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$4,207,000

Welcome to The Lake House. This beautiful, 6 bedroom, 8 bathroom house sits on 4.2 acres with valley views, a private lake along with a private redwood grove. Step into this amazing contemporary country home featuring abundant light, energy efficient metal roof with solar panels supporting tesla power walls, outside gym, dog run, and custom-built tree house. On the main level, there are 3 en suite bedrooms and a separate office, along with living/dining room, eat in kitchen and family room. The lower level offers 3 more bedrooms with a large family/playroom supported by a secondary kitchen area. There are over 4000 sq ft of terraces, with fire pit, for outdoor enjoyment as well as an attached 2 car garage and detached 2 car garage. The private lake is an ideal spot for swimming or fishing. Enjoy the privacy and tranquility of country living, with access to an extensive trail system. Only 3.9 miles from 280. PV schools.

6 Beds ⋅ 8 Baths ⋅ ML81935993 MLS

Welcome to The Lake House. This beautiful, 6 bedroom, 8 bathroom house sits on 4.2 acres with valley views, a private lake along with a private redwood grove. Step into this amazing contemporary country home featuring abundant light, energy efficient metal roof with solar panels supporting tesla power walls, outside gym, dog run, and custom-built tree house. On the main level, there are 3 en suite bedrooms and a separate office, along with living/dining room, eat in kitchen and family room. The lower level offers 3 more bedrooms with a large family/playroom supported by a secondary kitchen area. There are over 4000 sq ft of terraces, with fire pit, for outdoor enjoyment as well as an attached 2 car garage and detached 2 car garage. The private lake is an ideal spot for swimming or fishing. Enjoy the privacy and tranquility of country living, with access to an extensive trail system. Only 3.9 miles from 280. PV schools.

385 Old La Honda RD, Woodside

Listed by Debora Smith, 650-580-8286 from Sotheby's Intl Rlty
(If provided) CoList: from

Sold listing courtesy of Michael Galli from APR

$2,750,000

Discover an enchanting 5-bedroom, 4 and 1/2 bath retreat on 5+ acres of pristine Redwood forest, boasting Bay views yet only ~12 min to downtown Woodside. Adjacent to Wunderlich Park and El Corte Madera Open space, this gem also features coveted Woodside schools. The main floor Master suite features a private entrance to an outdoor hot tub that overlooks the Bay. The expansive floor-to-ceiling windows flood the interior with light. Entertain in style with a gourmet kitchen and host unforgettable gatherings in the adjacent dining area, which opens to the ~2200 sq ft outdoor deck, perfect for al fresco dining. The upper level houses three well-appointed bedrooms, ideal for family or guests. Unwind in the versatile game room or indulge in the sophisticated wine cellar, a haven for enthusiasts. Outside, revel in the private spa area, offering the ultimate relaxation amidst the Redwood tranquility. With 5 acres to explore, enjoy endless outdoor activities and bask in nature's embrace.

5 Beds ⋅ 5 Baths ⋅ ML81937466 MLS

Discover an enchanting 5-bedroom, 4 and 1/2 bath retreat on 5+ acres of pristine Redwood forest, boasting Bay views yet only ~12 min to downtown Woodside. Adjacent to Wunderlich Park and El Corte Madera Open space, this gem also features coveted Woodside schools. The main floor Master suite features a private entrance to an outdoor hot tub that overlooks the Bay. The expansive floor-to-ceiling windows flood the interior with light. Entertain in style with a gourmet kitchen and host unforgettable gatherings in the adjacent dining area, which opens to the ~2200 sq ft outdoor deck, perfect for al fresco dining. The upper level houses three well-appointed bedrooms, ideal for family or guests. Unwind in the versatile game room or indulge in the sophisticated wine cellar, a haven for enthusiasts. Outside, revel in the private spa area, offering the ultimate relaxation amidst the Redwood tranquility. With 5 acres to explore, enjoy endless outdoor activities and bask in nature's embrace.

16075 Skyline BLVD, Woodside

Listed by Scott Hayes, 650-245-5044 from Compass
(If provided) CoList: Karin Bird from Compass

Sold listing courtesy of Kelley Benetti from CBR

$10,055,000

Set on 3.4 acres in central Woodside bordering the 75-acre Fleishhacker Estate Conservancy this home was designed by renowned architect Goodwin Steinberg. Organic appointments that include copper chandeliers by Albert Guibara, stained glass windows by Hermann Lirk, and walls in clear vertical grain cedar and stone. Exceptional spaces for entertaining plus two separate offices for remote work. 4 bedrooms include a luxurious main-level primary suite + lower level w/3-bedrooms, including an en suite, central play area, large storage area or potential fitness room, & wine cellar. Upgraded 400 amp service including Tesla charger. Beautifully landscaped grounds, originally designed by Thomas Church, with enchanting gardens, inviting courtyards, open meadows, and a wraparound deck overlooking the sun-drenched pool. A private nature trail winds around the inside perimeter of the fenced property. Just over a mile from the Town Center. Highly-regarded Woodside School (K-8).

4 Beds ⋅ 5 Baths ⋅ ML81934420 MLS

Set on 3.4 acres in central Woodside bordering the 75-acre Fleishhacker Estate Conservancy this home was designed by renowned architect Goodwin Steinberg. Organic appointments that include copper chandeliers by Albert Guibara, stained glass windows by Hermann Lirk, and walls in clear vertical grain cedar and stone. Exceptional spaces for entertaining plus two separate offices for remote work. 4 bedrooms include a luxurious main-level primary suite + lower level w/3-bedrooms, including an en suite, central play area, large storage area or potential fitness room, & wine cellar. Upgraded 400 amp service including Tesla charger. Beautifully landscaped grounds, originally designed by Thomas Church, with enchanting gardens, inviting courtyards, open meadows, and a wraparound deck overlooking the sun-drenched pool. A private nature trail winds around the inside perimeter of the fenced property. Just over a mile from the Town Center. Highly-regarded Woodside School (K-8).

301 Olive Hill LN, Woodside

Listed by Mary & Brent Gullixson, 650-888-0860 from Compass
(If provided) CoList: from

Sold listing courtesy of Julie Baumann from APR

$12,099,888

Originally owned by socialite Adelaide Kirkbride, Canardia is a majestic 7+ acre Woodside equestrian estate. This special home has been extensively remodeled and reimagined to fit today's contemporary lifestyle. The main home features abundant light, high ceilings, energy efficient metal roof, dual pane windows and doors, hardwood flooring, remodeled bathrooms, and a gourmet chef's kitchen that features a huge center island, sub zero refrigerator, and 2 La Cornue stoves. This entertainer's paradise has hosted many gatherings, charities, fundraisers and weddings on its bountiful grounds with over 500 guests at a time. Other features of the property include a long scenic winding driveway, private lake with sand beach, a 6 stall remodeled stable, an outdoor kitchen, pool, pool house, multiple fountains, 3 wells, fire pits, a bocce ball court, a rose garden and large grassy areas. Only a short drive to Sand Hill Road, 280 and everything that San Francisco and Silicon Valley have to offer.

5 Beds ⋅ 6 Baths ⋅ ML81933807 MLS

Originally owned by socialite Adelaide Kirkbride, Canardia is a majestic 7+ acre Woodside equestrian estate. This special home has been extensively remodeled and reimagined to fit today's contemporary lifestyle. The main home features abundant light, high ceilings, energy efficient metal roof, dual pane windows and doors, hardwood flooring, remodeled bathrooms, and a gourmet chef's kitchen that features a huge center island, sub zero refrigerator, and 2 La Cornue stoves. This entertainer's paradise has hosted many gatherings, charities, fundraisers and weddings on its bountiful grounds with over 500 guests at a time. Other features of the property include a long scenic winding driveway, private lake with sand beach, a 6 stall remodeled stable, an outdoor kitchen, pool, pool house, multiple fountains, 3 wells, fire pits, a bocce ball court, a rose garden and large grassy areas. Only a short drive to Sand Hill Road, 280 and everything that San Francisco and Silicon Valley have to offer.

1550 Portola RD, Woodside

Listed by Monique Anton, 650-380-5512 from Modern Homes Realty
(If provided) CoList: from

Sold listing courtesy of Min Hui from ABAC

$13,000,000

New Price! Spectacular views of Western Hills from this light-filled 5BR/4.5BA approx 6,420 sq ft Central Woodside home on approx 3.27 fully usable acres close to Woodside Town Center shops, restaurants, freeway access and in the acclaimed Woodside School District. Efficient, mainly one level, floor plan w/large primary suite and separate living & family rooms & eat-in kitchen lead to outside deck overlooking large rear lawn and pool with adjacent spa. Separate approx 285 sq ft detached office with nearby chipping and putting green and attached potting shed to accommodate the grounds wonderful gardens; Detached 4-stall stable with tack room and hay storage, separate turnouts, large riding ring and surrounding corral. Come see this amazing estate in the heart of it all!

5 Beds ⋅ 5 Baths ⋅ ML81930413 MLS

New Price! Spectacular views of Western Hills from this light-filled 5BR/4.5BA approx 6,420 sq ft Central Woodside home on approx 3.27 fully usable acres close to Woodside Town Center shops, restaurants, freeway access and in the acclaimed Woodside School District. Efficient, mainly one level, floor plan w/large primary suite and separate living & family rooms & eat-in kitchen lead to outside deck overlooking large rear lawn and pool with adjacent spa. Separate approx 285 sq ft detached office with nearby chipping and putting green and attached potting shed to accommodate the grounds wonderful gardens; Detached 4-stall stable with tack room and hay storage, separate turnouts, large riding ring and surrounding corral. Come see this amazing estate in the heart of it all!

258 Kings Mountain RD, Woodside

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

Sold listing courtesy of David Bergman, CRS from NTERO

$33,500,000

Majestic Mediterranean and equestrian estate on secluded 8.7 acres in central Woodside. 4 bedroom/4.5 bath in main 6300 sq ft + residence includes expansive great room overlooking grounds with with additional study/5th bedroom option. Primary bedroom includes luxurious bath, two large walk in closets, and private rooftop deck with view of the grounds and western hills. Charming courtyard takes you to 3 studio guest apartments, detached office, gym and pathway to additional office/guest house. Breathtaking grounds feature stone terrace off the great room with outdoor fireplace, pool, spa, tennis court, historic 10 stall barn, paddock and riding arena all surrounded by natural grasses, expansive lawn, apple orchard, and stunning oak and redwood trees. This creekside setting allows for the ultimate in privacy and serenity just minutes to Town, Woodside Schools, and all the amenities of Silicon Valley living.

4 Beds ⋅ 5 Baths ⋅ ML81893802 MLS

Majestic Mediterranean and equestrian estate on secluded 8.7 acres in central Woodside. 4 bedroom/4.5 bath in main 6300 sq ft + residence includes expansive great room overlooking grounds with with additional study/5th bedroom option. Primary bedroom includes luxurious bath, two large walk in closets, and private rooftop deck with view of the grounds and western hills. Charming courtyard takes you to 3 studio guest apartments, detached office, gym and pathway to additional office/guest house. Breathtaking grounds feature stone terrace off the great room with outdoor fireplace, pool, spa, tennis court, historic 10 stall barn, paddock and riding arena all surrounded by natural grasses, expansive lawn, apple orchard, and stunning oak and redwood trees. This creekside setting allows for the ultimate in privacy and serenity just minutes to Town, Woodside Schools, and all the amenities of Silicon Valley living.

100 Why Worry LN, Woodside

Listed by Shena Hurley, 650-575-0991 from Golden Gate Sotheby's International Realty
(If provided) CoList: from

Sold listing courtesy of Alex Michas from OBOKWOAK

$20,750,000

Stately Italian villa sitting on roughly 7.7 acres on one of Woodsides most sought after cul-de-sac locations is now available. Incredible attention to detail and rare, highest end, European finishes makes this home a rare treasure and true sight to behold. Venetian plaster walls, brick barrel ceiling with oak beams, herringbone terra cotta flooring, and 300-year-old terracotta roof tiles imported from Italy to name a few. Majestic park-like grounds offer the ultimate private escape. Resort like amenities include pool, hot tub, tennis court, gym, vast lawns. Have dinner under the stars in your private redwood grove with tranquil creekside setting. Incredible guest house, additional gatehouse. This is one of Woodsides finest. Highly sought after Portola Valley schools.

5 Beds ⋅ 8 Baths ⋅ ML81925551 MLS

Stately Italian villa sitting on roughly 7.7 acres on one of Woodsides most sought after cul-de-sac locations is now available. Incredible attention to detail and rare, highest end, European finishes makes this home a rare treasure and true sight to behold. Venetian plaster walls, brick barrel ceiling with oak beams, herringbone terra cotta flooring, and 300-year-old terracotta roof tiles imported from Italy to name a few. Majestic park-like grounds offer the ultimate private escape. Resort like amenities include pool, hot tub, tennis court, gym, vast lawns. Have dinner under the stars in your private redwood grove with tranquil creekside setting. Incredible guest house, additional gatehouse. This is one of Woodsides finest. Highly sought after Portola Valley schools.

30 Trail LN, Woodside

Listed by Zachary Trailer, 650-906-8008 from Compass
(If provided) CoList: from

Sold listing courtesy of DeLeon Team from DLRPA