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$5,075,000

Welcome to The Barrel House. This distinctive property was built in 1973 and designed by Sidney Hoover, a distinguished local architect that was influenced by Frank Llyod Wright. The private two-story home boasts three bedrooms and two and a half baths along with an ADU which is attached to a two-car garage. The inspiration for this home came from the beauty of four enormous redwood water barrels that were used as the cornerstones of the residence. The abundant natural light is drawn through massive windows and skylights throughout to give you the feeling of living in the forest. An abundance of trees are scattered across the beautiful 1+acre parcel. The quiet serenity of the property is enhanced by the location which is accessed by a flag lot lane. The home is within a short distance to Woodside Elementary School and the Town Center for upmost convenience. If you have ever envisioned living in nature The Barrel House could be your dream come true!

3 Beds ⋅ 3 Baths ⋅ ML81938892 MLS

Welcome to The Barrel House. This distinctive property was built in 1973 and designed by Sidney Hoover, a distinguished local architect that was influenced by Frank Llyod Wright. The private two-story home boasts three bedrooms and two and a half baths along with an ADU which is attached to a two-car garage. The inspiration for this home came from the beauty of four enormous redwood water barrels that were used as the cornerstones of the residence. The abundant natural light is drawn through massive windows and skylights throughout to give you the feeling of living in the forest. An abundance of trees are scattered across the beautiful 1+acre parcel. The quiet serenity of the property is enhanced by the location which is accessed by a flag lot lane. The home is within a short distance to Woodside Elementary School and the Town Center for upmost convenience. If you have ever envisioned living in nature The Barrel House could be your dream come true!

3364 Woodside RD, Woodside

Listed by Chris Anderson, 650-207-7105 from Compass
(If provided) CoList: Grayson Martin from Compass

Sold listing courtesy of Dennis Phan from EXPCA

$2,300,000

Stunning Country retreat on approximately 1.35 acres just down the street from the renowned Alice's Restaurant, and Skywood Trading Post & Deli. Set beyond dual privacy gates, and with abundant off-street parking, this home offers a harmonious blend of comfort & elegance taking full advantage of the natural beauty. Fine hardwood floors throughout are complemented by beamed & paneled ceilings, nowhere more dramatic than in the spacious living room with fireplace, wood stove, and entire wall of glass opening to the rear grounds. An adjoining room is perfect for an office, and a formal dining room. The kitchen is bright & light in an all-white palette with vaulted sky-lit ceiling. There are 3 large bedrooms and 2.5 baths, one bedroom with full wall of custom cabinetry and integrated office space. The home's allure is heightened by the sun-swept level rear grounds, where an oversized spa, soothing water features, and a lily pond create an oasis for relaxation.

3 Beds ⋅ 3 Baths ⋅ ML81937507 MLS

Stunning Country retreat on approximately 1.35 acres just down the street from the renowned Alice's Restaurant, and Skywood Trading Post & Deli. Set beyond dual privacy gates, and with abundant off-street parking, this home offers a harmonious blend of comfort & elegance taking full advantage of the natural beauty. Fine hardwood floors throughout are complemented by beamed & paneled ceilings, nowhere more dramatic than in the spacious living room with fireplace, wood stove, and entire wall of glass opening to the rear grounds. An adjoining room is perfect for an office, and a formal dining room. The kitchen is bright & light in an all-white palette with vaulted sky-lit ceiling. There are 3 large bedrooms and 2.5 baths, one bedroom with full wall of custom cabinetry and integrated office space. The home's allure is heightened by the sun-swept level rear grounds, where an oversized spa, soothing water features, and a lily pond create an oasis for relaxation.

1600 La Honda RD, Woodside

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

Sold listing courtesy of Scott Sweeney from DWELL

$2,000,000

Your own piece of paradise awaits you. Close to the Woodside Village and highly acclaimed Woodside Elementary School K-8. Nestled among oak trees, this Woodside Glens home is tucked away on nearly half an acre overlooking a seasonal creek at the end of a quiet cul-de-sac with access to the Joan Olson Natural Preserve and trails. This move-in ready sunny home features abundant natural light and forest views from every room. The main level has three bedrooms and two bathrooms. The lower level includes rooms for an office, fitness/play space, and laundry. Highlights include hardwood floors, an updated kitchen with stainless steel appliances, dedicated off-street parking, and sunny spaces for flower/vegetable gardens. Enjoy the relaxed California indoor-outdoor lifestyle with a spacious deck off the main living area, with views of the property's seasonal creek and trail. This magical woodland retreat is conveniently located for commutes to SF and Silicon Valley, with 280 just minutes away.

3 Beds ⋅ 2 Baths ⋅ ML81937133 MLS

Your own piece of paradise awaits you. Close to the Woodside Village and highly acclaimed Woodside Elementary School K-8. Nestled among oak trees, this Woodside Glens home is tucked away on nearly half an acre overlooking a seasonal creek at the end of a quiet cul-de-sac with access to the Joan Olson Natural Preserve and trails. This move-in ready sunny home features abundant natural light and forest views from every room. The main level has three bedrooms and two bathrooms. The lower level includes rooms for an office, fitness/play space, and laundry. Highlights include hardwood floors, an updated kitchen with stainless steel appliances, dedicated off-street parking, and sunny spaces for flower/vegetable gardens. Enjoy the relaxed California indoor-outdoor lifestyle with a spacious deck off the main living area, with views of the property's seasonal creek and trail. This magical woodland retreat is conveniently located for commutes to SF and Silicon Valley, with 280 just minutes away.

160 Otis AVE, Woodside

Listed by Erika Demma, 650-888-6558 from Compass
(If provided) CoList: Deborah Kehrberg from Compass

Sold listing courtesy of Michael Warren from COMPS

$5,000,000

Welcome to this wonderful, gated, Woodside Estate. Situated on a 3.38 acre parcel at the end of a private lane, exemplifying Country living at its best. This custom-built home features massive rustic beams, unique millwork, high ceilings, and wide plank hardwood floors. The oversized great room/kitchen and living rooms encourage large gatherings. The bedroom wing consists of 3 en-suites, a bar area, powder & laundry rooms. Adjacent to the kitchen, there's an office, walk-in pantry, mud room, and spacious pet grooming parlor. The private yards are accented by tall redwoods, majestic oaks, beautiful rose gardens, raised potting beds and views of the western hills. A free form pool with rock surround and waterfall, and a quaint guest cottage with a 4th loft bedroom, round out the rear yard. Luxurious country living yet close to Woodside Elementary, Roberts Market, hiking, & cycling. Truly a tranquil, serene, and private place to live, work and play.

3 Beds ⋅ 5 Baths ⋅ ML81936454 MLS

Welcome to this wonderful, gated, Woodside Estate. Situated on a 3.38 acre parcel at the end of a private lane, exemplifying Country living at its best. This custom-built home features massive rustic beams, unique millwork, high ceilings, and wide plank hardwood floors. The oversized great room/kitchen and living rooms encourage large gatherings. The bedroom wing consists of 3 en-suites, a bar area, powder & laundry rooms. Adjacent to the kitchen, there's an office, walk-in pantry, mud room, and spacious pet grooming parlor. The private yards are accented by tall redwoods, majestic oaks, beautiful rose gardens, raised potting beds and views of the western hills. A free form pool with rock surround and waterfall, and a quaint guest cottage with a 4th loft bedroom, round out the rear yard. Luxurious country living yet close to Woodside Elementary, Roberts Market, hiking, & cycling. Truly a tranquil, serene, and private place to live, work and play.

170 Josselyn LN, Woodside

Listed by Peter Vece, 650-619-2799 from Golden Gate Sotheby's International Realty
(If provided) CoList: from

Sold listing courtesy of Jim Minkey from TODAY

$2,850,000

Serene, very private and very quiet 3+/- acre property, only 5 minutes to Woodside town center surrounded by oaks, redwood and manzanita trees. Set on a knoll the property borders Huddart Park and watershed property and features the highly desirable beautiful western hill views. The 3-bedroom, 2-bath (current 3rd bedroom used as office), inviting home has rustic tones with an abundance of natural light. Large primary bedroom with walk in closet and recently updated en-suite bathroom. Light and bright, well laid out kitchen and updated second bathroom. Multiple outdoor dining and seating areas to enjoy this peaceful natural setting and views, fruit trees and several flat areas for potential other applications. 2 covered horse stalls with runouts, tack room, sand arena/turnout area, larger main barn/workshop, outdoor shower. Barn is aprox. 20'x34' Easy trail access into Huddart Park, Woodside Elementary School, close access to 280 and Sand Hill. Truly must be seen to appreciate.

3 Beds ⋅ 2 Baths ⋅ ML81934979 MLS

Serene, very private and very quiet 3+/- acre property, only 5 minutes to Woodside town center surrounded by oaks, redwood and manzanita trees. Set on a knoll the property borders Huddart Park and watershed property and features the highly desirable beautiful western hill views. The 3-bedroom, 2-bath (current 3rd bedroom used as office), inviting home has rustic tones with an abundance of natural light. Large primary bedroom with walk in closet and recently updated en-suite bathroom. Light and bright, well laid out kitchen and updated second bathroom. Multiple outdoor dining and seating areas to enjoy this peaceful natural setting and views, fruit trees and several flat areas for potential other applications. 2 covered horse stalls with runouts, tack room, sand arena/turnout area, larger main barn/workshop, outdoor shower. Barn is aprox. 20'x34' Easy trail access into Huddart Park, Woodside Elementary School, close access to 280 and Sand Hill. Truly must be seen to appreciate.

486 Raymundo DR, Woodside

Listed by Chris Anderson, 650-207-7105 from Compass
(If provided) CoList: from

Sold listing courtesy of Roshan Izadi from APR

$1,480,000

A private picturesque 3-story chalet style retreat of redwood construction set back from the road on 3 acres of redwoods in Woodside just .7 mile north of Alice's Restaurant at Highway 84 adjacent to the County Fire Station. Well maintained in good condition with green forest views, the property backs up to Mid-Peninsula open space. The front door opens into the very spacious living, kitchen and dining areas on the mid-level of the home, warmed by central propane forced air heat and a fireplace complete with a firewood lift. Sturdy decks surround the newly recarpeted living areas on the main floor. Full bathrooms on each floor. The primary suite is on the top floor under redwood beamed ceilings with generous closet and storage spaces. The downstairs, ground floor living area hosts a family room, full bath, two bedrooms, a laundry area with kitchenette, all situated off of the covered parking area with its own entrance. Covered parking for three vehicles is situated under the dwelling.

3 Beds ⋅ 3 Baths ⋅ ML81918714 MLS

A private picturesque 3-story chalet style retreat of redwood construction set back from the road on 3 acres of redwoods in Woodside just .7 mile north of Alice's Restaurant at Highway 84 adjacent to the County Fire Station. Well maintained in good condition with green forest views, the property backs up to Mid-Peninsula open space. The front door opens into the very spacious living, kitchen and dining areas on the mid-level of the home, warmed by central propane forced air heat and a fireplace complete with a firewood lift. Sturdy decks surround the newly recarpeted living areas on the main floor. Full bathrooms on each floor. The primary suite is on the top floor under redwood beamed ceilings with generous closet and storage spaces. The downstairs, ground floor living area hosts a family room, full bath, two bedrooms, a laundry area with kitchenette, all situated off of the covered parking area with its own entrance. Covered parking for three vehicles is situated under the dwelling.

16990 Skyline BLVD, Woodside

Listed by Barry Mangan, 408-309-2596 from Intero Real Estate Services
(If provided) CoList: from

Sold listing courtesy of Thomas Beck from APR

$2,750,000

Complete privacy set way back from the street on 5.6 acres just one mile from famed Alice's Restaurant. Lodge style ambiance throughout with wood paneled wainscot and towering ceilings plus expansive windows and sliding glass doors. Spacious living room, formal dining room, large family room, and open design kitchen with high-end appliances. 2 offices plus 3 bedrooms and 3.5 baths. Private upstairs wing for primary suite with its own view deck plus second upstairs wing with 2 bedrooms. Miles of hiking, biking.

3 Beds ⋅ 4 Baths ⋅ ML81916837 MLS

Complete privacy set way back from the street on 5.6 acres just one mile from famed Alice's Restaurant. Lodge style ambiance throughout with wood paneled wainscot and towering ceilings plus expansive windows and sliding glass doors. Spacious living room, formal dining room, large family room, and open design kitchen with high-end appliances. 2 offices plus 3 bedrooms and 3.5 baths. Private upstairs wing for primary suite with its own view deck plus second upstairs wing with 2 bedrooms. Miles of hiking, biking.

18200 Skyline BLVD, Woodside

Listed by Scott Dancer, 650-888-8199 from Compass
(If provided) CoList: from

Sold listing courtesy of Scott Dancer from APR