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$4,207,000
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
$5,075,000
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
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
$2,750,000
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
$2,000,000
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
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
$10,055,000
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
$2,850,000
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
$1,275,000
2 Beds ⋅ 2 Baths ⋅ ML81933855 MLS
Must See! Views are incredible! Magnificent Redwood Trees in your own Back yard! Home is located in the Phleger Estate Area. You are in the forest, yet approximately 7 miles from Interstate 280 and Hwy 92. 2 lots together for a combined 3/4 of an acre. Plenty of room for parking, outdoor living spaces and the ability to make your home even larger. Currently configured with 2 bedrooms and 2 baths.

13503 Skyline BLVD, Woodside

Listed by James Light, 650-341-8193 from Bay Area Real Estate Services
(If provided) CoList: from

Sold listing courtesy of Rebecca Navarro from KWPA
$12,099,888
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
$1,480,000
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
$4,490,000
4 Beds ⋅ 3 Baths ⋅ ML81932636 MLS
This beautiful approximate 3000sq ft. Woodside Hills home offers stunning scenic views of the SF Bay Area. Enjoy 4th of July fireworks from the private patio and deck with built-in BBQ. Custom planter boxes and fruit trees adorn the 1.3 acre property. Cozy great room with fireplace, updated kitchen with quartz countertops, formal dining and living rooms. Master bedroom with remodeled bathroom and cedar-lined closet. Spacious laundry room with bonus area. 3-car garage with bonus room. Peaceful waterfall, art studio or extra storage. Convenient location, 17 solar panels, security system, landscaped. Perfect for growing families or telecommuters. Don't miss it!

190 Brookwood RD, Woodside

Listed by Loren Dakin, 650-714-8662 from Parc Agency Corporation
(If provided) CoList: from

Sold listing courtesy of Gary Campi from CAMPI
$13,000,000
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
$6,495,000
4 Beds ⋅ 5 Baths ⋅ ML81930021 MLS
Welcome to this completely remodeled & expanded 1-story Traditional style home in desirable Woodside Heights. Enjoy the space & ambiance of Woodside while being in the coveted Las Lomitas School District. This sophisticated home offers a perfect blend of single floor living & comfort while highlighting California's desirable indoor-outdoor living. Home features a 4 bedroom, 4.5 bathrooms with a dedicated office off the primary suite. There is a formal living room, dining room, family room, eat-in kitchen, & laundry room. Grounds feature a heated pool & spa, tennis court, outdoor fire pit, & landscaped gardens. Just some of the special features of the house include 11-foot high tray ceilings in the public rooms, beautiful hardwood floors, & full height windows. Outside, there are copper gutters & downspouts, slate roof, fully landscaped yard. Minutes from hiking & biking trails & the Town of Woodside, Menlo Park & Stanford, with easy access to Highway 280, this home is a must see!

417 Eleanor DR, Woodside

Listed by Hugh Cornish, 650-619-6461 from Coldwell Banker Realty
(If provided) CoList: Stephanie Elkins from Coldwell Banker Realty

Sold listing courtesy of Deborah Kehrberg from APR
$33,500,000
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
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
$2,500,000
4 Beds ⋅ 4 Baths ⋅ ML81924350 MLS
This exceptional home is situated on approx. 3/4 +acre, sunny usable lot and designed for indoor/outdoor living. Established natural landscape infuses the home through soaring windows, many skylights and French doors. The effect leaves one feeling far away from the hustle and bustle while just minutes from the Peninsula. Ideal for family living and entertaining. The gourmet kitchen is the heart of the home with an abundance of cabinets, extra-large center island, AGA stove and sun-filled eating nook. Open floor plan seamlessly connects the kitchen to living room on one side and cozy family room on the other. The large master suite found upstairs is a restful oasis with French doors and a private deck looking to the beautiful setting, spacious walk-in closet, and dreamy master bath with tub and sep. custom shower. Outdoor living at its finest with expanses of decks and garden sitting areas graced by majestic redwoods and established landscaping. Desirable Woodside/PV schools

36 Skyline DR, Woodside

Listed by Karin Bird, 650-207-0940 from Compass
(If provided) CoList: Scott Hayes from Compass

Sold listing courtesy of Christopher Eckert from KWPEN
$2,750,000
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
$2,230,000
4 Beds ⋅ 5 Baths ⋅ ML81899491 MLS
On the hunt for the ultimate Woodside getaway where you can leave behind the hustle and bustle of everyday life? Set on a majestic 2 acres, this spectacular residence provides an ideal blend of luxury and tranquility, all just moments from everything San Francisco has to offer. A long driveway, lush redwoods, and a contemporary façade greet you. Inside, discover a bright, welcoming layout with crisp white tones, soaring ceilings, and fine finishes throughout. Warm up in front of the stately fireplace in your well-sized living room or take advantage of one of the extensive decks framing verdant vistas. Your gourmet kitchen comes fitted with modern appliances, ample cabinetry, and an eat-in bar. Dine in your adjacent dining room where tray ceilings add to the captivating ambiance. At the end of a tiring day, rejuvenate in your secluded retreats, or savor a nightcap outdoors with 360 degrees of pure nature. As a bonus, you'll have a private library and an attached 7 garage.

35 Echo LN, Woodside

Listed by Douglas Heydon, 408-373-7844 from Century 21 Real Estate Alliance
(If provided) CoList: from

Sold listing courtesy of Douglas Heydon from ALNC

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