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Woodside Real Estate Homes & Condos

Featured Woodside Properties For sale

15 Hidden Valley LN, Woodside image
15 Hidden Valley LN, Woodside $38,800,000

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 $34,995,000

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
  • ML82038776 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
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
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
  • 9 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
2120 Stockbridge AVE, Woodside image
2120 Stockbridge AVE, Woodside $6,880,000

Welcome to this exquisite 5-bedroom, 3.5-bath home that combines elegance with an inviting, spacious floor plan. Step through the grand formal entry into a luxurious livi...

  • 5 Beds
  • 4 Baths
  • ML82056698 MLS
103 Toyon CT, Woodside image
103 Toyon CT, Woodside $5,495,000

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
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
950 Espinosa RD, Woodside image
950 Espinosa RD, Woodside $4,295,000

Stunning views of Stanford, San Francisco Bay, and the East Bay, just 10 minutes from downtown Woodside and 4 minutes to Alices Restaurant. Custom-built in 2004 on 1.4 a...

  • 4 Beds
  • 4 Baths
  • ML82037717 MLS
425 Summit Springs RD, Woodside image
425 Summit Springs RD, Woodside $3,998,000 ▼

Tranquil Woodside Retreat Nestled within one of Woodside's most sought-after enclaves, this enchanting single-family residence offers a rare blend of privacy, natural be...

  • 4 Beds
  • 3 Baths
  • ML82039737 MLS
3270 Woodside RD, Woodside image
3270 Woodside RD, Woodside $3,725,000 ▼

Move in today, expand tomorrow. Nearly one-half acre of level land less than one-half mile from the Woodside town center. Fresh paint, refinished hardwood floors, and num...

  • 3 Beds
  • 2 Baths
  • ML82050810 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
1100 Old La Honda RD, Woodside image
1100 Old La Honda RD, Woodside $3,195,000

Luxury retreat offers a serene escape on 9+ acres, secured by an electronic gate. Under 2 miles and just minutes to Alices restarant. Stunning style on one level, the hom...

  • 3 Beds
  • 3 Baths
  • ML82045702 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
232 Highland TER, Woodside image
232 Highland TER, Woodside $2,995,000

Set on approximately one-third acre in a serene Woodside setting, 232 Highland Terrace offers privacy, distinctive architecture, and exceptional indoor/outdoor living. Ma...

  • 4 Beds
  • 3 Baths
  • ML82060102 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
115 Forest View RD, Woodside image
115 Forest View RD, Woodside $1,950,000

Skyline corridor on nearly one-half acre with spectacular unobstructed ocean views and easy access to both the Peninsula and the coast. The two-story floor plan features ...

  • 3 Beds
  • 3 Baths
  • ML82059245 MLS
26 Big Tree RD, Woodside image
26 Big Tree RD, Woodside $1,888,000

An exceptional opportunity to own a premier property in the heart of Woodside, one of the Peninsula's most prestigious and sought-after communities. Located at 26 Big Tre...

  • 4 Beds
  • 4 Baths
  • ML82056831 MLS
221 Highland TER, Woodside image
221 Highland TER, Woodside $1,575,000 ▼

Architectural design takes advantage of expansive views of the western hills from most rooms. The front garden area of the property was carefully designed to create an ...

  • ML81968553 MLS
155 Native Sons RD, Woodside image
155 Native Sons RD, Woodside $998,000 ▼

Hidden at the end of a quiet country lane beneath a magnificent canopy of redwoods lies one of Kings Mountain's rarest opportunities, 3.63 private acres where nature, pri...

  • 1 Beds
  • 1 Baths
  • ML82038622 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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