Woodside CA Real Estate & Homes for Sale

This beautiful estate is nestled on nearly a 1.50 acre lot and is surrounded by beautiful redwood trees. This amazing, two-story mountain home offers unparalleled tranquility & privacy in a majestic setting. This rustic retreat boasts handcrafted wood features throughout the home, from the gorgeous detailing of the cabinetry in the loft, to the decorative pieces around the fireplace, to the beautiful wood beams adorning the ceilings. The first level features the kitchen that seamlessly flows into the dining room, a spacious and cozy living room, 2 bedrooms & 1 bathroom. The second level features a large, open loft, the primary bedroom suite & bathroom & two outdoor decks. While this home captivates so much history & exuberates timeless beauty, there is abundant potential to add in your own touches & transform this residence into your dream home. This property also offers a second dwelling unit with its own septic tank. The second dwelling is an unpermitted 2 bedroom, 2 bath unit with its own outdoor deck. Located in close proximity to the tech hubs of Silicon Valley, Stanford & the serene beauty of the Pacific coastline, this is an opportunity not to be missed. Don't let this chance slip away to own a slice of paradise in one of the most coveted neighborhoods in the area!

Experience country living just 30 minutes from the heart of Silicon Valley. Nestled in California's majestic Redwood Forest, this horse-zoned property blends natural beauty and equestrian potential. Set on a 2-acre lot with a HUGE open grass field, this home offers ample space for just about every lifestyle. Surrounded by lush greenery and open skies, it's a perfect retreat for those seeking a serene, private lifestyle. The expansive grounds provide endless possibilities for gardening, recreation, or creating your own outdoor oasis. Despite its secluded feel, youre close to top-rated schools and the 280 freeway, ensuring easy access to everything you need. The property is fenced, gated, and obscured by trees. The well-designed home features a fully equipped kitchen, spacious living room, high ceilings, and a welcoming family room, ideal for daily living and entertaining. Inside, cozy bedrooms offer a perfect haven after a long day. Tall windows and glass doors flood the floor plan with natural light. A bonus room under the house is perfect as a gym, recreation room, or playroom. Outside, a huge patio and wraparound deck overlook the expansive lot. Come live the life you deserve in this peaceful retreat.

Experience country living just 30 minutes from the heart of Silicon Valley. Nestled in California's majestic Redwood Forest, this horse-zoned property blends natural beauty and equestrian potential. Set on a 2-acre lot with a HUGE open grass field, this home offers ample space for just about every lifestyle. Surrounded by lush greenery and open skies, it's a perfect retreat for those seeking a serene, private lifestyle. The expansive grounds provide endless possibilities for gardening, recreation, or creating your own outdoor oasis. Despite its secluded feel, youre close to top-rated schools and the 280 freeway, ensuring easy access to everything you need. The property is fenced, gated, and obscured by trees. The well-designed home features a fully equipped kitchen, spacious living room, high ceilings, and a welcoming family room, ideal for daily living and entertaining. Inside, cozy bedrooms offer a perfect haven after a long day. Tall windows and glass doors flood the floor plan with natural light. A bonus room under the house is perfect as a gym, recreation room, or playroom. Outside, a huge patio and wraparound deck overlook the expansive lot. Come live the life you deserve in this peaceful retreat.

Located in the highly desirable Woodside Heights on a vast 41,000 sq ft lot! Featuring an open concept floor plan, soaring ceilings and an abundance of natural light this 4 bedroom, 3 bathroom, 2,990 sq ft villa sets the stage for gracious living and entertaining! Formal living room, fireplace and custom cabinets with access to the beautiful stone terrace. The large kitchen with dining bar opens to an inviting family room and adjacent spacious dining room. Paces away you have a separate laundry room, perfectly placed space for a home gym and beautiful wine cellar. Rounding out this level is a wonderful library/office and full bathroom. Just upstairs you have a private and spacious primary suite retreat with walk-in closet and spa-like bath! Down the hall, three additional bedrooms share a full hall bathroom. Relax or entertain outside in the elaborate yard with lush mature, landscaping boasting sweeping views and several seating areas. Located just minutes to Town Center, great schools and streamlined commute routes!

Located in the highly desirable Woodside Heights on a vast 41,000 sq ft lot! Featuring an open concept floor plan, soaring ceilings and an abundance of natural light this 4 bedroom, 3 bathroom, 2,990 sq ft villa sets the stage for gracious living and entertaining! Formal living room, fireplace and custom cabinets with access to the beautiful stone terrace. The large kitchen with dining bar opens to an inviting family room and adjacent spacious dining room. Paces away you have a separate laundry room, perfectly placed space for a home gym and beautiful wine cellar. Rounding out this level is a wonderful library/office and full bathroom. Just upstairs you have a private and spacious primary suite retreat with walk-in closet and spa-like bath! Down the hall, three additional bedrooms share a full hall bathroom. Relax or entertain outside in the elaborate yard with lush mature, landscaping boasting sweeping views and several seating areas. Located just minutes to Town Center, great schools and streamlined commute routes!

The allure of nature seamlessly intertwines with architectural brilliance at this exclusive vineyard estate on one of Woodsides most esteemed streets. Spanning over 4.399 acres, with the possibility of purchasing the adjacent lot of 3 acres for a total of 7.4 level acres, the entrance sets the tone of what lies within with an organic setting that begins with a serene lily pond and interconnected waterways with architecture by Atelier Ugo Sap of San Francisco and built by Van Acker Construction whose detail work is undeniable. The grand formal living room an antique mantelpiece adorn the wood burning fireplace and formal dining room grace the home for large gatherings. Dedicated office with fireplace, impressive open kitchen, breakfast and family room. Two levels with elevator, 6 bedrooms including luxurious primary suite, 6 full baths, and 2 half-baths including two main-level bedroom suites. Rustic-designed 1 bed/1 bath pool house with luxurious spa and kitchen. Additional structure for flexible use as gym, office or guest house with kitchenette and bath. Sparkling pool and magnificent grounds. Approximately 11,650 total square feet including 3-car garage. Cultivating wine, jam, honey and olive oil from the property. Acclaimed Woodside Elementary School and convenient location.

Enjoy sweeping Western Hill VIEWS from this gorgeous turnkey Cape Cod style home in the Woodside Elementary School district ! Resort like living awaits with a sparkling infinity POOL & spa, picturesque pinot noir VINEYARD & bucolic horse pasture. Entertain in the gorgeous POOL CABANA w/ kitchenette, full bathroom & sauna, surrounded by a beautiful huge brick patio. The home features elegant & spacious separate Living and Dining rooms, gourmet Kitchen with vaulted ceiling adjacent to cozy Fam Rm --all with outstanding VIEWS! Large separate office. Luxurious, MAIN level primary suite with gorgeous white marble bathroom, huge walk-in closet and more views! Rich hardwood, French doors, Carrera marble, custom cabinetry throughout. 5 CAR GARAGE--2 car attached +3 car NEW detached garage. HUGE deck off all main rooms overlooks the Western Hills. This is an exceptional home and property !

Enjoy sweeping Western Hill VIEWS from this gorgeous turnkey Cape Cod style home in the Woodside Elementary School district ! Resort like living awaits with a sparkling infinity POOL & spa, picturesque pinot noir VINEYARD & bucolic horse pasture. Entertain in the gorgeous POOL CABANA w/ kitchenette, full bathroom & sauna, surrounded by a beautiful huge brick patio. The home features elegant & spacious separate Living and Dining rooms, gourmet Kitchen with vaulted ceiling adjacent to cozy Fam Rm --all with outstanding VIEWS! Large separate office. Luxurious, MAIN level primary suite with gorgeous white marble bathroom, huge walk-in closet and more views! Rich hardwood, French doors, Carrera marble, custom cabinetry throughout. 5 CAR GARAGE--2 car attached +3 car NEW detached garage. HUGE deck off all main rooms overlooks the Western Hills. This is an exceptional home and property !

On one of Woodside most coveted streets the curved driveway leads you a peaceful setting of blooming trees & a charming 2 story home. A dramatic entry w/wall of glass looking out to redwoods welcomes you to this spacious home. The living room with its soaring beamed ceiling has French doors to the patio, a fireplace with an expansive hearth & is flooded w/ light from skylights. An adjacent library room w/ fireplace has a built-in cabinet for a TV. The formal dining room has a solarium room looking out to the redwoods. The country kitchen w/ a relaxing bay window sitting & fireplace has a view of the front garden & pool. The kitchen has a dining area, marble counters & walk-in pantry. One bedroom & bathroom is located off the kitchen. A large bedroom/entertainment room has a closet, bathroom & French doors to the pool area. The primary suite has a large sitting room w/ fireplace, built-in cabinets & sliding door to a balcony. The bedroom is spacious with French doors to 2 decks & ample closet space. The primary bathroom with marble has double sinks, tub & stall shower. Two additional bedrooms are located off a small sitting area & each bedroom has its own bath. Outdoors features patios overlooking redwoods, creek & grassy lawn creating peaceful indoor /outdoor living spaces.

On one of Woodside most coveted streets the curved driveway leads you a peaceful setting of blooming trees & a charming 2 story home. A dramatic entry w/wall of glass looking out to redwoods welcomes you to this spacious home. The living room with its soaring beamed ceiling has French doors to the patio, a fireplace with an expansive hearth & is flooded w/ light from skylights. An adjacent library room w/ fireplace has a built-in cabinet for a TV. The formal dining room has a solarium room looking out to the redwoods. The country kitchen w/ a relaxing bay window sitting & fireplace has a view of the front garden & pool. The kitchen has a dining area, marble counters & walk-in pantry. One bedroom & bathroom is located off the kitchen. A large bedroom/entertainment room has a closet, bathroom & French doors to the pool area. The primary suite has a large sitting room w/ fireplace, built-in cabinets & sliding door to a balcony. The bedroom is spacious with French doors to 2 decks & ample closet space. The primary bathroom with marble has double sinks, tub & stall shower. Two additional bedrooms are located off a small sitting area & each bedroom has its own bath. Outdoors features patios overlooking redwoods, creek & grassy lawn creating peaceful indoor /outdoor living spaces.

Welcome to 277 Grandview Drive, a contemporary Craftsman style haven in Woodside, CA offering privacy near Silicon Valley. The 4-bed, 4-bath main house with 2 offices spans 4920 sq ft on a 10+ acre lot. A 996 sq ft guest house, with an additional 1 bedroom and 1 bath, adds versatility (currently used as a music studio). The gated entrance reveals a welcoming design which includes an 8.4 kW solar system with battery backup. Inside, discover radiant heating, a chef's kitchen and two living rooms with surround sound. Outside, a fireplace, porch and deck offer relaxation and entertainment spaces, not to mention ultimate privacy. Adjacent to Thornewood Open Space, and built in 2008, this residence seamlessly combines modern amenities with eco-conscious features. Explore the harmonious blend of modern living and natural beauty.

Welcome to 277 Grandview Drive, a contemporary Craftsman style haven in Woodside, CA offering privacy near Silicon Valley. The 4-bed, 4-bath main house with 2 offices spans 4920 sq ft on a 10+ acre lot. A 996 sq ft guest house, with an additional 1 bedroom and 1 bath, adds versatility (currently used as a music studio). The gated entrance reveals a welcoming design which includes an 8.4 kW solar system with battery backup. Inside, discover radiant heating, a chef's kitchen and two living rooms with surround sound. Outside, a fireplace, porch and deck offer relaxation and entertainment spaces, not to mention ultimate privacy. Adjacent to Thornewood Open Space, and built in 2008, this residence seamlessly combines modern amenities with eco-conscious features. Explore the harmonious blend of modern living and natural beauty.

Originally conceived by the visionary architect Gardner Dailey in 1934, this exceptional estate is a testament to his architectural brilliance updated with a complete comprehensive renovation. The classic style of a country manor is presented, creating a visual symphony from the slate tile roof to the leaded glass windows and exceptional gardens. The views offered are nothing short of dazzling, encompassing verdant views of the bordering Menlo Country Club golf course, the sweeping panorama of San Francisco Bay, and the majestic silhouette of the East Bay hills. Set within a gated sanctuary of 1.5 acres, the home is adjacent to a 2.8 acre lot available for separate acquisition, enhancing the promise of exclusivity or with potential for further development. The palatial home spans more than 10,000 square feet of grace and sophistication. The journey into the home begins with a unique entrance a pedestrian gate beyond the gated driveway opens into a vast front courtyard with a magnificent heritage oak tree, lawns and patios, and a sparkling pool, creating an enchanting space for grand celebrations or private relaxation. Adjacent 2.8 acre parcel also available for sale. This is a once-in-a-lifetime property!

Originally conceived by the visionary architect Gardner Dailey in 1934, this exceptional estate is a testament to his architectural brilliance updated with a complete comprehensive renovation. The classic style of a country manor is presented, creating a visual symphony from the slate tile roof to the leaded glass windows and exceptional gardens. The views offered are nothing short of dazzling, encompassing verdant views of the bordering Menlo Country Club golf course, the sweeping panorama of San Francisco Bay, and the majestic silhouette of the East Bay hills. Set within a gated sanctuary of 1.5 acres, the home is adjacent to a 2.8 acre lot available for separate acquisition, enhancing the promise of exclusivity or with potential for further development. The palatial home spans more than 10,000 square feet of grace and sophistication. The journey into the home begins with a unique entrance a pedestrian gate beyond the gated driveway opens into a vast front courtyard with a magnificent heritage oak tree, lawns and patios, and a sparkling pool, creating an enchanting space for grand celebrations or private relaxation. Adjacent 2.8 acre parcel also available for sale. This is a once-in-a-lifetime property!

Contemporary with clean lines and total privacy, secluded in the redwoods on 5.6 acres just off Skyline with midway convenience to either Highway 92 or Woodside Road. Absolute privacy and most recently used as a professional recording studio. 3 beds plus an office or reading room with flexible use. Living room open to adjacent step up dining room just off the formal entry. Spacious kitchen with gas cooktop in the island, a large oven with microwave above, side by side refrigerator/freezer and nearby laundry room. The kitchen, informal dining, and family room are open to walls of glass overlooking the forest with access to the patio deck. Large primary suite with custom closet system and modern sleek bathroom. Significant backup generator in the event of power outages. Acclaimed Woodside Elementary School. Miles of hiking trails all around.

Welcome to your dream home at 250 Hardwick Rd in Woodside. Situated at the end of a quiet cul-de-sac, this exquisite property just completed a high-end, studs-out renovation and boasts stunning views of the Bay and East Bay hills. With dual oversized primary suites (4 bedrooms, 4 full bathrooms total), this home offers ample space for your growing family or those considering multigenerational living. As you step into the proper foyer, you'll be greeted by warm ambiance and stunning views that continue throughout the entire home. The open-plan kitchen is a chef's delight, featuring high-end appliances, integrated gas range, oversized kitchen island, and a walk-in pantry for all your culinary needs. The spacious family room is perfect for entertaining guests, with its vaulted ceilings and massive windows allowing for an abundance of natural light and stunning Woodside views! Both primary suites have been totally remodeled to perfection, featuring luxurious ensuite bathrooms, large walk-in closets, walk-in showers, and a gorgeous free-standing tub. The 1.6 acres of usable land, provides plenty of private outdoor space to enjoy the beautiful California weather. Just a short distance away, you'll find top-rated schools ensuring an excellent education for your children.

Welcome to your dream home at 250 Hardwick Rd in Woodside. Situated at the end of a quiet cul-de-sac, this exquisite property just completed a high-end, studs-out renovation and boasts stunning views of the Bay and East Bay hills. With dual oversized primary suites (4 bedrooms, 4 full bathrooms total), this home offers ample space for your growing family or those considering multigenerational living. As you step into the proper foyer, you'll be greeted by warm ambiance and stunning views that continue throughout the entire home. The open-plan kitchen is a chef's delight, featuring high-end appliances, integrated gas range, oversized kitchen island, and a walk-in pantry for all your culinary needs. The spacious family room is perfect for entertaining guests, with its vaulted ceilings and massive windows allowing for an abundance of natural light and stunning Woodside views! Both primary suites have been totally remodeled to perfection, featuring luxurious ensuite bathrooms, large walk-in closets, walk-in showers, and a gorgeous free-standing tub. The 1.6 acres of usable land, provides plenty of private outdoor space to enjoy the beautiful California weather. Just a short distance away, you'll find top-rated schools ensuring an excellent education for your children.

Majestic home set on 1.96 acre lot boasting with mature redwood trees, beautiful lush grounds with stunning views! Quaint entry porch & front door invites you into the spacious living room with cozy brick fireplace. Separate dining area, chefs kitchen with gas range and breakfast bar. Updated baths, recessed lighting, gorgeous hardwood flooring, dual-paned windows, 2 side storage sheds, large walkin basement accsessible from back yard under deck. Perfectly located in Central Woodside; this home is minutes to town center for convenient shopping, dining and the acclaimed Woodside School. Easy access to hiking trails, biking and horse back riding. Expansive deck to entertain guest while enjoying breathtaking views.

The allure of nature seamlessly intertwines with architectural brilliance at this exclusive vineyard estate on one of Woodsides most esteemed streets. Spanning over 4.399 acres, with the possibility of purchasing the adjacent lot of 3 acres for a total of 7.4 level acres, the entrance sets the tone of what lies within with an organic setting that begins with a serene lily pond and interconnected waterways with architecture by Atelier Ugo Sap of San Francisco and built by Van Acker Construction whose detail work is undeniable. The grand formal living room an antique mantelpiece adorn the wood burning fireplace and formal dining room grace the home for large gatherings. Dedicated office with fireplace, impressive open kitchen, breakfast and family room. Two levels with elevator, 6 bedrooms including luxurious primary suite, 6 full baths, and 2 half-baths including two main-level bedroom suites. Rustic-designed 1 bed/1 bath pool house with luxurious spa and kitchen. Additional structure for flexible use as gym, office or guest house with kitchenette and bath. Sparkling pool and magnificent grounds. Approximately 11,650 total square feet including 3-car garage. Cultivating wine, jam, honey and olive oil from the property. Acclaimed Woodside Elementary School and convenient location.

Perfectly and privately situated on nearly 9 sun-filled acres of land, options abound at this very special property: remodel the charming home or build new to create your own dream vision. The choice is yours. The land enjoys breathtaking 180 degree views of the Western Hills and there is a pool, spa, guest house and vast gardens. There is also a 1.2 mile hiking/biking trail encircling the property for a no-excuses healthy lifestyle right out the front door. Explore the endless possibilities. Approximately 9 acres (389,760 square feet; buyer to verify) Existing circa 1930 home with 4 bedrooms and 3 baths plus a one bedroom guest/pool house. Exceptional privacy and rural beauty Western hill views ~1 mile to Woodside town center. Woodside Elementary (K-8) School

Majestic home set on 1.96 acre lot boasting with mature redwood trees, beautiful lush grounds with stunning views! Quaint entry porch & front door invites you into the spacious living room with cozy brick fireplace. Separate dining area, chefs kitchen with gas range and breakfast bar. Updated baths, recessed lighting, gorgeous hardwood flooring, dual-paned windows, 2 side storage sheds, large walkin basement accsessible from back yard under deck. Perfectly located in Central Woodside; this home is minutes to town center for convenient shopping, dining and the acclaimed Woodside School. Easy access to hiking trails, biking and horse back riding. Expansive deck to entertain guest while enjoying breathtaking views.

Location, location! This lush jewel estate is located along central Woodside's most exclusive Mountain Home Road corridor. A rarely available opportunity to own a 1.25 flat acre property in the heart of the town's most prestigious neighborhood, discover an effortless blend of fine craftsmanship with luxurious elements and a touch of Hollywood style: 4(+1) brs, 4.5 ba plus an array of multi-functional spaces: a main-level suite easily converts to lounge/5th bedroom, the primary suite is enhanced by a private library/office/ walk-in closet, nursery or 2nd bedroom. Venture to the wine cellar with its own tasting room through a potential home theatre. An entertainer's dream for elegant al fresco afternoons by the pool and easy indoor/outdoor living, and the expansive grassed yard is as well suited for ball play as larger events, all framed for utmost privacy by pristine mature landscaping, a romantic rose garden, olive and fruit orchards. A short walk to town and the Woodside Elementary School, this garden estate balances peaceful seclusion with close proximity to all commuter routes and less than 20 minute drive to SFO Airport.

Location, location! This lush jewel estate is located along central Woodside's most exclusive Mountain Home Road corridor. A rarely available opportunity to own a 1.25 flat acre property in the heart of the town's most prestigious neighborhood, discover an effortless blend of fine craftsmanship with luxurious elements and a touch of Hollywood style: 4(+1) brs, 4.5 ba plus an array of multi-functional spaces: a main-level suite easily converts to lounge/5th bedroom, the primary suite is enhanced by a private library/office/ walk-in closet, nursery or 2nd bedroom. Venture to the wine cellar with its own tasting room through a potential home theatre. An entertainer's dream for elegant al fresco afternoons by the pool and easy indoor/outdoor living, and the expansive grassed yard is as well suited for ball play as larger events, all framed for utmost privacy by pristine mature landscaping, a romantic rose garden, olive and fruit orchards. A short walk to town and the Woodside Elementary School, this garden estate balances peaceful seclusion with close proximity to all commuter routes and less than 20 minute drive to SFO Airport.

Exceptional half acre+ with bay views in sought after Emerald Hills custom home built with meticulous attention to detail. Local artisan designed stone and ironwork. Outstanding floor plan with a focus on indoor-outdoor living the home seamlessly extending from the family room to a mostly covered, tiled deck with a fireplace, lounge, dining area and well-equipped outdoor kitchen offering a serene and inviting space for everyday living. Vaulted ceilings including living room with fireplace, formal dining room with fireplace, sun room and main floor bedroom suite. Granite chefs kitchen with views, breakfast room with outdoor patio, plus adjacent family room with fireplace. Upstairs luxurious primary suite with fireplace, vaulted ceiling, views and sitting room, plus two additional bedrooms and adjoining lounge or office. Lower-level flexible-use room for office, 2-car garage PLUS 735 square feet studio including half bath-possible ADU conversion. Approximately 5,173 square feet of conditioned space plus 2-car garage. Mostly float lot with vast lawn, huge entertaining spaces, privacy and views. Excellent Roy Cloud School, views and vast lawn, mostly flat land. One-of-a-kind enchanting home resting on gentle knoll-a must see.

Exceptional half acre+ with bay views in sought after Emerald Hills custom home built with meticulous attention to detail. Local artisan designed stone and ironwork. Outstanding floor plan with a focus on indoor-outdoor living the home seamlessly extending from the family room to a mostly covered, tiled deck with a fireplace, lounge, dining area and well-equipped outdoor kitchen offering a serene and inviting space for everyday living. Vaulted ceilings including living room with fireplace, formal dining room with fireplace, sun room and main floor bedroom suite. Granite chefs kitchen with views, breakfast room with outdoor patio, plus adjacent family room with fireplace. Upstairs luxurious primary suite with fireplace, vaulted ceiling, views and sitting room, plus two additional bedrooms and adjoining lounge or office. Lower-level flexible-use room for office, 2-car garage PLUS 735 square feet studio including half bath-possible ADU conversion. Approximately 5,173 square feet of conditioned space plus 2-car garage. Mostly float lot with vast lawn, huge entertaining spaces, privacy and views. Excellent Roy Cloud School, views and vast lawn, mostly flat land. One-of-a-kind enchanting home resting on gentle knoll-a must see.