County Planning & Building Department approved plan, this property is truly shovel-ready for your vision. The plans include a beautifully designed, light-filled 2,154-square-foot home featuring 3 bedrooms, 2.5 bathrooms, and a 400-square-foot deck perfect for soaking in the natural surroundings. A detached 400-square-foot, 2-car garage completes the package.Sellers are providing those approved plans, required studies + contact information for the various professionals who helped make this dream home possible and who are happy to help new owners build! Dont miss the opportunity to build your future!

1050 Los Trancos RD, Portola Valley

Listed by Ting Tan, 650-686-1885 from Compass
(If provided) CoList: Charlie Giang from Compass

Sold listing courtesy of Laura Bertolacci from DWELL

board logoThe data relating to real estate for sale on this display comes in part from the Internet Data Exchange program of the MLSListingsTM MLS system. Real estate listings held by brokerage firms other than JABEZ REALTY are marked with the Internet Data Exchange and detailed information about them includes the names of the listing brokers and listing agents.
Based on information from MLSListings MLS as of . All data, including all measurements and calculations of area, is obtained from various sources and has not been, and will not be, verified by broker or MLS. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.


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