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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 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.

4 Beds ⋅ 5 Baths ⋅ ML81958693 MLS

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 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.

290 Winding WAY, Woodside

Listed by Linda Hymes, 415-377-6061 from Intero Real Estate Services
(If provided) CoList: from

Sold listing courtesy of Josh Rubin from COMPS

$5,200,000

Welcome to Woodside Whisper, a fully gated property stands as an epitome of refined luxury & tranquil living.This distinguished single-family home spans across 4050 square feet of meticulously crafted living space on a 1 acre parcel. Boasting 4 spacious beds & 4.5 baths, this residence offers ample room for both relaxation & entertainment. Upon entering, guests are greeted by an inviting formal entrance characterized by abundant natural light & tasteful finishes. The gourmet kitchen, equipped w/high-end appliances & custom cabinetry, serves as the heart of the home, inspiring culinary creativity & gatherings. The primary suite exudes sophistication & serenity, featuring a luxurious en-suite bath w/huge walk-in closet. Additional bedrooms offer comfort & privacy, each thoughtfully appointed to ensure restful nights & rejuvenating mornings. Get your game on at the on-site sports court, perfect for basketball, pickleball, or tennis. Post-match, plunge into the saltwater pool or jacuzzi, or detox in the outdoor sauna it's wellness on your doorstep. The outdoor space is a dreamy landscape for enjoying the Californian sunshine. Chill on the vast patios, gather around the fire pit under the stars, or wander through the lush gardens it's all about serene outdoor living.

4 Beds ⋅ 6 Baths ⋅ ML81960173 MLS

Welcome to Woodside Whisper, a fully gated property stands as an epitome of refined luxury & tranquil living.This distinguished single-family home spans across 4050 square feet of meticulously crafted living space on a 1 acre parcel. Boasting 4 spacious beds & 4.5 baths, this residence offers ample room for both relaxation & entertainment. Upon entering, guests are greeted by an inviting formal entrance characterized by abundant natural light & tasteful finishes. The gourmet kitchen, equipped w/high-end appliances & custom cabinetry, serves as the heart of the home, inspiring culinary creativity & gatherings. The primary suite exudes sophistication & serenity, featuring a luxurious en-suite bath w/huge walk-in closet. Additional bedrooms offer comfort & privacy, each thoughtfully appointed to ensure restful nights & rejuvenating mornings. Get your game on at the on-site sports court, perfect for basketball, pickleball, or tennis. Post-match, plunge into the saltwater pool or jacuzzi, or detox in the outdoor sauna it's wellness on your doorstep. The outdoor space is a dreamy landscape for enjoying the Californian sunshine. Chill on the vast patios, gather around the fire pit under the stars, or wander through the lush gardens it's all about serene outdoor living.

165 Woodside DR, Woodside

Listed by Alan Canas, 415-298-8940 from Engel & Voelkers San Francisco
(If provided) CoList: from

Sold listing courtesy of Syed Baqar from MXR

$4,600,000

Nestled on 1.1 acres of tranquility in the exclusive enclave of Woodside, this exquisite residence promises a lifestyle of both convenience and serenity. A haven for those seeking the epitome of refinement, this home boasts a remodeled chef's kitchen adorned with ample cabinetry, top stainless appliances and honed quartzite counters. The heart of the home lies in the open kitchen-family great room with its vaulted ceiling, counter seating and breakfast nook. Three fireplaces, hardwood flooring and large windows throughout provide a light and airy ambiance of unparalleled comfort. The primary suite, with large walk-in closet and updated bath with dual sinks, is a private retreat with a sunny patio. Formal living and dining rooms present space for entertaining while the lower level bonus room provides versatile opportunities for a rec room, home office, gym or artist studio. Beyond the interior, the property offers multiple entertaining patios, lush lawn, mature trees, fruit tree orchard and backs to Menlo Country Club, ensuring a buffer of privacy. Ideal for the auto enthusiast, there is covered parking for 6 vehicles in the 3-car garage & carports. This residence transcends the ordinary, inviting discerning individuals to experience a life of unparalleled splendor in Woodside.

3 Beds ⋅ 4 Baths ⋅ ML81957056 MLS ⋅ Woodside Hills BLDG.

Nestled on 1.1 acres of tranquility in the exclusive enclave of Woodside, this exquisite residence promises a lifestyle of both convenience and serenity. A haven for those seeking the epitome of refinement, this home boasts a remodeled chef's kitchen adorned with ample cabinetry, top stainless appliances and honed quartzite counters. The heart of the home lies in the open kitchen-family great room with its vaulted ceiling, counter seating and breakfast nook. Three fireplaces, hardwood flooring and large windows throughout provide a light and airy ambiance of unparalleled comfort. The primary suite, with large walk-in closet and updated bath with dual sinks, is a private retreat with a sunny patio. Formal living and dining rooms present space for entertaining while the lower level bonus room provides versatile opportunities for a rec room, home office, gym or artist studio. Beyond the interior, the property offers multiple entertaining patios, lush lawn, mature trees, fruit tree orchard and backs to Menlo Country Club, ensuring a buffer of privacy. Ideal for the auto enthusiast, there is covered parking for 6 vehicles in the 3-car garage & carports. This residence transcends the ordinary, inviting discerning individuals to experience a life of unparalleled splendor in Woodside.

275 Woodside Dr., Woodside

Listed by Billy McNair, 650-862-3266 from Coldwell Banker Realty
(If provided) CoList: Tim Kerns from Coldwell Banker Realty

Sold listing courtesy of Vicky Yu from APR

$8,498,000

Through the private driveway at 11 Southgate Drive, something extraordinary awaits. Youre greeted by hand crafted iron gates which open to an expansive front courtyard, meticulously landscaped grounds, and an astounding, Ernest Coxhead designed 5,790-square foot Spanish Colonial home. The classic estate, built in 1929 as the original owners summer retreat, combines timeless design and luxury in a private, California setting with unmatched views of the Woodside hills, the sparkling Bay Area and beyond. Inside, youll find dramatic architecture, spacious living & entertaining areas, and distinct treatments throughout, with four bedrooms and bathrooms for family and guests. Outside, inspired by nearby historic Filoli gardens, youll enjoy the unique trees, plants, and flowers, as well as the resort-like backyard with large pool and entertainment areas. This is an extremely rare opportunity to enjoy the lifestyle of a more refined era all in the heart of world-renowned Silicon Valley. A world away, yet close to everything.

4 Beds ⋅ 5 Baths ⋅ ML81955662 MLS

Through the private driveway at 11 Southgate Drive, something extraordinary awaits. Youre greeted by hand crafted iron gates which open to an expansive front courtyard, meticulously landscaped grounds, and an astounding, Ernest Coxhead designed 5,790-square foot Spanish Colonial home. The classic estate, built in 1929 as the original owners summer retreat, combines timeless design and luxury in a private, California setting with unmatched views of the Woodside hills, the sparkling Bay Area and beyond. Inside, youll find dramatic architecture, spacious living & entertaining areas, and distinct treatments throughout, with four bedrooms and bathrooms for family and guests. Outside, inspired by nearby historic Filoli gardens, youll enjoy the unique trees, plants, and flowers, as well as the resort-like backyard with large pool and entertainment areas. This is an extremely rare opportunity to enjoy the lifestyle of a more refined era all in the heart of world-renowned Silicon Valley. A world away, yet close to everything.

11 Southgate DR, Woodside

Listed by Granoski,Weil Assoc., 650-269-8556 from Compass
(If provided) CoList: from

Sold listing courtesy of Keri Nicholas from PARCA

$16,800,000

New Price! This magnificent contemporary farmhouse is situated on 3+ flat acres with spectacular views of the Western Hills and is within easy walking distance to the Woodside School (preK-8th grade) and Town Center. A testament to timeless architecture, meticulous craftsmanship and designer details, the main home and guest house were newly constructed in 2012 by renowned builder, Pacific Peninsula Group. Nothing short of exceptional, the 4 bedroom main home has high end finishes and white oak floors throughout, a state-of-the-art chefs kitchen and a eye catching two-story great room with rustic wooden beams and a honed limestone two-sided gas-fed fireplace. This estate's flat 3+ acres, which include a detached 1,255 sf elegant one-bedroom guest house, are elegantly fully utilized between the natural front equestrian pasture, the rear pool, spa and large entertaining terrace, the wisteria-framed fire pit, a 6-raised bed vegetable garden, chicken coop, dog run and fenced corrals. Privacy, entertainment options and enviable location, this property has it all!

4 Beds ⋅ 6 Baths ⋅ ML81947147 MLS

New Price! This magnificent contemporary farmhouse is situated on 3+ flat acres with spectacular views of the Western Hills and is within easy walking distance to the Woodside School (preK-8th grade) and Town Center. A testament to timeless architecture, meticulous craftsmanship and designer details, the main home and guest house were newly constructed in 2012 by renowned builder, Pacific Peninsula Group. Nothing short of exceptional, the 4 bedroom main home has high end finishes and white oak floors throughout, a state-of-the-art chefs kitchen and a eye catching two-story great room with rustic wooden beams and a honed limestone two-sided gas-fed fireplace. This estate's flat 3+ acres, which include a detached 1,255 sf elegant one-bedroom guest house, are elegantly fully utilized between the natural front equestrian pasture, the rear pool, spa and large entertaining terrace, the wisteria-framed fire pit, a 6-raised bed vegetable garden, chicken coop, dog run and fenced corrals. Privacy, entertainment options and enviable location, this property has it all!

140 Olive Hill LN, Woodside

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

Sold listing courtesy of Liz Daschbach from COMPS

$6,035,000

Fantastic property! At 1.6 acres and at the end of the cul-de-sac, this 4 bed 6 full bath home has views of the Bay and East Bay mountain range. On the property there is a long private driveway, heated pool with pool house (full bathroom, kitchenette and changing room), tennis court, detached 3 car garage with attached workroom, and ample parking around the property. The home was originally built in the 50s, but a large addition in the early '90s increased the square footage, which totals roughly 5640 square feet (buyer to verify). There are 3 fireplaces - 2 of them wood burning. Each bedroom (2 on each side of the house) has its own full bathroom. There is a large laundry room that has area for crafting and workout equipment. The property is very private and quiet with wonderful views, which gives it an estate feel. New, high-end appliances in the expansive kitchen, upgraded lighting throughout and new flooring create a property that you can call home!

4 Beds ⋅ 6 Baths ⋅ ML81950242 MLS

Fantastic property! At 1.6 acres and at the end of the cul-de-sac, this 4 bed 6 full bath home has views of the Bay and East Bay mountain range. On the property there is a long private driveway, heated pool with pool house (full bathroom, kitchenette and changing room), tennis court, detached 3 car garage with attached workroom, and ample parking around the property. The home was originally built in the 50s, but a large addition in the early '90s increased the square footage, which totals roughly 5640 square feet (buyer to verify). There are 3 fireplaces - 2 of them wood burning. Each bedroom (2 on each side of the house) has its own full bathroom. There is a large laundry room that has area for crafting and workout equipment. The property is very private and quiet with wonderful views, which gives it an estate feel. New, high-end appliances in the expansive kitchen, upgraded lighting throughout and new flooring create a property that you can call home!

2195 Ward WAY, Woodside

Listed by Lisa Keith, 650-703-8644 from Golden Gate Sotheby's International Realty
(If provided) CoList: from

Sold listing courtesy of Dennis Phan from EXPCA

$6,850,000

Central Woodside / Woodside Knolls beauty! 4-bd, 3.5ba, 4,000 sq ft, 1,000+ sq ft ADU, pool & spa, flat backyard with full edible garden and kennels! Huge 3-car garage with workshop. Rebuilt and added onto in 2001-2004 so looks and feels newer! This property will not disappoint!!

4 Beds ⋅ 4 Baths ⋅ ML81952476 MLS

Central Woodside / Woodside Knolls beauty! 4-bd, 3.5ba, 4,000 sq ft, 1,000+ sq ft ADU, pool & spa, flat backyard with full edible garden and kennels! Huge 3-car garage with workshop. Rebuilt and added onto in 2001-2004 so looks and feels newer! This property will not disappoint!!

240 Laning DR, Woodside

Listed by Sean Foley, 650-207-6005 from Compass
(If provided) CoList: from

Sold listing courtesy of Christina Hengehold from CBR

$3,020,000

Fantastic cumulative price reduction by $855,000! A Game Changer! Home is on PUBLIC SEWER SYSTEM-not on septic system, Endless Potential for updating or perfect the way it is! 2,820 sq. ft. MOL, it is unknown if listed SF includes the big down stairs laundry room and recreation room, building plans show a rec room downstairs. Home w/high ceilings, big rooms, 3 massive & attractive fireplaces, downslope lot w/view of hills, peaceful/secluded. Big 3 car garage, downstairs recreation room staged as 2nd family room, possible 4th BR, big laundry room + bathroom, could be in-law suite for guests or home schooling, what's your pleasure? Entry level boasts big living room, dining room, family kitchen w/grand fire place, 2 baths & Powder Rm & 3 Bedrooms, Original Owner. Roof is 12 years old MOL & there are fire protection sprinklers atop the roof, Decks provide views of the hills, front wrap around patio could be changed to lawn, garden or play area. The home has been lovingly cared for & now ready for your TLC. Surrounded by more expensive Pride of Ownership Homes, ##### MATTERPORT FLOOR PLAN SHOWS MAIN FLOOR AS 2,732 SF & LOWER LEVEL @ 1,431 SF & "GROSS INTERNAL AREA" @ 4.163 ST EXLUDING garage area of 1,281 SF, BUYERS TO RELY ON THEIR OWN APPRAISAL FOR HOME'S SQUARE FEET #####

3 Beds ⋅ 4 Baths ⋅ ML81940521 MLS

Fantastic cumulative price reduction by $855,000! A Game Changer! Home is on PUBLIC SEWER SYSTEM-not on septic system, Endless Potential for updating or perfect the way it is! 2,820 sq. ft. MOL, it is unknown if listed SF includes the big down stairs laundry room and recreation room, building plans show a rec room downstairs. Home w/high ceilings, big rooms, 3 massive & attractive fireplaces, downslope lot w/view of hills, peaceful/secluded. Big 3 car garage, downstairs recreation room staged as 2nd family room, possible 4th BR, big laundry room + bathroom, could be in-law suite for guests or home schooling, what's your pleasure? Entry level boasts big living room, dining room, family kitchen w/grand fire place, 2 baths & Powder Rm & 3 Bedrooms, Original Owner. Roof is 12 years old MOL & there are fire protection sprinklers atop the roof, Decks provide views of the hills, front wrap around patio could be changed to lawn, garden or play area. The home has been lovingly cared for & now ready for your TLC. Surrounded by more expensive Pride of Ownership Homes, ##### MATTERPORT FLOOR PLAN SHOWS MAIN FLOOR AS 2,732 SF & LOWER LEVEL @ 1,431 SF & "GROSS INTERNAL AREA" @ 4.163 ST EXLUDING garage area of 1,281 SF, BUYERS TO RELY ON THEIR OWN APPRAISAL FOR HOME'S SQUARE FEET #####

41 Oak Haven WAY, Woodside

Listed by David Blewett, 650-867-4389 from Intero Real Estate Services
(If provided) CoList: from

Sold listing courtesy of Benjamin Wang from LEXI

$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

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