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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.

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

$2,250,000

Exceptional opportunity in Woodside Highlands on over half an acre of private, lush grounds. This light-filled 3-bedroom, 2-bath home is set on a quiet lot surrounded by mature trees, gardens, and fruit trees, offering a peaceful retreat in one of Portola Valleys most desirable neighborhoods. The main level features two bedrooms, one bath, hardwood floors, beautiful woodwork, and an oversized kitchen that opens to a sunny deckideal for indoor-outdoor living and entertaining. The lower level offers a flexible layout with a private bedroom or primary suite, full bath, and separate exterior entrance, perfect for guests, home office, or additional living space. Bonus room above the garage provides added versatility. Expansive multi-level grounds include wraparound patios, private garden areas, and tranquil natural surroundings. Elevated views overlook Portola Valley toward the East Bay Hills, offering stunning sunrises and full-moon views. Property offers excellent potential. Conveniently located near Town Center, Highway 280, scenic trails, and local favorites including the Alpine Inn. Served by top-rated Portola Valley schools, including Ormondale and Corte Madera.

3 Beds ⋅ 2 Baths ⋅ ML82034150 MLS

Exceptional opportunity in Woodside Highlands on over half an acre of private, lush grounds. This light-filled 3-bedroom, 2-bath home is set on a quiet lot surrounded by mature trees, gardens, and fruit trees, offering a peaceful retreat in one of Portola Valleys most desirable neighborhoods. The main level features two bedrooms, one bath, hardwood floors, beautiful woodwork, and an oversized kitchen that opens to a sunny deckideal for indoor-outdoor living and entertaining. The lower level offers a flexible layout with a private bedroom or primary suite, full bath, and separate exterior entrance, perfect for guests, home office, or additional living space. Bonus room above the garage provides added versatility. Expansive multi-level grounds include wraparound patios, private garden areas, and tranquil natural surroundings. Elevated views overlook Portola Valley toward the East Bay Hills, offering stunning sunrises and full-moon views. Property offers excellent potential. Conveniently located near Town Center, Highway 280, scenic trails, and local favorites including the Alpine Inn. Served by top-rated Portola Valley schools, including Ormondale and Corte Madera.

108 Santa Maria AVE, Portola Valley

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

Sold listing courtesy of James Steele from COMPS

$1,760,000

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.

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

$1,750,000

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.

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

$1,720,125

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.

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

$1,650,000

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.

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