San Gregorio, CA Houses for Sale

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

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

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 interiors feature wide-plank hardwood floors, soaring ceilings, and refined finishes that create a light-filled, airy atmosphere in harmony with its natural surroundings. Expansive formal rooms are complemented by multiple fireplaces,

Michael Repka Deleon Realty

A rare offering in coveted Emerald Hills, this beautifully reimagined residence blends timeless architecture with sophisticated modern living on over one-half acre of exceptionally level grounds. Framed by manicured landscaping and an expansive driveway, the home offers remarkable privacy, scale, and effortless elegance.Light-filled interiors showcase refined finishes, and a thoughtfully designed

Gagan Singh

Welcome to 904 Lakeview Way, a beautifully updated 3-bedroom, 3-bath home in one of Emerald Hills most sought-after and conveniently located neighborhoods. This inviting split-level floor plan features a dramatic high-ceiling living room with hardwood floors and a fireplace, flowing into the formal dining room where glass doors open to a serene backyard with a BBQ patio and lawn areaperfect for

Vicky Costantini Compass

NEW PRICE $200,000 PRICE REDUCTION! Exceptional Emerald Hills residence offering light-filled interiors and seamless indoor-outdoor living. Thoughtfully designed for everyday living and entertaining, this 5-bedroom, 4.5-bath home features formal living and dining rooms, private office/bonus room, and chefs kitchen opening to the family room. A ground-floor en-suite bedroom with separate garden

Teri Rossetto Shaughnessy Christie's International Real Estate Sereno

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 Tree Rd, this unique offering combines privacy, natural beauty, and convenient access to Silicon Valley, making it ideal for homeowners, investors, or those seeking a legacy property. Surrounded by mature trees and Woodside's

Matthew Dapolito Intero Real Estate Services

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

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 nearly 0.5 acre lot features abundant, 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 surrounded by windows which bring the

Stephen Rumberg Keller Williams Realty-Silicon Valley

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 living and dining rooms, a designer kitchen with Carrara marble finishes and wine bar, a welcoming family room, a lower-level recreation and media room, and a private bedroom with its own entrance and adjacent bath that is ideal

Hugh Cornish Coldwell Banker Realty

Spectacular Monterey Colonial home on 6+ private acres. Long gated driveway & large motor court. Estate shows tremendous character and beauty. Improvements include a stunning primary bath, a complete new roof & gutters & Exterior paint 2025. 3 expansive levels with grand public rooms, large eat-in kitchen, English Pub bar, recreation/media room and fitness room with sauna, wine room for approx.

Steve Lessard Compass

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, unobstructed views stretching clear across the Bayfrom vibrant sunrises over the water to shimmering city lights at night. Inside, three thoughtfully designed levels of living space are anchored by soaring ceilings, expansive glass,

Scott Hayes Compass

One-of-a-Kind Mountain Oasis on Spacious Sunny Lot! Charming 1930s log cabin cottage getaway with impeccable newer construction master suite addition, on fenced 1/3 acre of natural, drought resistant landscaping among dozens of majestic redwoods. Open kitchen with granite counters and new six-burner gas range. High ceilings, radiant heated hardwood and tile floors throughout. High quality

Allen Nazari Park Lane Capital Inc

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 what you do not see: neighbors. The Oak canopy and the open expanse of the Joan Olson Preserve fill the windows instead. Friends who visit call it the Treehouse. Built in 1959, the home keeps its mid-century bones: mahogany

Chris Iverson Golden Gate Sotheby's International Realty

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 opportunity, approximately 70% complete, with expired permits. Buyer to verify with County of San Mateo the existence and status of any past permits and the ability to resume construction towards completion. Grand scale luxury

Geoffrey Nelson Coldwell Banker Realty

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

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 for guidance in future opportunities. Positioned at the end of a private lane, the setting reflects the essence of Woodside

Mary Gullixson Compass

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, artisan tile, and beamed ceilings with the peace of mind of enterprise-grade infrastructure. The grounds are a private resort masterpiece designed for serene living,

Erika Demma Compass

Tucked at the end of a peaceful cul-de-sac in Woodside Hills, this beautifully reimagined single-level retreat pairs timeless ranch design with an unbeatable connection to nature. Panoramic views stretch across Hoover Tower, Moffett Field, the Dish, and Mount Hamilton — a backdrop that changes with the light throughout the day. Set on a full acre with a creekside property line, the grounds feel

Ella Naylor Compass

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 numerous updates make the home ready to enjoy, while the expansive property presents exceptional opportunities for future expansion or building new. The home has 3 bedrooms, 2 baths, an updated kitchen, living room with fireplace,

Hugh Cornish Coldwell Banker Realty

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, privacy, and possibility come together. Tucked away on picturesque Native Sons Road, this extraordinary property offers a peaceful woodland setting with an existing cottage and valuable infrastructure already in place, including a

Liliana Perazich Coldwell Banker Realty

PRIME LOCATION, Comprehensively Rebuilt, this comfortable Single-Story Home is located on its own corner and street, Hamilton Way, in a park-like fenced in setting. The home offers exceptional views in a neighborhood with serenity unmatched to any other. No expenses nor details were spared. A picture-windowed Primary Bedroom Suite with separate entrance and 3 large bedrooms make this 4 bedroom

Cher Rowland Intero Real Estate Services

Evoking the patina & permanence of a residence shaped over generations, this vineyard estate possesses an authenticity rarely achieved in contemporary construction. Completed in 2016 imbued with character of timeless European manor, it received the Julia Morgan Award for Classical Architecture, honoring its exceptional craftsmanship & architectural integrity. Hand-hewn beams, bespoke millwork,

Hugh Cornish Coldwell Banker Realty

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 2000, and in 2025, an entirely new guest house and entertainment complex was added to the estate. The classically styled main residence features nearly every room opening to the views and includes a state-of-the-art theater and

Mary Gullixson Compass

A grand entry welcomes you to a large traditional living room & formal dining room. Perfect for entertaining, the eat-in kitchen opens to a warm family room and patio slider for indoor-outdoor flow! The extra-large primary suite boasts canyon views, a walk-in closet, & spacious bath w/ separate toilet. Nestled in Emerald Hills near Edgewood Park & Handley Rock, with easy Edgewood Rd & I-280

Pam Tyson Compass

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 home features dramatic light-filled interiors with an open-concept design, SOARING CEILINGS, and abundant sliding glass doors and skylights. Bamboo floors, vertical grain cabinetry, and polished concrete counters. The main rooms

Scott Dancer Compass

Set upon an extraordinary 3.25-acre setting, and just west of Palo Alto sits this charming one-story home which offers a rare sense of seclusion and natural beauty, further enhanced by its adjacency to a protected 6-acre parcel that ensures enduring privacy. The grounds are a true sanctuary, featuring a 40-year-old native garden that blooms nearly year-round, and a spacious rear deck overlooks

Mercedes Roses Compass

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 vaulted beamed ceilings, angled transom windows, and abundant natural light. The main level has a spacious living room with fireplace, dining area opening to the view deck, an updated eat-in kitchen, plus the primary suite, two

Scott Dancer Compass