Woodside, CA Homes for Sale

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  /45

  $5,295,000 Open Sun 2PM - 4PM

  • 4 Beds
  • 3.5 Baths
  • 3,715 Sq Ft

  642 Woodside Way, Woodside, CA 94062

  Whole-Home Transformation & Amazing Views. This magical setting begins with a wine country-style garden entrance and continues out to sweeping western hill views and amazing privacy. A whole-home transformation created a luxurious indoor/outdoor space with designer finishes and an exceptionally bright and light ambiance. The floor plan is arranged with two distinct lower-level wings for the homes

  Erika Demma Compass

  642 Woodside Way, Woodside, CA 94062
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  /31

  $5,995,000

  • 4 Beds
  • 4 Baths
  • 2,970 Sq Ft

  1477 Portola Rd, Woodside, CA 94062

  Welcome to a breathtaking estate crafted from heart redwood, where timeless elegance meets modern luxury. The beautifully updated main residence features four spacious bedrooms along with a renovated kitchen and baths, designed for both comfort and style. Two inviting guest houses provide flexible living options, while a third guest unit serves as a bright, inspiring studio/gym. Soak up the sun

  Kristin Cashin Christie's International Real Estate Sereno

  1477 Portola Rd, Woodside, CA 94062
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  /32

  $6,488,000 Open Sun 1:30PM - 4:30PM

  • 5 Beds
  • 4 Baths
  • 4,190 Sq Ft

  2290 Stockbridge Ave, Woodside, CA 94062

  An extended driveway meanders through more than 1.3 acres of Woodside grounds, leading to this spacious and inviting home offering nearly 4,200 SF of space. Bright and airy interiors, adorned with maple floors and intricate millwork, have been thoughtfully updated over the years with modern living in mind, providing ideal spaces for entertaining or quiet evenings at home. Expansive formal rooms,

  Michael Repka Deleon Realty

  2290 Stockbridge Ave, Woodside, CA 94062
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  /3

  $5,799,000

  • 4 Beds
  • 4 Baths
  • 4,900 Sq Ft

  380 La Questa Way, Woodside, CA 94062

  First time on the market in almost 50 years. This unique setting close to horse trails in Central Woodside offers the opportunity to reimagine the potential of almost 3 park like acres. A private oasis for your dream home and minutes away from 280. Proximate to premier local shops and restaurants, Roberts Market, and highly rated Woodside Elementary School.

  Andrea Ivarsson Christie's International Real Estate Sereno

  380 La Questa Way, Woodside, CA 94062
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  /47

  $4,850,000 Open Sat 2PM - 4PM

  • 4 Beds
  • 3 Baths
  • 3,900 Sq Ft

  252 Raymundo Dr, Woodside, CA 94062

  IN THE HEART OF HORSE COUNTRY, this treasured family farm on 3 acres will provide enjoyment for years to come. Spacious and expansive, the classically simple and refreshed one-level home is designed for effortless indoor/outdoor living. Highlights include a dramatic great room, extra-large kitchen, 4 bedrooms, and seamless access to the pool and enchanting outdoor living spaces. Enhancing the

  Don DeFranco Compass

  252 Raymundo Dr, Woodside, CA 94062
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  /48

  $10,995,000 Open Sun 2PM - 4PM

  • 4 Beds
  • 4.5 Baths
  • 4,185 Sq Ft

  3295 Woodside Rd, Woodside, CA 94062

  A stately Hamptons-style retreat, this exquisite home offers complete privacy just blocks from Town Center and the acclaimed Woodside School. Set behind electronic gates on more than one acre of level land, the property is a showcase of timeless elegance and modern luxury with resort-like amenities. Extensively remodeled, the interiors feature refinished hardwood floors, fresh paint, and

  Erika Demma Compass

  3295 Woodside Rd, Woodside, CA 94062
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  /64

  $5,999,000

  • 5 Beds
  • 4.5 Baths
  • 7,300 Sq Ft

  22 Starwood Dr, Woodside, CA 94062

  This exceptional hilltop residence features dramatic bay views from Mt. Diablo to the coastal mountain range. The Hamptons-inspired shingle home has the ambiance of a resort retreat and the privacy that comes with being adjacent to 5000+ acres of Open Space yet minutes from the heart of Silicon Valley, A giant office suite, complete with lounge, meeting area and private deck is perfect for work

  Scott Hayes Compass

  22 Starwood Dr, Woodside, CA 94062
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  /24

  $4,495,000

  • 4 Beds
  • 3.5 Baths
  • 3,580 Sq Ft

  950 Espinosa Rd, Woodside, CA 94062

  Private retreat with stunning views of Stanford, San Francisco Bay, and the East Bay, just 10 minutes from downtown Woodside. Custom-built in 2004 on 1.4 acres with incredible quality and seismic integrity, this Craftsman home exudes European flair with imported Spanish tile and walnut floors, 12-foot ceilings, and fireplaces in the formal living and dining rooms. The French kitchen features

  Scott Dancer Compass

  950 Espinosa Rd, Woodside, CA 94062
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  /65

  $4,998,000

  • 4 Beds
  • 3 Baths
  • 2,960 Sq Ft

  250 Hardwick Rd, Woodside, CA 94062

  Situated at the end of a quiet cul-de-sac, this exquisite Woodside property has been tastefully renovated and boasts stunning views of the Bay and East Bay hills. With dual oversized primary suites (4 bedrooms, 4 full bathrooms total), this home offers ample space for your growing family or those considering multigenerational living. As you step into the proper foyer, you'll be greeted by warm

  Brian Brunetti Sotheby’s International Realty

  250 Hardwick Rd, Woodside, CA 94062
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  /98

  $7,628,000

  • 5 Beds
  • 6.5 Baths
  • 6,200 Sq Ft

  7 Oak Haven Way, Woodside, CA 94062

  Welcome to Serenity Hill Haven, a once-in-a-lifetime opportunity to own a stunning estate in the coveted Woodside Hills. A 6,200 sq.ft., 5-bedroom, 6.5-bathroom estate, perched on 2.180 acres & engulfs breathtaking Panoramic Bay Views. A sophisticated LR, highlighted by a fireplace & large windows that invite natural light, large walkout w/water feature & spectacular views. Separate DR & chef's

  Alan Canas Engel & Völkers

  7 Oak Haven Way, Woodside, CA 94062
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  /21

  $10,995,000

  • 4 Beds
  • 3 Baths
  • 3,021 Sq Ft

  275 Josselyn Ln, Woodside, CA 94062

  Perfectly and privately situated on nearly 9 sun-filled acres of land, options abound at this very special property: remodel the charming home or build new to create your own dream vision. The choice is yours. The land enjoys breathtaking 180 degree views of the Western Hills and there is a pool, spa, guest house and vast gardens. There is also a 1.2 mile hiking/biking trail encircling the

  Erika Demma Compass

  275 Josselyn Ln, Woodside, CA 94062
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  /33

  $8,995,000 Open Sun 2PM - 4PM

  • 4 Beds
  • 5.5 Baths
  • 5,642 Sq Ft

  333 Raymundo Dr, Woodside, CA 94062

  Amazing price for this stunning completely remodeled home! Located on 3 acres with complete privacy, and close-in convenience, this exceptional property epitomizes luxury living. The elegant sophistication of the interiors rivals luxury resorts with an extensive use of natural stones that transform walls into works of art. Natural light throughout. Book-matched precision is showcased on

  Erika Demma Compass

  333 Raymundo Dr, Woodside, CA 94062
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  /48

  $5,100,000 Open Sat 1PM - 3PM

  • 5 Beds
  • 7 Baths
  • 6,420 Sq Ft

  12 Colton Ct, Redwood City, CA 94062

  Introducing a stunning new listing in the highly sought-after Colton Court! This magnificent 5-bedroom, 5.5-bathroom home spans an impressive 6,420 square feet and is situated on a sprawling nearly half-acre lot. Each of the five bedrooms features its own ensuite bathroom, providing ultimate privacy and convenience. The thoughtfully designed layout includes a downstairs bedroom, perfect for

  Michele Harkov Compass

  12 Colton Ct, Redwood City, CA 94062
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  /2

  $13,900,000

  • 6 Beds
  • 8 Baths
  • 5,715 Sq Ft

  140 Eleanor Dr, Woodside, CA 94062

  Masterfully Renovated Bay-View Vineyard Estate. This extraordinary estate presents a masterfully executed whole-home renovation, captivating San Francisco Bay views, and resort-style amenities. Encompassing 1.8 acres of fully landscaped grounds, the property also includes a Chardonnay vineyard, two wine cellars, and expansive indoor and outdoor entertaining spaces designed for grand gatherings.

  Erika Demma Compass

  140 Eleanor Dr, Woodside, CA 94062
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  /47

  $825,000 Open Sat 12:30PM - 4:30PM

  • 1 Bed
  • 1 Bath
  • 910 Sq Ft

  13 & 15 Big Tree Way, Woodside, CA 94062

  Welcome to these cabins nestled in the quiet, redwood-lined hills of Woodside with the Portola Valley School System! Two vintage cabins (needs work) on a single lot - the perfect blend of rustic charm. Enjoy the peace of a small mountain community without being too far from modern essentials like groceries, shops, and entertainment. The front cabin welcomes you with a large deck, an inviting

  Doug Gonzalez Coldwell Banker Realty

  13 & 15 Big Tree Way, Woodside, CA 94062
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  /26

  $2,995,000

  • 3 Beds
  • 3 Baths
  • 1,678 Sq Ft

  171 Old la Honda Rd, Woodside, CA 94062

  Lakeview Lodge: A Storybook Sanctuary with Iconic Views and a Surprisingly Convenient Location. Every now and then, a property comes along that feels pulled from the pages of a storybook. Lakeview Lodge is one of those rare places, loved and nurtured by its owners for 29 years for the simplest reason: its just that special. Perched above the treetops with sweeping views of Stanfords Jasper Ridge,

  Ginny Kavanaugh Coldwell Banker Realty

  171 Old la Honda Rd, Woodside, CA 94062
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  /40

  $14,500,000

  • 5 Beds
  • 6 Baths
  • 6,135 Sq Ft

  258 Kings Mountain Rd, Woodside, CA 94062

  Panoramic Western Hills views set the stage for this stunning Central Woodside estate, nestled on approximately 3.2 flat, fully usable acres just moments from downtown shops, dining, and top-rated Woodside Elementary. Designed for both comfort and function, the primarily single-level layout includes a spacious primary suite, multiple living areas, and a bright eat-in kitchen opening to a large

  David Bergman Intero Real Estate Services

  258 Kings Mountain Rd, Woodside, CA 94062
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  /38

  $3,495,000

  • 3 Beds
  • 2 Baths
  • 2,850 Sq Ft

  9 Summit Rd, Woodside, CA 94062

  Embrace Nature 5.19 Acre Gated Magical Woodside Retreat. Contemporary style, huge windows, soaring ceilings that reach to amazing heights, pyramid copper roofs, 10 gig network intra-structure, and skylights. Unique style/constructionset in the magical setting of a majestic Redwood grove, surrounded by Silicon Valley Views. 3 bed, 2 bath home of ~2,850 sf. The open plan has a kitchen with custom

  Peter Cowperthwaite Golden Gate Sotheby's International Realty

  9 Summit Rd, Woodside, CA 94062
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  /3

  $999,000

  • Land
  • 0.34 Acre
  • $2,938,235 per Acre

  18 Montecito Rd, Redwood City, CA 94062

  This lot is located in a fantastic location. Fantastic price for close in Woodside. Great schools. Close to Portola Rd. Buyer to investigate the reports required by Town of Woodside for site approval and permits needed to build. You could potentially build approx 1332 sf. home with a 800sf ADU. Priced to sell. 2nd lot available #12 Montecito is 3.7 acre for 2,500,000. Buy both and have 4 acres

  Shawnna Sullivan Coldwell Banker Realty

  18 Montecito Rd, Redwood City, CA 94062
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  /49

  $2,195,000

  • 4 Beds
  • 2 Baths
  • 1,900 Sq Ft

  319 Highland Terrace, Woodside, CA 94062

  Tucked away in the enchanting Woodside Glens neighborhood, this circa mid-1930s cottage is wrapped with lush gardens on a level lot, presenting a rare opportunity not seen on the market in four generations. Thoughtfully maintained and updated, the home showcases its original charm with a leaded glass front door and handcrafted built-ins throughout. A welcoming foyer, inviting living spaces, and a

  Deborah Kehrberg Compass

  319 Highland Terrace, Woodside, CA 94062
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  /12

  $748,000

  • Land
  • 1.25 Acres
  • $596,539 per Acre

  559 Patrol Rd, Woodside, CA 94062

  Build your dream home on this over 1.2-acre lot in the prestigious town of Woodside. Surrounded by parks and enjoy trails made for hiking, biking, and horses. Conveniently close to Highway 280 providing easy access for all your commutes north to San Francisco and south to Silicon Valley while offering a peaceful setting yet close to Woodisde Town Center, Roberts Market and award winning Woodiside

  Greg Garcia Sequoia Realty Services

  559 Patrol Rd, Woodside, CA 94062
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  /86

  $15,998,000

  • 5 Beds
  • 5.5 Baths
  • 5,982 Sq Ft

  3 Vintage Ct, Woodside, CA 94062

  Stunning Custom Built 3 Level Home with Guest Cottage and Pool on 4.37+/- Acres with Stables and Riding Ring on Private Cul-de-Sac in Central Woodside. 5 Bedrooms. 5.5 Bathrooms. Living Room Features Vaulted Ceilings, Wood Floors, and Floor-to-Ceiling Windows. Spacious Kitchen with Large Island, Peninsula and Views of the Pool and a Pond. Intimate Family Room with Sliding Glass Doors to Pool.

  Keri Nicholas Parc Agency Corporation

  3 Vintage Ct, Woodside, CA 94062
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  $3,795,000 Open Sun 1PM - 4PM

  • 3 Beds
  • 3.5 Baths
  • 2,890 Sq Ft

  625 W Glen Way, Woodside, CA 94062

  Contemporary luxury with breathtaking western hill views from a close-in location with access to acclaimed Woodside Elementary School (K-8). Whole-home renovation in 2020 to 2022 with open concept design and three levels comprising 3 bedroom suites, dedicated office, 3.5 designer appointed baths, and spacious kitchen. Maple floors on the main level, towering vaulted all-wood ceilings, entire

  Scott Dancer Compass

  625 W Glen Way, Woodside, CA 94062
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  /19

  $16,995,000

  • 6 Beds
  • 7 Baths
  • 8,470 Sq Ft

  961 High Rd, Woodside, CA 94062

  Completely Renovated inside and out! This architectural Jewel with Dazzling Views! Originally imagined by the visionary architect Gardner Dailey in 1934, this exceptional estate is a testament to his architectural brilliance updated with a complete comprehensive renovation. The classic style of a country manor is presented, creating a visual symphony from the slate tile roof to the leaded glass

  Erika Demma Compass

  961 High Rd, Woodside, CA 94062
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  /18

  $4,995,000

  • Land
  • 2.84 Acres
  • $1,759,422 per Acre

  941 High Rd, Woodside, CA 94062

  2.8 Acres of Buildable Land Next to Menlo Country Club! This exceptional 2.8-acre vacant parcel presents an extraordinary opportunity in a prestigious setting, offering endless possibilities for building. Perfectly situated beside a magnificent high-end estate, also available for sale at 961 High Road, this property can stand on its own or combine with the neighboring estate for an unparalleled

  Erika Demma Compass

  941 High Rd, Woodside, CA 94062
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  /3

  $1,500,000

  • 2 Beds
  • 1 Bath
  • 1,690 Sq Ft

  4214 Jefferson Ave, Woodside, CA 94062

  Amazing opportunity to build a beautiful new home in Woodside just 2 miles from the town center and with access to acclaimed Woodside School (Pre K-8). Architectural plans, by the renowned firm, Mason Architects, have already been paid & approved by the City of Woodside. The plans include a 3,214 sf main home and 512 sq. ft ADU. The main level of the home features a formal living and dining room

  Casey Sternsmith Compass

  4214 Jefferson Ave, Woodside, CA 94062
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  /27

  $399,000

  • Land
  • 3.22 Acres
  • $123,913 per Acre

  0 Old Comstock Rd, Woodside, CA 94062

  Immerse yourself in nature on this beautiful, tree-filled parcel. Located at the end of the unpaved "Old Comstock Road," this gently sloping property offers ultimate privacy and a peaceful retreat. See the plot map for more details. The walk down the re-graded road is an experience in itself, leading you to a magnificent parcel surrounded by towering redwoods, expansive views, and the calming

  Aminta Sevilla Montclair Real Estate Services

  0 Old Comstock Rd, Woodside, CA 94062
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  /11

  $2,975,000

  • 4 Beds
  • 3 Baths
  • 3,980 Sq Ft

  885 Patrol Rd, Woodside, CA 94062

  Have vision and want to have the ultimate compound? This is a fixer with HUGE potential. This is a one-of-a-kind Nature-Lover's Tahoe-Style home and has so much upside and flat land. You will love what can be done here including adding an ADU to add even more sq footage (SB9). This is the perfect compound for a multi-generational family or place for Mom and Dad. Nestled on over 1.5 acres,

  Butch Haze Compass

  885 Patrol Rd, Woodside, CA 94062
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  /3

  $299,000

  • Land
  • 1.06 Acres
  • $283,144 per Acre

  0 Swett Rd, Woodside, CA 94062

  Opportunity to build and live in the prestigious rural community of Kings Mountain. Lots of stunning Redwoods. Water is available via the local water district. Septic will be needed. Parcel includes Ap #'s 067-222-080 & 067-222-100 for a total of approx 5.5 acres. Property extends from Swett Rd to Tunitas Creek Rd.

  David Cline Coldwell Banker Realty

  0 Swett Rd, Woodside, CA 94062
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  /19

  $13,850,000

  • 4 Beds
  • 8 Baths
  • 10,504 Sq Ft

  490 Las Pulgas Dr, Woodside, CA 94062

  Extraordinary residence with stunning panoramic San Francisco Bay views. Opulence and European inspiration at every turn. Impeccably crafted by renowned builder Markay Johnson in 2014 on a private gated lane with gated driveway. Lavish beauty throughout the home with hand-selected marble from Milan, elaborate millwork, Doric columns, intricate carvings, and gilded details. All-marble staircase

  Scott Dancer Compass

  490 Las Pulgas Dr, Woodside, CA 94062
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  /44

  $2,975,000 Open Sat 1PM - 3PM

  • 4 Beds
  • 2 Baths
  • 2,490 Sq Ft

  1 Hayfields Rd, Portola Valley, CA 94028

  Welcome to 1 Hayfields Road! Motivated Seller - best price on the flats of Portola Valley!!! Nestled in a serene and peaceful country setting, this inviting rancher offers the perfect balance of privacy and convenience. With stunning access to nearby trails, you can enjoy the natural beauty right outside your doorstep, whether you're hiking, biking, or simply soaking in the outdoors. Inside,

  Debora Smith Sotheby's Intl Rlty

  1 Hayfields Rd, Portola Valley, CA 94028
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  /37

  $3,298,000

  • 4 Beds
  • 4 Baths
  • 3,725 Sq Ft

  33 Bear Glen Dr, Woodside, CA 94062

  ARCHITECTURAL DIGEST MODERN OF ULTIMATE VIEWS! EXCLUSIVE GATED COMMUNITY, WOODSIDE SCHOOLS, HEART OF SILICON VALLEY LIFESTYLE! Bespoke architecturally singificant modern overlooking the Bay. Private natural wonderland with the Peninsula's best Bay vistas. Custom designed in 1991 by celebrated architect Paul Gilger, it's no wonder this home takes on cinematic qualities: around the same time Gilger

  Geoffrey Nelson Coldwell Banker Realty

  33 Bear Glen Dr, Woodside, CA 94062
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  /15

  $490,000

  • Land
  • 3.99 Acres
  • $122,807 per Acre

  446 Old la Honda Rd, Woodside, CA 94062

  Nestled amidst the estate-like homes of Woodside, this nearly 4-acre parcel offers a serene, secluded retreat. The location is incredible - less than 10 minutes away from Hwy 280 and the business world along Sand Hill Road and only 10 minutes from the hilltop restaraunt - Alices Restraunt. The property is accessed via a private shared road that brings you into the core of this gently sloped

  Joseph Suarez Coldwell Banker Realty

  446 Old la Honda Rd, Woodside, CA 94062
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  /10

  $1,998,000

  • Land
  • 1.97 Acres
  • $1,014,213 per Acre

  966 Godetia Dr, Woodside, CA 94062

  Nestled on 1.97 acres of serene, sun-drenched land, this exceptional property offers the perfect canvas to build your dream estate in Central Woodside. With access from both Godetia Way and Jefferson Avenue, this prime lot caters to developers, investors, and visionary buyers alike. Boasting two potential building sites, this verdant parcel provides a tranquil setting surrounded by natural

  Francesca Lampert Coldwell Banker Realty

  966 Godetia Dr, Woodside, CA 94062
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  /49

  $2,500,000

  • Land
  • 3.66 Acres
  • $683,434 per Acre

  12 Montecito Rd, Woodside, CA 94062

  New price is fantastic. A rare to find beautiful 4 acres property in fabulous Woodside! Sold separately or together. Very close to everything in private country setting with plenty of sunshine and majestic trees all around. A quick drive from Hwy 280 at Sand Hill Road. to Portola Rd. Build your dream home. Owner had plans to build a family compound. 2 lots available, lot #18 $999k for15kplus

  Shawnna Sullivan Coldwell Banker Realty

  12 Montecito Rd, Woodside, CA 94062
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  /10

  $690,000

  • Land
  • 3.00 Acres
  • $230,000 per Acre

  0-250 Heacox Rd, Woodside, CA 94062

  Price improvement. Excellent opportunity to build on this oak-studded parcel. Artist's rendering of home. 4000 ft2 home deemed possible by Lea and Braze engineers; price includes feasibility study, survey and septic perc test results. This land could be a great location for your estate home or quiet get-away. One mile from Thomas Fogarty Winery. Plenty of room for horses, animals and/or hobby

  Kim Hansen Golden Gate Sotheby's International Realty

  0-250 Heacox Rd, Woodside, CA 94062
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  /8

  $740,000

  • Land
  • 4.40 Acres
  • $168,182 per Acre

  0-220 Heacox Rd, Woodside, CA 94062

  Price reduction. Excellent opportunity to build on this peaceful, sun-drenched parcel that has nice flat area for development. Artist's rendering of home. 3800 ft2 home plus 1000 ft2 ADU deemed possible by Lea and Braze engineers; price includes feasibility study, survey and septic perc test results. This land could be a great location for your estate home or quiet get-away. Plenty of room for

  Kim Hansen Golden Gate Sotheby's International Realty

  0-220 Heacox Rd, Woodside, CA 94062
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  /31

  $159,000

  • Land
  • 2.01 Acres
  • $79,156 per Acre

  000 Purisima Rd, Woodside, CA 94062

  This is it! Your meditation getaway retreat is waiting with a vision! Approximately 2 acres of Peacefulness and Tranquility describe this unique location on Kings Mt in Woodside. Refresh your inner senses among glorious redwoods, spectacular views, and serene moments that can capture the feel of being in a remote mountain area while being a short distance from the hustle and bustle of everyday

  Dante Razzini Intero Real Estate Services

  000 Purisima Rd, Woodside, CA 94062
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  /3

  $1,500,000

  • Land
  • 0.59 Acre
  • $2,542,373 per Acre

  215 Grandview Dr, Woodside, CA 94062

  Plans included to build an appx 2000 square foot home, an appx 715 square foot ADU and a full 2 car garage with beautiful views of the bay, city and mountains. Conveniently located right off of Woodside Road. Plans available by request.

  Vicky Costantini Compass

  215 Grandview Dr, Woodside, CA 94062
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  /17

  $1,995,000

  • Land
  • 0.34 Acre
  • $5,941,036 per Acre

  221 Highland Terrace, Woodside, CA 94062

  Fully approved plans to build a modern home with standing seam roof, high interior ceilings, and peaceful views from every room. Designed by renown firm CJW Architechure of Portola Valley. 3615 total sq. ft. consisting of 3,175 livable & 440 garage. 3 bedroom, 2.5 bath house plus ADU with separate entrance 1 bedroom, 1 bath. All public utilities including public sewers and California water

  Scott Dancer Compass

  221 Highland Terrace, Woodside, CA 94062

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