San Gregorio, CA Homes for Sale

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  /44

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

  • 4 Beds
  • 2.5 Baths
  • 2,260 Sq Ft

  425 Summit Springs Rd, Woodside, CA 94062

  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 beauty, and timeless appeal. Set on expansive, level to gently sloping grounds, the property is ideal for equestrian use, featuring serene open spaces framed by mature trees and lush, thoughtfully designed landscaping. Bathed in

  

  Christienne Hadley

  Coldwell Banker Realty

  (650) 628-8507

  425 Summit Springs Rd, Woodside, CA 94062
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  /70

  $5,388,000 Open Sun 2:30PM - 4:30PM

  • 4 Beds
  • 3.5 Baths
  • 3,520 Sq Ft

  140 Ridgeway Rd, Woodside, CA 94062

  Set on beautifully landscaped grounds with sweeping Bay views, this impeccably maintained Woodside residence offers a rare blend of privacy, scale, and resort inspired living. Thoughtfully designed to balance formal and casual living, the home features a gracious entry introducing light filled interiors with high ceilings, refined millwork, and an elegant flow throughout. The living and dining

  Caroline Dinsmore The Agency

  140 Ridgeway Rd, Woodside, CA 94062
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  /51

  $11,988,000

  • 5 Beds
  • 5.5 Baths
  • 6,410 Sq Ft

  160 Phillip Rd, Woodside, CA 94062

  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 trees and lush foliage, it conveys a quiet sense of luxurious seclusion. Inside, more than 6,400 total SF includes a dramatic foyer with columns, expansive formal rooms, a chef's kitchen, private office, theater, and five

  Michael Repka Deleon Realty

  160 Phillip Rd, Woodside, CA 94062
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  /55

  $12,988,000

  • 6 Beds
  • 5.5 Baths
  • 6,340 Sq Ft

  1142 Moore Rd, Woodside, CA 94062

  Discover this exceptional opportunity to own a generational estate spanning 7 acres across 3 separate parcels, each with its own APN. Through a private gate & down a long winding driveway, you're greeted by a circular motor court with incredible views of the Santa Cruz Mountains. The main residence offers 4,340 sqft featuring 6 beds & 5.5 baths, with exceptional upgrades throughout. On the east

  Kia Amini Compass

  1142 Moore Rd, Woodside, CA 94062
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  /43

  $2,888,000 Open Sun 1PM - 3PM

  • 4 Beds
  • 4 Baths
  • 4,671 Sq Ft

  13370 Skyline Blvd, Redwood City, CA 94062

  This Custom built home is perched high on the Skyline ridge (approx. 2000' elevation) with the Pacific Ocean on one side the SF Bay on the other. Located in the exclusive Woodside neighborhood of Kings Mountain, this modern retreat was built with natural filtered light through the Redwoods in mind surrounded by about an acre of wooded privacy. Think open floor plan flow, soaring ceilings, and a

  Jonathan Lee A 2 M Real Estate

  13370 Skyline Blvd, Redwood City, CA 94062
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  /67

  $4,190,000 Open Sun 2PM - 4PM

  • 5 Beds
  • 3 Baths
  • 3,650 Sq Ft

  720 Temescal Way, Emerald Hills, CA 94062

  Set atop a coveted Emerald Hills street on a rare flat 12,183 sq ft lot, this beautifully staged 3650 residence offers an exceptional blend of comfort, style, and family-friendly living. The home features a spacious single-level layout with an expansive primary retreat, a dedicated office opening to the patio through elegant French doors, and a separate bedroom wing that creates ideal space for

  Vicky Costantini Compass

  720 Temescal Way, Emerald Hills, CA 94062
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  /37

  $6,988,000

  • 4 Beds
  • 4.5 Baths
  • 4,800 Sq Ft

  199 Hardwick Rd, Woodside, CA 94062

  Sweeping, unobstructed San Francisco Bay views define this contemporary estate set on more than an acre in Woodside Hills, with dramatic scenery enjoyed from nearly every room. Walls of glass, soaring ceilings, and refined finishes including marble, granite, and travertine floors create a striking yet warm aesthetic throughout approximately 4,800 square feet across two levels. The expansive

  Michael Repka Deleon Realty

  199 Hardwick Rd, Woodside, CA 94062
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  /78

  $2,099,000

  • 3 Beds
  • 2.5 Baths
  • 2,670 Sq Ft

  13872 Silver Sky Way, Woodside, CA 94062

  Spanning 2,670 square feet of living space, this home envelopes you with warmth and charm from the moment you enter. Sunlight filters through towering redwoods, creating a serene atmosphere throughout. Refinished hardwood floors and thoughtful modern updates blend timeless quality with everyday comfort. The spacious floor plan flows seamlessly, ideal for both daily living and entertaining. The

  Joakim Bye Ocean Element Real Estate

  13872 Silver Sky Way, Woodside, CA 94062
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  /65

  $3,780,000

  • 4 Beds
  • 4 Baths
  • 2,529 Sq Ft

  810 Glencrag Way, Woodside, CA 94062

  Hidden gem on nearly half an acre behind a private gated entry with professionally landscaped grounds, mature orchard trees, & year-round blooms. The exceptional single-level 3 bedroom, 3 bath 1,842 sqft main residence was completely renovated in 2017 & features an open, light-filled floor plan with skylights & French Oak floors throughout. The entry opens to a spacious living room with custom

  John Shroyer Golden Gate Sotheby's International Realty

  810 Glencrag Way, Woodside, CA 94062
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  /59

  $3,995,000

  • 6 Beds
  • 3.5 Baths
  • 5,390 Sq Ft

  90 Hayfields Rd, Portola Valley, CA 94028

  This home personifies tranquility. Nestled in a serene country setting just minutes from I-280 and top-rated Portola Valley schools, this beautifully updated 6-bedroom, 2- Office 3+-bathroom custom designed home perfectly balances rural privacy with modern convenience. The interior boasts an expansive, light-filled atmosphere defined by cathedral ceilings and large windows that frame the

  Peter Cowperthwaite Golden Gate Sotheby's International Realty

  90 Hayfields Rd, Portola Valley, CA 94028
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  /85

  $3,798,000

  • 4 Beds
  • 3 Baths
  • 2,682 Sq Ft

  2570 Purisima Creek Rd, Half Moon Bay, CA 94019

  Set on approximately 8.5 private acres in coveted Half Moon Bay, this beautifully remodeled contemporary ranch offers the rare combination of refined living and exceptional equestrian amenities just minutes from town. The home has been thoughtfully redesigned with a clean, modern aesthetic and an effortless indoor-outdoor flow. A dramatic living room anchored by an architectural steel fireplace

  Dana Cappiello Sotheby's Intl Rlty

  2570 Purisima Creek Rd, Half Moon Bay, CA 94019
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  /59

  $3,988,800 Open Sun 1:30PM - 4PM

  • 5 Beds
  • 4 Baths
  • 2,600 Sq Ft

  236 Ferndale Way, Emerald Hills, CA 94062

  Beautiful contemporary home built in 2002, privately set back on a serene 10,450 sq ft lot in sought-after Emerald Hills with direct access to Edgewood Park trails. Formal entry with statement staircase and honed travertine floors throughout the main level. Sunken living room with fireplace and formal dining room with rich moldings and elegant wainscoting, ideal for entertaining. The expansive

  Vicky Costantini Compass

  236 Ferndale Way, Emerald Hills, CA 94062
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  $4,688,800 Open Sun 2PM - 4PM

  • 4 Beds
  • 2.5 Baths
  • 3,052 Sq Ft

  1111 Eden Bower Ln, Redwood City, CA 94061

  Enjoy exceptional indoor-outdoor living in this stunning single-story ranch home in Redwood City. Spanning approx. 3,000 sq ft on a generous 13,000 sq ft lot, this home showcases sweeping Bay Area views, abundant natural light, and a seamless open floorplan with high ceilings and stylish tile floors. Walls of windows connect the main living spaces to the backyard oasis, featuring a pool with

  Vicky Costantini Compass

  1111 Eden Bower Ln, Redwood City, CA 94061
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  /65

  $6,695,000

  • 5 Beds
  • 5 Baths
  • 3,700 Sq Ft

  330 Ridgeway Rd, Woodside, CA 94062

  Set on a flat acre of gorgeously manicured grounds. This single story home borrows transitional architectural tones from the French countryside. The circular driveway leads up to a large 3 car garage. Five bedrooms that come with a separate guest house, sports court, large pool with covered grotto like spa, adjacent bath with changing room. Outdoor kitchen covered by a palapa, the perfect shade

  Mariana Pappalardo Compass

  330 Ridgeway Rd, Woodside, CA 94062
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  /38

  $4,695,000 Open Sun 2PM - 4PM

  • 4 Beds
  • 3.5 Baths
  • 2,910 Sq Ft

  175 Alta Mesa Rd, Woodside, CA 94062

  Known as the High Hilltop home, you will be surprised by this move-in-ready gems breathtaking views of the Western Hills, portions of the SF Bay and colorful sunsets. Closely adjacent to Kite Hill open space trail network and within easy and safe walking distance to the acclaimed Woodside School (pre-K to 8th) and Town Center restaurants and shops, this wonderful two-story home, situated in a

  Helen Miller Compass

  175 Alta Mesa Rd, Woodside, CA 94062
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  /24

  $3,688,000

  • 4 Beds
  • 8 Baths
  • 11,885 Sq Ft

  1 Reids Roost Rd, Redwood City, CA 94062

  SKY VILLA: RE-IMAGINE ROYALTY IN THE WOODS. Sky Villa is an opportunity to DREAM BIG with unmatched grandeur & privacy. An Italian Renaissance mansion engineered to commercial standards, but now awaiting your completion. Easy ingress/egress off Hwy 92 and Skyline presents this estate in sequestered privacy. A long driveway descends to the motor court & the Villa's monumental architectural scale.

  Geoffrey Nelson Coldwell Banker Realty

  1 Reids Roost Rd, Redwood City, CA 94062
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  /24

  $4,295,000

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

  950 Espinosa Rd, Woodside, CA 94062

  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 acres with INCREDIBLE QUALITY AND SEISMIC INTEGRITY, this home exudes quality features including walnut floors, 12-foot ceilings, and fireplaces in the living and dining rooms. The large kitchen features Carrara marble and zinc

  Scott Dancer Compass

  950 Espinosa Rd, Woodside, CA 94062
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  /18

  $3,750,000 Open Sun 2PM - 4PM

  • 3 Beds
  • 2.5 Baths
  • 2,790 Sq Ft

  573 Patrol Rd, Woodside, CA 94062

  A setting of extraordinary natural beauty defines this distinctive redwood retreat, where architecture and environment exist in quiet harmony. Designed by renowned builder Jerry Ellis, the home is masterfully engineered above a seasonal creek, where the gentle movement of water enhances the serene surroundings of more than 2 acres. Dramatic ceilings and expansive walls of glass create a seamless

  Scott Dancer Compass

  573 Patrol Rd, Woodside, CA 94062
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  /26

  $7,490,000

  • 4 Beds
  • 3.5 Baths
  • 7,274 Sq Ft

  835 La Honda Rd, Woodside, CA 94062

  7.7 gated acres with Views, Pool, Tennis Court, & Guest house. Bordered by Thornewood Open Space Preserve, and with incredible San Francisco Bay and western hill views. Main home with dramatic formal rooms, walls of glass, and tile or hardwood floors. Sleek modern kitchen with oversized island seating. Main level primary suite with views and spa-like bath plus secondary suite. Lower-level

  Scott Dancer Compass

  835 La Honda Rd, Woodside, CA 94062
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  /101

  $4,788,000 Open Sun 2PM - 4PM

  • 5 Beds
  • 3.5 Baths
  • 4,170 Sq Ft

  902 Fallen Leaf Way, Emerald Hills, CA 94062

  Set on an expansive 17,837 sq. ft. lot in desirable Emerald Hills, 902 Fallen Leaf Way offers privacy, scale, and effortless living. The 4,170 sq. ft. main home features 5 beds and 3.5 baths with a light-filled, open floor plan with partial hardwood floors. Eat-in kitchen with pantry opens to a spacious family room providing flexibility for gathering and relaxing. A large living room and dining

  Runa Magowan Coldwell Banker Realty

  902 Fallen Leaf Way, Emerald Hills, CA 94062
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  /35

  $4,498,000 Open Sun 2PM - 4PM

  • 4 Beds
  • 3.5 Baths
  • 3,365 Sq Ft

  199 Brookwood Rd, Woodside, CA 94062

  One Acre with Sweeping Bay Views in Woodside Hills. Sweeping San Francisco Bay views take center stage at this exceptional Woodside Hills property with fresh updates throughout. Spanning one acre, the elevated corner lot is positioned to capture the expansive views while also providing generous level areas for outdoor living. Enhancing the setting is the gentle sound of a meandering creek and

  Erika Demma Compass

  199 Brookwood Rd, Woodside, CA 94062
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  /61

  $3,500,000 Open Sun 2PM - 4PM

  • 4 Beds
  • 4.5 Baths
  • 3,130 Sq Ft

  808 Mohican Way, Redwood City, CA 94062

  808 Mohican is a large, beautifully improved home with a smart and adaptable floor plan, remodeled interiors, and strong potential for many different living needs. With its excellent location, top school district, and exceptional climate, it offers a rare opportunity to enjoy both comfort and long-term value.

  Anne Oliva Omarshall, Inc

  808 Mohican Way, Redwood City, CA 94062
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  /16

  $648,000

  • Land

  559 Patrol Rd, Woodside, CA 94062

  Build your dream home on this exceptional 1.2+ acre lot in the prestigious town of Woodside. Surrounded by open space and scenic parks, the property offers direct access to miles of trails perfect for hiking, biking, and horseback riding embracing the true Woodside lifestyle. Ideally located near Interstate 280, youll enjoy convenient access north to San Francisco and south to Silicon Valley, all

  Greg Garcia Sequoia Realty Services

  559 Patrol Rd, Woodside, CA 94062
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  /17

  $1,749,000

  • Land
  • 14,627 Sq Ft
  • $5,208,457 per Acre

  221 Highland Terrace, Woodside, CA 94062

  Build up to 3615 total sq. ft. consisting of 3,175 livable & 440 garage. All public utilities including public sewers and California water service. Highland Terrace has long been one of the most desirable streets in the Woodside community of "The Glens". This lot was held for decades by the prior owner of the adjacent home. Truly a rare opportunity find a vacant parcel where you can create a new

  Scott Dancer Compass

  221 Highland Terrace, Woodside, CA 94062
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  /2

  $1,100,000

  • Land
  • 25,439 Sq Ft
  • $1,883,562 per Acre

  215 Grandview Dr, Woodside, CA 94062

  Spacious lot with a view on beautiful Grandview in Woodside! Bring your contractor to build your dream home!

  Vicky Costantini Compass

  215 Grandview Dr, Woodside, CA 94062
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  /16

  $715,000

  • 2 Beds
  • 1 Bath
  • 916 Sq Ft

  4004 Farm Hill Blvd Unit 303, Redwood City, CA 94061

  Great opportunity to purchase this private top-floor condo in the sought-after Farm Hill Vista Community! Light and bright with a large balcony off the living room and master bedroom overlooking tranquil, verdant views. The nicely updated kitchen overlooks the lush central grass area and the pool and has plenty of storage/pantry. The expansive living room and dining area are filled with natural

  Leslie Woods Christie's International Real Estate Sereno

  4004 Farm Hill Blvd Unit 303, Redwood City, CA 94061
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  /6

  $450,000

  • Land
  • 5.64 Acres
  • $79,764 per Acre

  LOT27 Old la Honda Rd, Woodside, CA 94062

  Tucked into the tranquil forested hills of Woodside, this serene 5.64-acre parcel offers an immersive escape into nature. Surrounded by mature trees, quiet trails, and peaceful open space, the property is perfect for those seeking solitude, fresh air, and natural beauty—just minutes from the 280 freeway and an easy route to Silicon Valley. Enjoy hiking, biking, or simply relaxing beneath the

  Mike Continillo Villa Propertes

  LOT27 Old la Honda Rd, Woodside, CA 94062
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  /45

  $2,350,000

  • 3 Beds
  • 2 Baths
  • 2,200 Sq Ft

  235 Hillside Dr, Woodside, CA 94062

  MOTIVATED SELLER! Nestled under Woodside's heritage oaks, this 1929 Woodside Glens retreat offers a rare blend of vintage character, privacy, and views. Spanning approximately 2,200 sq. ft. on a nearly 0.5 acre lot, this home features verdant scenery and a wrap-around deck to take it all in. The main level boasts a large, open-beam living room anchored by a cozy wood-burning stove, and is

  Stephen Rumberg Keller Williams Realty-Silicon Valley

  235 Hillside Dr, Woodside, CA 94062
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  /12

  $2,998,000

  • Land
  • 1.28 Acres
  • $2,346,955 per Acre

  0 W California Way, Redwood City, CA 94062

  DREAM ON: magnificent Emerald Hills is inviting developers, investors, and future homeowners to bring their vision to life on these five adjacent uphill parcels, perched gracefully atop a peaceful hill, nestled in the heart of Silicon Valley just minutes from the vibrant Redwood City Downtown. This serene location offers the perfect balance of privacy, convenience, sweeping canyon views, public

  AnaMaria Cojocaru Berkshire Hathaway HomeServices DrysdaleProperties

  0 W California Way, Redwood City, CA 94062
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  /19

  $1,549,000

  • 4 Beds
  • 1 Bath
  • 1,420 Sq Ft

  12450 Skyline Blvd, Redwood City, CA 94062

  Tucked away in the serene hills of Woodside, this rare 4-bedroom, 1-bath fixer offers an exceptional opportunity to create a true estate on over an acre of land. Surrounded by natural beauty and capturing sweeping ocean views, the property provides a peaceful, private setting that feels worlds away, yet remains conveniently close to major freeway access. This is a dream opportunity for

  Ulrich Gabriel Luxe Realty Group

  12450 Skyline Blvd, Redwood City, CA 94062
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  /10

  $4,499,000

  • Land

  941 High Rd, Woodside, CA 94062

  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, offering endless possibilities for building. The vacant land, bordering the Menlo Country Club, offers gently rolling terrain with open meadows, wildflowers, perimeter trees, and views of the East Bay hills. With a serene landscape

  Erika Demma Compass

  941 High Rd, Woodside, CA 94062
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  /65

  $14,900,000

  • 4 Beds
  • 4.5 Baths
  • 7,155 Sq Ft

  600 Moore Rd, Woodside, CA 94062

  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 meticulously renovated sanctuary blends old-world artistry, hand-painted murals, artisan tile, and beamed ceilings with the peace of mind of enterprise-grade infrastructure. The grounds are a private resort masterpiece designed

  Erika Demma Compass

  600 Moore Rd, Woodside, CA 94062
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  /13

  $12,998,000

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

  490 Las Pulgas Dr, Woodside, CA 94062

  Extraordinary residence on 5.32 acres with opulence and European inspiration at every turn. Impeccably crafted by renowned builder Markay Johnson in 2014 on a private gated lane with gated driveway and sweeping views of San Francisco Bay. Lavish beauty throughout the home with hand-selected marble from Milan, elaborate millwork, Doric columns, intricate carvings, and gilded details. All-marble

  Scott Dancer Compass

  490 Las Pulgas Dr, Woodside, CA 94062
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  /42

  $2,395,000

  • 4 Beds
  • 3 Baths
  • 2,760 Sq Ft

  255 Allen Rd, Redwood City, CA 94062

  An exceptional Woodside estate set on approximately 6.6 acres, this private 4-bed, 3-bath residence offers a rare opportunity to experience refined living surrounded by nature. Encompassing approximately 2,760 sq ft, the home is thoughtfully designed to capture captivating views of the surrounding mountains & clear across the Bay while providing a serene retreat just moments from local amenities.

  Ricky Flores Golden Gate Sotheby's International Realty

  255 Allen Rd, Redwood City, CA 94062
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  /19

  $1,749,000

  • Land
  • 23,343 Sq Ft
  • $3,263,669 per Acre

  000 Lakeview Way, Redwood City, CA 94062

  Build Your Dream Home in Prestigious Emerald Hills! An exceptional opportunity to design and build your custom residence in one of the Peninsula's most desirable neighborhoods. This prime 23,345 SqFt conforming lot offers sweeping Bay views, privacy, and a gently contoured setting ideal for a beautiful home with a private driveway. Extensive groundwork is complete: recorded lot split approved by

  Jessica Eva Golden Gate Sotheby's International Realty

  000 Lakeview Way, Redwood City, CA 94062
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  /40

  $2,699,000 Open Sun 2PM - 4PM

  • 2 Beds
  • 2.5 Baths
  • 1,150 Sq Ft

  271 Sylvan Way, Emerald Hills, CA 94062

  A Sprawling Creative Compound & Historic Shangri-La in Emerald Hills - Rarely does a property offer the intimacy of a soulful retreat and the scale of a private park. Set on a breathtaking 28,000+ sq. ft. lot (3 parcels), 271 Sylvan Way is a 1928 summer retreat lovingly transformed into a one-of-a-kind sanctuary. The Warmth of this home meets history with panoramic 180-degree views of Edgewood

  Pamela Tyson Compass

  271 Sylvan Way, Emerald Hills, CA 94062
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  /42

  $2,800,000

  • 4 Beds
  • 2 Baths
  • 1,860 Sq Ft

  3950 Brookline Way, Emerald Hills, CA 94062

  Tucked away in the hills above Redwood City, Emerald Hills offers a picturesque hillside community surrounded by natural beauty. This Emerald Hills property offers potential for multi-generational living with 2 separate homes. On combined lots of about 16,459 sf total, each home has a separate drive, separate utilities, and designated address. The primary home has about 1860 sf, featuring decks

  Marilyn Koron Coldwell Banker Realty

  3950 Brookline Way, Emerald Hills, CA 94062
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  /46

  $2,339,000

  • 3 Beds
  • 2 Baths
  • 1,560 Sq Ft

  108 Santa Maria Ave, Portola Valley, CA 94028

  Exceptional opportunity in Woodside Highlands on over half an acre of private, lush grounds. This light-filled 3-bedroom, 2-bath home is set on a quiet lot surrounded by mature trees, gardens, and fruit trees, offering a peaceful retreat in one of Portola Valleys most desirable neighborhoods. The main level features two bedrooms, one bath, hardwood floors, beautiful woodwork, and an oversized

  Janeen Poutre Coldwell Banker Realty

  108 Santa Maria Ave, Portola Valley, CA 94028
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  /13

  $699,000

  • 2 Beds
  • 1 Bath
  • 1,110 Sq Ft

  14826 Skyline Blvd Unit 3, Redwood City, CA 94062

  Tucked along Skyline Boulevard, this 2-bedroom, 1-bath Woodside condo with its own private one car garage and laundry offers a lifestyle thats becoming increasingly hard to find: quiet, privacy, and nature; without giving up proximity to Silicon Valley and the Peninsula. Only 10-15 minutes to hwy 280 and set among towering redwoods, open sky, an ocean view and steps away from trails. This home

  Stephanie Nash Compass

  14826 Skyline Blvd Unit 3, Redwood City, CA 94062
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  /8

  $13,500,000

  • 2 Beds
  • 3.5 Baths
  • 3,200 Sq Ft

  309 Olive Hill Ln, Woodside, CA 94062

  Discover an exceptional opportunity to create a dream home or reimagine the existing Neoclassical residence on one of central Woodsides most desirable streets. Spanning just over 3.4 acres, this expansive property showcases rare Bay views. There is an existing planning study by Pacific Peninsula Architects for guidance in future opportunities. Positioned at the end of a private lane, the setting

  Mary Gullixson Compass

  309 Olive Hill Ln, Woodside, CA 94062

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