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Woodside Real Estate Homes & Condos

Featured Woodside Properties For sale

7 Blue Ridge LN, Woodside image
7 Blue Ridge LN, Woodside $65,000,000

Completed in 2023 on Woodside's most premier central corridor, a Cul De Sac off Mountain Home Road. This 3 acre Tuscan inspired estate property is a masterpiece of design...

  • 5 Beds
  • 6 Baths
  • ML82032838 MLS
15 Hidden Valley LN, Woodside image
15 Hidden Valley LN, Woodside $35,000,000 ▼

This extraordinary Woodside estate spans 6.4 level acres w/sun-swept vineyards & western hill views. The compound comprises multiple architecturally significant buildings...

  • 6 Beds
  • 9 Baths
  • ML82045742 MLS
307 Olive Hill LN, Woodside image
307 Olive Hill LN, Woodside $29,995,000

This exceptional property spans more than 3 acres with sweeping western hill views and 9,880 square feet of total living space. The main home was completely rebuilt in 20...

  • 8 Beds
  • 7 Baths
  • ML82065658 MLS
180 Farm RD, Woodside image
180 Farm RD, Woodside $21,995,000 ▼

Evoking the patina & permanence of a residence shaped over generations, this vineyard estate possesses an authenticity rarely achieved in contemporary construction. Compl...

  • 4 Beds
  • 5 Baths
  • ML82054839 MLS
235 Harcross RD, Woodside image
235 Harcross RD, Woodside $19,950,000

Newly constructed modern residence by Keightley Builders defined by exceptional architecture, abundant natural light, and a private knoll-top setting. 8,275 sf of living ...

  • 5 Beds
  • 7 Baths
  • ML82064103 MLS
600 Moore RD, Woodside image
600 Moore RD, Woodside $14,900,000

A rare, fully realized legacy compound offering the soul of a European retreat in the heart of Woodside. Hidden within 3.2 acres of curated gardens and ancient oaks, this...

  • 7 Beds
  • 9 Baths
  • ML82057953 MLS
388 Albion AVE, Woodside image
388 Albion AVE, Woodside $14,800,000

One of the most premier locations in Central Woodside! Within walking distance to the Town Center shops & restaurants and highly acclaimed Woodside Elementary K-8. This e...

  • 2 Beds
  • 2 Baths
  • ML82064344 MLS
389 Moore RD, Woodside image
389 Moore RD, Woodside $12,995,000

Spectacular Monterey Colonial home on 6+ private acres. Long gated driveway & large motor court. Estate shows tremendous character and beauty. Improvements include a stun...

  • 7 Beds
  • 8 Baths
  • ML82045810 MLS
309 Olive Hill LN, Woodside image
309 Olive Hill LN, Woodside $11,000,000 ▼

Discover an exceptional opportunity to create a dream home or reimagine the existing Neoclassical residence on one of central Woodsides most desirable streets. Spanning j...

  • 2 Beds
  • 4 Baths
  • ML82039836 MLS
160 Phillip RD, Woodside image
160 Phillip RD, Woodside $10,988,000 ▼

Set on more than 2.5 acres of quintessential Woodside grounds, this spectacular estate balances timeless elegance with easy comfort. Behind gates and surrounded by mature...

  • 5 Beds
  • 6 Baths
  • ML82037743 MLS
1543 Portola RD, Woodside image
1543 Portola RD, Woodside $6,995,000

An extensive remodel completed in 2023 transformed this classic New England Colonial with designer style and a fresh approach to modern living. The remodeling went well b...

  • 5 Beds
  • 4 Baths
  • ML82065045 MLS
643 W Glen WAY, Woodside image
643 W Glen WAY, Woodside $5,200,000

Framed by majestic trees w/ sweeping views of Woodside & the Santa Cruz mountains, this remodeled California Mediterranean home brings the outdoors in. A bright foyer w/ ...

  • 4 Beds
  • 4 Baths
  • ML82065037 MLS
103 Toyon CT, Woodside image
103 Toyon CT, Woodside $4,950,000 ▼

More than one-third acre creates an exceptional setting for this spacious home with 4 bedrooms, 3.5 baths, and multiple living areas designed for today. There are formal ...

  • 4 Beds
  • 4 Baths
  • ML82046648 MLS
775 W California WAY, Woodside image
775 W California WAY, Woodside $4,850,000

775 West California Way is calling you home! Located in the highly regarded Woodside School District and ideally situated near Woodside Town Center, this meticulously mai...

  • 4 Beds
  • 3 Baths
  • ML82063093 MLS
25 Corto LN, Woodside image
25 Corto LN, Woodside $4,850,000

Rarely available flat lot and ideally located close to Woodside Town Center, this inviting single-level ranch-style home combines timeless appeal with exceptional flexibi...

  • 3 Beds
  • 3 Baths
  • ML82062831 MLS
61 Oak Haven WAY, Woodside image
61 Oak Haven WAY, Woodside $4,588,000 ▼

Nestled among majestic oak trees on nearly 1.2 acres in Woodside Hills, this home is set well back from the street via a long paver driveway. Spanning 4,150 SF, the inter...

  • 4 Beds
  • 4 Baths
  • ML82050181 MLS
941 High RD, Woodside image
941 High RD, Woodside $4,499,000

2.8 Acres of Buildable Land Next to Menlo Country Club. This exceptional nearly 3 acre vacant parcel presents an extraordinary opportunity in a prestigious setting, offer...

  • ML82042331 MLS
63 Ridge CT, Woodside image
63 Ridge CT, Woodside $3,489,000

Beautifully updated interiors & striking architectural character define this exceptional home in the Glens newly built in 2007. Tucked away at the end of a peaceful cul-d...

  • 4 Beds
  • 3 Baths
  • ML82062642 MLS
411 Glenwood AVE, Woodside image
411 Glenwood AVE, Woodside $3,389,000

There is a particular quiet at 411 Glenwood Avenue. Stand on the main level and look through walls of glass. The first thing you notice is the treetops. The second is wh...

  • 3 Beds
  • 2 Baths
  • ML82059026 MLS
1 Reids Roost RD, Woodside image
1 Reids Roost RD, Woodside $3,088,000 ▲

SKY VILLA: RE-IMAGINE ROYALTY IN THE WOODS. Sky Villa is an opportunity to dream big with unmatched grandeur & privacy. This is a bank-owned, non-livable development oppo...

  • 4 Beds
  • 8 Baths
  • ML82017325 MLS
160 Redland RD, Woodside image
160 Redland RD, Woodside $2,750,000

Some houses announce themselves, this one settles quietly into the redwoods of Skylonda, a 1967 mid-century modern by architect Edwin Wadsworth where the light comes firs...

  • 4 Beds
  • 3 Baths
  • ML82063276 MLS
255 Allen RD, Woodside image
255 Allen RD, Woodside $2,299,000

Panoramic Views, Absolute Privacy Perched high above the valley on over six acres, this rare 4-bedroom, 3-bath mountain sanctuary pairs total seclusion with sweeping, un...

  • 4 Beds
  • 3 Baths
  • ML82058136 MLS
20255 Skyline BLVD, Woodside image
20255 Skyline BLVD, Woodside $2,195,000 ▼

Spanning approximately 2.92 usable acres of gently rolling meadows with picture-postcard views, this classic horse property offers miles-away tranquility just 20 minutes ...

  • 3 Beds
  • 3 Baths
  • ML82042155 MLS
235 Hillside DR, Woodside image
235 Hillside DR, Woodside $2,150,000 ▼

BEST VALUE IN WOODSIDE!! Nestled under Woodside's heritage oaks, this 1929 Woodside Glens retreat offers a rare blend of vintage character, privacy, and views. The nearl...

  • 3 Beds
  • 2 Baths
  • ML82032924 MLS
225 Old Ranch RD, Woodside image
225 Old Ranch RD, Woodside $2,100,000

Welcome to this exceptional 3-bedroom, 2.5-bath Woodside home, built in 2004 and tucked away in a private, secure setting on an expansive 31,798 sq. ft. lot. Surrounded b...

  • 3 Beds
  • 3 Baths
  • ML82065637 MLS

Based on information from the Multiple Listing Service of Hicentral MLS, Ltd. Listings last updated on . Information is deemed reliable but not guaranteed. Copyright: 2026 by HiCentral MLS, Ltd. IDX information is provided exclusively for consumers' personal, non-commercial use. It may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

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All measurements and all calculations of area (i.e., Sq Ft and Acreage) are approximate. Broker has represented to MetroList that Broker has a valid listing signed by seller authorizing placement in the MLS. Above information is provided by Seller and/or other sources and has not been verified by Broker. Copyright 2026 MetroList Services, Inc. The data relating to real estate for sale on this web site comes in part from the Broker Reciprocity Program of MetroList® MLS. All information has been provided by seller/other sources and has not been verified by broker. All interested persons should independently verify the accuracy of all information. Last updated .

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