San Gregorio, CA Homes for Sale with Acreage

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

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

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

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

Set on 1.5 acres at the end of a quiet cul-de-sac in Central Woodside, the property offers a beautifully completely updated estimated 2,105 sq ft retreat in the highly regarded Woodside School District. The refreshed home features wide-plank oak hardwood floors, new dual-pane windows, LED lighting, and a new metal roof with added skylights. The renovated kitchen showcases shaker cabinetry, white

Helen Miller Compass

Spectacular Monterey colonial home on 6+ private acres. Long gated driveway & large motor court the estate shows tremendous original 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

Steve Lessard 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, 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

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

*NOW REDUCED FOR SALE ON OFFER DATE THURSDAY JULY 9, 12 NOON* 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

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

Set on quiet Native Sons Road, this approximately 3.63-acre property offers privacy, natural beauty, and an opportunity to restore or reimagine a home in one of the Peninsulas most beloved mountain communities. A charming cottage surrounded by mature trees and near El Corte de Madera Open Space Preserve, the setting feels peaceful and inspiring. The existing residence is ready for a new vision,

Liliana Perazich Coldwell Banker Realty

One of Woodside's premier estates, encompassing nearly 10,000 square feet across all structures, this property offers exceptional scale, quality, and lifestyle, highlighted by a classically styled main residence and a brand-new guest house crafted with authentic European detail. The main home is luxuriously appointed across two levels, with nearly every room opening to the outdoors. A

Mary Gullixson Compass

Set upon an extraordinary 3.25-acre setting, this charming one-story home 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 this serene landscape, creating a

Mercedes Roses 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